Compound ID | 897

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GSQ 11203

Class: RNA synthesis inhibitor (hetero ARomatic Polyamide [HARP])

Spectrum of activity: Gram-negative
Details of activity: Noncovalent binding in the minor groove of DNA results in inhibition of DNA replication and DNA-dependent RNA transcription and subsequent bacterial growth.
Institute where first reported: Oscient Pharmaceuticals
Year first mentioned: 2001
Highest developmental phase: Preclinical
Development status: Inactive
Reason Dropped: Symmetrical compounds- not very drug like- and acted on the minor groove of DNA, which made them very active but relatively non-selective- (JS, 2) Additionally, Oscient went bankrupt in 2009. HARPs were first worked on by Genesoft which merged with Oscient - and change of personnel working on the project- (LS)
Chemical structure(s):
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Molecular weight: 637.69
Iso. SMILES: O=C(NC1=CN(C)C(C(NC2=CNC(C(NC3=CN(C)C(C(NCCN4CCOCC4)=O)=C3)=O)=C2)=O)=C1)C5=NC=C6C=CC=CC6=C5
InChI Key: SSTSKWKTDNGUIG-UHFFFAOYSA-N
Can. SMILES: CN1C=C(C=C1C(=O)NCCN2CCOCC2)NC(=O)C3=CC(=CN3)NC(=O)C4=CC(=CN4C)NC(=O)C5=CC6=C(C=CC=C6)C=N5
InChI: InChI=1S/C33H35N9O5/c1-40-19-24(15-28(40)32(45)34-7-8-42-9-11-47-12-10-42)39-31(44)27-14-23(18-36-27)37-33(46)29-16-25(20-41(29)2)38-30(43)26-13-21-5-3-4-6-22(21)17-35-26/h3-6,13-20,36H,7-12H2,1-2H3,(H,34,45)(H,37,46)(H,38,43)(H,39,44)
External links:
Citations:
  • https://www.ncbi.nlm.nih.gov/pubmed/23507040
  • http://www.ncbi.nlm.nih.gov/pmc/articles/PMC253762/
  • https://journals.asm.org/doi/full/10.1128/aac.47.11.3448-3457.2003?site=AntimicrobAgentsChemother&utm_campaign=TrendMD_AACCLIN_0&utm_medium=trendmdantimicrobagentschemother&utm_source=TrendMDAntimicrobAgentsChemother

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