133485-56-0

Usage

Physical appearance

white to off-white crystalline solid

Primary use

intermediate in the synthesis of pharmaceuticals and agrochemicals

Common use

antifungal medication for athlete's foot and ringworm

Additional properties

fungicidal and antibacterial

Upstream product

• 133485-55-9 2-n-butyl-1-(2-chlorophenyl)-methyl-5-hydroxymethyl-1H-imidazole 
• 17849-38-6 2-Chlorobenzyl alcohol 
• 133486-42-7 2-n-butyl-5-(acetoxymethyl)-1-<(2-chlorophenyl)methyl>imidazole 
• 133486-41-6 1-acetyl-4-acetoxymethyl-2-n-butylimidazole 
• 68283-19-2 2-n-butyl-4-(hydroxymethyl)imidazole 

Downstream Products

• 134405-48-4 (E)-3-<2-butyl-1-<(2-chlorophenyl)methyl>imidazol-5-yl>-2-phenyl-2-propenoic acid 
• 1026169-28-7 3-[2-Butyl-3-(2-chloro-benzyl)-3H-imidazol-4-yl]-3-hydroxy-2-pyridin-3-ylmethyl-propionic acid methyl ester 
• 1027865-27-5 3-[2-Butyl-3-(2-chloro-benzyl)-3H-imidazol-4-yl]-3-hydroxy-2-pyridin-2-ylmethyl-propionic acid methyl ester 
• 133486-28-9 methyl-3-[2-n-butyl-1-(2-chlorophenyl)methyl-1H-imidazol-5-yl]-3-hydroxy-2-[(pyridin-4-yl)methyl]propanoate 
• 1026329-68-9 (E)-3-[2-Butyl-3-(2-chloro-benzyl)-3H-imidazol-4-yl]-2-methyl-acrylic acid methyl ester 
• 1027502-75-5 3-[2-Butyl-3-(2-chloro-benzyl)-3H-imidazol-4-yl]-3-hydroxy-2-(3,4,5-trimethoxy-benzyl)-propionic acid methyl ester 
• 133485-75-3 2-n-butyl-1-(2-chlorophenyl)methyl-5-(α-hydroxy)ethyl-1H-imidazole 
• 141771-53-1 methyl (E,E)-5-<2-butyl-1-<(2-chlorophenyl)methyl>imidazol-5-yl>-2,4-pentadienoate 
• 133485-50-4 (Z)-3-[2-Butyl-3-(2-chloro-benzyl)-3H-imidazol-4-yl]-2-furan-3-ylmethyl-acrylic acid methyl ester 
• 133485-50-4 (E)-3-[2-Butyl-3-(2-chloro-benzyl)-3H-imidazol-4-yl]-2-furan-3-ylmethyl-acrylic acid methyl ester 
• 134405-38-2 2-[1-[2-Butyl-3-(2-chloro-benzyl)-3H-imidazol-4-yl]-meth-(Z)-ylidene]-4-phenyl-butyric acid methyl ester 
• 134405-38-2 2-[1-[2-Butyl-3-(2-chloro-benzyl)-3H-imidazol-4-yl]-meth-(E)-ylidene]-4-phenyl-butyric acid methyl ester 
• 134406-27-2 (Z)-3-[2-Butyl-3-(2-chloro-benzyl)-3H-imidazol-4-yl]-2-naphthalen-2-ylmethyl-acrylic acid methyl ester 
• 134405-42-8 (E)-3-[2-Butyl-3-(2-chloro-benzyl)-3H-imidazol-4-yl]-2-naphthalen-2-ylmethyl-acrylic acid methyl ester 

Relevant academic research and scientific papers

Substituted [1H-imidazol-5-ylialkanoic acids having angiotension II receptor antagonist activity

Angiotensin II receptor antagonists having the formula: STR1 which are useful in regulating hypertension and in the treatment of congestive heart failure, renal failure, and glaucoma, pharmaceutical compositions including these antagonists, and methods of using these compounds to produce angiotensin II receptor antagonism in mammals.

SUBSTITUTED IMIDAZOLES HAVING ANGIOTENSIN II RECEPTOR BLOCKING ACTIVITY

Angiotensin II receptor antagonists having the formula: STR1 which are useful in regulating hypertension and in the treatment of congestive heart failure, renal failure, and glaucoma, pharmaceutical compositions including these antagonists, and methods of

Substituted 5-(alkyl)carboxamide imidazoles

Angiotensin II receptor antagonists having the formula: STR1 which are useful in regulating hypertension and in the treatment of congestive heart failure, renal failure, and glaucoma pharmaceutical compositions including these antagonists, and methods of

Imidazolyl-alkenoic acids useful as angiotensin II receptor antagonists

Angiotensin II receptor antagonists having the formula: STR1 which are useful in regulating hypertension and in the treatment of congestive heart failure, renal failure, and glaucoma, pharmaceutical compositions including these antagonists, and methods of using these compounds to produce angiotensin II receptor antagonism in mammals.

Substituted 5-((tetrazolyl)alkenyl)imidazoles and pharmaceutical methods of use thereof

Angiotensin II receptor antagonists having the formula: STR1 which are useful in regulating hypertension and in the treatment of congestive heart failure, renal failure, and glaucoma, pharmaceutical compositions including these antagonists, and methods of

Potent Nonpeptide Angiotensin II Receptor Antagonists. 2. (1-Carboxybenzyl)imidazole-5-acrylic Acids

The further evolution of the imidazole-5-acrylic acid series of nonpeptide angiotensin II receptor antagonists is detailed (for Part 1, see: J.Med.Chem. 1992, 35, 3858).Modifications of the N-benzyl ring substitution were undertaken in an effort to mimic the Tyr4 residue of angiotensin II.Introduction of a p-carboxylic acid on the N-benzyl ring resulted in the discovery of compounds with nanomolar affinity for the receptor and good oral activity.SAR studies of these potent antagonists revealed that the thienyl ring, the (E)-acrylic acid, and the imidazole ring in addition to the two acid groups were important for high potency.Also, overlay comparisons of the parent diacid with both angiotensin II and a representative biphenylyltetrazole nonpeptide angiotensin II receptor antagonist are presented.The parent diacid analog, SKF 108566 or (E)-3--2-propenoic acid, is currently in clinical development for the treatment of hypertension.

Substituted N-(imidazolyl)alkyl alanine derivatives

Angiotensin II receptor antagonists having the formula: STR1 which are useful in regulating hypertension and in the treatment of congestive heart failure, renal failure, and glaucoma, pharmaceutical compositions including these antagonists, and methods of

Imidazole-5-acrylic Acids: Potent Nonpeptide Angiotensin II Receptor Antagonists Designed Using a Novel Peptide Pharmacophore Model

A series a novel nonpeptide angiotensin II receptor antagonists containing a substituted (E)-acrylic acid has been developed.The overlay of 1, an imidazole-5-acetic acid found in the patent literature, on a novel pharmacophore model of AII suggested that extension of the acid side chain and attachment of a second aryl residue to mimic the C-terminal phenylalanine region of AII would lead to increased activity.A study of extended acid side chains at C-5 of the imidazole nucleus led to the discovery of the (E)-acrylic acid 5 as a promising starting point for further exploration.As predicted by the modeling, substitution of a benzyl group on the acrylic acid side chain to mimic the phenylalanine gave increased potency.An extensive study of the SAR of the newly introduced aromatic ring revealed that electron-rich heteroaryl rings provided improved activity, most notably in the in vivo rat models.Compound 40, (E)-3-imidazol-5-yl>-2--2-propenoic acid, has been shown to be a potent, competitive, and orally active small molecule AT-1 receptor antagonist.It exhibits a 2 orders of magnitude increase in binding affinity and a 10-fold improvement in in vivo potency as compared to compound 1 and represents an important milestone in the development of even more potent nonpeptide angiotensin II receptor antagonists.