Compound ID | 898

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GSQ 2287

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: 627.12
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=C(Cl)C=CS5
InChI Key: SQYDTKOMMYRVPW-UHFFFAOYSA-N
Can. SMILES: CN1C=C(C=C1C(=O)NCCN2CCOCC2)NC(=O)C3=CC(=CN3)NC(=O)C4=CC(=CN4C)NC(=O)C5=C(C=CS5)Cl
InChI: InChI=1S/C28H31ClN8O5S/c1-35-15-18(12-22(35)26(39)30-4-5-37-6-8-42-9-7-37)33-25(38)21-11-17(14-31-21)32-27(40)23-13-19(16-36(23)2)34-28(41)24-20(29)3-10-43-24/h3,10-16,31H,4-9H2,1-2H3,(H,30,39)(H,32,40)(H,33,38)(H,34,41)
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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