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29th November 2012 @ 05:10
Reaction Scheme PY14.png

DMF (5.0 mL) was stirred under a nitrogen atmosphere in an ice-bath. Phosphoryl chloride (1.18 mL, 12.7 mmol, 1.2 equiv.) was added and the reaction stirred for 25 minutes. Reaction still colourless. A solution of pyrrole PMY 1-6 (2.00 g, 10.5 mmol, 1 equiv.) in DMF (5 mL) was added dropwise over 5 minutes. The reaction was removed from the ice-bath and allowed to warm to room temperature. After 45 minutes, reaction was complete by TLC. Poured over ice (100 ml). pH adjusted to 6 (approx. 20% NaOH) and left stirring overnight. In the morning, pH was 3. 20% NaOH added until pH 11 and left for a further 30 minutes. The solid was filtered and washed with water. The solid was a wet beige paste. Recrystallised (MeCN/water) to obtain a first crop of tan free-flowing powder (2.05 g, 89%).



crystals filterd
Solid prior to recrystallisation.

Hazard and Risk Assessment:
As for Scale up (3 mmol): Formylation of 1-(4-fluorophenyl)-2,5-dimethyl-1H-pyrrole (PMY 2-2).
Linked Posts
This post is linked by:
3rd November 2012 @ 04:19
List: OSM-S-1_to

This page is no longer actively edited. The active spreadsheet of all OSM compounds is here. The corresponding visualisation of the data is here. Note that in the below the structure given for OSM-S-56 is slightly wrong (an isomer). The correct structure may be seen here or via the above links.

OSM-S-139OSM-S-140

OSM-S-141OSM-S-142OSM-S-143OSM-S-144

OSM-S-145OSM-S-146OSM-S-147OSM-S-148OSM-S-149

OSM-S-150OSM-S-151OSM-S-152OSM-S-153OSM-S-154

OSM-S-155OSM-S-156OSM-S-157OSM-S-158OSM-S-159

OSM-S-167OSM-S-168OSM-S-169OSM-S-170OSM-S-171

OSM-S-172OSM-S-173OSM-S-174OSM-S-175

OSM-S-187OSM-S-188OSM-S-189OSM-S-190OSM-S-191OSM-S-192 OSM-S-193OSM-S-194OSM-S-195OSM-S-196OSM-S-197OSM-S-198OSM-S-199OSM-S-200OSM-S-201OSM-S-202OSM-S-203OSM-S-204OSM-S-205OSM-S-209OSM-S-210OSM-S-211OSM-S-212OSM-S-213OSM-S-214  OSM-S-215   OSM-S-216  OSM-S-217OSM-S-223OSM-S-224OSM-S-225

OSM-S-227 OSM-S-228 OSM-S-229 OSM-S-230

OSM-S-236OSM-S-237OSM-S-238 OSM-S-239

OSM-S-240 OSM-S-241 OSM-S-242 OSM-S-243

OSM-S-244 OSM-S-245

OSM-S-254OSM-S-255OSM-S-256OSM-S-257 OSM-S-258     OSM-S-262 OSM-S-263 OSM-S-264 OSM-S-265 OSM-S-266 OSM-S-267 OSM-S-268 OSM-S-269OSM-S-270OSM-S-271 OSM-S-272

 

 

OSM-E Compounds

OSM-E-1OSM-E-2OSM-E-3OSM-E-4

OSM-E-5OSM-E-6OSM-E-7OSM-E-8

OSM-E-9OSM-E-10OSM-E-11OSM-E-12

OSM-E-13OSM-S-14

 

OSM-L Compounds

OSM-L-1OSM-L-2

Attached Files
3rd November 2012 @ 02:57
A procedure for the Paal-Knorr synthesis of 1-(4-Fluoro-phenyl)-2,5-dimethyl-1H-pyrrole.

Reaction Scheme

4-fluoroaniline (10.4 mL, 110 mmol, 1.1 equiv.) and 2,5-hexanedione (11.7 mL, 100 mmol, 1 equiv.) were heated to 110 °C (oil bath temp.). After 15 hours, reaction was cooled to room temperature. The mixture was dissolved in hot EtOH (15 mL) and a mixture of EtOH (30 mL) and aqueous solution of 10% citric acid (15 mL). The reaction was slowly cooled to approx. 10 °C with periodic shaking. The resulting crystals were filted and washed with water (approx. 200 mL) to obtain the product as pale tan crystals (14.98 g, 79%) after drying under vacuum at room temperature. A further crop of brown crystals (1.89 g, 10%) could be obtained from mother liquor.

Data:
1H and 13C 300 MHz Data

mpt: 48-49 °C (EtOH/water)
m/z (APCI+) 190 [M+H]+, 100%.

References:

Manetti, F.; Magnani, M.; Castagnolo, D.; Passalacqua, L.; Botta, M.; Corelli, F.; Saddi, M.; Deidda, D; De Logu, A. ChemMedChem, 2006, 1, 973–989. doi: 10.1002/cmdc.200600026

Original Experiment:
Scale-up (100 mmol) of Paal-Knorr Synthesis of 1-aryl-2,5-dimethyl Pyrrole Core (PMY 1-6)

Structural Information
InChI=1S/C6H6FN/c7-5-1-3-6(8)4-2-5/h1-4H,8H2
and
InChI=1S/C6H10O2/c1-5(7)3-4-6(2)8/h3-4H2,1-2H3
gives: InChI=1S/C12H12FN/c1-9-3-4-10(2)14(9)12-7-5-11(13)6-8-12/h3-8H,1-2H3
Linked Posts
This post is linked by:
3rd November 2012 @ 02:54

By clicking here this page can be viewed using the Chemicalize website which will display the sturtures of the compounds when you mouse over the InChI strings.

OSM_ID

3D7_IC50_nM_Avery Link / InChI
OSM-S-1   InChI=1S/C12H12FN/c1-9-3-4-10(2)14(9)12-7-5-11(13)6-8-12/h3-8H,1-2H3
OSM-S-2 60% @ 120000 InChI=1S/C13H12FNO/c1-9-7-11(8-16)10(2)15(9)13-5-3-12(14)4-6-13/h3-8H,1-2H3
OSM-S-3 11960 InChI=1S/C15H16FNO2/c1-4-19-15(18)14-9-10(2)17(11(14)3)13-7-5-12(16)6-8-13/h5-9H,4H2,1-3H3
OSM-S-4 75% @ 120000 InChI=1S/C13H12FNO2/c1-8-7-12(13(16)17)9(2)15(8)11-5-3-10(14)4-6-11/h3-7H,1-2H3,(H,16,17)
OSM-S-5 404 InChI=1S/C15H15FN2O3/c1-9-7-13(15(20)21-8-14(17)19)10(2)18(9)12-5-3-11(16)4-6-12/h3-7H,8H2,1-2H3,(H2,17,19)
OSM-S-6 345 InChI=1S/C26H25FN4O4/c1-16-14-22(17(2)30(16)20-12-10-19(27)11-13-20)26(34)35-15-23(32)28-24-18(3)29(4)31(25(24)33)21-8-6-5-7-9-21/h5-14H,15H2,1-4H3,(H,28,32)
OSM-S-7 7800 InChI=1S/C26H34FN3O2/c1-18-17-24(19(2)29(18)23-15-13-20(27)14-16-23)25(31)30(22-11-7-4-8-12-22)26(32)28-21-9-5-3-6-10-21/h13-17,21-22H,3-12H2,1-2H3,(H,28,32)
OSM-S-8 100% @ 80000 InChI=1S/C24H23FN4O2/c1-15-14-21(16(2)28(15)19-12-10-18(25)11-13-19)23(30)26-22-17(3)27(4)29(24(22)31)20-8-6-5-7-9-20/h5-14H,1-4H3,(H,26,30)
OSM-S-9 47 InChI=1S/C24H20FN3O2S/c1-15-13-18(16(2)27(15)21-11-9-19(25)10-12-21)14-22-23(30)26-24(31-22)28(17(3)29)20-7-5-4-6-8-20/h4-14H,1-3H3/b22-14-
OSM-S-10 176 InChI=1S/C22H18FN3OS/c1-14-12-16(15(2)26(14)19-10-8-17(23)9-11-19)13-20-21(27)25-22(28-20)24-18-6-4-3-5-7-18/h3-13H,1-2H3,(H,24,25,27)/b20-13-
OSM-S-11   InChI=1S/C13H14FNO/c1-9-7-11(8-16)10(2)15(9)13-5-3-12(14)4-6-13/h3-7,16H,8H2,1-2H3
OSM-S-12 70% @ 120000 InChI=1S/C13H13NO2/c1-9-8-12(13(15)16)10(2)14(9)11-6-4-3-5-7-11/h3-8H,1-2H3,(H,15,16)
OSM-S-13 70% @ 120000 InChI=1S/C14H15NO2/c1-9-4-6-12(7-5-9)15-10(2)8-13(11(15)3)14(16)17/h4-8H,1-3H3,(H,16,17)
OSM-S-14 25% @ 120000 InChI=1S/C14H12F3NO2/c1-8-7-12(13(19)20)9(2)18(8)11-5-3-10(4-6-11)14(15,16)17/h3-7H,1-2H3,(H,19,20)
OSM-S-15   InChI=1S/C9H9NO3/c11-8(12)6-10-9(13)7-4-2-1-3-5-7/h1-5H,6H2,(H,10,13)(H,11,12)
OSM-S-16 >80000 InChI=1S/C20H20N4O3/c1-14-18(20(27)24(23(14)2)16-11-7-4-8-12-16)22-17(25)13-21-19(26)15-9-5-3-6-10-15/h3-12H,13H2,1-2H3,(H,21,26)(H,22,25)
OSM-S-17   InChI=1S/C18H24N4O4/c1-12-15(20-14(23)11-19-17(25)26-18(2,3)4)16(24)22(21(12)5)13-9-7-6-8-10-13/h6-10H,11H2,1-5H3,(H,19,25)(H,20,23)
OSM-S-18   InChI=1S/C13H16N4O2/c1-9-12(15-11(18)8-14)13(19)17(16(9)2)10-6-4-3-5-7-10/h3-7H,8,14H2,1-2H3,(H,15,18)
OSM-S-19 25-80% @ 80000 InChI=1S/C15H16FN3O2/c1-9-7-13(15(21)18-8-14(17)20)10(2)19(9)12-5-3-11(16)4-6-12/h3-7H,8H2,1-2H3,(H2,17,20)(H,18,21)
OSM-S-20   InChI=1S/C13H11ClFNO/c1-8-7-12(13(14)17)9(2)16(8)11-5-3-10(15)4-6-11/h3-7H,1-2H3
OSM-S-21 31000 InChI=1S/C26H26FN5O3/c1-16-14-22(17(2)31(16)20-12-10-19(27)11-13-20)25(34)28-15-23(33)29-24-18(3)30(4)32(26(24)35)21-8-6-5-7-9-21/h5-14H,15H2,1-4H3,(H,28,34)(H,29,33)
OSM-S-22   InChI=1S/C13H13FN2O/c1-8-7-12(13(15)17)9(2)16(8)11-5-3-10(14)4-6-11/h3-7H,1-2H3,(H2,15,17)
OSM-S-23   InChI=1S/C13H14N2O2/c1-3-17-13(16)12-9-14-15(10(12)2)11-7-5-4-6-8-11/h4-9H,3H2,1-2H3
OSM-S-24   InChI=1S/C11H10N2O2/c1-8-10(11(14)15)7-12-13(8)9-5-3-2-4-6-9/h2-7H,1H3,(H,14,15)
OSM-S-25   InChI=1S/C12H13N/c1-10-8-9-11(2)13(10)12-6-4-3-5-7-12/h3-9H,1-2H3
OSM-S-26   InChI=1S/C13H15N/c1-10-4-8-13(9-5-10)14-11(2)6-7-12(14)3/h4-9H,1-3H3
OSM-S-27   InChI=1S/C13H12F3N/c1-9-3-4-10(2)17(9)12-7-5-11(6-8-12)13(14,15)16/h3-8H,1-2H3
OSM-S-28 55% @ 120000 InChI=1S/C13H13NO/c1-10-8-12(9-15)11(2)14(10)13-6-4-3-5-7-13/h3-9H,1-2H3
OSM-S-29 could not determine InChI=1S/C14H15NO/c1-10-4-6-14(7-5-10)15-11(2)8-13(9-16)12(15)3/h4-9H,1-3H3
OSM-S-30 85% @ 120000 InChI=1S/C16H19NO2/c1-5-19-16(18)15-10-12(3)17(13(15)4)14-8-6-11(2)7-9-14/h6-10H,5H2,1-4H3
OSM-S-31 80% @ 120000 InChI=1S/C15H17NO2/c1-4-18-15(17)14-10-11(2)16(12(14)3)13-8-6-5-7-9-13/h5-10H,4H2,1-3H3
OSM-S-32 85% @ 120000 InChI=1S/C16H16F3NO2/c1-4-22-15(21)14-9-10(2)20(11(14)3)13-7-5-12(6-8-13)16(17,18)19/h5-9H,4H2,1-3H3
OSM-S-33   InChI=1S/C14H11F6N/c1-8-3-4-9(2)21(8)12-6-10(13(15,16)17)5-11(7-12)14(18,19)20/h3-7H,1-2H3
OSM-S-34   InChI=1S/C14H12F3NO/c1-9-7-11(8-19)10(2)18(9)13-5-3-12(4-6-13)14(15,16)17/h3-8H,1-2H3
OSM-S-35 26 InChI=1S/C22H19N3OS/c1-15-13-17(16(2)25(15)19-11-7-4-8-12-19)14-20-21(26)24-22(27-20)23-18-9-5-3-6-10-18/h3-14H,1-2H3,(H,23,24,26)/b20-14-
OSM-S-36   InChI=1S/C15H11F6NO/c1-8-3-10(7-23)9(2)22(8)13-5-11(14(16,17)18)4-12(6-13)15(19,20)21/h3-7H,1-2H3
OSM-S-37 15 InChI=1S/C23H21N3OS/c1-15-9-11-20(12-10-15)26-16(2)13-18(17(26)3)14-21-22(27)25-23(28-21)24-19-7-5-4-6-8-19/h4-14H,1-3H3,(H,24,25,27)/b21-14-
OSM-S-38 2 InChI=1S/C23H18F3N3OS/c1-14-12-16(15(2)29(14)19-10-8-17(9-11-19)23(24,25)26)13-20-21(30)28-22(31-20)27-18-6-4-3-5-7-18/h3-13H,1-2H3,(H,27,28,30)/b20-13-
OSM-S-39 0.78 InChI=1S/C24H17F6N3OS/c1-13-8-15(9-20-21(34)32-22(35-20)31-18-6-4-3-5-7-18)14(2)33(13)19-11-16(23(25,26)27)10-17(12-19)24(28,29)30/h3-12H,1-2H3,(H,31,32,34)/b20-9-
OSM-S-40   InChI=1S/C15H17NO2/c1-4-18-15(17)13-7-9-14(10-8-13)16-11(2)5-6-12(16)3/h5-10H,4H2,1-3H3
OSM-S-41   InChI=1S/C11H12N2/c1-9-6-7-10(2)13(9)11-5-3-4-8-12-11/h3-8H,1-2H3
OSM-S-42 could not determine InChI=1S/C25H19F3N4OS/c1-16-14-18(17(2)32(16)21-10-8-19(9-11-21)25(26,27)28)15-22-23(33)31(13-12-29)24(34-22)30-20-6-4-3-5-7-20/h3-11,14-15H,13H2,1-2H3/b22-15-,30-24-
OSM-S-43 3120 InChI=1S/C25H19F3N4OS/c1-16-14-18(17(2)32(16)21-10-8-19(9-11-21)25(26,27)28)15-22-23(33)30-24(34-22)31(13-12-29)20-6-4-3-5-7-20/h3-11,14-15H,13H2,1-2H3/b22-15-
OSM-S-44   InChI=1S/C12H12N2O/c1-9-7-11(8-15)10(2)14(9)12-5-3-4-6-13-12/h3-8H,1-2H3
OSM-S-45 12 InChI=1S/C25H20F3N3O2S/c1-15-13-18(16(2)30(15)21-11-9-19(10-12-21)25(26,27)28)14-22-23(33)29-24(34-22)31(17(3)32)20-7-5-4-6-8-20/h4-14H,1-3H3/b22-14-
OSM-S-46   InChI=1S/C16H17NO3/c1-4-20-16(19)13-5-7-15(8-6-13)17-11(2)9-14(10-18)12(17)3/h5-10H,4H2,1-3H3
OSM-S-47   InChI=1S/C15H12N2OS/c18-14-11-19-15(16-12-7-3-1-4-8-12)17(14)13-9-5-2-6-10-13/h1-10H,11H2/b16-15-
OSM-S-48 169 InChI=1S/C25H23N3O3S/c1-4-31-24(30)18-10-12-21(13-11-18)28-16(2)14-19(17(28)3)15-22-23(29)27-25(32-22)26-20-8-6-5-7-9-20/h5-15H,4H2,1-3H3,(H,26,27,29)/b22-15-
OSM-S-49 63 InChI=1S/C24H21N3O2S/c1-16-14-19(17(2)26(16)20-10-6-4-7-11-20)15-22-23(29)25-24(30-22)27(18(3)28)21-12-8-5-9-13-21/h4-15H,1-3H3/b22-15-
OSM-S-50 326 InChI=1S/C25H23N3O2S/c1-16-10-12-22(13-11-16)27-17(2)14-20(18(27)3)15-23-24(30)26-25(31-23)28(19(4)29)21-8-6-5-7-9-21/h5-15H,1-4H3/b23-15-
OSM-S-51 307 InChI=1S/C21H18N4OS/c1-14-12-16(15(2)25(14)19-10-6-7-11-22-19)13-18-20(26)24-21(27-18)23-17-8-4-3-5-9-17/h3-13H,1-2H3,(H,23,24,26)/b18-13-
OSM-S-52 54 InChI=1S/C29H22F3N3OS/c1-19-17-21(20(2)34(19)25-15-13-22(14-16-25)29(30,31)32)18-26-27(36)35(24-11-7-4-8-12-24)28(37-26)33-23-9-5-3-6-10-23/h3-18H,1-2H3/b26-18-,33-28-
OSM-S-53   InChI=1S/C9H10N2O2/c1-7(12)10-9(13)11-8-5-3-2-4-6-8/h2-6H,1H3,(H2,10,11,12,13)
OSM-S-54 34 InChI=1S/C28H26F3N3OS/c1-18-16-20(19(2)33(18)24-14-12-21(13-15-24)28(29,30)31)17-25-26(35)34(23-10-6-7-11-23)27(36-25)32-22-8-4-3-5-9-22/h3-5,8-9,12-17,23H,6-7,10-11H2,1-2H3/b25-17-,32-27-
OSM-S-55 could not determine InChI=1S/C16H12N2OS/c19-15-14(11-12-7-3-1-4-8-12)20-16(18-15)17-13-9-5-2-6-10-13/h1-11H,(H,17,18,19)/b14-11-
OSM-S-56 333 InChI=1S/C12H15N5O3S/c1-15(2)12(18)17-9-13-11(14-17)21(19,20)16(3)10-7-5-4-6-8-10/h4-9H,1-3H3
OSM-S-57 >40000 InChI=1S/C13H13N3O3/c1-9-11(13(18)19-8-12(14)17)7-15-16(9)10-5-3-2-4-6-10/h2-7H,8H2,1H3,(H2,14,17)
OSM-S-58 >40000 InChI=1S/C15H18FN3O/c1-10-7-12(8-18-9-15(17)20)11(2)19(10)14-5-3-13(16)4-6-14/h3-7,18H,8-9H2,1-2H3,(H2,17,20)
OSM-S-59 >40000 InChI=1S/C16H18FN3O2/c1-10-8-14(16(22)19(3)9-15(18)21)11(2)20(10)13-6-4-12(17)5-7-13/h4-8H,9H2,1-3H3,(H2,18,21)
OSM-S-60 >40000 InChI=1S/C16H20FN3O/c1-11-8-13(9-19(3)10-16(18)21)12(2)20(11)15-6-4-14(17)5-7-15/h4-8H,9-10H2,1-3H3,(H2,18,21)
OSM-S-61 >40000 InChI=1S/C17H19FN2O4/c1-10-8-14(16(22)19-15(9-21)17(23)24-3)11(2)20(10)13-6-4-12(18)5-7-13/h4-8,15,21H,9H2,1-3H3,(H,19,22)/t15-/m0/s1
OSM-S-62 >40000 InChI=1S/C17H15FN2O3/c1-10-8-14(16-19-15(9-23-16)17(21)22-3)11(2)20(10)13-6-4-12(18)5-7-13/h4-9H,1-3H3
OSM-S-63 >40000 InChI=1S/C17H17FN2O3/c1-10-8-14(16-19-15(9-23-16)17(21)22-3)11(2)20(10)13-6-4-12(18)5-7-13/h4-8,15H,9H2,1-3H3/t15-/m0/s1
OSM-S-64 >40000 InChI=1S/C10H11N3OS/c1-6-15-9-8(1)11-7-12-10(9)13-2-4-14-5-3-13/h1,6-7H,2-5H2
OSM-S-65 >40000 InChI=1S/C6H3IN2OS/c7-4-1-3-5(11-4)6(10)9-2-8-3/h1-2H,(H,8,9,10)
OSM-S-66 >40000 InChI=1S/C9H9N3S/c1-2-4-8(5-3-1)6-13-9-10-7-11-12-9/h1-5,7H,6H2,(H,10,11,12)
OSM-S-67 438 InChI=1S/C12H14N4OS/c1-15(2)12(17)16-9-13-11(14-16)18-8-10-6-4-3-5-7-10/h3-7,9H,8H2,1-2H3
OSM-S-68 >40000 InChI=1S/C17H19FN2O3/c1-10-9-14(15(21)23-17(3,4)16(19)22)11(2)20(10)13-7-5-12(18)6-8-13/h5-9H,1-4H3,(H2,19,22)
OSM-S-69 >40000 InChI=1S/C7H7NO3S/c1-11-7(10)6-5(8-4-9)2-3-12-6/h2-4H,1H3,(H,8,9)
OSM-S-70 94000 InChI=1S/C6H3ClN2S/c7-6-5-4(1-2-10-5)8-3-9-6/h1-3H
OSM-S-71 >40000 InChI=1S/C6H5N3S/c7-6-5-4(1-2-10-5)8-3-9-6/h1-3H,(H2,7,8,9)
OSM-S-72 >40000 InChI=1S/C18H13N3O2S2/c22-25(23,14-9-5-2-6-10-14)21-17-15-11-16(13-7-3-1-4-8-13)24-18(15)20-12-19-17/h1-12H,(H,19,20,21)
OSM-S-73 >40000 InChI=1S/C15H16N4O2S2/c1-10-4-5-11(8-13(10)23(20,21)19(2)3)18-15-14-12(6-7-22-14)16-9-17-15/h4-9H,1-3H3,(H,16,17,18)
OSM-S-74 17600 InChI=1S/C19H18N4O3S3/c1-20-29(24,25)17-8-7-14(27-17)10-21-19-18-15(22-11-23-19)9-16(28-18)12-3-5-13(26-2)6-4-12/h3-9,11,20H,10H2,1-2H3,(H,21,22,23)
OSM-S-75 >40000 InChI=1S/C18H20N4O3S2/c1-25-14-2-4-15(5-3-14)27(23,24)22-9-6-13(7-10-22)21-18-17-16(8-11-26-17)19-12-20-18/h2-5,8,11-13H,6-7,9-10H2,1H3,(H,19,20,21)
OSM-S-76 >40000 InChI=1S/C14H14N4O2S2/c1-9(10-3-2-4-11(7-10)22(15,19)20)18-14-13-12(5-6-21-13)16-8-17-14/h2-9H,1H3,(H2,15,19,20)(H,16,17,18)/t9-/m1/s1
OSM-S-77 >40000 InChI=1S/C16H18N4O3S2/c1-4-23-13-6-5-11(9-14(13)25(21,22)20(2)3)19-16-15-12(7-8-24-15)17-10-18-16/h5-10H,4H2,1-3H3,(H,17,18,19)
OSM-S-78 >40000 InChI=1S/C19H16N4O2S2/c20-27(24,25)15-7-5-13(6-8-15)11-21-19-16-3-1-2-4-17(16)22-18(23-19)14-9-10-26-12-14/h1-10,12H,11H2,(H2,20,24,25)(H,21,22,23)
OSM-S-79 >40000 InChI=1S/C13H12N4O2S2/c14-21(18,19)10-3-1-2-9(6-10)7-15-13-12-11(4-5-20-12)16-8-17-13/h1-6,8H,7H2,(H2,14,18,19)(H,15,16,17)
OSM-S-80 80% @ 40000 InChI=1S/C23H21N3O5S2/c1-29-17-4-2-16(3-5-17)21-14-20-22(32-21)23(25-15-24-20)31-18-6-8-19(9-7-18)33(27,28)26-10-12-30-13-11-26/h2-9,14-15H,10-13H2,1H3
OSM-S-81 >40000 InChI=1S/C17H21N3O2/c1-12-10-15(17(22)18-11-16(21)19(3)4)13(2)20(12)14-8-6-5-7-9-14/h5-10H,11H2,1-4H3,(H,18,22)
OSM-S-82 9400 InChI=1S/C16H17FN2O3/c1-10-8-14(16(21)22-9-15(20)18-3)11(2)19(10)13-6-4-12(17)5-7-13/h4-8H,9H2,1-3H3,(H,18,20)
OSM-S-83 >40000 InChI=1S/C17H19N3O2/c1-12-10-15(17(22)19-9-8-18-16(21)11-19)13(2)20(12)14-6-4-3-5-7-14/h3-7,10H,8-9,11H2,1-2H3,(H,18,21)
OSM-S-84 70% @ 40000 InChI=1S/C17H20BrN3O2/c1-11-9-15(17(23)20(4)10-16(22)19-3)12(2)21(11)14-7-5-13(18)6-8-14/h5-9H,10H2,1-4H3,(H,19,22)
OSM-S-85 >40000 InChI=1S/C23H22N4O3S/c1-15-12-20(16(2)27(15)18-9-5-4-6-10-18)22-25-26-23(30-22)31-14-21(28)24-17-8-7-11-19(13-17)29-3/h4-13H,14H2,1-3H3,(H,24,28)
OSM-S-86 >40000 InChI=1S/C23H22F3N3O2/c1-4-28(13-21(30)27-22-19(25)6-5-7-20(22)26)23(31)18-12-14(2)29(15(18)3)17-10-8-16(24)9-11-17/h5-12H,4,13H2,1-3H3,(H,27,30)
OSM-S-87 85% @ 40000 InChI=1S/C21H24N4O3/c1-13-7-6-8-17(9-13)25-14(2)10-18(16(25)4)21(27)24(5)12-20(26)22-19-11-15(3)28-23-19/h6-11H,12H2,1-5H3,(H,22,23,26)
OSM-S-88 14700 InChI=1S/C21H29ClN4O/c1-15-12-17(16(2)26(15)20-6-4-18(22)5-7-20)13-24-19-8-10-25(11-9-19)14-21(27)23-3/h4-7,12,19,24H,8-11,13-14H2,1-3H3,(H,23,27)
OSM-S-89 24700 InChI=1S/C20H27ClN4O/c1-4-23-20(26)19-10-16(22)12-24(19)11-15-9-13(2)25(14(15)3)18-8-6-5-7-17(18)21/h5-9,16,19H,4,10-12,22H2,1-3H3,(H,23,26)/t16-,19+/m1/s1
OSM-S-90 >40000 InChI=1S/C21H28N2O2/c1-4-17-5-7-20(8-6-17)23-15(2)13-19(16(23)3)14-22-11-9-18(10-12-22)21(24)25/h5-8,13,18H,4,9-12,14H2,1-3H3,(H,24,25)
OSM-S-91 11300 InChI=1S/C17H19FN2O3/c1-11-9-15(17(22)23-10-16(21)19(3)4)12(2)20(11)14-7-5-13(18)6-8-14/h5-9H,10H2,1-4H3
OSM-S-92 >40000 InChI=1S/C12H10FN3O3/c13-9-1-3-10(4-2-9)16-6-8(5-15-16)12(18)19-7-11(14)17/h1-6H,7H2,(H2,14,17)
OSM-S-93 >40000 InChI=1S/C15H17FN2O/c1-10-9-14(15(19)17(3)4)11(2)18(10)13-7-5-12(16)6-8-13/h5-9H,1-4H3
OSM-S-94 96% @ 40000 InChI=1S/C17H21FN2/c1-13-11-15(12-19-9-3-4-10-19)14(2)20(13)17-7-5-16(18)6-8-17/h5-8,11H,3-4,9-10,12H2,1-2H3
OSM-S-95 4800 InChI=1S/C25H30FN3/c1-19-16-22(20(2)29(19)25-10-8-23(26)9-11-25)17-27-24-12-14-28(15-13-24)18-21-6-4-3-5-7-21/h3-11,16,24,27H,12-15,17-18H2,1-2H3
OSM-S-96 >40000 InChI=1S/C15H12FN3O3/c1-9-12(14-18-13(8-22-14)15(20)21-2)7-17-19(9)11-5-3-10(16)4-6-11/h3-8H,1-2H3
OSM-S-97 >40000 InChI=1S/C16H16FNO3/c1-10-9-14(15(19)7-8-16(20)21)11(2)18(10)13-5-3-12(17)4-6-13/h3-6,9H,7-8H2,1-2H3,(H,20,21)
OSM-S-98 >40000 InChI=1S/C18H21FN2O2/c1-12-11-16(17(22)9-10-18(23)20(3)4)13(2)21(12)15-7-5-14(19)6-8-15/h5-8,11H,9-10H2,1-4H3
OSM-S-99 >40000 InChI=1S/C18H20FNO4/c1-5-23-17(21)13(4)24-18(22)16-10-11(2)20(12(16)3)15-8-6-14(19)7-9-15/h6-10,13H,5H2,1-4H3/t13-/m1/s1
OSM-S-100 >40000 InChI=1S/C16H16FNO4/c1-9-8-14(16(21)22-11(3)15(19)20)10(2)18(9)13-6-4-12(17)5-7-13/h4-8,11H,1-3H3,(H,19,20)/t11-/m1/s1
OSM-S-101 >40000 InChI=1S/C16H13FN2O3/c1-9-7-13(15-18-14(8-22-15)16(20)21)10(2)19(9)12-5-3-11(17)4-6-12/h3-8H,1-2H3,(H,20,21)
OSM-S-102 >40000 InChI=1S/C17H19FN2O2/c1-11-10-15(16(21)8-9-17(22)19-3)12(2)20(11)14-6-4-13(18)5-7-14/h4-7,10H,8-9H2,1-3H3,(H,19,22)
OSM-S-103 61% @ 40000 InChI=1S/C16H17FN2O2/c1-10-9-14(15(20)7-8-16(18)21)11(2)19(10)13-5-3-12(17)4-6-13/h3-6,9H,7-8H2,1-2H3,(H2,18,21)
OSM-S-104 >40000 InChI=1S/C14H10FN3O3/c1-8-11(13-17-12(7-21-13)14(19)20)6-16-18(8)10-4-2-9(15)3-5-10/h2-7H,1H3,(H,19,20)
OSM-S-105 >40000 InChI=1S/C14H11FN4O2/c1-8-11(14-18-12(7-21-14)13(16)20)6-17-19(8)10-4-2-9(15)3-5-10/h2-7H,1H3,(H2,16,20)
OSM-S-106 36 InChI=1S/C12H10N4O2S2/c13-12-11-9(15-6-16-12)5-10(19-11)7-2-1-3-8(4-7)20(14,17)18/h1-6H,(H2,13,15,16)(H2,14,17,18)
OSM-S-107 92% @ 40,000 InChI=1S/C17H17FN4S/c18-14-3-1-13(2-4-14)11-21-6-8-22(9-7-21)17-16-15(5-10-23-16)19-12-20-17/h1-5,10,12H,6-9,11H2
OSM-S-108 1200 InChI=1S/C16H15N3OS/c1-10-8-12(11(2)17-10)9-14-15(20)19-16(21-14)18-13-6-4-3-5-7-13/h3-9,17H,1-2H3,(H,18,19,20)/b14-9-
OSM-S-109 262 InChI=1S/C22H18N4O3S/c1-14-12-16(15(2)25(14)18-8-10-19(11-9-18)26(28)29)13-20-21(27)24-22(30-20)23-17-6-4-3-5-7-17/h3-13H,1-2H3,(H,23,24,27)/b20-13-
OSM-S-110 2300 InChI=1S/C22H18N4O4S/c1-13-10-15(14(2)25(13)17-6-8-18(9-7-17)26(29)30)11-20-21(28)24-22(31-20)23-16-4-3-5-19(27)12-16/h3-12,27H,1-2H3,(H,23,24,28)/b20-11-
OSM-S-111 146 InChI=1S/C23H21N3O2S/c1-15-13-17(16(2)26(15)19-9-11-20(28-3)12-10-19)14-21-22(27)25-23(29-21)24-18-7-5-4-6-8-18/h4-14H,1-3H3,(H,24,25,27)/b21-14-
OSM-S-112 1600 InChI=1S/C23H21N3O3S/c1-14-11-16(15(2)26(14)18-7-9-20(29-3)10-8-18)12-21-22(28)25-23(30-21)24-17-5-4-6-19(27)13-17/h4-13,27H,1-3H3,(H,24,25,28)/b21-12-
OSM-S-113 >40000 InChI=1S/C21H18N4O2S/c1-13-11-15(14(2)25(13)19-5-3-4-10-22-19)12-18-20(27)24-21(28-18)23-16-6-8-17(26)9-7-16/h3-12,26H,1-2H3,(H,23,24,27)/b18-12-
OSM-S-114 1200 InChI=1S/C22H19N3O2S/c1-14-11-16(15(2)25(14)18-8-4-3-5-9-18)12-20-21(27)24-22(28-20)23-17-7-6-10-19(26)13-17/h3-13,26H,1-2H3,(H,23,24,27)/b20-12-
OSM-S-115 1800 InChI=1S/C22H19N3O2S/c1-14-12-16(15(2)25(14)18-6-4-3-5-7-18)13-20-21(27)24-22(28-20)23-17-8-10-19(26)11-9-17/h3-13,26H,1-2H3,(H,23,24,27)/b20-13-
OSM-S-116 11000 InChI=1S/C16H17FN2O3/c1-9-8-14(16(21)22-11(3)15(18)20)10(2)19(9)13-6-4-12(17)5-7-13/h4-8,11H,1-3H3,(H2,18,20)/t11-/m1/s1
OSM-S-117 >40,000 InChI=1S/C10H11N3OS/c1-6-15-9-8(1)11-7-12-10(9)13-2-4-14-5-3-13/h1,6-7H,2-5H2
OSM-S-118 >40,000 InChI=1S/C12H8N2S/c1-2-4-9(5-3-1)11-12-10(6-7-15-12)13-8-14-11/h1-8H
OSM-S-119 >40,000 InChI=1S/C12H6Br2N2S/c13-8-10-11(17-12(8)14)9(15-6-16-10)7-4-2-1-3-5-7/h1-6H
OSM-S-120 >40,000 InChI=1S/C12H7BrN2S/c13-10-6-9-12(16-10)11(15-7-14-9)8-4-2-1-3-5-8/h1-7H
OSM-S-121 95% @ 40,000 InChI=1S/C6H2BrClN2S/c7-4-1-3-5(11-4)6(8)10-2-9-3/h1-2H
OSM-S-122 >40,000 InChI=1S/C18H12N2S/c1-3-7-13(8-4-1)16-11-15-18(21-16)17(20-12-19-15)14-9-5-2-6-10-14/h1-12H
OSM-S-123 >40,000 InChI=1S/C12H9N3S/c13-12-11-9(14-7-15-12)6-10(16-11)8-4-2-1-3-5-8/h1-7H,(H2,13,14,15)
OSM-S-124 62% @ 40,000 InChI=1S/C17H17N3O2S/c1-21-13-4-2-12(3-5-13)15-10-14-16(23-15)17(19-11-18-14)20-6-8-22-9-7-20/h2-5,10-11H,6-9H2,1H3
OSM-S-125 >40,000 InChI=1S/C10H10BrN3OS/c11-8-5-7-9(16-8)10(13-6-12-7)14-1-3-15-4-2-14/h5-6H,1-4H2
OSM-S-126 39% @ 40,000 InChI=1S/C16H15N3OS/c1-2-4-12(5-3-1)14-10-13-15(21-14)16(18-11-17-13)19-6-8-20-9-7-19/h1-5,10-11H,6-9H2
OSM-S-127 42% @ 40,000 InChI=1S/C16H16N4O3S2/c17-25(21,22)12-3-1-2-11(8-12)14-9-13-15(24-14)16(19-10-18-13)20-4-6-23-7-5-20/h1-3,8-10H,4-7H2,(H2,17,21,22)
OSM-S-128 54% @ 40,000 InChI=1S/C16H17N3S/c1-16(2,3)11-6-4-10(5-7-11)13-8-12-14(20-13)15(17)19-9-18-12/h4-9H,1-3H3,(H2,17,18,19)
OSM-S-129 >40,000 InChI=1S/C12H10N4O2S2/c13-12-11-9(15-6-16-12)5-10(19-11)7-1-3-8(4-2-7)20(14,17)18/h1-6H,(H2,13,15,16)(H2,14,17,18)
OSM-S-130 >40,000 InChI=1S/C15H14N4OS/c1-19(2)15(20)10-5-3-9(4-6-10)12-7-11-13(21-12)14(16)18-8-17-11/h3-8H,1-2H3,(H2,16,17,18)
OSM-S-131 >40,000 InChI=1S/C13H11N3OS/c1-17-9-4-2-8(3-5-9)11-6-10-12(18-11)13(14)16-7-15-10/h2-7H,1H3,(H2,14,15,16)
OSM-S-132 >40,000 InChI=1S/C17H16N4O2S/c18-16-15-13(19-10-20-16)9-14(24-15)11-1-3-12(4-2-11)17(22)21-5-7-23-8-6-21/h1-4,9-10H,5-8H2,(H2,18,19,20)
OSM-S-133 73% @ 40,000 InChI=1S/C15H14N4OS/c1-19(2)15(20)10-5-3-4-9(6-10)12-7-11-13(21-12)14(16)18-8-17-11/h3-8H,1-2H3,(H2,16,17,18)
OSM-S-134 >40,000 InChI=1S/C18H19N5OS/c1-22-6-8-23(9-7-22)18(24)13-4-2-12(3-5-13)15-10-14-16(25-15)17(19)21-11-20-14/h2-5,10-11H,6-9H2,1H3,(H2,19,20,21)
OSM-S-135 >40,000 InChI=1S/C13H10N4OS/c14-12-11-9(16-6-17-12)5-10(19-11)7-2-1-3-8(4-7)13(15)18/h1-6H,(H2,15,18)(H2,14,16,17)
OSM-S-136 15000 InChI=1S/C17H16BrFN4S/c18-15-9-14-16(24-15)17(21-11-20-14)23-7-5-22(6-8-23)10-12-1-3-13(19)4-2-12/h1-4,9,11H,5-8,10H2
OSM-S-137 17000 InChI=1S/C23H22FN5O2S2/c24-18-6-4-16(5-7-18)14-28-8-10-29(11-9-28)23-22-20(26-15-27-23)13-21(32-22)17-2-1-3-19(12-17)33(25,30)31/h1-7,12-13,15H,8-11,14H2,(H2,25,30,31)
OSM-S-138 23000 InChI=1S/C22H20N4OS/c1-14-12-16(15(2)26(14)19-10-8-17(23)9-11-19)13-20-21(27)25-22(28-20)24-18-6-4-3-5-7-18/h3-13H,23H2,1-2H3,(H,24,25,27)/b20-13-
OSM-S-139   InChI=1S/C6H4BrN3S/c7-4-1-3-5(11-4)6(8)10-2-9-3/h1-2H,(H2,8,9,10)
OSM-S-140  

InChI=1S/C6H5BrN4S/c7-4-1-3-5(12-4)6(11-8)10-2-9-3/h1-2H,8H2,(H,9,10,11) 

OSM-S-141  

InChI=1S/C8H9N3S/c1-11(2)8-7-6(3-4-12-7)9-5-10-8/h3-5H,1-2H3

OSM-S-142   InChI=1S/C18H19N5OS/c1-22-5-7-23(8-6-22)18(24)13-4-2-3-12(9-13)15-10-14-16(25-15)17(19)21-11-20-14/h2-4,9-11H,5-8H2,1H3,(H2,19,20,21)
OSM-S-143   InChI=1S/C12H8ClN3O2S2/c13-12-11-9(15-6-16-12)5-10(19-11)7-2-1-3-8(4-7)20(14,17)18/h1-6H,(H2,14,17,18)
OSM-S-144   InChI=1S/C16H18N4O3S2/c1-20(2)6-7-23-16-15-13(18-10-19-16)9-14(24-15)11-4-3-5-12(8-11)25(17,21)22/h3-5,8-10H,6-7H2,1-2H3,(H2,17,21,22)
OSM-S-145   InChI=1S/C14H14N4O2S2/c1-18(2)14-13-11(16-8-17-14)7-12(21-13)9-4-3-5-10(6-9)22(15,19)20/h3-8H,1-2H3,(H2,15,19,20)
OSM-S-146   InChI=1S/C17H26BNO6S/c1-15(2,3)23-14(20)19-26(21,22)13-10-8-9-12(11-13)18-24-16(4,5)17(6,7)25-18/h8-11H,1-7H3,(H,19,20)
OSM-S-147   InChI=1S/C6H6N2O2/c1-10-6(9)5-4-7-2-3-8-5/h2-4H,1H3
OSM-S-148   InChI=1S/C6H6N2O3/c1-11-6(9)5-4-8(10)3-2-7-5/h2-4H,1H3
OSM-S-149   InChI=1S/C6H5ClN2O2/c1-11-6(10)4-2-8-3-5(7)9-4/h2-3H,1H3
OSM-S-150   InChI=1S/C5H3ClN2O2/c6-4-2-7-1-3(8-4)5(9)10/h1-2H,(H,9,10)
OSM-S-151   InChI=1S/C12H18BNO4S/c1-11(2)12(3,4)18-13(17-11)9-6-5-7-10(8-9)19(14,15)16/h5-8H,1-4H3,(H2,14,15,16)
OSM-S-152   InChI=1S/C13H20BNO4S/c1-12(2)13(3,4)19-14(18-12)10-7-6-8-11(9-10)20(16,17)15-5/h6-9,15H,1-5H3
OSM-S-153   InChI=1S/C14H22BNO4S/c1-13(2)14(3,4)20-15(19-13)11-8-7-9-12(10-11)21(17,18)16(5)6/h7-10H,1-6H3
OSM-S-154   InChI=1S/C7H8BrNO2S/c1-9-12(10,11)7-4-2-3-6(8)5-7/h2-5,9H,1H3
OSM-S-155   InChI=1S/C8H10BrNO2S/c1-10(2)13(11,12)8-5-3-4-7(9)6-8/h3-6H,1-2H3
OSM-S-156   InChI=1S/C9H16O4S/c1-3-12-8(10)5-6-14-7-9(11)13-4-2/h3-7H2,1-2H3
OSM-S-157   InChI=1S/C7H12O2S/c1-2-9-7(8)6-4-3-5-10-6/h6H,2-5H2,1H3
OSM-S-158   InChI=1S/C8H6F3NO3S/c1-15-6(13)5-4(2-3-16-5)12-7(14)8(9,10)11/h2-3H,1H3,(H,12,14)
OSM-S-159   InChI=1S/C10H10IN3OS/c11-8-5-7-9(16-8)10(13-6-12-7)14-1-3-15-4-2-14/h5-6H,1-4H2
OSM-S-160   InChI=1S/C9H12F3NO3/c1-16-7(14)5-3-2-4-6(5)13-8(15)9(10,11)12/h5-6H,2-4H2,1H3,(H,13,15)
OSM-S-161   InChI=1S/C13H10BrN3O2S2/c1-8-2-4-9(5-3-8)21(18,19)17-13-12-10(15-7-16-13)6-11(14)20-12/h2-7H,1H3,(H,15,16,17)
OSM-S-162   InChI=1S/C15H13N3S/c1-10-8-11-4-2-3-5-13(11)18(10)15-14-12(6-7-19-14)16-9-17-15/h2-7,9-10H,8H2,1H3
OSM-S-163   InChI=1S/C13H11BrN2O/c14-10-5-4-8-12(9-10)16-13(17)15-11-6-2-1-3-7-11/h1-9H,(H2,15,16,17)
OSM-S-164   InChI=1S/C12H17BO2/c1-11(2)12(3,4)15-13(14-11)10-8-6-5-7-9-10/h5-9H,1-4H3
OSM-S-165   InChI=1S/C10H11N3S2/c1-4-15-9-8(1)11-7-12-10(9)13-2-5-14-6-3-13/h1,4,7H,2-3,5-6H2
OSM-S-166  

InChI=1S/C13H10ClN3S/c1-17(10-4-2-9(14)3-5-10)13-12-11(6-7-18-12)15-8-16-13/h2-8H,1H3 

OSM-S-167   InChI=1S/C7H6BrN3S/c1-9-7-6-4(10-3-11-7)2-5(8)12-6/h2-3H,1H3,(H,9,10,11)
OSM-S-168   InChI=1S/C7H7N3S/c1-8-7-6-5(2-3-11-6)9-4-10-7/h2-4H,1H3,(H,8,9,10)
OSM-S-169   InChI=1S/C8H8BrN3S/c1-12(2)8-7-5(10-4-11-8)3-6(9)13-7/h3-4H,1-2H3
OSM-S-170   InChI=1S/C10H12BrN3OS/c1-14(2)3-4-15-10-9-7(12-6-13-10)5-8(11)16-9/h5-6H,3-4H2,1-2H3
OSM-S-171   InChI=1S/C6H4N2OS/c9-6-5-4(1-2-10-5)7-3-8-6/h1-3H,(H,7,8,9)
OSM-S-172   InChI=1S/C7H6N2OS/c1-10-7-6-5(2-3-11-6)8-4-9-7/h2-4H,1H3
OSM-S-173   InChI=1S/C8H10BrNO2S/c1-10(2)13(11,12)8-5-3-7(9)4-6-8/h3-6H,1-2H3
OSM-S-174   InChI=1S/C11H14N4S/c1-14-3-5-15(6-4-14)11-10-9(2-7-16-10)12-8-13-11/h2,7-8H,3-6H2,1H3
OSM-S-175   InChI=1S/C18H11F3N6O2/c19-14-7-11(5-6-23-14)24-17(28)13-8-22-9-15-25-26-16(27(13)15)10-1-3-12(4-2-10)29-18(20)21/h1-9,18H,(H,23,24,28)
OSM-S-176 250 InChI=1S/C20H14ClF2N5O2/c21-14-3-1-2-12(8-14)9-25-19(29)16-10-24-11-17-26-27-18(28(16)17)13-4-6-15(7-5-13)30-20(22)23/h1-8,10-11,20H,9H2,(H,25,29)
OSM-S-177 >10000 InChI=1S/C20H15F2N5O2/c21-20(22)29-16-7-5-13(6-8-16)18-25-24-12-27(18)17(9-23)19(28)26-10-14-3-1-2-4-15(14)11-26/h1-9,12,20H,10-11H2/b17-9+
OSM-S-178 1330 InChI=1S/C20H14ClF2N5O2/c21-14-5-1-12(2-6-14)9-25-19(29)16-10-24-11-17-26-27-18(28(16)17)13-3-7-15(8-4-13)30-20(22)23/h1-8,10-11,20H,9H2,(H,25,29)
OSM-S-179 >10000 InChI=1S/C19H19F2N5O3/c20-19(21)29-14-3-1-13(2-4-14)17-25-24-16-11-22-10-15(26(16)17)18(27)23-9-12-5-7-28-8-6-12/h1-4,10-12,19H,5-9H2,(H,23,27)
OSM-2-180  >10000 InChI=1S/C23H22F2N8O2/c24-23(25)35-17-6-4-16(5-7-17)21-30-29-20-14-26-13-18(33(20)21)22(34)28-15-31-9-11-32(12-10-31)19-3-1-2-8-27-19/h1-8,13-14,23H,9-12,15H2,(H,28,34)
OSM-S-181  >10000 InChI=1S/C19H20F2N6O3/c20-19(21)30-14-3-1-13(2-4-14)17-25-24-16-12-22-11-15(27(16)17)18(28)23-5-6-26-7-9-29-10-8-26/h1-4,11-12,19H,5-10H2,(H,23,28)
OSM-S-182  >10000 InChI=1S/C17H15F2N5O2/c18-17(19)26-12-5-3-11(4-6-12)15-22-21-14-10-20-9-13(24(14)15)16(25)23-7-1-2-8-23/h3-6,9-10,17H,1-2,7-8H2
OSM-S-183 3560 InChI=1S/C23H19F2N5O2/c24-23(25)32-17-10-8-16(9-11-17)21-28-27-20-14-26-13-19(30(20)21)22(31)29-12-4-7-18(29)15-5-2-1-3-6-15/h1-3,5-6,8-11,13-14,18,23H,4,7,12H2
OSM-S-184 >10000 InChI=1S/C18H18F2N6O4S/c1-31(28,29)25-8-6-24(7-9-25)17(27)14-10-21-11-15-22-23-16(26(14)15)12-2-4-13(5-3-12)30-18(19)20/h2-5,10-11,18H,6-9H2,1H3
OSM-S-185 >10000 InChI=1S/C17H15F2N5O3/c18-17(19)27-12-3-1-11(2-4-12)15-22-21-14-10-20-9-13(24(14)15)16(25)23-5-7-26-8-6-23/h1-4,9-10,17H,5-8H2

OSM-S-186

1350

InChI=1S/C21H17F2N5O2/c1-13(14-5-3-2-4-6-14)25-20(29)17-11-24-12-18-26-27-19(28(17)18)15-7-9-16(10-8-15)30-21(22)23/h2-13,21H,1H3,(H,25,29)/t13-/m0/s1

OSM-S-187

 

InChI=1S/C20H15N5O/c21-12-16-6-8-17(9-7-16)20-24-23-18-13-22-14-19(25(18)20)26-11-10-15-4-2-1-3-5-15/h1-9,13-14H,10-11H2

OSM-S-188   InChI=1S/C20H15N5S/c21-12-16-6-8-17(9-7-16)20-24-23-18-13-22-14-19(25(18)20)26-11-10-15-4-2-1-3-5-15/h1-9,13-14H,10-11H2
OSM-S-189   InChI=1S/C20H14ClN5O/c21-17-4-2-1-3-15(17)9-10-27-19-13-23-12-18-24-25-20(26(18)19)16-7-5-14(11-22)6-8-16/h1-8,12-13H,9-10H2
OSM-S-190   InChI=1S/C20H15ClN6/c21-17-3-1-2-14(10-17)8-9-24-18-12-23-13-19-25-26-20(27(18)19)16-6-4-15(11-22)5-7-16/h1-7,10,12-13,24H,8-9H2
OSM-S-191   InChI=1S/C19H15Cl2N5/c20-15-6-4-14(5-7-15)19-25-24-18-12-22-11-17(26(18)19)23-9-8-13-2-1-3-16(21)10-13/h1-7,10-12,23H,8-9H2
OSM-S-192   InChI=1S/C13H15N3O3/c1-9-12(14-11(18)8-17)13(19)16(15(9)2)10-6-4-3-5-7-10/h3-7,17H,8H2,1-2H3,(H,14,18)
OSM-S-193   InChI=1S/C5H8O3/c1-5(2)7-3-4(6)8-5/h3H2,1-2H3
OSM-S-194   InChI=1S/C22H24N2O/c1-2-6-17(7-3-1)16-24-13-11-22(12-14-24)21-19(10-15-25-22)18-8-4-5-9-20(18)23-21/h1-9,23H,10-16H2
OSM-S-195   InChI=1S/C20H22ClNO/c21-19-8-4-7-18-17(19)9-14-23-20(18)10-12-22(13-11-20)15-16-5-2-1-3-6-16/h1-8H,9-15H2
OSM-S-196   InChI=1S/C22H27NO3/c1-24-20-14-18-8-13-26-22(19(18)15-21(20)25-2)9-11-23(12-10-22)16-17-6-4-3-5-7-17/h3-7,14-15H,8-13,16H2,1-2H3
OSM-S-197   InChI=1S/C15H17N2O/c1-2-4-13-11(3-1)12-5-10-18-15(14(12)17-13)6-8-16-9-7-15/h1-4,16H,5-10H2
OSM-S-198   InChI=1S/C18H21NOS/c1-2-4-15(5-3-1)14-19-10-8-18(9-11-19)17-16(6-12-20-18)7-13-21-17/h1-5,7,13H,6,8-12,14H2
OSM-S-199   InChI=1S/C24H25N2O3/c1-2-4-20-18(3-1)19-7-12-29-24(23(19)25-20)8-10-26(11-9-24)16-17-5-6-21-22(15-17)28-14-13-27-21/h1-6,15H,7-14,16H2
OSM-S-200   InChI=1S/C22H23NOS/c1-2-6-17(7-3-1)16-23-13-11-22(12-14-23)21-19(10-15-24-22)18-8-4-5-9-20(18)25-21/h1-9H,10-16H2
OSM-S-201   InChI=1S/C20H14ClF2N5O2/c1-11-14(21)3-2-4-15(11)25-19(29)16-9-24-10-17-26-27-18(28(16)17)12-5-7-13(8-6-12)30-20(22)23/h2-10,20H,1H3,(H,25,29)
OSM-S-202  

InChI=1S/C19H12ClF2N5O2/c20-12-2-1-3-13(8-12)24-18(28)15-9-23-10-16-25-26-17(27(15)16)11-4-6-14(7-5-11)29-19(21)22/h1-10,19H,(H,24,28)

OSM-S-203    InChI=1S/C19H11ClN6O/c20-14-2-1-3-15(8-14)23-19(27)16-10-22-11-17-24-25-18(26(16)17)13-6-4-12(9-21)5-7-13/h1-8,10-11H,(H,23,27)
OSM-S-204    InChI=1S/C19H11ClF3N5O2/c20-12-2-1-3-13(16(12)21)25-18(29)14-8-24-9-15-26-27-17(28(14)15)10-4-6-11(7-5-10)30-19(22)23/h1-9,19H,(H,25,29)
OSM-S-205     InChI=1S/C19H10ClFN6O/c20-13-2-1-3-14(17(13)21)24-19(28)15-9-23-10-16-25-26-18(27(15)16)12-6-4-11(8-22)5-7-12/h1-7,9-10H,(H,24,28)
OSM-S-206   InChI=1S/C21H11F8N5O2/c22-19(23)36-14-3-1-10(2-4-14)17-33-32-16-9-30-8-15(34(16)17)18(35)31-13-6-11(20(24,25)26)5-12(7-13)21(27,28)29/h1-9,19H,(H,31,35)
OSM-S-207   InChI=1S/C21H14F3N5O2/c22-16-3-1-2-13-10-28(11-15(13)16)20(30)17-8-25-9-18-26-27-19(29(17)18)12-4-6-14(7-5-12)31-21(23)24/h1-9,21H,10-11H2
OSM-S-208   InChI=1S/C21H15F2N5O2/c1-29-18(15-6-7-16(22)17(23)8-15)12-30-20-11-25-10-19-26-27-21(28(19)20)14-4-2-13(9-24)3-5-14/h2-8,10-11,18H,12H2,1H3
OSM-S-209   InChI=1S/C18H21NOS/c1-2-4-15(5-3-1)14-19-10-8-18(9-11-19)16-7-13-21-17(16)6-12-20-18/h1-5,7,13H,6,8-12,14H2
OSM-S-210  

InChI=1S/C20H23NO3S/c1-2-17-18(23-11-10-22-17)13-15(1)14-21-7-5-20(6-8-21)16-4-12-25-19(16)3-9-24-20/h1-2,4,12-13H,3,5-11,14H2

OSM-S-211   InChI=1S/C19H21NO3S/c1-2-16-17(22-13-21-16)11-14(1)12-20-7-5-19(6-8-20)15-4-10-24-18(15)3-9-23-19/h1-2,4,10-11H,3,5-9,12-13H2
OSM-S-212   InChI=1S/C18H20ClNOS/c19-15-3-1-14(2-4-15)13-20-9-7-18(8-10-20)16-6-12-22-17(16)5-11-21-18/h1-4,6,12H,5,7-11,13H2
OSM-S-213    InChI=1S/C18H18BrNO2S/c19-14-3-1-13(2-4-14)17(21)20-9-7-18(8-10-20)15-6-12-23-16(15)5-11-22-18/h1-4,6,12H,5,7-11H2
OSM-S-214    InChI=1S/C24H27FN2OS/c1-17-15-19(18(2)27(17)21-5-3-20(25)4-6-21)16-26-11-9-24(10-12-26)22-8-14-29-23(22)7-13-28-24/h3-6,8,14-15H,7,9-13,16H2,1-2H3
OSM-S-215    InChI=1S/C17H25NOS/c1-2-4-14(5-3-1)18-10-8-17(9-11-18)15-7-13-20-16(15)6-12-19-17/h7,13-14H,1-6,8-12H2
OSM-S-216    InChI=1S/C18H19NO2S/c20-17(14-4-2-1-3-5-14)19-10-8-18(9-11-19)15-7-13-22-16(15)6-12-21-18/h1-5,7,13H,6,8-12H2
OSM-S-217    InChI=1S/C14H18ClNO3S/c15-5-9-18-13(17)16-6-3-14(4-7-16)11-2-10-20-12(11)1-8-19-14/h2,10H,1,3-9H2
OSM-S-218   InChI=1S/C21H15F2N5O2/c1-29-18(15-6-7-16(22)17(23)8-15)12-30-20-11-25-10-19-26-27-21(28(19)20)14-4-2-13(9-24)3-5-14/h2-8,10-11,18H,12H2,1H3
OSM-S-219   InChI=1S/C12H6ClN5/c13-10-6-15-7-11-16-17-12(18(10)11)9-3-1-8(5-14)2-4-9/h1-4,6-7H
OSM-S-220   InChI=1S/C15H14F2I/c1-9-6-10(2)15(11(3)7-9)18-12-4-5-13(16)14(17)8-12/h4-8H,1-3H3/q+1
OSM-S-221   InChI=1S/C12H13NO4/c14-11(13-6-7-17-12(13)15)9-16-8-10-4-2-1-3-5-10/h1-5H,6-9H2
OSM-S-222   InChI=1S/C9H8F2O3/c1-14-9(13)8(12)5-2-3-6(10)7(11)4-5/h2-4,8,12H,1H3
OSM-S-223   InChI=1S/C4H5ClN4/c5-3-1-7-2-4(8-3)9-6/h1-2H,6H2,(H,8,9) 
OSM-S-224    InChI=1S/C12H8ClN5/c13-11-7-15-8-12(17-11)18-16-6-10-3-1-9(5-14)2-4-10/h1-4,6-8H,(H,17,18)/b16-6+ 
OSM-S-225    InChI=1S/C12H8ClN5/c13-11-7-15-8-12(17-11)18-16-6-10-3-1-9(5-14)2-4-10/h1-4,6-8H,(H,17,18)/b16-6+ 
OSM-S-226   InChI=1S/C11H13F2NOSi/c1-16(2,3)15-11(7-14)8-4-5-9(12)10(13)6-8/h4-6,11H,1-3H3
OSM-S-227   InChI=1S/C12H9Cl2N3O/c1-7-8(13)3-2-4-9(7)17-12(18)10-5-15-6-11(14)16-10/h2-6H,1H3,(H,17,18)
OSM-S-228   InChI=1S/C11H6Cl2FN3O/c12-6-2-1-3-7(10(6)14)17-11(18)8-4-15-5-9(13)16-8/h1-5H,(H,17,18)
OSM-S-229   InChI=1S/C12H9Cl2N3O/c1-7-2-3-8(13)4-9(7)17-12(18)10-5-15-6-11(14)16-10/h2-6H,1H3,(H,17,18)
OSM-S-230   InChI=1S/C11H10ClN5O/c12-7-2-1-3-8(4-7)15-11(18)9-5-14-6-10(16-9)17-13/h1-6H,13H2,(H,15,18)(H,16,17)
OSM-S-231   InChI=1S/C12H12ClN5O/c1-7-8(13)3-2-4-9(7)17-12(19)10-5-15-6-11(16-10)18-14/h2-6H,14H2,1H3,(H,16,18)(H,17,19)
OSM-S-232   InChI=1S/C11H9ClFN5O/c12-6-2-1-3-7(10(6)13)17-11(19)8-4-15-5-9(16-8)18-14/h1-5H,14H2,(H,16,18)(H,17,19)
OSM-S-233   InChI=1S/C12H12ClN5O/c1-7-2-3-8(13)4-9(7)17-12(19)10-5-15-6-11(16-10)18-14/h2-6H,14H2,1H3,(H,16,18)(H,17,19)
OSM-S-234   InChI=1S/C19H14ClF2N5O2/c20-13-2-1-3-14(8-13)25-18(28)16-10-23-11-17(26-16)27-24-9-12-4-6-15(7-5-12)29-19(21)22/h1-11,19H,(H,25,28)(H,26,27)/b24-9+
OSM-S-235   InChI=1S/C20H16ClF2N5O2/c1-12-15(21)3-2-4-16(12)27-19(29)17-10-24-11-18(26-17)28-25-9-13-5-7-14(8-6-13)30-20(22)23/h2-11,20H,1H3,(H,26,28)(H,27,29)/b25-9+
     
OSM-S-258   InChI=1S/C18H14ClN5O/c19-15-4-2-1-3-13(15)7-10-25-17-12-21-11-16-22-23-18(24(16)17)14-5-8-20-9-6-14/h1-6,8-9,11-12H,7,10H2
OSM-S-259   InChI=1S/C18H11ClF2N4O/c19-13-4-2-12(3-5-13)18-24-23-16-8-22-9-17(25(16)18)26-10-11-1-6-14(20)15(21)7-11/h1-9H,10H2
OSM-S-260   InChI=1S/C20H14F4N4O2/c21-15-6-1-12(9-16(15)22)7-8-29-18-11-25-10-17-26-27-19(28(17)18)13-2-4-14(5-3-13)30-20(23)24/h1-6,9-11,20H,7-8H2
OSM-S-261   InChI=1S/C20H18ClN5O/c21-16-8-6-15(7-9-16)20-25-24-18-11-23-12-19(26(18)20)27-13-17(22)10-14-4-2-1-3-5-14/h1-9,11-12,17H,10,13,22H2/t17-/m1/s1
     
OSM-L-01 3200 InChI=1S/C28H22FN3OS/c1-19-16-21(20(2)31(19)25-15-9-10-22(29)18-25)17-26-27(33)32(24-13-7-4-8-14-24)28(34-26)30-23-11-5-3-6-12-23/h3-18H,1-2H3/b26-17-,30-28-
chloroquine 18.7 InChI=1S/C18H26ClN3/c1-4-22(5-2)12-6-7-14(3)21-17-10-11-20-18-13-15(19)8-9-16(17)18/h8-11,13-14H,4-7,12H2,1-3H3,(H,20,21)/t14-/m1/s1
artemisinin 6 InChI=1S/C15H22O5/c1-8-4-5-11-9(2)12(16)17-13-15(11)10(8)6-7-14(3,18-13)19-20-15/h8-11,13H,4-7H2,1-3H3/t8-,9-,10+,11+,13-,14-,15-/m1/s1
artesunate   InChI=1S/C19H28O8/c1-10-4-5-13-11(2)16(23-15(22)7-6-14(20)21)24-17-19(13)12(10)8-9-18(3,25-17)26-27-19/h10-13,16-17H,4-9H2,1-3H3,(H,20,21)/t10-,11-,12+,13+,16-,17-,18-,19-/m1/s1
Pyrimethamine 11 InChI=1S/C12H13ClN4/c1-2-9-10(11(14)17-12(15)16-9)7-3-5-8(13)6-4-7/h3-6H,2H2,1H3,(H4,14,15,16,17)
Tafenoquine 451 InChI=1S/C24H28F3N3O3/c1-14-11-20(32-4)30-22-18(29-15(2)7-6-10-28)13-19(31-3)23(21(14)22)33-17-9-5-8-16(12-17)24(25,26)27/h5,8-9,11-13,15,29H,6-7,10,28H2,1-4H3/t15-/m0/s1
Pyronaridine   InChI=1S/C29H32ClN5O2/c1-37-26-9-8-24-28(33-26)27(23-7-6-21(30)16-25(23)32-24)31-22-14-19(17-34-10-2-3-11-34)29(36)20(15-22)18-35-12-4-5-13-35/h6-9,14-16,32-33H,2-5,10-13,17-18H2,1H3
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