Chemical Information | |
Antiviral agent ID | DrugRepV_7865 | |
Antiviral agent name | (2S)-N-[(2S)-1-(1,3-benzothiazol-2-yl)-1-oxo-3-[(3S)-2-oxopyrrolidin-3-yl]propan-2-yl]-2-[[2-(4-methoxyphenyl)acetyl]amino]-4-methylpentanamide | |
IUPAC Name | (2S)-N-[(2S)-1-(1,3-benzothiazol-2-yl)-1-oxo-3-[(3S)-2-oxopyrrolidin-3-yl]propan-2-yl]-2-[[2-(4-methoxyphenyl)acetyl]amino]-4-methylpentanamide | |
SMILES (canonical) | CC(C)CC(C(=O)NC(CC1CCNC1=O)C(=O)C2=NC3=CC=CC=C3S2)NC(=O)CC4=CC=C(C=C4)OC | |
SMILES (isomeric) | CC(C)C[C@@H](C(=O)N[C@@H](C[C@@H]1CCNC1=O)C(=O)C2=NC3=CC=CC=C3S2)NC(=O)CC4=CC=C(C=C4)OC | |
Molecular Formula | C29H34N4O5S | |
Molecular Weight (g/mol) | 550.7 | |
InChl | InChI=1S/C29H34N4O5S/c1-17(2)14-23(31-25(34)15-18-8-10-20(38-3)11-9-18)28(37)32-22(16-19-12-13-30-27(19)36)26(35)29-33-21-6-4-5-7-24(21)39-29/h4-11,17,19,22-23H,12-16H2,1-3H3,(H,30,36)(H,31,34)(H,32,37)/t19-,22-,23-/m0/s1 | |
Common Name | (2S)-N-[(2S)-1-(1,3-benzothiazol-2-yl)-1-oxo-3-[(3S)-2-oxopyrrolidin-3-yl]propan-2-yl]-2-[[2-(4-meth | |
Structural Information | |
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Clinical Information | |
Biological Information | |
Secondary Indication | Severe acute respiratory syndrome coronavirus (SARS-CoV) NA NA | |
Secondary Indication (Approaches) | Experimental | |
Secondary Indication (Drug concentration) | 43 μM
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Secondary Indication (Cell based assay) | Fluorometric protease inhibitory assay
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Secondary Indication (Change) | Decrease
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Secondary Indication (Type of Inhibition) | IC50 [ 50 % ] | |
Reference | Thanigaimalai P, Konno S, Yamamoto T, Koiwai Y, Taguchi A, Takayama K, Yakushiji F, Akaji K, Kiso Y, Kawasaki Y, Chen SE, Naser-Tavakolian A, Schon A, Freire E, Hayashi Y..Design, synthesis, and biological evaluation of novel dipeptide-type SARS-CoV 3CL protease inhibitors: structure-activity relationship study..Eur J Med Chem. 2013 Jul;65:436-47. doi: 10.1016/j.ejmech.2013.05.005. PMCID: PMC7115367. PMID:23747811
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Comment | The preliminary SAR study of the peptidomimetic compounds with potent inhibitory activities revealed several structural features that boosted the inhibitory activity: (i) a benzothiazole warhead at the S1' position, (ii) a ?-lactam unit at the S1-position, (iii) an appropriately hydrophobic leucine moiety at the S2-position, and (iv) a hydrogen bond between the N-arylglycine unit and a backbone hydrogen bond donor at the S3-position.
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