OpenSourceMalaria:GSK Arylpyrrole Series

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(Put in new section for other incidences of series.)
(added synthesis of near-neighbours)
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TCMDC-124456, CHEMBL548395, CHEMBL: [https://www.ebi.ac.uk/chembldb/index.php/compound/inspect/640006 640006]
TCMDC-124456, CHEMBL548395, CHEMBL: [https://www.ebi.ac.uk/chembldb/index.php/compound/inspect/640006 640006]
CCn1c(cc(c1C)C=C2C(=O)NC(=Nc3ccccc3)S2)C
CCn1c(cc(c1C)C=C2C(=O)NC(=Nc3ccccc3)S2)C
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 +
Potential synthesis strategy toward near-neighbours:
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 +
Experimental information available from [http://malaria.ourexperiment.org/uri/32 PMY 13-1], [http://malaria.ourexperiment.org/uri/33 PMY 14-1] and [http://malaria.ourexperiment.org/uri/39 PMY 16-1].
4) Other known incidences of these molecules/this series<br>
4) Other known incidences of these molecules/this series<br>
Related compounds are known to inhibit the proteasome, according to [http://www.nature.com/nature/journal/v467/n7312/abs/nature09299.html this Nature paper].<br>
Related compounds are known to inhibit the proteasome, according to [http://www.nature.com/nature/journal/v467/n7312/abs/nature09299.html this Nature paper].<br>

Revision as of 22:34, 1 November 2011

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1) The initial two leads have the general structure:

GSK Tres Cantos Arylpyrrole Generic Structure


These compounds are currently under study by the Todd lab at the University of Sydney and the Medicines for Malaria Venture, Geneva. As an open source project, anyone may participate:
Coordination/Discussion site
Electronic Lab Notebooks
Compounds are commercially-available
Series was listed as one of the most promising leads from TCAMS set (though lacking aryl F)

2) The two known series examples:

TCMDC 123812

TCMDC123812


InChI=1/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)
SMILES: O=C(N)COC(=O)c2c(n(c1ccc(F)cc1)c(c2)C)C
CAS Registry Number: 733026-12-5
Chemspider page
ChEMBL Page
Resynthesis:

TCMDC 123794

TCMDC123794


InChI=1/C26H25FN4O4/c1-16-14-22(17(2)30(16)20-12-10-19(27)11-13-20)26(34)35-15-23(32)28-24-18(3)29(4)31(25(24)33)21-8-6-5-7-9-21/h5-14H,15H2,1-4H3,(H,28,32)
SMILES: Fc1ccc(cc1)n2c(cc(c2C)C(=O)OCC(=O)NC=4C(=O)N(c3ccccc3)N(C=4C)C)C
Chemspider page
ChEMBL Page
Resynthesis:

The proposed resynthesis strategy for these two compounds:

Proposed Strategy

3) Known "Near Neighbours" contained in the Tres Cantos set

Known GSK Arylpyrrole Near Neighbours

Data/links for these compounds:

TCMDC-123563, CHEMBL546966, CHEMBL page: 637010 Cc1ccc(cc1)n2c(cc(c2C)C(=O)CN3C(=O)C(NC3=O)Cc4ccccc4)C

TCMDC-125698, CHEMBL587989, CHEMBL: 627784 Cc1cc(c(n1c2ccc(cc2)Cl)C)C=C3C(=O)N(C(=Nc4ccccc4)S3)C5CCCC5

TCMDC-125697, CHEMBL581336, CHEMBL: 640978 CCOC(=O)c1ccc(cc1)n2c(cc(c2C)C=C3C(=O)N(C(=Nc4ccccc4)S3)C5CCCC5)C

TCMDC-125659, CHEMBL528140, CHEMBL: 626220 Cc1ccnc(c1)n2c(cc(c2C)C=C3C(=O)N(C(=Nc4ccccc4)S3)Cc5ccco5)C

TCMDC-124103, CHEMBL588465, CHEMBL: 643107 Cc1cc(cc(c1)n2c(cc(c2C)C=C3C(=O)NC(=Nc4ccc(cc4)Cl)S3)C)C

TCMDC-124456, CHEMBL548395, CHEMBL: 640006 CCn1c(cc(c1C)C=C2C(=O)NC(=Nc3ccccc3)S2)C

Potential synthesis strategy toward near-neighbours:

Experimental information available from PMY 13-1, PMY 14-1 and PMY 16-1.

4) Other known incidences of these molecules/this series

Related compounds are known to inhibit the proteasome, according to this Nature paper.

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