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21st January 2014 @ 10:25
Osm: OSM-S-1_to_OSM-S-10

OSM-S-2

Context

OSM Series 1

Original Sources

Preparation of 1-(4-fluorophenyl)-2,5-dimethyl-1H-pyrrole-3-carbaldehyde (OSM-S-2)

Formylation of 1-(4-fluorophenyl)-2,5-dimethyl-1H-pyrrole (PMY 2-1)

Scale up (3 mmol): Formylation of 1-(4-fluorophenyl)-2,5-dimethyl-1H-pyrrole (PMY 2-2)

Scale up (11 mmol): Formylation of 1-(4-fluorophenyl)-2,5-dimethyl-1H-pyrrole (PMY 2-3)

Scale up (11 mmol): Formylation of 1-(4-fluorophenyl)-2,5-dimethyl-1H-pyrrole (PMY 2-4)

Preparation of 1-(4-fluorophenyl)-2,5-dimethyl-1H-pyrrole-3-carbaldehyde (PMY 2-5)

Preparation of 1-(4-fluorophenyl)-2,5-dimethyl-1H-pyrrole-3-carbaldehyde

TCMDC_AP AEW 2-1

Formylation of 1-(4-fluorophenyl)-2,5-dimethyl-1H-pyrrole (AEW 2-2)

Synthesis of 1-(4-fluorophenyl)-2,5-dimethyl-1H-pyrrole-3-carbaldehyde (AEW 2-3)

Biological Evaluation

First Set of Biological Data

Second Analysis of First Set of Compounds (Avery)

Re-evaluation of TCMDC-123794, TCMDC-123812 and others by GSK Tres Cantos

GSK DHODH Assay

Synonyms

PMY 2, AEW 2

CC(N1C2=CC=C(F)C=C2)=C(C=O)C=C1C

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

COLPZCHNJIVKMV-UHFFFAOYSA-N

1-(4-fluorophenyl)-2,5-dimethyl-1H-pyrrole-3-carbaldehyde

Literature

Reported here and here and here though data incomplete.

Procedure used for synthesis: http://dx.doi.org/10.1021/jm00098a013 and  http://dx.doi.org/10.1002/cmdc.200600026

See also community suggestion for synthesis advice that was employed.

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26th March 2013 @ 05:28
Osm: OSM-S-1_to_OSM-S-10

OSM-S-10

Original Sources

Hydrolysis of acyl-iminothiazolidinone PMY 14-1 (PMY 16-1)

Attempt: Synthesis of phenyliminothiazolidinone-substituted arylpyrrole (PMY 14-1)

Synthesis of phenyliminothiazolidinone-substituted arylpyrrole (PMY 14-2)

Synthesis of phenyliminothiazolidinone-substituted arylpyrrole (PMY 14-3)

Synthesis of 4-Fluoro substituted near neighbour (PMY 14-4)

Resynthesis of (2Z,5Z)-5-((1-(4-fluorophenyl)-2,5-dimethyl-1H-pyrrol-3-yl)methylene)-2-(phenylimino)thiazolidin-4-one (AEW 80-1, OSM-S-10)

Reduction of 4-fluoro near-neighbour (N-H) Michael-acceptor (PMY 39-1)

Biological Data

3D7, K1 and HEK293 - Avery - Second Round of Evaluation by the Avery Lab

3D7 - GSK - Second Round of Evaluation by GSK Tres Cantos

Metabolism - Metabolism and Solubility Results

Plasma - Human and Mouse Plasma Stability of OSM-S-5/PMY 10-6

Pharmacokinetics - Pharmacokinetics of OSM-S-5/TCMDC-123812/PMY 10-6

Synonyms

PMY 14, AEW 80

CC(N1C2=CC=C(F)C=C2)=C(/C=C(C(N/3)=O)\SC3=N/C4=CC=CC=C4)C=C1C

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-

IMCPBTMVWRMBHR-MOSHPQCFSA-N

(2Z,5Z)-5-((1-(4-fluorophenyl)-2,5-dimethyl-1H-pyrrol-3-yl)methylene)-2-(phenylimino)thiazolidin-4-one

Attached Files
26th March 2013 @ 05:22
Osm: OSM-S-1_to_OSM-S-10

OSM-S-9

Original Sources

Acetylation of 4-fluoro near neighbour PMY 14-4 (PMY 35-1)

Accidental synthesis: Synthesis of phenyliminothiazolidinone-substituted arylpyrrole (PMY 14-1)

Accidental synthesis: Synthesis of phenyliminothiazolidinone-substituted arylpyrrole (PMY 14-2)

Biological Data

3D7, K1 and HEK293 - Avery - Second Analysis of First Set of Compounds (Avery)

3D7 - GSK - Re-evaluation of TCMDC-123794, TCMDC-123812 and others by GSK Tres Cantos

Metabolism - Metabolism and Solubility Results

Plasma - Human and Mouse Plasma Stability of OSM-S-5/PMY 10-6

Pharmacokinetics - Pharmacokinetics of OSM-S-5/TCMDC-123812/PMY 10-6

Late stage gametocyte testing of a sample set of GSK-Arylpyrrole Series

GSK DHODH Assay

Synonyms

PMY 14, PMY 35

FC1=CC=C(C=C1)N2C(C)=CC(/C=C(SC(N(C3=CC=CC=C3)C(C)=O)=N4)/C4=O)=C2C

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-

WFLINPFRLHPFGO-HMAPJEAMSA-N

(Z)-N-(5-((1-(4-fluorophenyl)-2,5-dimethyl-1H-pyrrol-3-yl)methylene)-4-oxo-4,5-dihydrothiazol-2-yl)-N-phenylacetamide

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26th March 2013 @ 05:20
Osm: OSM-S-1_to_OSM-S-10

OSM-S-8

Original Sources

Coupling of acid PMY 8-2 and 4-aminoantipyrine for a linker-less analogue of TCMDC-123794 (PMY 12-1)

Coupling of acid PMY 8-2 and 4-aminoantipyrine for a linker-less analogue of TCMDC-123794 (PMY 12-2)

Failed: Coupling of acid PMY 8-2 and 4-aminoantipyrine using EDC for a linker-less analogue of TCMDC-123794 (PMY 12-3)

Coupling of acid PMY 8-2 and 4-aminoantipyrine using T3P for a linker-less analogue of TCMDC-123794 (PMY 12-4)

Coupling of acid PMY 8-3 and 4-aminoantipyrine using T3P for a linker-less analogue of TCMDC-123794 (PMY 12-5)

Repeat synthesis of N-(1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-yl)-1-(4-fluorophenyl)-2,5-dimethyl-1H-pyrrole-3-carboxamide, OSM-S-8 (AEW 62-1)

Biological Data

3D7, K1 and HEK293 - Avery - Second Analysis of First Set of Compounds (Avery)

3D7 - GSK - Re-evaluation of TCMDC-123794, TCMDC-123812 and others by GSK Tres Cantos

3D7 - Ralph - Second Round Biological evaluation by James Pham and Stuart Ralph

GSK DHODH Assay

Synonyms

PMY 12, AEW 62

FC1=CC=C(N2C(C)=CC(C(NC3=C(C)N(C)N(C4=CC=CC=C4)C3=O)=O)=C2C)C=C1

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)

NVKLEDPUHCCJRE-UHFFFAOYSA-N

N-(1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-yl)-1-(4-fluorophenyl)-2,5-dimethyl-1H-pyrrole-3-carboxamide

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