Studies on Griseolic Acid Derivatives. VII. : Synthesis and Phosphodiesterase Inhibitory Activity of the C^<4′>-C^<5′> Hydrogenated Products of Griseolic Acid and Their Base-Exchanged Derivatives
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概要
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Addition reactions of the C^<4′>-C^<5′> double bond of griseolic acid were investigated. C^<4′>-C^<5′>Dihydrogrisiolic acid was obtained by reduction of the adduct having halogen at the 4′-position.The ring juncture of the two five-membered rings of the C^<4′>-C^<5′> dihydro derivaticves was of all-"cis"configuration. Acetolysis of the protected dihydrogriseolic acid gave the corresponding 1′-acetoxy sugar derivative. Reaction of this sugar derivative with silylated bases gave guanine and uracil derivatives of the dihydrogriseolic acid. The cyclic nucleotide phosphodiesterase (PDE)-inhibitory activity of the C^<4′>-C^<5′> cis dihydrogriseolic acid derivative was weaker than that of griseolic acid.The uracil derivative of C^<4′>-C^<5′> cis dihydrogriseolic acid completely lost the inhibitory activity against both adenosine 3′, 5′-cyclic monophosphate (cAMP) and guanosine 3′, 5′-cyclic monophosphate (cGMP) PDE, whereas the guanine derivative showed reduced inhibitory activity against cAMP PDE, but retained its activity against cGMP PDE. It was also apparent that the C^<4′>-C^<5′>trans dihydro derivative which was obtained as a minor product from the same culture broth of griseolic acid had almost the same inhibitory activity as griseolic acid.
- 公益社団法人日本薬学会の論文
- 1988-10-25
著者
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桑野 晴光
Analytical and Metabolic Research Laboratories
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飯島 康輝
三共活性研
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桑野 晴光
三共分代研
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室伏 良信
Chemical Research Laboratories:sankyo Company Ltd.
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山崎 光郎
Biological Research Laboratories, Sankyo Co., Ltd.
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木村 美佐子
Chemical Research Laboratories:sankyo Company Ltd.
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飯島 康輝
Biological Research Laboratories
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金子 正勝
Chemical Research Laboratories
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