| Chemical Information | |
| Antiviral agent ID | DrugRepV_6391 | |
| Antiviral agent name | (2S)-6-amino-2-[(2S)-2-[(4-{[(5Z)-3-benzyl-2,4-dioxo-1,3-thiazolidin-5-ylidene]methyl}phenyl)formamido]-5-carbamimidamidopentanamido]-N-[(1S)-1-carbamoylpentyl]hexanamide | |
| IUPAC Name | (2S)-6-amino-2-[(2S)-2-[(4-{[(5Z)-3-benzyl-2,4-dioxo-1,3-thiazolidin-5-ylidene]methyl}phenyl)formamido]-5-carbamimidamidopentanamido]-N-[(1S)-1-carbamoylpentyl]hexanamide |  |
| 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(=O)N(CC3=CC=CC=C3)C2=O)C=C1)C(N)=O | |
| Molecular Formula | C36H49N9O6S | |
| Molecular Weight (g/mol) | 735.91 | |
| InChl | InChI=1/C36H49N9O6S/c1-2-3-12-26(30(38)46)42-32(48)27(13-7-8-19-37)44-33(49)28(14-9-20-41-35(39)40)43-31(47)25-17-15-23(16-18-25)21-29-34(50)45(36(51)52-29)22-24-10-5-4-6-11-24/h4-6,10-11,15-18,21,26-28H,2-3,7-9,12-14,19-20,22,37H2,1H3,(H2,38,46)(H,42,48)(H,43,47)(H,44,49)(H4,39,40,41)/b29-21-/t26-,27-,28-/s2 | |
| Structural Information | |
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| Clinical Information | |
| Biological Information | |
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Secondary Indication | Dengue virus (DENV) 2 NA |   |
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Secondary Indication (Approaches) | Experimental | |
| Secondary Indication (Methods) | In-vitro | |
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Secondary Indication (Model system) [cell lines/ animal models] | Huh-7
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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) | >50 μM
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Secondary Indication (Cell based assay) | Renilla luciferase assay
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Secondary Indication (Change) | Decrease
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Secondary Indication (Type of Inhibition) | EC50 [ 50 % ] | |
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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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