150598-37-1Relevant articles and documents
Intramolecular conjugate addition of α,β-unsaturated lactones having an alkanenitrile side chain: Stereocontrolled construction of carbocycles with quaternary carbon atoms
Yoshimura, Fumihiko,Torizuka, Makoto,Mori, Genki,Tanino, Keiji
supporting information; scheme or table, p. 251 - 254 (2012/03/08)
An efficient method for constructing carbocycles with all-carbon quaternary stereocenters has been developed on the basis of a stereoselective cyclization reaction of ,-unsaturated lactones having an alkanenitrile side chain. Treatment of the substrate with lithium hexamethyldisilazide (LiHMDS) in the presence of triisopropylsilyl chloride (TIPSCl) led to the generation of the corresponding -cyano carbanion species which readily underwent an intramolecular conjugate addition reaction. It was found that thecombined use of trimethylsilyl trifluoromethanesulfonate (TMSOTf) and triethylamine is also effective for the cyclization reaction without using a strong base. Interestingly, different ste-reochemical outcomes were observed in the two cyclization methods. Georg Thieme Verlag Stuttgart - New York.
CARBOXYLIC ACID LEUKOTRIENE B4 ANTAGONISTS
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, (2008/06/13)
Compounds of the formula STR1 wherein X is O or CH 2 ; Y is O,--CH 2--CH 2,--CH=CH--,--C C--, or--OCH 2 C 6 H 4--;Z is--CH 2--CH 2--,--CH=CH--or--C C--;f, h, k, m and t, independently, are 0 or 1;n is an integer from 1 to 12; R 1 is hydrogen, lower alkyl, lower alkenyl, cycloalkyl, or aralkyl; andA is B or--O--B, wherein B is a mono-, di-or tricyclic aromatic or heteroaromatic moiety substituted by the group--COR 2,--(O) t--(W) s--COR 2 or--(CH=CH) p COR 2 and which may also contain up to 4 additional substituents selected, independently, from the group consisting of halogen, cyano, lower alkyl, lower alkoxy, sulfonamido, alkanoyl, aroyl,--(Q) k--(W) s'--E or--(Q) k--(W) s"--C 6 H 4--(W) s'"--E, provided that no more than one of said substituents is--(Q) k--(W) s'--E or--(Q) k--(W). sub.s"--C 6 H 4--(W) s'"--E, and wherein E is COR 2 or R 2, W is--CR 3 R 4--, Q is O or carbonyl, p is an integer from 1 to 2, s and s', independently, are an integer from 1-12, s" and s'", independently, are an integer from 0 to 12, C 6 H 4 is a 1,2-, 1,3-, or 1,4-phenylene moiety, and R 2 is hydroxy, lower alkoxy or NR 3 R 4, wherein R 3 and R 4, each occurrence, independently, are hydrogen or lower alkyl,their geometric and optical isomers and, when R 2 is hydroxy, pharmaceutically acceptable salts thereof with bases. The compounds of formula I are potent leukotriene B 4 antagonists and are therefore useful in the treatment of inflammatory diseases, such as psoriasis, inflammatory bowel disease, asthma, allergy, arthritis, dermatitis, gout, pulmonary disease, ischemia/reperfusion injury, and trauma induced inflammation, such as spinal cord injury. "