- 著者
- 室伏 良信 木村 美佐子 桑野 晴光 飯島 康輝 山崎 光郎 金子 正勝
- 出版者
- 公益社団法人日本薬学会
- 雑誌
- Chemical & pharmaceutical bulletin (ISSN:00092363)
- 巻号頁・発行日
- vol.36, no.10, pp.3760-3769, 1988-10-25
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.
1 0 0 0 OA Synthesis of 9-(β-D-Arabinofuranosyl) adenine 5'-Phosphate starting from Adenosine 5'-Phosphate
- 著者
- 金子 正勝 木村 美佐子 清水 文治 矢野 純一 池原 森男
- 出版者
- The Pharmaceutical Society of Japan
- 雑誌
- Chemical and Pharmaceutical Bulletin (ISSN:00092363)
- 巻号頁・発行日
- vol.25, no.8, pp.1892-1898, 1977-08-25 (Released:2008-03-31)
- 被引用文献数
- 2 2
9-(β-D-Arabinofuranosyl) adenine 5'-phosphate was obtained from adenosine 5'-phosphate via the novel intermediate 8, 2'-O-cycloadenosine 5'-phosphate. In contrast to the synthesis of 9-(β-D-arabinofuranosyl) adenine, it was difficult to cleave this compound by hydrogen sulfide directly to 8, 2'-O-cycloadenosine 5'-phosphate because of a considerable degree of dephosphorylation. However N-acylated 8, 2'-O-cycloadenosine 5'-phosphate was readily cleaved at the cyclo-bond by hydrogen sulfide. Desulfurization of 8-mercapto-9-(β-D-arabinofuranosyl) adenine 5'-phosphate gave the desired pure crystalline product.'