137292-30-9

Basic information

• Product Name: 5-[(1-cyclohexyl-2-imidazol-1-yl-3-phenyl-propylidene)amino]oxypentano ic acid
• Synonyms: 5-[(1-cyclohexyl-2-imidazol-1-yl-3-phenyl-propylidene)amino]oxypentano ic acid;Pentanoic acid, 5-(((1-cyclohexyl-2-(1H-imidazol-1-yl)-3-phenylpropylidene)amino)oxy)-, (E)-(+-)-
• CAS NO: 137292-30-9
• Molecular Formula: C₂₃H₃₁N₃O₃
• Molecular Weight: 0
• Mol File: 137292-30-9.mol

Chemical Properties

• Boiling Point: 619.5°Cat760mmHg
• Flash Point: 328.5°C
• Appearance: /
• Density: 1.17g/cm³
• Vapor Pressure: 3.29E-16mmHg at 25°C
• Refractive Index: 1.589
• CAS DataBase Reference: 5-[(1-cyclohexyl-2-imidazol-1-yl-3-phenyl-propylidene)amino]oxypentano ic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 5-[(1-cyclohexyl-2-imidazol-1-yl-3-phenyl-propylidene)amino]oxypentano ic acid(137292-30-9)
• EPA Substance Registry System: 5-[(1-cyclohexyl-2-imidazol-1-yl-3-phenyl-propylidene)amino]oxypentano ic acid(137292-30-9)

Safety Data

• Hazardous Substances Data: 137292-30-9(Hazardous Substances Data)

Usage

InChI:InChI=1/C23H31N3O3/c27-22(28)13-7-8-16-29-25-23(20-11-5-2-6-12-20)21(26-15-14-24-18-26)17-19-9-3-1-4-10-19/h1,3-4,9-10,14-15,18,20-21H,2,5-8,11-13,16-17H2,(H,27,28)/b25-23+

Upstream product

• 14660-52-7 ethyl 5-bromovalerate 
• 142223-42-5 ethyl (+/-)-(E+Z)-5-<<<1-cyclohexyl-2-(1H-imidazol-1-yl)-3-phenylpropylidene>amino>oxy>pentanoate 

Downstream Products

• 1025912-19-9 5-[1-Cyclohexyl-2-imidazol-1-yl-3-phenyl-prop-(E)-ylideneaminooxy]-pentanoic acid benzyloxy-amide 
• 1027294-29-6 5-[1-Cyclohexyl-2-imidazol-1-yl-3-phenyl-prop-(E)-ylideneaminooxy]-pentanoyl chloride 

Relevant articles and documents

Substituted 1-(alkoxy-iminoalkyl) imidazole derivatives and their use in treating disease related to an enhancement of thromboxane-A2 syntheis

1-(Alkoxy-iminoalkyl)imidazole derivatives of formula STR1 wherein R is hydrogen or C1 -C4 alkyl; A is C1 -C4 alkylene optionally substituted by phenyl optionally substituted by halogen or trifluoromethyl; R is

Agents combining thromboxane receptor antagonism with thromboxane synthase inhibition: [[[2-(1H-imidazol-1-yl)ethylidene]amino]oxy]alkanoic acids

A new class of compounds combining thromboxane-A2 (TxA2) receptor antagonism and thromboxane synthase inhibition is described. A first series of (E)- and (Z)-[[[2-(1H-imidazol-1-yl)ethylidene]amino]oxy]pentanoic acids showed relevant thromboxane synthase inhibition associated with weak TxA2 receptor antagonism, while a series of (±)-(E)-[[[2-(1H-imidazol-1-yl)-3- phenylpropylidene]amino]oxy]pentanoic acids, structurally derived from the former, showed potent and well-balanced dual activity. Structural requirements for significant single and dual activity are discussed. Two close congeners of the latter series, (±)-(E)-5-[[[1-cyclohexyl-2-(1H- imidazol-1-yl)-3-phenylpropylidene]amino]oxy]pentanoic acid 23c and its p- fluorophenyl analog 23m, inhibited TxB2 production in vitro, in rat whole blood during clotting, with IC50 of 0.06 and 0.37 μM and antagonized the binding of [3H]SQ 29548 to washed human platelets, with IC50 of 0.08 and 0.02 μM, respectively. These two compounds were selected for further pharmacological evaluation and were shown to antagonize U46619-induced platelet aggregation in human platelet rich plasma with IC50 of 0.30 and 0.44 μM, respectively. They were both orally available, and in particular 23m caused a long lasting ex vivo TxA2 synthase inhibition in the fed rat. The levorotatory enantiomer of 23c, stereospecifically synthesized as a model compound, was found to be more potent than racemic 23c with regard to TxA2 receptor antagonism (IC50 = 0.04 μM) and equivalent to the latter with regard to TxA2 synthase inhibition. A molecular modeling study concerning the levorotatory enantiomer of 23c (S), TxA2, and representative TxA2 antagonists of different classes led to the definition of a putative pharmacophoric model for the TxA2 receptor ligands.