Chemical Information | |
Antiviral agent ID | DrugRepV_6352 | |
Antiviral agent name | methyl 2-[(5Z)-5-[(4-{[(1S)-1-{[(1S)-5-amino-1-{[(1S)-1-carbamoylpentyl]carbamoyl}pentyl]carbamoyl}-4-carbamimidamidobutyl]carbamoyl}phenyl)methylidene]-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]hexanoate | |
IUPAC Name | methyl 2-[(5Z)-5-[(4-{[(1S)-1-{[(1S)-5-amino-1-{[(1S)-1-carbamoylpentyl]carbamoyl}pentyl]carbamoyl}-4-carbamimidamidobutyl]carbamoyl}phenyl)methylidene]-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]hexanoate | |
SMILES (isomeric) | CCCC[C@H](NC(=O)[C@H](CCCCN)NC(=O)[C@H](CCCNC(N)=N)NC(=O)C1=CC=C(\C=C2/SC(=S)N(C(CCCC)C(=O)OC)C2=O)C=C1)C(N)=O | |
Molecular Formula | C36H55N9O7S2 | |
Molecular Weight (g/mol) | 790.01 | |
InChl | InChI=1/C36H55N9O7S2/c1-4-6-11-24(29(38)46)42-31(48)25(12-8-9-19-37)44-32(49)26(13-10-20-41-35(39)40)43-30(47)23-17-15-22(16-18-23)21-28-33(50)45(36(53)54-28)27(14-7-5-2)34(51)52-3/h15-18,21,24-27H,4-14,19-20,37H2,1-3H3,(H2,38,46)(H,42,48)(H,43,47)(H,44,49)(H4,39,40,41)/b28-21-/t24-,25-,26-,27?/s2 | |
Structural Information | |
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Clinical Information | |
Biological Information | |
Secondary Indication | Dengue virus (DENV) 2 NA | |
Secondary Indication (Approaches) | Experimental | |
Secondary Indication (Methods) | In-vitro | |
Secondary Indication (Mode of viral infection) | Adsorption
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Secondary Indication (Mode of drug delivery) | Culture
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Secondary Indication (Drug concentration) | 11.6 ± 1.2 μM
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Secondary Indication (Cell based assay) | Protease Assay
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Secondary Indication (Change) | Decrease
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Secondary Indication (Type of Inhibition) | IC50 [ 50 % ] | |
Reference | Nitsche C, Schreier VN, Behnam MA, Kumar A, Bartenschlager R, Klein CD..Thiazolidinone-peptide hybrids as dengue virus protease inhibitors with antiviral activity in cell culture..J Med Chem. 2013 Nov 14;56(21):8389-403. doi: 10.1021/jm400828u. Epub 2013 Oct 22. PMID:24083834
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Comment | The most promising in vitro affinities were observed for thiazolidinedione-based peptide hybrids containing hydrophobic groups with Ki values between 1.5 and 1.8 μM and competitive inhibition mechanisms. Rhodanine-capped peptide hybrids with hydrophobic substituents have, in correlation with their membrane permeability, a more pronounced antiviral activity in cell culture than the thiazolidinediones.
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