136285-48-8

Upstream product

• 4518-10-9 Methyl 3-aminobenzoate 
• 638-29-9 n-valeryl chloride 

Downstream Products

• 136285-49-9 methyl 4-nitro-3-valerylaminobenzoate 
• 174482-77-0 3-pentanamidobenzoic acid 
• 133085-92-4 2-Butyl-3-[2'-(1H-tetrazol-5-yl)-biphenyl-4-ylmethyl]-3H-benzoimidazole-5-carboxylic acid methyl ester 
• 136285-50-2 3-[(2'-Cyano-biphenyl-4-ylmethyl)-pentanoyl-amino]-4-nitro-benzoic acid methyl ester 
• 133085-96-8 2-Butyl-1-[[2'-(1H-tetrazol-5-yl)biphenyl-4-yl)methyl]benzimidazole-6-carboxylic acid 
• 136285-51-3 2-Butyl-3-(2'-cyano-biphenyl-4-ylmethyl)-3H-benzoimidazole-5-carboxylic acid methyl ester 

Relevant academic research and scientific papers

Copper-catalyzed synthesis of benzoxazoles via a regioselective C-H functionalization/C-O bond formation under an air atmosphere

(Chemical Equation Presented) An efficient method for the synthesis of functionalized benzoxazoles is described that involves a copper(II)-catalyzed regioselective C-H functionalization/C-O bond formation protocol. The use of dichlorobenzene as a solvent at 160°C allows the use of air as the terminal oxidant in the catalytic synthesis of benzoxazoles in a process that has high functional group tolerance. The presence of a directing group at the meta position markedly improves the reaction efficacy and a variety of 7-substituted benzoxazoles are selectively produced under mild reaction conditions. The mechanism of the reaction is also discussed in this report.

Benzene derivatives and pharmaceutical composition

A benzene derivative of the formula (I): STR1 wherein R 1 is hydrogen, C 1-6 -alkyl, C 1-6 -haloalkyl, --NH 2, --NHR 21 ; R 2 is hydroxyl, --OR 22, three- to seven-membered saturated cycloaliphatic amino optionally interrupted by one or more nitrogen, oxygen or sulfur atoms, --NHR 23, --N(R 24) 2, --NH 2 ; R 4 is hydrogen, C 1-6 -alkyl, or --C( O)R 25 ; R 7 is --CO--, --SO 2 --; R 8 is --CO--, single bond; R 12 is --R 11 --R 5 ; R 11 is --N(R 5)--, --NH--, --O--, --N(R 26)--, --N(C( O)R 27)--, --N(C( O)NH 2)--, --N(C( O)NHR 28)--; R 13 is hydrogen, C 1-6 -alkyl, C 1-6 -haloalkyl, --NHC( O)(CH 2) m C 6 H 5, --NHC( O)R 29, --NHC( O)CH(C 6 H 5) 2, --NH 2, --NHR 30, --(CH 2) n C 6 H 5 ; Z is C, CH, N; A is CH, N; R 5 is hydrogen, --CH 2 C 6 H 4 COOH, --CH 2 C 6 H 4 COOR 31, --CH 2 C 6 H 4 OH, --CH 2 C 6 H 4 OR 32, --CH 2 C 6 H 4 NH 2, --CH 2 C 6 H 4 N(R 33) 2, --CH 2 C 6 H 4 -azole, --CH 2 C 6 H 4 NHR 34, --CH 2 C 6 H 4 C 6 H 4 R 14 ; R 14 is azole, --COOH; R 21 to R 34 are independently C 1-6 -alkyl or C 1-6 -haloalkyl; m is 0 to 6; n is 0 to 6; t is 0 or 1, with the proviso that when Z is N, R 5 is hydrogen, --CH 2 C 6 H 4 COOH, --CH 2 C 6 H 4 COOR 31, --CH 2 C 6 H 4 OH, --CH 2 C 6 H 4 OR 32, --CH 2 C 6 H 4 NH 2, --CH 2 C 6 H 4 N(R 33) 2, --CH 2 C 6 H 4 -azole, or --CH 2 C 6 H 4 NHR 34, or a salt thereof, and a pharmaceutical composition comprising said benzene derivative or a pharmaceutically acceptable salt thereof, and a pharmaceutically acceptable carrier are disclosed.

Nonpeptide angiotensin II receptor antagonists. Synthesis and biological activity of benzimidazoles

A series of substituted 2-butylbenzimidazoles bearing a biphenylylmethyl moiety at the 1-position was prepared via three synthetic routes and evaluated for angiotensin II (AII) receptor antagonistic activity (in vitro and in vivo). Binding affinity was determined using bovine adrenal cortical membrane. Substitution at the 4-, 5-, or 6-position reduced the affinity relative to that of the unsubstituted compound (13a). However, most of the compounds with a substituent at the 7-position showed binding affinity comparable to that of DuP 753 (losartan). In functional studies, a carboxyl group was found to be very important for antagonistic activity against AII. Comparison of 2-butyl-1-[[2'-(1H-tetrazol-5-yl)biphenyl-4-yl]methyl]-1H- benzimidazole-4-,-5-,-6-, and -7-carboxylic acids (15a-d) in an AII-induced rabbit aortic ring contraction assay clearly demonstrated the importance of the substitutional position of the carboxyl group. In an in vivo assay, oral administration of benzimidazole-7-carboxylic acids caused long-lasting inhibition of the AII-induced pressor response in rats. The optimum substituent at the 7-position of the benzimidazole ring was found to be a carboxyl or an ester group. The representative compound, 2-butyl-1-[[2'-(1H- tetrazol-5-yl)biphenyl-4-yl]methyl]-1H-benzimidazole-7-carboxylic acid (15d, CV-11194), inhibited the specific binding of [125I]AII to bovine adrenal cortical membrane with an IC50 value of 5.5 x 10-7 M. The AII-induced contraction of rabbit aortic strips was antagonized by CV-11194 (IC50 value, 5.5 x 10-11 M), while the compound had no effect on the contraction induced by norepinephrine or KCl. Orally administered CV-11194 at doses of 0.3-10 mg/kg dose-dependently inhibited the AII-induced pressor response in rats and dogs. CV-11194 at 1 mg/kg po reduced blood pressure in spontaneously hypertensive rats (SHR). The three-dimensional molecular structure of CV- 11194 was determined by X-ray diffraction.

Benzimidazole derivatives and their use

Novel imidazole derivatives of the formula (I): STR1 wherein R1 is an optionally substituted alkyl group, R2 and R3 are independently a group capable of forming an anion or a group which can be changed thereinto, ring A is a benzene ring optionally having, besides the group shown by R2, further substituents, and X shows linkage of phenylene group and phenyl group directly or through a spacer whose atomic length is not more than 2 and a salt thereof, show antagonistic actions to angiotensin II, thus being useful as therapeutics for cardiovascular diseases.