(11beta)-11,18-环氧-21-羟基孕甾-4-烯-3,20-二酮 | 2507-88-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧杂环己烷
• 中文名称: (11beta)-11,18-环氧-21-羟基孕甾-4-烯-3,20-二酮
• 英文名称: 18-Deoxyaldosterone
• 英文别名: (11beta)-11,18-Epoxy-21-hydroxypregn-4-ene-3,20-dione；(1R,2S,5S,6S,14R,15S,16S)-2-(2-hydroxyacetyl)-14-methyl-17-oxapentacyclo[14.2.1.01,5.06,15.09,14]nonadec-9-en-11-one
• CAS: 2507-88-2
• 化学式: C₂₁H₂₈O₄
• 分子量: 344.451
• InChiKey: ZEBLTAXSHAKMDJ-SNCGNRLASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  25
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.81
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (11beta)-11,18-环氧-21-羟基孕甾-4-烯-3,20-二酮 在 Krebs-Ringer-bicarbonate-glucose buffer 、 male CHBB-Thom rat adrenal mitochondria 、 还原型辅酶II(NADPH)四钠盐 作用下， 生成 11beta,18-环氧-18,21-二羟基孕甾-4-烯-3,20-二酮
  参考文献：
  名称：

  Inhibition of aldosterone formation by cortisol in rat adrenal mitochondria

  摘要：

  In this work we confirm by a metabolic method the existence of at least two enzymes with 11 beta- and 18-hydroxylase activities in rat adrenal mitochondria. The method was based on the ability of cortisol (F), a foreign alternative substrate, to inhibit competitively metabolite productions from various precursors. F inhibited a) aldosterone (ALDO) production from 11-deoxycorticosterone (DOG) without affecting the yields of corticosterone (B) and 18-hydroxy-11-deoxycorticosterone (18-OHDOC); b) 18-hydroxycorticosterone and aldosterone productions from B (K-i = 2.5 +/- 0.5 mu M); and c) ALDO production from 18-OHDOC. These results suggest the existence of two categories of enzymes with both 11 beta- and 18-hydroxylase activities, one comprising those that catalyze the conversions of DOC to B and 18-OHDOC (F-insensitive reactions [FIS]) and the other one comprising the enzymes involved in the conversions of B to 18-OHB and ALDO and that of 18-OHDOC to ALDO (F-sensitive reactions [FS]). The cloned enzymes CYP11B1 and CYP11B2 would pertain respectively to the FIS and FS categories.

  DOI：

  10.1016/0039-128x(94)00064-j
• 作为产物：
  描述：

  11β,21-dihydroxy-5-pregnene-3,20-dione-18-oic acid 3,20-di-(ethylene glycol)ketal(18(*)11) lactone 在 sodium hydroxide 、 对甲苯磺酸 作用下， 以 二氯甲烷 、 溶剂黄146 为溶剂， 反应 3.0h， 生成 (11beta)-11,18-环氧-21-羟基孕甾-4-烯-3,20-二酮
  参考文献：
  名称：

  18-脱氧醛固酮，其化学和微生物还原产品

  摘要：

  用双-（甲氧基乙氧基）氢化铝铝还原二缩酮1，得到结晶的18-羟基皮质酮二缩酮（2），这是形成18-脱氧醛固酮乙酸酯的中间体（4b）。的迄今未报告但预期代谢物4制备如下：的氢化4b中提供的fα-和5β异构体6和图5b，并从那里的四-和六氢衍生物10，11，8,9和7，以及3-脱氧化合物12和13。的厌氧发酵4B与梭菌paraputrificum得到高产率的四氢衍生物8b。

  DOI：

  10.1016/0040-4020(82)80058-6

文献信息

• US4081538A
  申请人：——

  公开号：US4081538A

  公开（公告）日：1978-03-28
• Inhibition of aldosterone formation by cortisol in rat adrenal mitochondria
  作者：Laura Matković、Celso E. Gomez-Sanchez、Carlos P. Lantos、Eduardo N. Cozza

  DOI：10.1016/0039-128x(94)00064-j

  日期：1995.6

  In this work we confirm by a metabolic method the existence of at least two enzymes with 11 beta- and 18-hydroxylase activities in rat adrenal mitochondria. The method was based on the ability of cortisol (F), a foreign alternative substrate, to inhibit competitively metabolite productions from various precursors. F inhibited a) aldosterone (ALDO) production from 11-deoxycorticosterone (DOG) without affecting the yields of corticosterone (B) and 18-hydroxy-11-deoxycorticosterone (18-OHDOC); b) 18-hydroxycorticosterone and aldosterone productions from B (K-i = 2.5 +/- 0.5 mu M); and c) ALDO production from 18-OHDOC. These results suggest the existence of two categories of enzymes with both 11 beta- and 18-hydroxylase activities, one comprising those that catalyze the conversions of DOC to B and 18-OHDOC (F-insensitive reactions [FIS]) and the other one comprising the enzymes involved in the conversions of B to 18-OHB and ALDO and that of 18-OHDOC to ALDO (F-sensitive reactions [FS]). The cloned enzymes CYP11B1 and CYP11B2 would pertain respectively to the FIS and FS categories.
• 18-Deoxyaldosterone, its chemical and microbial reduction products
  作者：M. Harnik、Y. Aharonowitz、R. Lamed

  DOI：10.1016/0040-4020(82)80058-6

  日期：1982.1

  Reduction of the diketal 1 with sodium aluminum bis-(methoxyethoxy) hydride afforded the crystalline 18-hydroxycorticosterone diketal (2), an intermediate in the formation of 18-deoxyaldosterone acetate (4b). The hitherto unreported but anticipated metabolites of 4 were prepared as follows: hydrogenations of 4b furnished the fα- and 5β isomers 6 and 5b, and thence the tetra- and hexahydro derivatives

  用双-（甲氧基乙氧基）氢化铝铝还原二缩酮1，得到结晶的18-羟基皮质酮二缩酮（2），这是形成18-脱氧醛固酮乙酸酯的中间体（4b）。的迄今未报告但预期代谢物4制备如下：的氢化4b中提供的fα-和5β异构体6和图5b，并从那里的四-和六氢衍生物10，11，8,9和7，以及3-脱氧化合物12和13。的厌氧发酵4B与梭菌paraputrificum得到高产率的四氢衍生物8b。