557112-42-2

Basic information

• Product Name: Butanoic acid, 3-oxo-, 3-cyclohexylpropyl ester
• CAS NO: 557112-42-2
• Molecular Formula: C13H22O3
• Molecular Weight: 226.316
• Mol File: 557112-42-2.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: Butanoic acid, 3-oxo-, 3-cyclohexylpropyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: Butanoic acid, 3-oxo-, 3-cyclohexylpropyl ester(557112-42-2)
• EPA Substance Registry System: Butanoic acid, 3-oxo-, 3-cyclohexylpropyl ester(557112-42-2)

Safety Data

• Hazardous Substances Data: 557112-42-2(Hazardous Substances Data)

Upstream product

• 1124-63-6 3-cyclohexylpropan-1-ol 
• 5394-63-8 2,2,6-trimethyl-4H-1,3-dioxin-4-one 
• 42490-66-4 2,2,6-trimethyl-4H-1,3-dioxin-4-one 

Downstream Products

• 1027261-86-4 3-Oxo-2-[1-(2-phenyl-3H-imidazol-4-yl)-meth-(Z)-ylidene]-butyric acid 3-cyclohexyl-propyl ester 
• 196707-76-3 bis[(3-cyclohexyl)propyl] 1,4-dihydro-2,6-dimethyl-4-(1-methyl-5-nitroimidazol-2-yl)-3,5-pyridinedicarboxylate 

Relevant articles and documents

Lipophilic 4-imidazoly-1,4-dihydropyridines: Synthesis, calcium channel antagonist activity and protection against pentylenetetrazole-induced seizure

A group of alkyl, cycloalkyl and aryl ester analogs of nifedipine, in which the o-nitrophenyl group at position 4 is replaced by a 2-phenyl-4(5)-imidazolyl substituent, were synthesized and evaluated as calcium channel antagonist using the high K+ contraction of guinea-pig ileal longitudinal smooth muscle, and the activity of 5a-d, 8b and 8f against pentylenetetrazole (PTZ)-induced seizure was assessed. The results for symmetrical esters showed that lengthening of the methylene chain in C3 and C5 ester substituents increased activity. When increasing of the length is accompanied by increasing the hindrance, the activity decreased. In contrast to symmetrical derivatives, comparison of the activities of asymmetrical esters showed that increasing the length of the methylene chain was accompanied by a decrease in their activity. The results demonstrate that 8a was more active, and 5c and 8f were similar in effect to that of the reference drug nifedipine. The time-course of anticonvulsant effect on PTZ-induced seizure threshold of said compounds was assessed and showed that increasing the lipophilicity decreases the time needed for maximum effect. Mice treated with intraperitoneal injection of 25 mg/kg of these derivatives all exhibited increase seizure threshold as compared with control.

Synthesis and calcium-channel antagonist activity of nifedipine analogues containing nitroimidazolyl substituent in guinea-pig ileal smooth muscle

Alkyl, cycloalkyl or aryl ester analogues of nifedipine, in which the ortho-nitrophenyl group at position 4 is replaced by 1-methyl-5-nitro-2-imidazolyl substituent, were synthesized and evaluated as calcium-channel antagonists using the high K+ contraction of guinea-pig ileal longitudinal smooth muscle. The results for the symmetrical esters showed that increasing the length of methylene chain (n > 2) decreases activity. The relative activity profile for asymmetrical esters was cyclopentyl > cyclohexyl > cyclopropyl. Comparison of esters having the same methylene space showed that the cyclohexyl compounds were more active than the corresponding phenyl derivatives. In addition, asymmetrical esters possessing one R2 substituent (methyl > ethyl) indicated that increasing the length of methylene chain in the R1-substituent decreased activity. Our results demonstrate that several compounds were more active than the reference drug nifedipine. The symmetrical cyclohexyl ester (n = 0) and the asymmetrical (R1 = cyclohexyl, R2 = Me, n = 0) derivatives were the most potent antagonists tested.