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OpenSourceMalaria / Series5

Open Source Malaria Series Five. 1-substituted isoquinolines
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Batch of compounds sent for potency evaluation March 2020 #5

Open kwanchristopher opened 4 years ago

kwanchristopher commented 4 years ago

The following compounds have been sent off for potency evaluation, and results will be updated when we get them back.

MMV Number SMILES InChI InChI Key
MMV1803705 OC1=C(O)C=C(C2=C1)CCNC32CC4=C(CC3)C=CC=C4.Cl InChI=1S/C18H19NO2.ClH/c20-16-9-13-6-8-19-18(15(13)10-17(16)21)7-5-12-3-1-2-4-14(12)11-18;/h1-4,9-10,19-21H,5-8,11H2;1H RIDZJARMAREEJP-UHFFFAOYSA-N
MMV1803706 OC1=C(C=C2[C@]3(NCCC2=C1)CCC4=C(C3)C=CC=C4)O.Cl InChI=1S/C18H19NO2.ClH/c20-16-9-13-6-8-19-18(15(13)10-17(16)21)7-5-12-3-1-2-4-14(12)11-18;/h1-4,9-10,19-21H,5-8,11H2;1H/t18-;/m0./s1 RIDZJARMAREEJP-FERBBOLQSA-N
MMV1803707 OC1=C(C=C2[C@]3(NCCC2=C1)CCC4=C(C3)C=C(OC)C=C4)O.Cl InChI=1S/C19H21NO3.ClH/c1-23-15-3-2-12-4-6-19(11-14(12)8-15)16-10-18(22)17(21)9-13(16)5-7-20-19;/h2-3,8-10,20-22H,4-7,11H2,1H3;1H/t19-;/m0./s1 IGGBNLPFOUKYOW-FYZYNONXSA-N
MMV1803708 OC1=C(C=C2C3(NCCC2=C1)CC4=C(C3)C=CC=C4)O.Cl InChI=1S/C17H17NO2.ClH/c19-15-7-11-5-6-18-17(14(11)8-16(15)20)9-12-3-1-2-4-13(12)10-17;/h1-4,7-8,18-20H,5-6,9-10H2;1H GNKQHAAQOOVOJY-UHFFFAOYSA-N
MMV1803709 OC1=C(C=C2C3(NCCC2=C1)CCCCC3)F.Cl InChI=1S/C14H18FNO.ClH/c15-12-9-11-10(8-13(12)17)4-7-16-14(11)5-2-1-3-6-14;/h8-9,16-17H,1-7H2;1H BKYCZWYQINENQB-UHFFFAOYSA-N
MMV1803710 OC1=C(C=C2C(C)(CCC3=CC=CC=C3)NCCC2=C1)O.Cl InChI=1S/C18H21NO2.ClH/c1-18(9-7-13-5-3-2-4-6-13)15-12-17(21)16(20)11-14(15)8-10-19-18;/h2-6,11-12,19-21H,7-10H2,1H3;1H KQUXIBHECOJVSN-UHFFFAOYSA-N
MMV1803711 O=C(O)C(F)(F)F.OC1=C(O)C=C([C@@]2(C[C@@H]3C(C[C@H]2C3)=O)NCC4)C4=C1 InChI=1S/C15H17NO3.C2HF3O2/c17-12-5-10-3-9(12)7-15(10)11-6-14(19)13(18)4-8(11)1-2-16-15;3-2(4,5)1(6)7/h4,6,9-10,16,18-19H,1-3,5,7H2;(H,6,7)/t9-,10-,15+;/m1./s1 JWSWKVDFQMKCPO-VGCSDMGASA-N
MMV1803712 OC1=C(O)C=C(C(CCC2=O)N2CC3)C3=C1 InChI=1S/C12H13NO3/c14-10-5-7-3-4-13-9(1-2-12(13)16)8(7)6-11(10)15/h5-6,9,14-15H,1-4H2 LJIDRFNRDLYHNC-UHFFFAOYSA-N
MMV1803713 OC1=C(O)C=C(C(CCCC2=O)N2CC3)C3=C1 InChI=1S/C13H15NO3/c15-11-6-8-4-5-14-10(2-1-3-13(14)17)9(8)7-12(11)16/h6-7,10,15-16H,1-5H2 GEMGWRKYXXKBSX-UHFFFAOYSA-N
MMV1803714 OC1=C(O)C=C(C@HN2CC3)C3=C1 InChI=1S/C13H15NO3/c15-11-6-8-4-5-14-10(2-1-3-13(14)17)9(8)7-12(11)16/h6-7,10,15-16H,1-5H2/t10-/m0/s1 GEMGWRKYXXKBSX-JTQLQIEISA-N
MMV1803715 O[C@@H]1C2=CC(O)=C(O)C=C2C@@HN[C@H]1C.Cl InChI=1S/C16H16BrNO3.ClH/c1-8-16(21)11-7-14(20)13(19)6-10(11)15(18-8)9-4-2-3-5-12(9)17;/h2-8,15-16,18-21H,1H3;1H/t8-,15+,16-;/m0./s1 HWUQKGYCGJFPFQ-BOJOSIOESA-N
MMV1803716 OC1=CC=C(C(CCC2=O)N2CC3)C3=C1 InChI=1S/C12H13NO2/c14-9-1-2-10-8(7-9)5-6-13-11(10)3-4-12(13)15/h1-2,7,11,14H,3-6H2 DJZBGQPEAGNGGC-UHFFFAOYSA-N
MMV1803717 OC1=CC=C2C3(NCCC2=C1)CCCCC3.Cl InChI=1S/C14H19NO.ClH/c16-12-4-5-13-11(10-12)6-9-15-14(13)7-2-1-3-8-14;/h4-5,10,15-16H,1-3,6-9H2;1H UPSOQYNICIHNTL-UHFFFAOYSA-N
MMV1803718 OC1=C(C=C2C3(NCCC2=C1)CCC3)O.Cl InChI=1S/C12H15NO2.ClH/c14-10-6-8-2-5-13-12(3-1-4-12)9(8)7-11(10)15;/h6-7,13-15H,1-5H2;1H NMFFWBYHIPJPLJ-UHFFFAOYSA-N
MMV1803719 OC1=C(C=C2C3(NCCC2=C1)CCCC3)O.Cl InChI=1S/C13H17NO2.ClH/c15-11-7-9-3-6-14-13(4-1-2-5-13)10(9)8-12(11)16;/h7-8,14-16H,1-6H2;1H SKZRHEYHDUAXJS-UHFFFAOYSA-N
MMV1803720 OC1=C(O)C=C2CCNC@HCC3=CC=CC=C3.Cl InChI=1S/C16H17NO2.ClH/c18-15-9-12-6-7-17-14(13(12)10-16(15)19)8-11-4-2-1-3-5-11;/h1-5,9-10,14,17-19H,6-8H2;1H/t14-;/m0./s1 IZPZTGBVHOZPHH-UQKRIMTDSA-N
MMV1803721 O=C(O)C(F)(F)F.OC1=CC=C(C[C@H]2C3=CC(O)=C(O)C=C3CCN2)C=C1 InChI=1S/C16H17NO3.C2HF3O2/c18-12-3-1-10(2-4-12)7-14-13-9-16(20)15(19)8-11(13)5-6-17-14;3-2(4,5)1(6)7/h1-4,8-9,14,17-20H,5-7H2;(H,6,7)/t14-;/m0./s1 NXGIYILCGUQKCZ-UQKRIMTDSA-N
MMV1803722 OC1=CC(C[C@H]2C3=CC=C(O)C=C3CCN2)=CC=C1.Cl InChI=1S/C16H17NO2.ClH/c18-13-3-1-2-11(8-13)9-16-15-5-4-14(19)10-12(15)6-7-17-16;/h1-5,8,10,16-19H,6-7,9H2;1H/t16-;/m0./s1 AKQAQJXWDWOBII-NTISSMGPSA-N
MMV1803723 O=C(O)C(F)(F)F.FC1=CC(C[C@H]2C3=CC=C(O)C=C3CCN2)=CC=C1O InChI=1S/C16H16FNO2.C2HF3O2/c17-14-7-10(1-4-16(14)20)8-15-13-3-2-12(19)9-11(13)5-6-18-15;3-2(4,5)1(6)7/h1-4,7,9,15,18-20H,5-6,8H2;(H,6,7)/t15-;/m0./s1 JYDADDLZMCWFJS-RSAXXLAASA-N
MMV1803724 O=C(O)C(F)(F)F.OC1=CC=C2C(CCN[C@H]2CC3=CC=CC=C3Br)=C1 InChI=1S/C16H16BrNO.C2HF3O2/c17-15-4-2-1-3-12(15)10-16-14-6-5-13(19)9-11(14)7-8-18-16;3-2(4,5)1(6)7/h1-6,9,16,18-19H,7-8,10H2;(H,6,7)/t16-;/m0./s1 IERYVJLFKSFDCM-NTISSMGPSA-N
MMV1803725 O=C(O)C(F)(F)F.OC(C1=CC(O)=C(O)C=C21)CN[C@H]2CC3=CC=CC=C3 InChI=1S/C16H17NO3.C2HF3O2/c18-14-7-11-12(8-15(14)19)16(20)9-17-13(11)6-10-4-2-1-3-5-10;3-2(4,5)1(6)7/h1-5,7-8,13,16-20H,6,9H2;(H,6,7)/t13-,16?;/m0./s1 WQBGOLKVAGEBGS-MRTSDAHRSA-N
MMV1803726 O=C(O)C(F)(F)F.OC(C=C1CCN2)=CC=C1[C@@H]2C3=CC=CC=C3 InChI=1S/C15H15NO.C2HF3O2/c17-13-6-7-14-12(10-13)8-9-16-15(14)11-4-2-1-3-5-11;3-2(4,5)1(6)7/h1-7,10,15-17H,8-9H2;(H,6,7)/t15-;/m0./s1 CLLPUVUFQNMMID-RSAXXLAASA-N
MMV1803727 O=C(O)C(F)(F)F.OC1=C(O)C=C2CCNC@HC3=CC=CC=C3 InChI=1S/C15H15NO2.C2HF3O2/c17-13-8-11-6-7-16-15(12(11)9-14(13)18)10-4-2-1-3-5-10;3-2(4,5)1(6)7/h1-5,8-9,15-18H,6-7H2;(H,6,7)/t15-;/m0./s1 HTVVXYCVXPXNTA-RSAXXLAASA-N
MMV1803728 O=CC(F)(F)F.COC(C(OC)=C1)=CC=C1C@@(C)[C@H]2C3=CC(O)=C(O)C=C3CCN2 InChI=1S/C15H21NO2.C2HF3O2/c17-13-8-11-6-7-16-15(12(11)9-14(13)18)10-4-2-1-3-5-10;3-2(4,5)1(6)7/h8-10,15-18H,1-7H2;(H,6,7)/t15-;/m0./s1 OORILZUKRWCZAG-RSAXXLAASA-N
MMV1803729 O=CC(F)(F)F.COC(C(OC)=C1)=CC=C1C@@(C)[C@H]2C3=CC(O)=C(O)C=C3CCN2 InChI=1S/C12H17NO2.C2HF3O2/c1-7(2)12-9-6-11(15)10(14)5-8(9)3-4-13-12;3-2(4,5)1(6)7/h5-7,12-15H,3-4H2,1-2H3;(H,6,7)/t12-;/m0./s1 NPWWUZDGBRFLLV-YDALLXLXSA-N
MMV1803730 O=C(O)C(F)(F)F.CC@@HCC InChI=1S/C13H19NO2.C2HF3O2/c1-3-8(2)13-10-7-12(16)11(15)6-9(10)4-5-14-13;3-2(4,5)1(6)7/h6-8,13-16H,3-5H2,1-2H3;(H,6,7)/t8-,13+;/m1./s1 UWDDSNBPIIDDQP-LXOGKALOSA-N
MMV1803731 O=C(O)C(F)(F)F.COC(C(OC)=C1)=CC=C1C@@(C)[C@H]2C3=CC(O)=C(O)C=C3CCN2 InChI=1S/C19H23NO4.C2HF3O2/c1-11(12-4-5-17(23-2)18(9-12)24-3)19-14-10-16(22)15(21)8-13(14)6-7-20-19;3-2(4,5)1(6)7/h4-5,8-11,19-22H,6-7H2,1-3H3;(H,6,7)/t11-,19+;/m1./s1 HWOSOLJARYWCIC-YATOIDHLSA-N
jonjoncardoso commented 3 years ago

Hi!

I'm catching up on OSM repos I missed for the past few months and I just found out about Series 5.

Do we have the potency results for these compounds? I'm curious to run a QSAR model on these

mattodd commented 3 years ago

Yes, we do, sorry we've been really slow on this one because the compounds came back inactive, including the ones that are supposed to have some activity. @edwintse I know this will take a little bit of time, but can you first post the Dundee data (ELN and here if possible), and then post a summary of the sequence of events since then, including your resynthesis of the actives and the associated discussion we had (by email sorry) about the identity/purity of the lit compounds?