α-Methylene-γ-butyrolactones : Synthesis and Vasorelaxing Activity Assay of Coumarin, Naphthalene, and Quinoline Derivatives

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概要

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• Certain α-methylene-γ-butyrolactone derivatives of coumarin, naphthalene, and quinoline were synthesized and evaluated for vasorelaxing effects on isolated rat thoracic aorta. The 7-[(2,3,4,5-tetrahydro-2-methyl-4-methylene-5-oxo-2-furanyl)methoxy]-2H-1-benzopyran-2-ones, which have an aliphatic methyl substituent at the lactone C_2,were more active than their C_2-phenyl counterparts against high-K^+ (80 mM) medium, Ca^<2+> (1.9 mM)-induced vasoconstriction and the norepinephrine (NE, 3 μM)-induced phasic and tonic constrictions (2a vs. 2b; 2c vs. 2d; 2e vs. 2f; 2g vs. 2h). Although 3-chloro-7-[(2,3,4,5-tetrahydro-2-methyl-4-methylene-5-oxo-2-furanyl)methoxy]-4-methyl-2H-1-benzopyran-2-one (2g) demonstrated the most potent inhibitory activities on the NE-induced phasic and tonic constrictions at concentrations of as low as 10 μg/ml, it possesses both affinity for NE-receptor and intrinsic activity to trigger the vasoconstriction. However, 8-[(2,3,4,5-tetrahydro-2-methyl-4-methylene-5-oxo-2-furanyl)-methoxy]quinoline (10a) and other quinoline derivatives (11a, 12a) are pure irreversible non-competitive blockers of NE-receptor with no intrinsic activity. The aromatic ring played an important role in the vasorelaxing effects of α-methylene-γ-butyrolactones; naphthalene was inactive, quinolines exhibited only affinity to the α-receptor, and coumarins possessed both affinity and intrinsic activity.

• 公益社団法人日本薬学会の論文
• 1998-06-15

著者

• Tzeng C‐c

  Kaohsiung Medical Univ. Kaohsiung City Twn

• Teng C‐m

  National Taiwan Univ. Taipei Twn

• Teng Che-ming

  Pharmacological Institute College Of Medicine National Taiwan University

• CHEN Yeh-Long

  School of Chemistry, Kaohsiung Medical College

• WANG Tai-Chi

  School of Chemistry, Kaohsiung Medical College

• TZENG Cherng-Chyi

  School of Chemistry, Kaohsiung Medical College

• Chen Y‐l

  Kaohsiung Medical Coll. Kaohsiung Twn

• Chang Ya-ling

  School Of Chemistry Kaohsiung Medical College:department Of Chemistry National Sun Yat-sen Universit

• Wang T‐c

  Tajen Inst. Of Technol. Pintung Twn

• Chang N‐c

  National Sun Yat‐sen Univ. Kaohsiung Twn

• CHANG Nein-Chen

  Department of Chemistry, National Sun Yat-Sen University

• CHANG Ya-Ling

  Pharmacological Institute, College of Medicine, National Taiwan University

• Tzeng Cherng-chyi

  School Of Chemistry Kaohsiung Medical University

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• α-Methylene-γ-butyrolactones : Synthesis and Vasorelaxing Activity Assay of Coumarin, Naphthalene, and Quinoline Derivatives
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