6603-71-0Relevant articles and documents
SYNTHESIS OF CYCLOHEXYLALIPHATIC ACIDS AND THEIR PHARMACOLOGICAL PROPERTIES
Kuchar, Miroslav,Brunova, Bohumila,Grimova, Jaroslava,Vanecek, Stanislav,Holubek, Jiri
, p. 2896 - 2908 (2007/10/02)
A series of substituted cyclohexylacetic acids I has been obtained by hydrogenation of the unsaturated analogues II and III.Esters of these analogues were prepared by the Horner-Wittig reaction of the corresponding cyclohexanones IV and/or 2-cyclohexenones V with triethyl phosphonoacetate.These esters were obtained in two isomeric forms (Z and E), differing in the double bond in the exo-position.The derivatives with a substituent in the 2-position exhibited a partial shift of the double bond to the cyclohexane ring; this shift was especially marked in the 2-phenyl derivative.With the acids I-III, activation of fibrinolysis was assessed by the hanging clot method; the anti-inflammatory effect was assessed by inhibition of two experimental model inflammations.The regression equation relating fibrinolytic capacity to lipophilicity was a quadratic one, the logarithm of optimum lipophilicity being log Popt = 5.55.A qualitative assessment of the anti-inflammatory effect in relation to lipophilicity suggests that log Popt is probably higher than with arylaliphatic acids.These acids seem to have an active site different from that of the acids I-III.
Stereochemistry of 1,4-Addition of Nucleophiles to Ethyl Cyclohexylidenecyanoacetates
Nasipuri, Dhanonjoy,Sarkar, Ashis,Konar, Samir K.
, p. 2840 - 2845 (2007/10/02)
The stereochemistry of 1,4-addition of several nucleophiles such as cyanide, sodium borohydride, and methylmagnesium iodide to three substituted ethyl cyclohexylidenecyanoacetates (1-3) has been determined.A higher preference for equatorial attack is observed in these compounds than in related cyclohexanones, which is considerably diminished by the use of aprotic polar solvents.The results do not show any appreciable contribution of product stability control, recently shown to be important for hydride reduction of cyclohexanones, and have been rationalized on thebasis of a six-center cyclic transition state in which steric factors play a dominant role.These compounds have also been reduced by catalytic hydrogenation (Pd/C), and, interestingly, with unhindered systems (1, 2) hydrogenation takes place more from the axial side (40-60percent) as compared to cyclohexanones.
