Next batch of compounds sent for biological testing August 2019 Sydney

[maratsydney]

Results are at bottom of thread!

• Control compounds : MMV897698 as the reference compound (#572); MMV663915 resynthesis by SSP students of this year; additional test for OHOH pfizer compound Synthesis of "The OHOH" - a benzylic hydroxylation product #36.
• SSP compounds: set of compounds made by SSP program students at Sydney University earlier this year, in some cases tele-substituted products were isolated as well.
• Miscellaneous compounds: most of these compounds were made as a part of investigation of tele-substitution reaction.

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MMV Number	SMILES	InChI	InChI Key
MMV1794865	CC1=CC=C(C2=NN=C3C=NC=C(OCCC4=CC=CC=C4)N32)C=C1	"InChI=1S/C20H18N4O/c1-15-7-9-17(10-8-15)20-23-22-18-13-21-14-19(24(18)20)25-12-11-16-5-3-2-4-6-16/h2-10,13-14H,11-12H2,1H3"	SXWAAPADJHJBSD-UHFFFAOYSA-N
MMV1794866	COC1=C(C2=NN=C3C=NC=C(OCCC4=CC=CC=C4)N32)C=CC=C1	"InChI=1S/C20H18N4O2/c1-25-17-10-6-5-9-16(17)20-23-22-18-13-21-14-19(24(18)20)26-12-11-15-7-3-2-4-8-15/h2-10,13-14H,11-12H2,1H3"	WZBPFRAHGWVSIJ-UHFFFAOYSA-N
MMV1794867	C1(CCOC2=CN=CC(N23)=NN=C3C4=CC5=C(OCC5)C=C4)=CC=CC=C1	"InChI=1S/C21H18N4O2/c1-2-4-15(5-3-1)8-10-27-20-14-22-13-19-23-24-21(25(19)20)17-6-7-18-16(12-17)9-11-26-18/h1-7,12-14H,8-11H2"	CZAGUUPDYUFYFD-UHFFFAOYSA-N
MMV1794868	C1(CCOC2=NC=CN3C2=NN=C3C4=CC5=C(OCC5)C=C4)=CC=CC=C1	"InChI=1S/C21H18N4O2/c1-2-4-15(5-3-1)8-12-27-21-20-24-23-19(25(20)11-10-22-21)17-6-7-18-16(14-17)9-13-26-18/h1-7,10-11,14H,8-9,12-13H2"	OPUDZTPTHQKNEJ-UHFFFAOYSA-N
MMV1794869	CCOC1=C(C2=NN=C3C=NC=C(OCCC4=CC=CC=C4)N32)C=CC=C1	"InChI=1S/C21H20N4O2/c1-2-26-18-11-7-6-10-17(18)21-24-23-19-14-22-15-20(25(19)21)27-13-12-16-8-4-3-5-9-16/h3-11,14-15H,2,12-13H2,1H3"	JITNRDHUIGIPAG-UHFFFAOYSA-N
MMV1794870	CCOC1=C(C2=NN=C3C(OCCC4=CC=CC=C4)=NC=CN32)C=CC=C1	"InChI=1S/C21H20N4O2/c1-2-26-18-11-7-6-10-17(18)19-23-24-20-21(22-13-14-25(19)20)27-15-12-16-8-4-3-5-9-16/h3-11,13-14H,2,12,15H2,1H3"	QFOPXLJIKBWQFM-UHFFFAOYSA-N
MMV1794871	COC1=C(OC)C=C(C2=NN=C3C=NC=C(OCCC4=CC=CC=C4)N32)C=C1OC	"InChI=1S/C22H22N4O4/c1-27-17-11-16(12-18(28-2)21(17)29-3)22-25-24-19-13-23-14-20(26(19)22)30-10-9-15-7-5-4-6-8-15/h4-8,11-14H,9-10H2,1-3H3"	UAVMJQLWBOZKCU-UHFFFAOYSA-N
MMV1794872	COC1=C(OC)C=C(C2=NN=C3C(OCCC4=CC=CC=C4)=NC=CN32)C=C1OC	"InChI=1S/C22H22N4O4/c1-27-17-13-16(14-18(28-2)19(17)29-3)20-24-25-21-22(23-10-11-26(20)21)30-12-9-15-7-5-4-6-8-15/h4-8,10-11,13-14H,9,12H2,1-3H3"	YKTLOJBEONQUEK-UHFFFAOYSA-N
MMV897698	FC(OC1=CC=C(C2=NN=C3C=NC=C(OCCC4=CC=CC=C4)N32)C=C1)F	"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"	AVBCIJLYABLIRW-UHFFFAOYSA-N
MMV663915	ClC1=CC=C(C2=NN=C3C=NC=C(OCCC4=CC=CC=C4)N32)C=C1	"InChI=1S/C19H15ClN4O/c20-16-8-6-15(7-9-16)19-23-22-17-12-21-13-18(24(17)19)25-11-10-14-4-2-1-3-5-14/h1-9,12-13H,10-11H2"	VURCFSOLNXCMTN-UHFFFAOYSA-N
MMV1581295	OCC(C1=CC=CC=C1)(O)COC2=CN=CC(N23)=NN=C3C4=CC=C(OC(F)F)C=C4	"InChI=1S/C21H18F2N4O4/c22-20(23)31-16-8-6-14(7-9-16)19-26-25-17-10-24-11-18(27(17)19)30-13-21(29,12-28)15-4-2-1-3-5-15/h1-11,20,28-29H,12-13H2"	LVBNVRWXODMMAV-UHFFFAOYSA-N
MMV1794873	FC(OC1=CC=C(C2=NN=C3C=NC=C(N32)OCC4(C5=CC=CC=C5)COC(C)(OC4)C)C=C1)F	"InChI=1S/C25H24F2N4O4/c1-24(2)33-15-25(16-34-24,18-6-4-3-5-7-18)14-32-21-13-28-12-20-29-30-22(31(20)21)17-8-10-19(11-9-17)35-23(26)27/h3-13,23H,14-16H2,1-2H3"	GOGFQEYNHYWLHG-UHFFFAOYSA-N
MMV1794874	FC1=C(C=C(C=C1)CCOC2=CN=CC3=NN=C(C4=C5C(OCO5)=CC=C4)N32)F	"InChI=1S/C20H14F2N4O3/c21-14-5-4-12(8-15(14)22)6-7-27-18-10-23-9-17-24-25-20(26(17)18)13-2-1-3-16-19(13)29-11-28-16/h1-5,8-10H,6-7,11H2"	GDVWTTMGYDZCGA-UHFFFAOYSA-N
MMV1794875	C1(CCOC2=CN=CC3=NN=C(C4=C5C(OCO5)=CC=C4)N32)=CC=CC=C1	"InChI=1S/C20H16N4O3/c1-2-5-14(6-3-1)9-10-25-18-12-21-11-17-22-23-20(24(17)18)15-7-4-8-16-19(15)27-13-26-16/h1-8,11-12H,9-10,13H2"	ZKHRIXZJEWPHMI-UHFFFAOYSA-N
MMV1794876	COC1=C(C2=NN=C3C=NC=C(OCCC4=CC=CC=C4)N32)C(OC)=CC=C1	"InChI=1S/C21H20N4O3/c1-26-16-9-6-10-17(27-2)20(16)21-24-23-18-13-22-14-19(25(18)21)28-12-11-15-7-4-3-5-8-15/h3-10,13-14H,11-12H2,1-2H3"	LKTVWEBNZPWPDK-UHFFFAOYSA-N
MMV1794877	COC1=C(C2=NN=C3C(O)=NC=CN32)C(OC)=CC=C1	"InChI=1S/C13H12N4O3/c1-19-8-4-3-5-9(20-2)10(8)11-15-16-12-13(18)14-6-7-17(11)12/h3-7H,1-2H3,(H,14,18)"	ICMDKBWEFQQGOD-UHFFFAOYSA-N
MMV1794878	COC1=C(C2=NN=C3C=NC=C(OCCC4=CC=CC=C4)N32)C(OC)=CC(OC)=C1	"InChI=1S/C22H22N4O4/c1-27-16-11-17(28-2)21(18(12-16)29-3)22-25-24-19-13-23-14-20(26(19)22)30-10-9-15-7-5-4-6-8-15/h4-8,11-14H,9-10H2,1-3H3"	ZQEVPGQJEYESQM-UHFFFAOYSA-N
MMV1794879	O=[N+](C1=C(C2=NN=C3C=NC=C(N32)OCCC4=CC=CC=C4)C=CC=C1)[O-]	"InChI=1S/C19H15N5O3/c25-24(26)16-9-5-4-8-15(16)19-22-21-17-12-20-13-18(23(17)19)27-11-10-14-6-2-1-3-7-14/h1-9,12-13H,10-11H2"	UOFWUVKZVYVQRS-UHFFFAOYSA-N
MMV1794880	CC(C)(C)C(C=C1)=CC=C1C2=NN=C(N32)C=NC=C3OCCC4=CC=CC=C4	"InChI=1S/C23H24N4O/c1-23(2,3)19-11-9-18(10-12-19)22-26-25-20-15-24-16-21(27(20)22)28-14-13-17-7-5-4-6-8-17/h4-12,15-16H,13-14H2,1-3H3"	XMBJCSCDNCISLS-UHFFFAOYSA-N
MMV1794881	CC(C)(C)C1=CC(C2=NN=C(N32)C=NC=C3OCCC4=CC=CC=C4)=CC(C(C)(C)C)=C1	"InChI=1S/C27H32N4O/c1-26(2,3)21-14-20(15-22(16-21)27(4,5)6)25-30-29-23-17-28-18-24(31(23)25)32-13-12-19-10-8-7-9-11-19/h7-11,14-18H,12-13H2,1-6H3"	CHHYGUPKJUPRRL-UHFFFAOYSA-N
MMV1794882	C12=NN=C(C3=C4C=CC=CC4=CC5=C3C=CC=C5)N1C=CN=C2OCCC6=CC=CC=C6	"InChI=1S/C27H20N4O/c1-2-8-19(9-3-1)14-17-32-27-26-30-29-25(31(26)16-15-28-27)24-22-12-6-4-10-20(22)18-21-11-5-7-13-23(21)24/h1-13,15-16,18H,14,17H2"	FZWWTLMHHVGZQM-UHFFFAOYSA-N
MMV1794883	C12=NN=C(C3=C4C=CC=CC4=CC5=C3C=CC=C5)N1C(OCCC6=CC=CC=C6)=CN=C2	"InChI=1S/C27H20N4O/c1-2-8-19(9-3-1)14-15-32-25-18-28-17-24-29-30-27(31(24)25)26-22-12-6-4-10-20(22)16-21-11-5-7-13-23(21)26/h1-13,16-18H,14-15H2"	VQFDEGMDKXYPAC-UHFFFAOYSA-N
MMV1794884	COC1=C(C2=NN=C3C(O)=NC=CN32)C(OC)=CC(OC)=C1	"InChI=1S/C14H14N4O4/c1-20-8-6-9(21-2)11(10(7-8)22-3)12-16-17-13-14(19)15-4-5-18(12)13/h4-7H,1-3H3,(H,15,19)"	JFPIHAZCCHRKRA-UHFFFAOYSA-N

2019.08.16 - Dundee Shipment.zip

[MFernflower]

@edwintse Deleting previous comments as I have updated main post

[maratsydney]

So as competition is over - here are results for the august batch:

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Control and retest:

• Control OSM-S-369 showed result 362 nM comparable to previous 251nM, 301nM, 534 nM;
• OSM-S-293 remade by SSP students confirmed high potency 136 nM (previous 166 nM);
• OHOH compound OSM-S-556 was retested again but once again we were unable to replicate potency of original biosynthesis 605 nM (previous 659 nM, 146 nM).

General observations:

• Tele-substitution products are generally inactive, what is in alignment with previous results;
• Sterically bulky substituents (eg. antracenyl or tertbutylphenyl) on triazole ring are not tolerated;
• Electron rich aromatic substituents on triazole ring are not tolerated;
• fluorinated compound OSM-S-662 (1.71 uM) showed significantly higher potency than non-fluorinated analogue OSM-S-693 (14.25 uM);
• OSM-S-651 (0.367 uM) has surprisingly higher potency than unprotected analogue OSM-S-609 (6.132 uM), presumably due to lower polarity and thus improved cell penetration

results.zip