1007881-98-2

Basic information

• Product Name: (S)-tert-butyl 2-(5-(4-broMophenyl)-1h-iMidazol-2-yl)pyrrolidine-1-carboxylate
• Synonyms: (S)-tert-butyl 2-(2-(4-bromophenyl)-2-oxoethylcarbamoyl)pyrrolidine-1-carboxylate;tert-butyl (2S)-2-[[2-(4-bromophenyl)-2-oxoethyl]carbamoyl]pyrrolidine-1-carboxylate
• CAS NO: 1007881-98-2
• Molecular Formula: C₁₈H₂₃BrN₂O₄
• Molecular Weight: 392.29018
• EINECS: -0
• Mol File: 1007881-98-2.mol

Chemical Properties

• Appearance: /
• Storage Temp.: 2-8°C
• CAS DataBase Reference: (S)-tert-butyl 2-(5-(4-broMophenyl)-1h-iMidazol-2-yl)pyrrolidine-1-carboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-tert-butyl 2-(5-(4-broMophenyl)-1h-iMidazol-2-yl)pyrrolidine-1-carboxylate(1007881-98-2)
• EPA Substance Registry System: (S)-tert-butyl 2-(5-(4-broMophenyl)-1h-iMidazol-2-yl)pyrrolidine-1-carboxylate(1007881-98-2)

Safety Data

• Hazardous Substances Data: 1007881-98-2(Hazardous Substances Data)

Usage

Uses

Used in Medicinal Chemistry:
(S)-tert-butyl 2-(5-(4-bromophenyl)-1H-imidazol-2-yl)pyrrolidine-1-carboxylate is used as a potential candidate in medicinal chemistry for its structural similarities with pharmacologically active compounds. Its unique molecular composition, including the pyrrolidine, imidazol, and bromophenyl groups, may contribute to its interaction with biological targets, offering opportunities for the development of new therapeutic agents.
Used in Drug Design and Development:
In the pharmaceutical industry, (S)-tert-butyl 2-(5-(4-bromophenyl)-1H-imidazol-2-yl)pyrrolidine-1-carboxylate is used as a starting material or a building block in drug design and development. Its complex molecular structure allows for the possibility of creating novel drugs with specific therapeutic effects, potentially leading to the discovery of new treatments for various diseases and conditions.

Upstream product

• 15761-39-4 1-(tert-butoxycarbonyl)-L-proline 
• 5467-72-1 α-amino-4-bromoacetophenone hydrochloride 
• 7644-04-4 4-bromophenacylamine 
• 99-73-0 para-bromophenacyl bromide 
• 59936-29-7 (S)-N-(tert-butoxycarbonyl)proline methyl ester 

Downstream Products

• 1007882-04-3 (S)-tert-butyl 2-(5-(4-bromophenyl)-1H-imidazol-2-yl)pyrrolidine-1-carboxylate 
• 1085706-68-8 (S)-tert-butyl 2-(5-(4-bromophenyl)oxazol-2-yl)pyrrolidine-1-carboxylate 
• 1256384-71-0 tert-butyl (2S)-2-[5-(4-bromophenyl)-1,3-thiazol-2-yl]pyrrolidine-1-carboxylate 
• 1007882-12-3 (S)-tert-butyl 2-(5-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1H-imidazol-2-yl)pyrrolidine-1-carboxylate 
• 1256384-76-5 di-tert-butyl (2S,2'S)-2,2’-(biphenyl-4,4'-diyldi-1,3-thiazole-5,2-diyl)dipyrrolidine-1-carboxylate 
• 1282563-99-8 5,5'-biphenyl-4,4'-diylbis{2-[(2S)-pyrrolidin-2-yl]-1,3-thiazole} 
• 1310694-94-0 (S)-tert-butyl 2-(4-(4'-(2-((S)-1-(tert-butoxycarbonyl)pyrrolidin-2-yl)-1H-imidazol-5-yl)biphenyl-4-yl)thiazol-2-yl)pyrrolidine-1-carboxylate 
• 1256384-74-3 tert-butyl (2S)-2-{5-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]-1,3-thiazol-2-yl}pyrrolidine-1-carboxylate 
• 1310694-74-6 di-tert-butyl (biphenyl-4,4'-diylbis{1,3-thiazole-5,2-diyl-(2S)-pyrrolidine-2,1-diyl[(1R)-2-oxo-1-phenylethane-2,1-diyl]})biscarbamate 
• 1310694-75-7 N,N’-(biphenyl-4,4'-diylbis{1,3-thiazole-5,2-diyl-(2S)-pyrrolidine-2,1-diyl[(1R)-2-oxo-1-phenylethane-2,1-diyl]})dicyclopropanecarboxamide 
• 1310695-07-8 N,N’-(biphenyl-4,4'-diylbis{1,3-thiazole-5,2-diyl(2S)pyrrolidine-2,1-diyl[(1R)-2-oxo-1-phenylethane-2,1-diyl]})diacetamide 
• 1310695-08-9 N-{(1R)-2-[(2S)-2-{5-[4’-(2-{(2S)-1-[(2S)-2-(acetylamino)-2-phenylacetyl]pyrrolidin-2-yl}-1,3-thiazol-5-yl)biphenyl-4-yl]-1,3-thiazol-2-yl}pyrrolidin-1-yl]-2-oxo-1-phenylethyl}acetamide 
• 1310695-52-3 C₄₀H₄₈N₆O₆S₂ 
• 1228968-41-9 2-[5-(4-ethynyl-phenyl)-1H-imidazol-2-yl]-pyrrolidine-1-carboxylic acid tert-butyl ester 

Relevant articles and documents

The Discovery of Conformationally Constrained Bicyclic Peptidomimetics as Potent Hepatitis C NS5A Inhibitors

HCV NS5A inhibitors are the backbone of directly acting antiviral treatments against the hepatitis C virus (HCV). While these therapies are generally highly curative, they are less effective in some specific HCV patient populations. In the search for broader-acting HCV NS5A inhibitors that address these needs, we explored conformational restrictions imposed by the [7,5]-azabicyclic lactam moiety incorporated into daclatasvir (1) and related HCV NS5A inhibitors. Unexpectedly, compound 5 was identified as a potent HCV genotype 1a and 1b inhibitor. Molecular modeling of 5 bound to HCV genotype 1a suggested that the use of the conformationally restricted lactam moiety might have resulted in reorientation of its N-terminal carbamate to expose a new interaction with the NS5A pocket located between amino acids P97 and Y93, which was not easily accessible to 1. The results also suggest new chemistry directions that exploit the interactions with the P97-Y93 site toward new and potentially improved HCV NS5A inhibitors.

A novel, potent, and orally bioavailable thiazole HCV NS5A inhibitor for the treatment of hepatitis C virus

A medicinal chemistry program based on the small-molecule HCV NS5A inhibitor daclatasvir has led to the discovery of dimeric phenylthiazole compound 8, a novel and potent HCV NS5A inhibitor. The subsequent SAR studies and optimization revealed that the cycloalkyl amide derivatives 27a-29a exhibited superior potency against GT1b with GT1b EC50 values at picomolar concentration. Interestingly, high diastereospecificity for HCV inhibition was observed in this class with the (1R,2S,1′R,2′S) diastereomer displaying the highest GT1b inhibitory activity. The best inhibitor 27a was found to be 3-fold more potent (GT1b EC50 = 0.003 nM) than daclatasvir (GT1b EC50 = 0.009 nM) against GT1b, and no detectable in vitro cytotoxicity was observed (CC50 > 50 μM). Pharmacokinetic studies demonstrated that compound 27a had an excellent pharmacokinetic profiles with a superior oral exposure and desired bioavailability after oral administration in both rats and dogs, and therefore it was selected as a developmental candidate for the treatment of HCV infection.

Monoglycosyl-containing heterocyclic compound for inhibiting hepatitis C viruses and preparation method

The invention discloses a monoglycosyl-containing heterocyclic compound for inhibiting hepatitis C viruses and a preparation method. The monoglycosyl-containing heterocyclic compound has a chemical structure represented by a formula I shown in the description. The monoglycosyl-containing heterocyclic compound disclosed by the invention can be used for effectively inhibiting protease of the hepatitis C viruses and treating infection of the hepatitis C viruses (HCV).

5,5-FUSED ARYLENE OR HETEROARYLENE HEPATITIS C VIRUS INHIBITORS

Provided herein are 5,5-fused heteroarylene hepatitis C virus inhibitor compounds, for example, of Formula I, IA, or IB, pharmaceutical compositions comprising the compounds, and processes of preparation thereof. Also provided are methods of their use for the treatment of an HCV infection in a host in need thereof.

Novel spiroketal pyrrolidine GSK2336805 potently inhibits key hepatitis C virus genotype 1b mutants: From lead to clinical compound

Rapid clinical progress of hepatitis C virus (HCV) replication inhibitors, including these selecting for resistance in the NS5A region (NS5A inhibitors), promises to revolutionize HCV treatment. Herein, we describe our explorations of diverse spiropyrrolidine motifs in novel NS5A inhibitors and a proposed interaction model. We discovered that the 1,4-dioxa-7-azaspiro[4.4]nonane motif in inhibitor 41H (GSK2236805) supported high potency against genotypes 1a and 1b as well as in genotype 1b L31V and Y93H mutants. Consistent with this, 41H potently suppressed HCV RNA in the 20-day RNA reduction assay. Pharmacokinetic and safety data supported further progression of 41H to the clinic.

ANTIVIRAL COMPOUNDS

The present invention discloses compounds of Formulae I and II, wherein the variables in Formulae I and II are defined as described herein. Also disclosed are pharmaceutical compositions containing such compounds and methods for using the compounds of Formulae I and II in the treatment of HCV infection.

COMBINATION TREATMENTS FOR HEPATITIS C

The present invention features a method for the treatment of Hepatitis C in a human in need thereof comprising administering a first compound of Formula (II) or (IIB) described herein or a pharmaceutically acceptable salt thereof in combination with a second compound having a structure of Formula (I), (III), (IIIB), or (IIIC), and optionally a third compound comprising one or more alternative Hepatitis C treatment agents.

NOVEL HEPATITIS C VIRUS INHIBITORS

The invention provides compounds of formula (I): wherein Rings A and A' are independently 5-membered optionally substituted aromatic heterocycles; Q is C(=O)NR1R1' or formula U is C(R4)2, O, S, S(=O)2, C(R4)2C(R4)2, CH2O, OCH2, CH2S, SCH2, CH2S(=O)2, S(=O)CH2 or C=C(Ru )2; X is CH2, CHR12, CR12R12, O, S, S(=O)2 or NRx; m is 0, 1, 2 or 3; n is 0, 1, 2 or 3; the other variables are as defined in the claims, which are of use in the treatment or prophylaxis of hepatitis C virus infection, and related aspects.

HEPATITIS C VIRUS INHIBITORS

The present disclosure relates to compounds, compositions and methods for the treatment of hepatitis C virus (HCV) infection. Also disclosed are pharmaceutical compositions containing such compounds and methods for using these compounds in the treatment of HCV infection.

Phenyl Ethynyl Derivatives As Hepatitis C Virus Inhibitors

Inhibitors of HCV replication of formula I including stereochemically isomeric forms, and salts, hydrates, solvates thereof, wherein R and R* have the meaning defined in the claims. The present invention also relates to processes for preparing said compounds, pharmaceutical compositions containing them and their use, alone or in combination with other HCV inhibitors, in the treatment or prophylaxis of HCV.