120555-31-9Relevant articles and documents
SYNTHESIS OF AN ORALLY ACTIVE PAF ANTAGONIST OF THE N-PENTADIENAMIDE CLASS
Manchand, Percy S.,Schwartz, Alan,Wolff, Steven,Belica, Peter S.,Madan, Pradeep,et al.
, p. 1351 - 1369 (2007/10/02)
The PAF antagonist -5-(4-methoxyphenyl)-N--2,4-decadienamide (2) was synthesized from (S)-α-methyl-3-pyridinebutanol (14), which was obtained either from ethyl lactate or by enantioselective kinetic hydrolysis of its racemate using the lipase derived from Pseudomonas cepacia (syn.P. fluorescens).Mesylation of 14, followed by azide displacement and hydrogenation, produced amine (7), which was coupled with the p-nitrophenol ester (8) to give 2.The direct coupling of (E,E)-5-(4-methoxyphenyl)-2,4-decadienoic acid (27) with azide(24) in the presence of tri-n-butylphosphine also gave 2.Acid (27) was prepared by a vinylogous Reformatsky reaction between ketone (25) and methyl 4-bromocrotonate.
Pentadieneamides
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, (2008/06/13)
Compounds of the formula STR1 Y is O ir S, *A is paraphenylene or *----(CH2)n----(X)m --(CH2)r ----, X is O, S or --CH=CH--, n or r, independently, are integers from 0 to 3, s is an integer from 0 to 1, m is an integer from 0 to 1, provided that when m is 1, n+s must be at least 2, R1 and R2, independently, are hydrogen, lower alkyl, cycloalkyl, lower alkenyl, Het, aryl, R3, R4 and R8, independently, are hydrogen, lower alkyl, aryl, R5 and R6, independently, are hydrogen or lower alkyl, R7 is hydrogen, lower alkyl, cycloalkyl, Het-lower alkyl or aryl, Het is a monocyclic 5- or 6-membered hetero aromatic or a bicyclic heteroaromatic radical containing one or two hetero atoms selected from nitrogen, oxygen and sulfur, which radical may be substituted by lower alkyl, halogen or aryl, and the asterisk denotes the point of attachment, and when R6 and R7 are different, their enantiomers and racemic mixtures thereof, when R1 and R2 are different, their geometric isomers, and pharmaceutically acceptable acid addition salts thereof, are described. The compounds of formula I exhibit activity as platelet activating factor (PAF) antagonists and are, therefore, useful in disease states characerized by excess platelet activating factor or for the prevention and treatment of cardiovascular disease, pulmonary diseases, immunological disorders, inflammatory diseases, dermatological disorders, shock or transplant rejection.
