| Chemical Information | |
| Antiviral agent ID | DrugRepV_6361 | |
| Antiviral agent name | (2S)-6-amino-2-[(2S)-5-carbamimidamido-2-[(4-{[(5Z)-3-cyclohexyl-2,4-dioxo-1,3-thiazolidin-5-ylidene]methyl}phenyl)formamido]pentanamido]-N-[(1S)-1-carbamoylpentyl]hexanamide | |
| IUPAC Name | (2S)-6-amino-2-[(2S)-5-carbamimidamido-2-[(4-{[(5Z)-3-cyclohexyl-2,4-dioxo-1,3-thiazolidin-5-ylidene]methyl}phenyl)formamido]pentanamido]-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(C3CCCCC3)C2=O)C=C1)C(N)=O | |
| Molecular Formula | C35H53N9O6S | |
| Molecular Weight (g/mol) | 727.93 | |
| InChl | InChI=1/C35H53N9O6S/c1-2-3-12-25(29(37)45)41-31(47)26(13-7-8-19-36)43-32(48)27(14-9-20-40-34(38)39)42-30(46)23-17-15-22(16-18-23)21-28-33(49)44(35(50)51-28)24-10-5-4-6-11-24/h15-18,21,24-27H,2-14,19-20,36H2,1H3,(H2,37,45)(H,41,47)(H,42,46)(H,43,48)(H4,38,39,40)/b28-21-/t25-,26-,27-/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 (Mode of viral infection) | Adsorption
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Secondary Indication (Mode of drug delivery) | Culture
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Secondary Indication (Drug concentration) | 3.4 ± 0.1 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 % ] | |
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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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