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26th January 2017 @ 22:51

A new set of 20 Series 4 Triazolopyrazine compounds were sent to have their efficacy evaluated against Plasmodium falciparum in-vitro at Dundee.

N.B. Potency values are an average of 2 runs. In certain cases (MMV897697, MMV897698, MMV897699, MMV897700, MMV897708, MMV897714), the 2 runs gave more-divergent-than-ideal values, however the averages are still reported.

The following results were obtained:

Brief comments:

Thioether, sulfoxide and sulfone were inactive again. The comparative ether compounds showed good to moderate activity.

Left hand cubane bioisosteres showed good to moderate activty. Right hand isosteres were inactive.

All ether-triazole linked compounds were inactive.

Both 3- and 4-OMe compounds were active

MMV897708 showed slightly reduced activity to the OCHF2 analogue (MMV672687). MMV897707 was inactive compared with the active OCHF2 analogue (MMV897763).

Compounds with a methylated benzylic position showed moderate activity.

MMV897706 and MMV897705 were inactive.

Strings:

MMV693164 OSM-S-363

FC(F)OC1=CC=C(C2=NN=C3C=NC=C(N32)SCCC4=CC=CC=C4)C=C1       InChI=1S/C20H16F2N4OS/c21-20(22)27-16-8-6-15(7-9-16)19-25-24-17-12-23-13-18(26(17)19)28-11-10-14-4-2-1-3-5-14/h1-9,12-13,20H,10-11H2

MMV693167 OSM-S-364

O=S(CCC1=CC=CC=C1)C(N23)=CN=CC2=NN=C3C4=CC=C(OC(F)F)C=C4 InChI=1S/C20H16F2N4O2S/c21-20(22)28-16-8-6-15(7-9-16)19-25-24-17-12-23-13-18(26(17)19)29(27)11-10-14-4-2-1-3-5-14/h1-9,12-13,20H,10-11H2

MMV693166 OSM-S-365

FC(F)OC1=CC=C(C2=NN=C3C=NC=C(N32)S(CCC4=CC=CC=C4)(=O)=O)C=C1 InChI=1S/C20H16F2N4O3S/c21-20(22)29-16-8-6-15(7-9-16)19-25-24-17-12-23-13-18(26(17)19)30(27,28)11-10-14-4-2-1-3-5-14/h1-9,12-13,20H,10-11H2

MMV897697 OSM-S-368

FC(F)OC1=CC=C(C2=NN=C3C=NC=C(N32)OCC4=CC=CC=C4)C=C1     InChI=1S/C19H14F2N4O2/c20-19(21)27-15-8-6-14(7-9-15)18-24-23-16-10-22-11-17(25(16)18)26-12-13-4-2-1-3-5-13/h1-11,19H,12H2

MMV897698 OSM-S-369

FC(F)OC1=CC=C(C2=NN=C3C=NC=C(N32)OCCC4=CC=CC=C4)C=C1   InChI=1S/C20H16F2N4O2/c21-20(22)28-16-8-6-15(7-9-16)19-25-24-17-12-23-13-18(26(17)19)27-11-10-14-4-2-1-3-5-14/h1-9,12-13,20H,10-11H2

MMV897699 OSM-S-370

FC(F)OC(C=C1)=CC=C1C2=NN=C3C=NC=C(OCCCC45C6C7C4C8C7C6C58)N32 InChI=1S/C23H20F2N4O2/c24-22(25)31-11-4-2-10(3-5-11)21-28-27-12-8-26-9-13(29(12)21)30-7-1-6-23-18-15-14-16(18)20(23)17(14)19(15)23/h2-5,8-9,14-20,22H,1,6-7H2

MMV897700 OSM-S-371

FC(F)OC(C=C1)=CC=C1C2=NN=C3C=NC=C(OCCC45C6C7C4C8C7C6C58)N32 InChI=1S/C22H18F2N4O2/c23-21(24)30-10-3-1-9(2-4-10)20-27-26-11-7-25-8-12(28(11)20)29-6-5-22-17-14-13-15(17)19(22)16(13)18(14)22/h1-4,7-8,13-19,21H,5-6H2

MMV897704 OSM-S-375

FC(C=C1)=C(F)C=C1CCOC2=CN=CC3=NN=C(C45C6C7C4C8C7(I)C6C58)N32 InChI=1S/C21H15F2IN4O/c22-9-2-1-8(5-10(9)23)3-4-29-12-7-25-6-11-26-27-19(28(11)12)20-13-16-14(20)18-15(20)17(13)21(16,18)24/h1-2,5-7,13-18H,3-4H2

MMV897710 OSM-S-382

IC12C3C4C5(C3C1C5C24)C6=NN=C7C=NC=C(C(NC8=CC(C(F)(F)F)=NC=C8)=O)N76 InChI=1S/C20H12F3IN6O/c21-20(22,23)8-3-6(1-2-26-8)27-16(31)7-4-25-5-9-28-29-17(30(7)9)18-10-13-11(18)15-12(18)14(10)19(13,15)24/h1-5,10-15H,(H,26,27,31)

MMV897701 OSM-S-372

FC(F)OC1=CC=C(C2=NN=C3C=NC=C(N32)OCC4=CN(CC5=CC=CC=C5)N=N4)C=C1 InChI=1S/C22H17F2N7O2/c23-22(24)33-18-8-6-16(7-9-18)21-28-27-19-10-25-11-20(31(19)21)32-14-17-13-30(29-26-17)12-15-4-2-1-3-5-15/h1-11,13,22H,12,14H2

MMV897702 OSM-S-373

FC(F)OC1=CC=C(C2=NN=C3C=NC=C(N32)OCC4=CN(C5=CC=CC=C5)N=N4)C=C1 InChI=1S/C21H15F2N7O2/c22-21(23)32-17-8-6-14(7-9-17)20-27-26-18-10-24-11-19(30(18)20)31-13-15-12-29(28-25-15)16-4-2-1-3-5-16/h1-12,21H,13H2

MMV897703 OSM-S-374

ClC1=CN=CC(N2N=NC(COC(N34)=CN=CC3=NN=C4C5=CC=C(C=C5)OC(F)F)=C2)=N1 InChI=1S/C19H12ClF2N9O2/c20-14-5-23-6-15(25-14)30-9-12(26-29-30)10-32-17-8-24-7-16-27-28-18(31(16)17)11-1-3-13(4-2-11)33-19(21)22/h1-9,19H,10H2

MMV897711 OSM-S-383

FC(F)OC(C=C1)=CC=C1C2=NN=C3C=NC=C(OCCC4=CC(OC)=CC=C4)N32 InChI=1S/C21H18F2N4O3/c1-28-17-4-2-3-14(11-17)9-10-29-19-13-24-12-18-25-26-20(27(18)19)15-5-7-16(8-6-15)30-21(22)23/h2-8,11-13,21H,9-10H2,1H3

MMV897712 OSM-S-384

FC(F)OC(C=C1)=CC=C1C2=NN=C3C=NC=C(OCCC4=CC=C(OC)C=C4)N32 InChI=1S/C21H18F2N4O3/c1-28-16-6-2-14(3-7-16)10-11-29-19-13-24-12-18-25-26-20(27(18)19)15-4-8-17(9-5-15)30-21(22)23/h2-9,12-13,21H,10-11H2,1H3

MMV897708 OSM-S-376

OC(C1=CC(F)=C(F)C=C1)COC2=CN=CC3=NN=C(C4=CC=C(C#N)C=C4)N32 InChI=1S/C20H13F2N5O2/c21-15-6-5-14(7-16(15)22)17(28)11-29-19-10-24-9-18-25-26-20(27(18)19)13-3-1-12(8-23)2-4-13/h1-7,9-10,17,28H,11H2

MMV897707 OSM-S-378

FC1=C(F)C=CC(C(N(C)C)COC2=CN=CC3=NN=C(C4=CC=C(C#N)C=C4)N32)=C1 InChI=1S/C22H18F2N6O/c1-29(2)19(16-7-8-17(23)18(24)9-16)13-31-21-12-26-11-20-27-28-22(30(20)21)15-5-3-14(10-25)4-6-15/h3-9,11-12,19H,13H2,1-2H3

MMV897713 OSM-S-385

FC(F)OC(C=C1)=CC=C1C2=NN=C3C=NC=C(OC(C)C4=CC=C(F)C(F)=C4)N32 InChI=1S/C20H14F4N4O2/c1-11(13-4-7-15(21)16(22)8-13)29-18-10-25-9-17-26-27-19(28(17)18)12-2-5-14(6-3-12)30-20(23)24/h2-11,20H,1H3

MMV897714 OSM-S-386

FC(F)OC(C=C1)=CC=C1C2=NN=C3C=NC=C(OC(C)C4=CC=C(C#N)C=C4)N32 InChI=1S/C21H15F2N5O2/c1-13(15-4-2-14(10-24)3-5-15)29-19-12-25-11-18-26-27-20(28(18)19)16-6-8-17(9-7-16)30-21(22)23/h2-9,11-13,21H,1H3

MMV897706 OSM-S-387

FC(C=C1)=C(F)C=C1CCOC2=CN=CC3=NN=C([H])N32                           InChI=1S/C13H10F2N4O/c14-10-2-1-9(5-11(10)15)3-4-20-13-7-16-6-12-18-17-8-19(12)13/h1-2,5-8H,3-4H2

MMV897705 OSM-S-388

OC1=CN=CC2=NN=C(N3CCCCC3)N21                                                     InChI=1S/C10H13N5O/c16-9-7-11-6-8-12-13-10(15(8)9)14-4-2-1-3-5-14/h6-7,16H,1-5H2

Attached Files
Nov 2016 Compound Results.cdx
Nov 2016 Compound Results.png
Nov 2016 Compound Results.xlsx