Conformational Studies of Semotiadil (SD-3211), a Novel Ca^<2+> Antagonist

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概要

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• The stereochemistry of a novel Ca^<2+> antagonist, semotiadil, 1,was investigated using X-ray crystallography and CD. The X-ray structure was analyzed using its diastereomeric salt with (S)-(+)-mandelic acid (2); 1 (mandelate). The R absolute configuration of 1,which was previously determined by chemical transformation of the optically-active synthetic precursor, was directly confirmed by this analysis. The hydrogen bonding, electrostatic and the hydrophobic interactions, which stabilize the crystal structure, were observed in the crystal. CD spectra of 1 (mandelate) and the hydrogen fumarate of 1 (SD-3211; 1 (fumarate)) in ethanolic solution exhibited similar spectral patterns. The CD bands from each chromophore were unambiguously assigned and the conformation of the benzothiazine ring was determined using the helicity rule. The X-ray and CD data confirmed the P-conformation of the benzothiazine ring and the existence of the 2-phenyl ring in an equatorial position in both of the crystal and ethanolic solution states. These findings were in good agreement with our previous results regarding the conformational analysis of 2-arylbenzothiazine derivatives.

• 社団法人日本薬学会の論文
• 1993-10-15

著者

• 大石 宏文

  Osaka University of Pharmaceutical Sciences

• 石田 寿昌

  Osaka University of Pharmaceutical Sciences

• 河嶋 洋一

  Central Research Laboratories, Santen Pharmaceutical Co., Ltd.,

• 河嶋 洋一

  参天製薬(株)生産技術部

• 河嶋 洋一

  Central Research Laboratories Santen Pharmaceutical Co. Ltd.

• 太田 淳稔

  Central Research Laboratories, Santen Pharmaceutical Co., Ltd.,

• 太田 淳稔

  参天製薬(株)眼科研究所

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