6,7-dihydrocanrenonoic acid | 63815-34-9

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 类固醇和类固醇衍生物
• 英文名称: 6,7-dihydrocanrenonoic acid
• 英文别名: 3-(3-Oxo-17-beta-hydroxy-4-androsten-17a-yl)propionic acid；3-[(8R,9S,10R,13S,14S,17R)-17-hydroxy-10,13-dimethyl-3-oxo-2,6,7,8,9,11,12,14,15,16-decahydro-1H-cyclopenta[a]phenanthren-17-yl]propanoic acid
• CAS: 63815-34-9
• 化学式: C₂₂H₃₂O₄
• 分子量: 360.494
• InChiKey: JDJDVENIGIFHAG-WNHSNXHDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  26
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  74.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  螺内酯EP杂质C 在 葡萄糖 、 adult Sprague-Dawley rat testicular tissue 、 Krebs-Ringer bicarbonate buffer 、 氧气 作用下， 以 乙醇 为溶剂， 反应 4.0h， 以14.4%的产率得到16α-hydroxy-6,7-dihydrocanrenone
  参考文献：
  名称：

  Metabolism of spirolactones by the rat testis in vitro

  摘要：

  Spironolactone (SPIR) has been shown in numerous clinical studies to produce sexual disorders. We studied the metabolism of canrenone (CAN), the main metabolite of SPIR, and of the analogue 6,7-dihydrocanrenone (DHC) by the rat testis in vitro. The metabolites produced during a 4 h incubation period were isolated by HPLC and identified by nmr-, ms-, ir- and uv-spectrometry. SPIR was not metabolised in a detectable amount. CAN was converted to canrenoic acid, several hydroxylated (15 beta-, 16 alpha-, 19-, 2OR- and 21S-OH-CAN) and one reduced metabolite (3 alpha-OH-CAN). When DHC was incubated, an analogous pattern was detected. It is concluded that CAN and DHC serve as substrates for steroid metabolism in the rat testis.

  DOI：

  10.1016/0039-128x(83)90136-8

文献信息

• Processes for preparation of 9,11-epoxy steroids and intermediates useful therein
  申请人：G.D. Searle & Company

  公开号：US20030055274A1

  公开（公告）日：2003-03-20

  Multiple novel reaction schemes, novel process steps and novel intermediates are provided for the synthesis of epoxymexrenone and other compounds of formula (I) wherein: —A—A— represents the group —CHR 4 —CHR 5 — or —CR 4 ═CR 5 —, R 3 , R 4 and R 5 are independently selected from the group consisting of hydrogen, halo, hydroxy, lower alkyl, lower alkoxy, hydroxyalkyl, alkoxyalkyl, hydroxycarbonyl, cyano, aryloxy; R 1 represents an alpha-oriented lower alkoxycarbonyl or hydroxyalkyl radical; —B—B— represents the group —CHR 6 —CHR 7 — or an alpha- or beta-oriented group (III), where R 6 and R 7 are independently selected from the group consisting of hydrogen, halo, lower alkoxy, acyl, hydroxyalkyl, alkoxyalkyl, hydroxycarbonyl, alkyl, alkoxycarbonyl, acyloxyalkyl, cyano and aryloxy; and R 8 and R 9 are independently selected from the group consisting of hydrogen, hydroxy, halo, lower alkoxy, acyl, hydroxyalkyl, alkoxyalkyl, hydroxycarbonyl, alkyl, alkoxycarbonyl, acyloxyalkyl, cyano and aryloxy, or R 8 and R 9 together comprise a carbocyclic or heterocyclic ring structure, or R 8 or R 9 together with R 6 or R 7 comprise a carbocyclic or heterocyclic ring structure fused to the pentacyclic D ring. 1

  提供了多种新颖的反应方案、新颖的工艺步骤和新颖的中间体，用于合成环氧甲基孟酮和其他式（I）化合物，其中：—A—A—代表基团—CHR4—CHR5—或—CR4═CR5—，R3、R4和R5独立地选自氢、卤素、羟基、低碳基、低烷氧基、羟基烷基、烷氧基烷基、羟基羰基、氰基、芳氧基的群；R1代表α定向的低碳基羧酸酯或羟基烷基基团；—B—B—代表基团—CHR6—CHR7—或α-或β定向的基团（III），其中R6和R7独立地选自氢、卤素、低烷氧基、酰基、羟基烷基、烷氧基烷基、羟基羰基、烷基、烷氧基羧酸酯、酰氧基烷基、氰基和芳氧基的群；而R8和R9独立地选自氢、羟基、卤素、低烷氧基、酰基、羟基烷基、烷氧基烷基、羟基羰基、烷基、烷氧基羧酸酯、酰氧基烷基、氰基和芳氧基的群，或者R8和R9一起组成碳环或杂环结构，或者R8或R9与R6或R7一起组成与五环D环融合的碳环或杂环结构。
• Processes for preparations of 9,11-epoxy steroids and intermediates useful therein
  申请人：Ng S. John

  公开号：US20080027237A1

  公开（公告）日：2008-01-31

  Multiple novel reaction schemes, novel process steps and novel intermediates are provided for the synthesis of 9,11-epoxy steroids.

  为合成9,11-环氧类固醇提供了多种新的反应方案、新的工艺步骤和新的中间体。
• Nouveaux dérivés stéroides 3-céto delta 4 ou delta 1-4 substitués en position 7, leur préparation, leur application comme médicaments et les compositions les renfermant
  申请人：ROUSSEL-UCLAF

  公开号：EP0055170A1

  公开（公告）日：1982-06-30

  L'invention concerne les produits (I'): R est R1 [alkyle, alkényle ou alkynyle 1-8C] ou R2,/R2 = -(CH2)n-R3 (n = 1-8, R3 = OH libre ou protégé, NH2, NH2 protégé alkyl ou dialkylamino, COOH libre, estérifié ou salifié, Halogène/X et Y = ou X = OH et Y = CH2-CH2-CO2M où M = H, métal alcalin ou NH4, Ra = H ou CH3, le pointillé symbolise une liaison éventuelle et le trait ondulé une liaison a ou β, étant entendu essentiellement que R est différent de R1 ou de R2 où n = 1 et R3 = halogène quand la liaison 1 (2) est simple et Ra = CH3. L'invention concerne également la préparation des produits (I'), leur application comme médicaments notamment anti aldostérone et les compositions les renfermant.

  本发明涉及产品（I'）： R 是 R1[烷基、烯基或炔基 1-8C]或 R2,/R2 = -(CH2)n-R3 （n = 1-8，R3 = 游离的或受保护的 OH、NH2、受保护的 NH2 烷基或二烷基氨基、游离的、酯化的或盐化的 COOH、卤素/X 和 Y =）。 或 X = OH 和 Y = CH2-CH2-CO2-CO2M，其中 M = H、碱金属或 NH4，Ra = H 或 CH3，虚线表示可能的键，波浪线表示键 a 或 β，基本上可以理解 R 不同于 R1 或 R2，其中 n = 1 和 R3 = 卤素（当键 1 (2) 为单键时）以及 Ra = CH3。 本发明还涉及产品（I'）的制备、其作为医药产品（尤其是抗睾酮药物）的用途以及含有它们的组合物。
• Process for preparation of 9, 11- epoxy steroids and intermediates useful therein
  申请人：G.D. SEARLE & CO.

  公开号：EP1148061A2

  公开（公告）日：2001-10-24

  Multiple novel reaction schemes, novel process steps and novel intermediates are provided for the synthesis of epoxymexrenone and other compounds of Formula I wherein: -A-A- represents the group -CHR4-CHR5- or -CR4=CR5- R3 R4 and R5 are independently selected from the group consisting of hydrogen, halo, hydroxy, lower alkyl, lower alkoxy, hydroxyalkyl, alkoxyalkyl, hydroxycarbonyl, cyano, aryloxy; R1 represents an alpha-oriented lower alkoxycarbonyl or hydroxyalkyl radical; -B-B- represents the group -CHR6-CHR7- or an alpha- or beta- oriented group: where R6 and R7 are independently selected from the group consisting of hydrogen, halo, lower alkoxy, acyl, hydroxyalkyl, alkoxyalkyl, hydroxycarbonyl, alkyl, alkoxycarbonyl, acyloxyalkyl, cyano and aryloxy; and R8 and R9 are independently selected from the group consisting of hydrogen, hydroxy, halo, lower alkoxy, acyl, hydroxyalkyl, alkoxyalkyl, hydroxycarbonyl, alkyl, alkoxycarbonyl, acyloxyalkyl, cyano and aryloxy, or R8 and R9 together comprise a carbocyclic or heterocyclic ring structure, or R8 or R9 together with R6 or R7 comprise a carbocyclic or heterocyclic ring structure fused to the pentacyclic D ring.

  提供了多种新型反应方案、新型工艺步骤和新型中间体，用于合成环氧甲壬酮和其他式 I 的化合物 其中 -A-A- 代表基团 -CHR4-CHR5- 或 -CR4=CR5- R3 R4 和 R5 独立选自由氢、卤素、羟基、低级烷基、低级烷氧基、羟基烷基、烷氧基烷基、羟基羰基、氰基、芳氧基组成的组； R1 代表α 向低级烷氧基羰基或羟基烷基； -B-B-代表基团-CHR6-CHR7-或α-或β-基团： 其中 R6 和 R7 独立地选自氢、卤素、低级烷氧基、酰基、羟基烷基、烷氧基烷基、羟基羰基、烷基、烷氧基羰基、酰氧基烷基、氰基和芳氧基组成的组；以及 R8 和 R9 独立地选自氢、羟基、卤代、低级烷氧基、酰基、羟基烷基、烷氧基烷基、羟基羰基、烷基、烷氧基羰基、酰氧基烷基、氰基和芳氧基组成的组，或 R8 和 R9 共同组成碳环或杂环环结构，或 R8 或 R9 与 R6 或 R7 共同组成与五环 D 环融合的碳环或杂环环结构。
• Processes for preparation of 3-keto-7alpha-alkoxycarbonyl-delta-4,5- steroids and intermediates useful therein
  申请人：G.D. SEARLE & CO.

  公开号：EP1223174A2

  公开（公告）日：2002-07-17

  Multiple novel reaction schemes, novel process steps and novel intermediates are provided for the synthesis of epoxymexrenone and other compounds of Formula I wherein: -A-A- represents the group -CHR4-CHR5- or -CR4=CR5- R3, R4 and R5 are independently selected from the group consisting of hydrogen, halo, hydroxy, lower alkyl, lower alkoxy, hydroxyalkyl, alkoxyalkyl, hydroxycarbonyl, cyano, varyloxy; R1 represents an alpha-oriented lower alkoxycarbonyl or hydroxyalkyl radical; -B-B- represents the group -CHR6-CHR7- or an alpha- or beta- oriented group: where R6 and R7 are independently selected from the group consisting of hydrogen, halo, lower alkoxy, acyl, hydroxyalkyl, alkoxyalkyl, hydroxycarbonyl, alkyl, alkoxycarbonyl, acyloxyalkyl, cyano and aryloxy; and R8 and R9 are independently selected from the group consisting of hydrogen, hydroxy, halo, lower alkoxy, acyl, hydroxyalkyl, alkoxyalkyl, hydroxycarbonyl, alkyl, alkoxycarbonyl, acyloxyalkyl, cyano and aryloxy, or R8 and R9 together comprise a carbocyclic or heterocyclic ring structure, or R8 or R9 together with R6 or R7 comprise a carbocyclic or heterocyclic ring structure fused to the pentacyclic D ring.

  提供了多种新型反应方案、新型工艺步骤和新型中间体，用于合成环氧甲壬酮和其他式 I 的化合物 其中 -A-A-代表基团-CHR4-CHR5-或-CR4=CR5- R3、R4 和 R5 独立地选自氢、卤素、羟基、低级烷基、低级烷氧基、羟基烷基、烷氧基烷基、羟基羰基、氰基、变化氧基组成的组； R1 代表α 向低级烷氧基羰基或羟基烷基； -B-B-代表基团-CHR6-CHR7-或α-或β-基团： 其中 R6 和 R7 独立地选自氢、卤素、低级烷氧基、酰基、羟基烷基、烷氧基烷基、羟基羰基、烷基、烷氧基羰基、酰氧基烷基、氰基和芳氧基组成的组；以及 R8 和 R9 独立地选自氢、羟基、卤代、低级烷氧基、酰基、羟基烷基、烷氧基烷基、羟基羰基、烷基、烷氧基羰基、酰氧基烷基、氰基和芳氧基组成的组，或 R8 和 R9 共同组成碳环或杂环环结构，或 R8 或 R9 与 R6 或 R7 共同组成与五环 D 环融合的碳环或杂环环结构。