OSDDMalaria:GSK Arylpyrrole Series:desired compounds

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The .cdx file is available via a [https://dl.dropbox.com/u/3557122/Top%2010%20Synthetics_final.cdx public dropbox]
The .cdx file is available via a [https://dl.dropbox.com/u/3557122/Top%2010%20Synthetics_final.cdx public dropbox]
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=== SMILES/InChi ===
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=== Synthetic SMILES/InChi ===
sA: FC1=CC=C(N2C(C)=CC(C(OC(C)(C)C(N)=O)=O)=C2C)C=C1
sA: FC1=CC=C(N2C(C)=CC(C(OC(C)(C)C(N)=O)=O)=C2C)C=C1
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sJ: FC1=CC=C(N2N=CC(C(OCC(N)=O)=O)=C2)C=C1
sJ: FC1=CC=C(N2N=CC(C(OCC(N)=O)=O)=C2)C=C1
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)
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)
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== Commercial Smiles/InChi list ==
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cA: O=C(N(C)C)CNCC1=C(C)N(C(C)=C1)C2=CC=CC=C2
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InChI=1S/C17H23N3O/c1-13-10-15(11-18-12-17(21)19(3)4)14(2)20(13)16-8-6-5-7-9-16/h5-10,18H,11-12H2,1-4H3
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cB: FC1=CC=C(N2C(C)=CC(C(OCC(N)=O)=O)=C2C)C=C1
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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)
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cC: O=C(N1CCNC(C1)=O)C2=C(C)N(C(C)=C2)C3=CC=CC=C3
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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)
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cD: O=C(NC)CN(C)CC1=C(C)N(C(C)=C1)C2=CC=C(Br)C=C2
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InChI=1S/C17H22BrN3O/c1-12-9-14(10-20(4)11-17(22)19-3)13(2)21(12)16-7-5-15(18)6-8-16/h5-9H,10-11H2,1-4H3,(H,19,22)
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cE: O=C(NC1=CC=CC(OC)=C1)CSC2=NN=C(O2)C3=C(C)N(C(C)=C3)C4=CC=CC=C4
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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)
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cF: FC1=CC=C(N2C(C)=CC(C(N(CC)CC(NC3=C(F)C=CC=C3F)=O)=O)=C2C)C=C1
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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)
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cG: O=C(NC1=NOC(C)=C1)CN(C)C(C2=C(C)N(C(C)=C2)C3=CC(C)=CC=C3)=O
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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)
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cH: ClC1=CC=C(N2C(C)=CC(CNC3CCN(CC(NC)=O)CC3)=C2C)C=C1
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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)
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cI: O=C(NCC)[C@H](C[C@@H](N)C1)N1CC2=C(C)N(C(C)=C2)C3=CC=CC=C3Cl
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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
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cJ: CCC1=CC=C(N2C(C)=CC(CN3CCC(C(O)=O)CC3)=C2C)C=C1
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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)
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cK (additional): FC1=CC=C(N2C(C)=CC(C(OCC(N(C)C)=O)=O)=C2C)C=C1
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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
== Original List Desired Analogues ==
== Original List Desired Analogues ==

Revision as of 00:32, 31 July 2012

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The decisions about the compounds discussed below is being carried out at The Synaptic Leap


Contents

Finalised List

This finalised list of desired synthetic compounds is the result of the compounds consultation. The descriptors "sA" etc are temporary and will be replaced with appropriate designators when acquired in reality. We are also interested in the secondary and tertiary amide analogues of these compounds as well. for compound sH, other heterocycles would be of interest.

Desired compounds
Desired compounds

The .cdx file is available via a public dropbox

Synthetic SMILES/InChi

sA: FC1=CC=C(N2C(C)=CC(C(OC(C)(C)C(N)=O)=O)=C2C)C=C1 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)


sB: FC1=CC=C(N2C(C)=CC(C3=NC(C(N)=O)=CO3)=C2C)C=C1 InChI=1S/C16H14FN3O2/c1-9-7-13(16-19-14(8-22-16)15(18)21)10(2)20(9)12-5-3-11(17)4-6-12/h3-8H,1-2H3,(H2,18,21)


sC (alanine derivative shown): FC1=CC=C(N2C(C)=CC(C(N(C)C(C)C(N)=O)=O)=C2C)C=C1 InChI=1S/C17H20FN3O2/c1-10-9-15(17(23)20(4)12(3)16(19)22)11(2)21(10)14-7-5-13(18)6-8-14/h5-9,12H,1-4H3,(H2,19,22)


sD: FC1=CC=C(N2C(C)=CC(COCC(N)=O)=C2C)C=C1 InChI=1S/C15H17FN2O2/c1-10-7-12(8-20-9-15(17)19)11(2)18(10)14-5-3-13(16)4-6-14/h3-7H,8-9H2,1-2H3,(H2,17,19)


sE: FC1=CC=C(N2C(C)=CC(S(N(C)CC(N)=O)(=O)=O)=C2C)C=C1 InChI=1S/C15H18FN3O3S/c1-10-8-14(23(21,22)18(3)9-15(17)20)11(2)19(10)13-6-4-12(16)5-7-13/h4-8H,9H2,1-3H3,(H2,17,20)


sF: FC1=CC=C(N2C(C)=CC(C3=NOC(C(N)=O)=N3)=C2C)C=C1 InChI=1S/C15H13FN4O2/c1-8-7-12(14-18-15(13(17)21)22-19-14)9(2)20(8)11-5-3-10(16)4-6-11/h3-7H,1-2H3,(H2,17,21)


sG: FC1=CC=C(N2N=CC(C3=NC(C(N)=O)=CO3)=C2C)C=C1 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)


sH: O=C1CCCN1CC(C=C(N2C3=CC=CC=C3)C)=C2C InChI=1S/C17H20N2O/c1-13-11-15(12-18-10-6-9-17(18)20)14(2)19(13)16-7-4-3-5-8-16/h3-5,7-8,11H,6,9-10,12H2,1-2H3


sI: FC1=CC=C(N2C(C=CN=C3OCC(N)=O)=C3C=N2)C=C1 InChI=1S/C14H11FN4O2/c15-9-1-3-10(4-2-9)19-12-5-6-17-14(11(12)7-18-19)21-8-13(16)20/h1-7H,8H2,(H2,16,20)


sJ: FC1=CC=C(N2N=CC(C(OCC(N)=O)=O)=C2)C=C1 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)

Commercial Smiles/InChi list

cA: O=C(N(C)C)CNCC1=C(C)N(C(C)=C1)C2=CC=CC=C2 InChI=1S/C17H23N3O/c1-13-10-15(11-18-12-17(21)19(3)4)14(2)20(13)16-8-6-5-7-9-16/h5-10,18H,11-12H2,1-4H3


cB: FC1=CC=C(N2C(C)=CC(C(OCC(N)=O)=O)=C2C)C=C1 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)


cC: O=C(N1CCNC(C1)=O)C2=C(C)N(C(C)=C2)C3=CC=CC=C3 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)


cD: O=C(NC)CN(C)CC1=C(C)N(C(C)=C1)C2=CC=C(Br)C=C2 InChI=1S/C17H22BrN3O/c1-12-9-14(10-20(4)11-17(22)19-3)13(2)21(12)16-7-5-15(18)6-8-16/h5-9H,10-11H2,1-4H3,(H,19,22)


cE: O=C(NC1=CC=CC(OC)=C1)CSC2=NN=C(O2)C3=C(C)N(C(C)=C3)C4=CC=CC=C4 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)


cF: FC1=CC=C(N2C(C)=CC(C(N(CC)CC(NC3=C(F)C=CC=C3F)=O)=O)=C2C)C=C1 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)


cG: O=C(NC1=NOC(C)=C1)CN(C)C(C2=C(C)N(C(C)=C2)C3=CC(C)=CC=C3)=O 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)


cH: ClC1=CC=C(N2C(C)=CC(CNC3CCN(CC(NC)=O)CC3)=C2C)C=C1 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)


cI: O=C(NCC)[C@H](C[C@@H](N)C1)N1CC2=C(C)N(C(C)=C2)C3=CC=CC=C3Cl 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


cJ: CCC1=CC=C(N2C(C)=CC(CN3CCC(C(O)=O)CC3)=C2C)C=C1 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)


cK (additional): FC1=CC=C(N2C(C)=CC(C(OCC(N(C)C)=O)=O)=C2C)C=C1 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

Original List Desired Analogues

This is a list of compounds we are currently targeting or would like to have access to. If you happen to have some of these compounds, or their close analogues, in your labs or would like to make them then please get in touch. The compounds highlighted in red are current priority compounds, please get in touch on The Synaptic Leap with your views.

Desired compounds
Desired compounds

The .cdx file is available via a public dropbox

The near neighbour compounds could be available from the authors of this paper


SMARTS Filter

A SMARTS filter was carried out on the above compounds with the following summary (All fail on the Alarm NMR):

total: 24

passed: 6 (25.0%)

failed: 18 (75.0%)

failed glaxo_unsuitable_leads: 0 (0.0%)

failed glaxo_unsuitable_natprod: 0 (0.0%)

failed glaxo_reactive: 0 (0.0%)

failed ursu_reactive: 0 (0.0%)

failed lint_blake-v2: 1 (4.2%)

failed oprea_filters: 1 (4.2%)

failed MLSMR_excluded: 12 (50.0%)

failed MLSMR_allowed: 1 (4.2%)

failed toxic: 0 (0.0%)

failed pains: 15 (62.5%)

Commercially available analogues of desired compounds

This is a list of commercially available analogues of the above compounds. The cores of each of the different classes in the above list were searched by eMolecules.com and by supplier websites. Partial search carried out by via Molport.

Desired compounds
Desired compounds

The .cdx file is available via a public dropbox

SMILES list

CNC(=O)COC(=O)c1cc(C)n(c2ccc(F)cc2)c1C

Fc1ccc(cc1)n1c(C)cc(C(=O)OCC(=O)N(C)C)c1C

CCN(CC(=O)Nc1c(F)cccc1F)C(=O)c1cc(C)n(c2ccc(F)cc2)c1C

O=C1NCCN(C1)C(=O)c1cc(C)n(c2ccccc2)c1C

O=C(Nc1noc(C)c1)CN(C)C(=O)c1cc(C)n(c2cccc(C)c2)c1C

CNC(=O)CN(C)C(=O)c1cc(C)n(c2ccc(Br)cc2)c1C

CN(C)C(=O)CNC(=O)c1cc(C)n(c2ccccc2)c1C

CNC(=O)CN1CCC(CC1)NCc1cc(C)n(c2ccc(Cl)cc2)c1C

COc1cccc(NC(=O)CSc2nnc(o2)c2cc(C)n(c3ccccc3)c2C)c1

O=C(CSc1nnc(o1)c1cc(C)n(c2ccccc2)c1C)Nc1cccc(C)c1C 

O=C(NCC)[C@H](C[C@@H](N)C1)N1CC2=C(C)N(C(C)=C2)C3=CC=CC=C3Cl

O=C(NC1=O)/C(S1)=C([H])/C(C=C(N2C3=CN=CC=C3)C)=C2C

O=C(NC1=O)/C(S1)=C([H])/C(C=C(N2C3=CC=NC=C3)C)=C2C

CC(N1C2=CC=CC=C2)=C(/C([H])=C(S3)/C(NC3=O)=O)C=C1C4=CC=CC=C4

CN1C=C(/C=C2C(N/C(S/2)=N\C3=CC=C(F)C=C3)=O)C4=C1C=CC=C4

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