design and synthesis of a conformationally rigid mimic of the dihydropyrimidine calcium channel modulator sq 32,926设计和合成构象上的刚性dihydropyrimidine钙通道的模拟调制器32926平方.pdfVIP

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design and synthesis of a conformationally rigid mimic of the dihydropyrimidine calcium channel modulator sq 32,926设计和合成构象上的刚性dihydropyrimidine钙通道的模拟调制器32926平方.pdf

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design and synthesis of a conformationally rigid mimic of the dihydropyrimidine calcium channel modulator sq 32,926设计和合成构象上的刚性dihydropyrimidine钙通道的模拟调制器32926平方

Molecules 2000, 5, 227-239 molecules ISSN 1420-3049 Design and Synthesis of a Conformationally Rigid Mimic of the Dihydropyrimidine Calcium Channel Modulator SQ 32,926 ‡ Birgit Jauk, Tetiana Pernat and C. Oliver Kappe* Institute of Chemistry / Organic and Bioorganic Chemistry, Karl-Franzens-University Graz, Heinrich- strasse 28, A-8010 Graz, Austria Tel.: (43)-(316)-380-5352, Fax: (43)-(316)-380-9840, E-mail: oliver.kappe@kfunigraz.ac.at, URL: http://www-ang.kfunigraz.ac.at/~kappeco ‡ Presented in part at The First International Electronic Conference on Synthetic Organic Chemistry (ECSOC-1), September, 1-30, 1997. URL: http://www.unibas.ch/mdpi/ecsoc/ Synthesis and Reactions of Biginelli Compounds, 21. For part 20, see [30]. *Author to whom correspondence should be addressed. Received: 9 February 2000 / Accepted: 29 February 2000 / Published: 3 March 2000 Abstract: A conformationally rigid polyheterocycle (3) which mimics the putative receptor- bound conformation of dihydropyridine-type calcium channel modulators is prepared in a seven-step reaction sequence based on a Biginelli-type cyclocondensation reaction. Keywords: Dihydropyrimidines, Biginelli reaction, isomünchnones, 1,3-dipolar cycloaddi- tion reactions, AM1 calculations, conformation. Introduction 4-Aryl-1,4-dihydropyridines (DHPs, e.g nifedipine, 1) are the most studied class of organic calcium channel modulators and, since their introduction into clinical medicine in 1975, have become almost indispensable for the treatment of cardiovascular diseases such as hypertension, cardiac arrhythmias, or angina [1]. More than 25 years after the introduction of nifedipine (1