INSECT PHEROMONES AND THEIR ANALOGS. XII. SYNTHESIS OF THE ISOMERIC DEC-5-ENYL ACETATES - THE SEX PHEROMONES OF Anarsia lineatella AND Agrotis segetum
A new route for the synthesis of dec-5E- and -5Z-enyl acetates - the sex pheromones of the peach-tree borer and of the turnip moth - is proposed which is based on the two-stage hydroxyethylation of hex-1-yne using 2-chloroethyl vinyl ethers and ethylene oxide.
Odinokov, V. N.,Balezina, G. G.,Ishmuratov, G. Yu.,Vakhitov, R. Sh.,Tolstikov, G. A.
Palladium-Catalyzed Intramolecular Addition of Amines to Acetylenes. Synthesis of Cyclic Imines
Intramolecular aminopalladation of alkynylamines gave intermediary alkenylpalladium compounds that hydrolyzed and isomerized to thermodynamically stable cyclic imines.Treatment of 3-alkynylamines with a catalytic amount of PdCl2(MeCN)2 gave exclusively 1-
Evaluation and optimization of antifibrotic activity of cinnamoyl anthranilates
Tranilast is an anti-inflammatory drug in use for asthma and atopic dermatitis. In studies over the last decade it has been revealed that tranilast can reduce fibrosis occurring in the kidney during diabetes, thereby delaying and/or preventing kidney dysfunction. We report a structure-activity study aimed at optimizing the antifibrotic activity of tranilast. A series of cinnamoyl anthranilates were prepared and assessed for their ability to prevent TGF-β-stimulated production of collagen in cultured renal mesangial cells. We reveal derivatives with improved potency and reduced cellular toxicity relative to tranilast. 3-Methoxy-4-propargyloxycinnamoyl anthranilate reduces albuminuria in a rat model of progressive diabetes, and thus has potential as an innovative treatment for diabetic nephropathy.
Zammit, Steven C.,Cox, Alison J.,Gow, Renae M.,Zhang, Yuan,Gilbert, Richard E.,Krum, Henry,Kelly, Darren J.,Williams, Spencer J.
supporting information; experimental part
p. 7003 - 7006
(2010/07/08)
THERAPEUTIC COMPOUNDS
Substituted cinnamoyl anthranilate compounds exhibiting anti-fibrotic activity; or derivatives thereof, analogues thereof, pharmaceutically acceptable salts thereof, and metabolites thereof; with the proviso that the compound is not Tranilast.
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Page/Page column 80
(2008/06/13)
Syntheses of Monounsaturated Sex Pheromones of Lepidoptera via 3-Alkyn-1-ols
3-Alkyn-1-ols as intermediate synthons in the preparation of some Lepidoteran sex pheromones were utilized.Characteristic fragmentations reflecting the position of the triple bond were found in the mass spectra of 3-alkyn-1-ols and alkyn-1-yl acetates in contrast to 1-tert-butoxy-alkynes.A partial isomerization of 1-tosyloxy-3-(Z)-octene to 1-bromo-3-(E)-octene within the reaction with NaBr in DMF was noticed by GC and 13C-n.m.r., for which a mechanism involving homoconjugation in an intermediate non-classical carbonium ion was suggested.
Pop, Lidia,Oprean, I.,Barabas, A.,Hodosan, F.
p. 867 - 878
(2007/10/02)
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