7,17-dioxoandrost-5-ene-3β,16α-diyl diacetate | 112375-87-8

• 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: 7,17-dioxoandrost-5-ene-3β,16α-diyl diacetate
• 英文别名: 3β,16α-diacetoxy-androst-5-ene-7,17-dione；3β,16α-Diacetoxy-androst-5-en-7,17-dion；5-androstene-3β,16α-diol-7,17-dione；[(3S,8R,9S,10R,13S,14S,16R)-16-acetyloxy-10,13-dimethyl-7,17-dioxo-2,3,4,8,9,11,12,14,15,16-decahydro-1H-cyclopenta[a]phenanthren-3-yl] acetate
• CAS: 112375-87-8
• 化学式: C₂₃H₃₀O₆
• 分子量: 402.488
• InChiKey: RYSQOTKTQGWIAR-DQHFKTQHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  29
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.74
• 拓扑面积：
  86.7
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  7,17-dioxoandrost-5-ene-3β,16α-diyl diacetate 在 sodium tetrahydroborate 、 sodium hydroxide 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 生成 HE-3354
  参考文献：
  名称：

  Novel components of the human metabolome: The identification, characterization and anti-inflammatory activity of two 5-androstene tetrols

  摘要：

  Two natural 5-androstene steroid tetrols, androst-5-ene-3 beta,7 beta,16 alpha,17 beta-tetrol (HE3177) and androst-5-ene-3 alpha,7 beta,16 alpha,17 beta-tetrol (HE3413), were discovered in human plasma and urine. These compounds had significant aqueous solubility, did not bind or transactivate steroid-binding nuclear hormone receptors. and were not immunosuppressive in murine mixed-lymphocyte studies. Both compounds appear to be metabolic end products, as they were resistant to primary and secondary metabolism. Both were orally bioavailable, and were very well tolerated in a two-week dose-intensive toxicity study in mice. Anti-inflammatory properties were found with exogenous administration of these compounds in rodent disease models of multiple sclerosis, lung injury, chronic prostatitis, and colitis. (C) 2010 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.steroids.2010.10.005
• 作为产物：
  描述：

  3β,16α-dihydroxy-17,17-dimethoxyandrost-5-ene 在 3,5-二甲基吡唑 、 chromium(VI) oxide 、 对甲苯磺酸一水合物 作用下， 以 吡啶 、 二氯甲烷 、 水 、 丙酮 为溶剂， 反应 124.0h， 生成 7,17-dioxoandrost-5-ene-3β,16α-diyl diacetate
  参考文献：
  名称：

  Derivatives of 16α-hydroxy-dehydroepiandrosterone with an additional 7-oxo or 7-hydroxy substituent: Synthesis and gas chromatography/mass spectrometry analysis

  摘要：

  Derivatives of 16 alpha-hydroxy-dehydroepiandrosterone, which have an additional oxygen substituent at position 7 (oxo or hydroxy group), were synthesized. Firstly, 17,17-dimethoxyandrost-5-ene-3 beta, 16 alpha-diyl diacetate was prepared and then oxidized with a complex of chromium(VI) oxide and 2,5-dimethylpyrazole to the respective 7-oxo derivative. This key intermediate was both deprotected or reduced by L-Selectride (R) or sodium borohydride in the presence of cerium(III) chloride and then deprotected to give 7-oxo, 7 alpha-hydroxy and 7 beta-hydroxy derivatives of 16 alpha-hydroxy-dehydroepiandrosterone. The target compounds were characterized by H-1 and C-13 NMR spectra and in the form of O-methyloxime-trimethylsilyl derivatives, by gas chromatography/mass spectrometry methods. (c) 2005 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.steroids.2005.04.002

文献信息

• WO2008/39566
  申请人：——

  公开号：——

  公开（公告）日：——
• Okada et al., Journal of Biological Chemistry, 1959, vol. 234, p. 1688,1690
  作者：Okada et al.

  DOI：——

  日期：——
• STEROID TETROL SOLID STATE FORMS
  申请人：White Steven K.

  公开号：US20120220560A1

  公开（公告）日：2012-08-30

  The invention relates to solid state forms of androst-5-ene-3β,7β,16α,17β-tetrol, formulations containing or prepared from such solid state forms and use of these materials for modulating unwanted inflammation including acute and chronic non-productive inflammation. The formulations can be used to prevent, treat or slow the progression of conditions related to autoimmunity and metabolic disorders such as arthritis, multiple sclerosis, ulcerative colitis, Type 1 diabetes and Type 2 diabetes.
• [EN] STEROID TETROL SOLID STATE FORMS<br/>[FR] FORMES À L'ÉTAT SOLIDE DE TÉTROL STÉROÏDE
  申请人：HARBOR BIOSCIENCES INC

  公开号：WO2012083161A1

  公开（公告）日：2012-06-21

  The invention relates to solid state forms of androst-5-ene-3β,7β,16α,17β- tetrol, formulations containing or prepared from such solid state forms and use of these materials for modulating unwanted inflammation including acute and chronic non-productive inflammation. The formulations can be used to prevent, treat or slow the progression of conditions related to autoimmunity and metabolic disorders such as arthritis, multiple sclerosis, ulcerative colitis, Type 1 diabetes and Type 2 diabetes.