DrugRepV|Encyclopedia for antivirals

Chemical, Structural, Clinical and Biological details of Antiviral agents ID: DrugRepV_7860

Chemical Information
Antiviral agent ID DrugRepV_7860
Antiviral agent name benzyl N-[(2S)-1-[[(2S)-1-(1,3-benzothiazol-2-yl)-1-oxo-3-[(3S)-2-oxopyrrolidin-3-yl]propan-2-yl]amino]-3-methyl-1-oxobutan-2-yl]carbamate
IUPAC Name benzyl N-[(2S)-1-[[(2S)-1-(1,3-benzothiazol-2-yl)-1-oxo-3-[(3S)-2-oxopyrrolidin-3-yl]propan-2-yl]amino]-3-methyl-1-oxobutan-2-yl]carbamate
SMILES (canonical) CC(C)C(C(=O)NC(CC1CCNC1=O)C(=O)C2=NC3=CC=CC=C3S2)NC(=O)OCC4=CC=CC=C4
SMILES (isomeric) CC(C)[C@@H](C(=O)N[C@@H](C[C@@H]1CCNC1=O)C(=O)C2=NC3=CC=CC=C3S2)NC(=O)OCC4=CC=CC=C4
Molecular Formula C27H30N4O5S
Molecular Weight (g/mol) 522.6

InChl InChI=1S/C27H30N4O5S/c1-16(2)22(31-27(35)36-15-17-8-4-3-5-9-17)25(34)29-20(14-18-12-13-28-24(18)33)23(32)26-30-19-10-6-7-11-21(19)37-26/h3-11,16,18,20,22H,12-15H2,1-2H3,(H,28,33)(H,29,34)(H,31,35)/t18-,20-,22-/m0/s1

Common Name benzyl N-[(2S)-1-[[(2S)-1-(1,3-benzothiazol-2-yl)-1-oxo-3-[(3S)-2-oxopyrrolidin-3-yl]propan-2-yl]ami
Structural Information

Clinical Information
Biological Information
Secondary Indication Severe acute respiratory syndrome coronavirus (SARS-CoV) NA NA
Secondary Indication (Approaches) Experimental
Secondary Indication (Drug concentration) 1.71 μM
Secondary Indication (Cell based assay) Fluorometric protease inhibitory assay
Secondary Indication (Change) Decrease
Secondary Indication (Type of Inhibition) Ki [ NA NA ]
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
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.

Copyright © 2019. CSIR-Institute of Microbial Technology, Chandigarh, INDIA.

Chemical Information
Antiviral agent ID	DrugRepV_7860
Antiviral agent name	benzyl N-[(2S)-1-[[(2S)-1-(1,3-benzothiazol-2-yl)-1-oxo-3-[(3S)-2-oxopyrrolidin-3-yl]propan-2-yl]amino]-3-methyl-1-oxobutan-2-yl]carbamate
IUPAC Name	benzyl N-[(2S)-1-[[(2S)-1-(1,3-benzothiazol-2-yl)-1-oxo-3-[(3S)-2-oxopyrrolidin-3-yl]propan-2-yl]amino]-3-methyl-1-oxobutan-2-yl]carbamate
SMILES (canonical)	CC(C)C(C(=O)NC(CC1CCNC1=O)C(=O)C2=NC3=CC=CC=C3S2)NC(=O)OCC4=CC=CC=C4
SMILES (isomeric)	CC(C)[C@@H](C(=O)N[C@@H](C[C@@H]1CCNC1=O)C(=O)C2=NC3=CC=CC=C3S2)NC(=O)OCC4=CC=CC=C4
Molecular Formula	C27H30N4O5S
Molecular Weight (g/mol)	522.6
InChl	InChI=1S/C27H30N4O5S/c1-16(2)22(31-27(35)36-15-17-8-4-3-5-9-17)25(34)29-20(14-18-12-13-28-24(18)33)23(32)26-30-19-10-6-7-11-21(19)37-26/h3-11,16,18,20,22H,12-15H2,1-2H3,(H,28,33)(H,29,34)(H,31,35)/t18-,20-,22-/m0/s1
Common Name	benzyl N-[(2S)-1-[[(2S)-1-(1,3-benzothiazol-2-yl)-1-oxo-3-[(3S)-2-oxopyrrolidin-3-yl]propan-2-yl]ami
Structural Information

Clinical Information
Biological Information
Secondary Indication	Severe acute respiratory syndrome coronavirus (SARS-CoV) NA NA
Secondary Indication (Approaches)	Experimental
Secondary Indication (Drug concentration)	1.71 μM
Secondary Indication (Cell based assay)	Fluorometric protease inhibitory assay
Secondary Indication (Change)	Decrease
Secondary Indication (Type of Inhibition)	Ki [ NA NA ]
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
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.