Art

J-GLOBAL ID：200902155153338510   Reference number：96A1032046

Chemical Modification and Structure-activity Relationships of Pyripyropenes. 2. 1,11-Cyclic Analogs.

ピリピロペン類の化学的修飾と構造活性相関 2 1,11-環状類縁体

Author (6)： OBATA R (Kitasato Univ., Tokyo, JPN) ,  SUNAZUKA T (Kitasato Univ., Tokyo, JPN) ,  KATO Y (Kitasato Univ., Tokyo, JPN) ,  TOMODA H (Kitasato Univ., Tokyo, JPN) ,  HARIGAYA Y (Kitasato Univ., Tokyo, JPN) ,  OHMURA S (Kitasato Univ., Tokyo, JPN)
Material： Journal of Antibiotics  (J Antibiot)
Volume： 49  Issue： 11  Page： 1149-1156  Publication year： Nov. 1996 
JST Material Number： G0489A  ISSN： 0021-8820  Document type： Article
Article type： 原著論文  Country of issue： Japan (JPN)  Language： ENGLISH (EN)

Thesaurus term： enzyme inhibitor ,...
Semi thesaurus term： hydroxyl group ,...

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JST classification (2)： Synthesis of antibiotics  (GX04000Z) ,  Basic research of drugs acting on lipid metabolism  (GW13040M)

Substance index (30)： Pyripyropene A ,  4,4a,4bβ,5,6,6a,12,12aβ,12b,13,14,14aβ-Dodecahydro-6α,12α-dihydroxy-2α,4aα,6aα,12bα-tetramethyl-9-(3-pyridinyl)-2H,11H-1,3,7,10-tetraoxabenzo[b]chrysen-11-one ,  4,4a,4bβ,5,6,6a,12,12aβ,12b,13,14,14aβ-Dodecahydro-6α,12α-dihydroxy-2,2,4aα,6aα,12bα-pentamethyl-9-(3-pyridinyl)-2H,11H-1,3,7,10-tetraoxabenzo[b]chrysen-11-one ,  4,4a,4bβ,5,6,6a,12,12aβ,12b,13,14,14aβ-Dodecahydro-6α,12α-dihydroxy-2α-ethyl-4aα,6aα,12bα-trimethyl-9-(3-pyridinyl)-2H,11H-1,3,7,10-tetraoxabenzo[b]chrysen-11-one ,  4,4a,4bβ,5,6,6a,12,12aβ,12b,13,14,14aβ-Dodecahydro-6α,12α-dihydroxy-2α-vinyl-4aα,6aα,12bα-trimethyl-9-(3-pyridinyl)-2H,11H-1,3,7,10-tetraoxabenzo[b]chrysen-11-one ,  4,4a,4bβ,5,6,6a,12,12aβ,12b,13,14,14aβ-Dodecahydro-6α,12α-dihydroxy-2α-isopropyl-4aα,6aα,12bα-trimethyl-9-(3-pyridinyl)-2H,11H-1,3,7,10-tetraoxabenzo[b]chrysen-11-one ,  4,4a,4bβ,5,6,6a,12,12aβ,12b,13,14,14aβ-Dodecahydro-6α,12α-dihydroxy-2α-tert-butyl-4aα,6aα,12bα-trimethyl-9-(3-pyridinyl)-2H,11H-1,3,7,10-tetraoxabenzo[b]chrysen-11-one ,  4,4a,4bβ,5,6,6a,12,12aβ,12b,13,14,14aβ-Dodecahydro-6α,12α-dihydroxy-2α-methoxy-4aα,6aα,12bα-trimethyl-9-(3-pyridinyl)-2H,11H-1,3,7,10-tetraoxabenzo[b]chrysen-11-one ,  4,4a,4bβ,5,6,6a,12,12aβ,12b,13,14,14aβ-Dodecahydro-6α,12α-dihydroxy-2α-phenyl-4aα,6aα,12bα-trimethyl-9-(3-pyridinyl)-2H,11H-1,3,7,10-tetraoxabenzo[b]chrysen-11-one ,  4,4a,4bβ,5,6,6a,12,12aβ,12b,13,14,14aβ-Dodecahydro-6α,12α-dihydroxy-2α-phenyl-2,4aα,6aα,12bα-tetramethyl-9-(3-pyridinyl)-2H,11H-1,3,7,10-tetraoxabenzo[b]chrysen-11-one ,  4,4a,4bβ,5,6,6a,12,12aβ,12b,13,14,14aβ-Dodecahydro-6α,12α-dihydroxy-2α-(2-methylphenyl)-4aα,6aα,12bα-trimethyl-9-(3-pyridinyl)-2H,11H-1,3,7,10-tetraoxabenzo[b]chrysen-11-one ,  4,4a,4bβ,5,6,6a,12,12aβ,12b,13,14,14aβ-Dodecahydro-6α,12α-dihydroxy-2α-(3-methylphenyl)-4aα,6aα,12bα-trimethyl-9-(3-pyridinyl)-2H,11H-1,3,7,10-tetraoxabenzo[b]chrysen-11-one ,  4,4a,4bβ,5,6,6a,12,12aβ,12b,13,14,14aβ-Dodecahydro-6α,12α-dihydroxy-2α-(4-methylphenyl)-4aα,6aα,12bα-trimethyl-9-(3-pyridinyl)-2H,11H-1,3,7,10-tetraoxabenzo[b]chrysen-11-one ,  4,4a,4bβ,5,6,6a,12,12aβ,12b,13,14,14aβ-Dodecahydro-6α,12α-dihydroxy-2α-(2-fluorophenyl)-4aα,6aα,12bα-trimethyl-9-(3-pyridinyl)-2H,11H-1,3,7,10-tetraoxabenzo[b]chrysen-11-one ,  4,4a,4bβ,5,6,6a,12,12aβ,12b,13,14,14aβ-Dodecahydro-6α,12α-dihydroxy-2α-(3-fluorophenyl)-4aα,6aα,12bα-trimethyl-9-(3-pyridinyl)-2H,11H-1,3,7,10-tetraoxabenzo[b]chrysen-11-one ,  4,4a,4bβ,5,6,6a,12,12aβ,12b,13,14,14aβ-Dodecahydro-6α,12α-dihydroxy-2α-(4-fluorophenyl)-4aα,6aα,12bα-trimethyl-9-(3-pyridinyl)-2H,11H-1,3,7,10-tetraoxabenzo[b]chrysen-11-one ,  4,4a,4bβ,5,6,6a,12,12aβ,12b,13,14,14aβ-Dodecahydro-6α,12α-dihydroxy-2α-(4-methoxyphenyl)-4aα,6aα,12bα-trimethyl-9-(3-pyridinyl)-2H,11H-1,3,7,10-tetraoxabenzo[b]chrysen-11-one ,  4,4a,4bβ,5,6,6a,12,12aβ,12b,13,14,14aβ-Dodecahydro-6α,12α-dihydroxy-2α-(4-nitrophenyl)-4aα,6aα,12bα-trimethyl-9-(3-pyridinyl)-2H,11H-1,3,7,10-tetraoxabenzo[b]chrysen-11-one ,  4,4a,4bβ,5,6,6a,12,12aβ,12b,13,14,14aβ-Dodecahydro-6α,12α-dihydroxy-4aα,6aα,12bα-trimethyl-9-(3-pyridinyl)spiro[1,3,7,10-tetraoxabenzo[b]chrysene-2(11H),1′-cyclopentan]-11-one ,  4,4a,4bβ,5,6,6a,12,12aβ,12b,13,14,14aβ-Dodecahydro-6α,12α-dihydroxy-4aα,6aα,12bα-trimethyl-9-(3-pyridinyl)spiro[1,3,7,10-tetraoxabenzo[b]chrysene-2(11H),1′-cyclohexan]-11-one ,  4,4a,4bβ,5,6,6a,12,12aβ,12b,13,14,14aβ-Dodecahydro-6α,12α-dihydroxy-4aα,6aα,12bα-trimethyl-9-(3-pyridinyl)-2H,11H-1,3,7,10-tetraoxabenzo[b]chrysene-2,11-dione ,  4,4a,4bβ,5,6,6a,12,12aβ,12b,13,14,14aβ-Dodecahydro-6α-hydroxy-2,2,4aα,6aα,12bα-pentamethyl-9-(3-pyridinyl)-2H,11H-1,3,7,10-tetraoxabenzo[b]chrysen-11-one ,  4,4a,4bβ,5,6,6a,12,12aβ,12b,13,14,14aβ-Dodecahydro-6α-(pentanoyloxy)-2,2,4aα,6aα,12bα-pentamethyl-9-(3-pyridinyl)-2H,11H-1,3,7,10-tetraoxabenzo[b]chrysen-11-one ,  4,4a,4bβ,5,6,6a,12,12aβ,12b,13,14,14aβ-Dodecahydro-6α-acetoxy-12α-hydroxy-2,2,4aα,6aα,12bα-pentamethyl-9-(3-pyridinyl)-2H,11H-1,3,7,10-tetraoxabenzo[b]chrysen-11-one ,  4,4a,4bβ,5,6,6a,12,12aβ,12b,13,14,14aβ-Dodecahydro-2α-phenyl-6α-acetoxy-12α-hydroxy-4aα,6aα,12bα-trimethyl-9-(3-pyridinyl)-2H,11H-1,3,7,10-tetraoxabenzo[b]chrysen-11-one ,  4,4a,4bβ,5,6,6a,12,12aβ,12b,13,14,14aβ-Dodecahydro-6α-(pentanoyloxy)-12α-hydroxy-2α-phenyl-4aα,6aα,12bα-trimethyl-9-(3-pyridinyl)-2H,11H-1,3,7,10-tetraoxabenzo[b]chrysen-11-one ,  4,4a,4bβ,5,6,6a,12,12aβ,12b,13,14,14aβ-Dodecahydro-6α-(pentanoyloxy)-12α-hydroxy-2α,4aα,6aα,12bα-tetramethyl-9-(3-pyridinyl)-2H,11H-1,3,7,10-tetraoxabenzo[b]chrysen-11-one ,  4,4a,4bβ,5,6,6a,12,12aβ,12b,13,14,14aβ-Dodecahydro-6α-(pentanoyloxy)-12α-hydroxy-2α-phenyl-2,4aα,6aα,12bα-tetramethyl-9-(3-pyridinyl)-2H,11H-1,3,7,10-tetraoxabenzo[b]chrysen-11-one ,  4,4a,4bβ,5,6,6a,12,12aβ,12b,13,14,14aβ-Dodecahydro-6α-(pentanoyloxy)-12α-hydroxy-4aα,6aα,12bα-trimethyl-9-(3-pyridinyl)spiro[1,3,7,10-tetraoxabenzo[b]chrysene-2(11H),1′-cyclohexan]-11-one ,  4,4a,4bβ,5,6,6a,12,12aβ,12b,13,14,14aβ-Dodecahydro-6α-(pentanoyloxy)-12α-hydroxy-4aα,6aα,12bα-trimethyl-9-(3-pyridinyl)spiro[1,3,7,10-tetraoxabenzo[b]chrysene-2(11H),1′-cyclopentan]-11-one

Reference (6)：

• 1) OMURA, S.; H. TOMODA, Y. K. KIM & H. NISHIDA: Pyripyropenes, highly potent inhibitors of acyl-CoA: cholesterol acyltransferase produced by Aspergillus fumigatus. J. Antibiotics 46: 1168-1169, 1993
• 2) OBATA, R.; T. SUNAZUKA, L. ZHUORONG, H. TOMODA & S. OMURA: Structure-activity relationships of pyripyropenes fungal acyl-CoA: cholesterol acyltransferase inhibitors. J. Antibiotics 48: 749-750, 1995
• 3) OBATA, R.; T. SUNAZUKA, H. TOMODA, Y. HARIGAYA & S. OMURA: Chemical modification and structure-activity relationships of pyripyropenes; Potent, bioavailable inhibitor of acyl-CoA: cholesterol acyltransferase. Bioorg. & Med. Chem. Lett. 5: 2683-2688, 1995
• 4) NARASAKA, K.: Trends in synthetic carbohydrate chemistry. In ACS symposium series 386. Ed., D. HORTON et aJ., p. 290, American Chemical Society, Washington DC, 1989
• 5) LEWBART, M. L. & J. J. SCHNEIDER: Preparation and properties of steroidal 17, 20-acetonides epimeric at C-20. I. Derivatives of 5β-pregnan-3a-ol. J. Org. Chem. 34: 3505-3512, 1969

Terms in the title (4)： 化学的修飾 ,  構造活性相関 ,  環状 ,  類縁体