16α-bromo-3β-hydroxyandrost-5-en-17-one | 1093-91-0

• 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: 16α-bromo-3β-hydroxyandrost-5-en-17-one
• 英文别名: 16α-Brom-3β-hydroxy-androst-5-en-17-on；3β-Hydroxy-16α-brom-androst-5-en-17-on；(3S,10R,13S,16R)-16-bromo-3-hydroxy-10,13-dimethyl-1,2,3,4,7,8,9,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-17-one
• CAS: 1093-91-0；55821-49-3；74644-60-3；151434-12-7
• 化学式: C₁₉H₂₇BrO₂
• 分子量: 367.326
• InChiKey: WQCCGDRKRHLVJM-UAFBDMIJSA-N

物化性质

• 熔点：
  179-180 °C(Solv: water (7732-18-5); methanol (67-56-1))
• 沸点：
  462.1±45.0 °C(Predicted)
• 密度：
  1.35±0.1 g/cm3(Predicted)
• 溶解度：
  氯仿（微溶）、乙酸乙酯（微溶）

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  22
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.84
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  16α-bromo-3β-hydroxyandrost-5-en-17-one 在 lithium bromide monohydrate 、 lithium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 8.0h， 以31%的产率得到3β-hydroxyandrosta-5,8(14),15-trien-17-one
  参考文献：
  名称：

  Synthesis and biological evaluation of 3β-androsta-5,8(14),15-trien-17-one derivatives as potential anticancer agents

  摘要：

  A novel and operationally simple method for highly efficient synthesis of promising anti-cancer 3 beta-hydroxy-16-arylandrosta-5,8(14),15-trien-17-ones was reported. Compounds were tested for their cytotoxic activities against A549, SKOV3, MKN-45 and MDA-MB-435 cancer cell lines. The preliminary results showed that compounds 5e, g were the most active especially against cancer cell lines tested. (C) 2016 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.steroids.2016.05.004
• 作为产物：
  描述：

  dehydroepiandrosterone 在 copper(ll) bromide 作用下， 以 甲醇 为溶剂， 反应 8.0h， 以82%的产率得到16α-bromo-3β-hydroxyandrost-5-en-17-one
  参考文献：
  名称：

  Synthesis and biological evaluation of 3β-androsta-5,8(14),15-trien-17-one derivatives as potential anticancer agents

  摘要：

  A novel and operationally simple method for highly efficient synthesis of promising anti-cancer 3 beta-hydroxy-16-arylandrosta-5,8(14),15-trien-17-ones was reported. Compounds were tested for their cytotoxic activities against A549, SKOV3, MKN-45 and MDA-MB-435 cancer cell lines. The preliminary results showed that compounds 5e, g were the most active especially against cancer cell lines tested. (C) 2016 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.steroids.2016.05.004

文献信息

• Drug Screen and Treatment Method
  申请人：Flores-Riveros Jaime

  公开号：US20080221074A1

  公开（公告）日：2008-09-11

  The invention relates to methods identify or characterize compounds that can be used to treat specified clinical disorders such as hyperglycemia and type 2 diabetes. Compounds that can be used in these methods include 4α-fluoro-17α-ethynylandrost-5-ene-3β,7β,17β-triol, 4α-fluoro-17α-ethynylandrost-5-ene-3β,7α,17β-triol, 4α-fluoro-17α-ethynylandrost-5-ene-3α,7β,17β-triol and 4α-fluoro-17α-ethynylandrost-5-ene-3β,17β-triol-7-one.

  本发明涉及用于治疗特定临床疾病，如高血糖和2型糖尿病的化合物的鉴定或表征方法。可以在这些方法中使用的化合物包括4α-氟-17α-乙炔基雄烯-5-烯-3β，7β，17β-三醇，4α-氟-17α-乙炔基雄烯-5-烯-3β，7α，17β-三醇，4α-氟-17α-乙炔基雄烯-5-烯-3α，7β，17β-三醇和4α-氟-17α-乙炔基雄烯-5-烯-3β，17β-三醇-7-酮。
• Drug Screening and Treatment Methods
  申请人：Flores-Riveros Jaime

  公开号：US20080146532A1

  公开（公告）日：2008-06-19

  The invention relates to methods identify or characterize compounds that can be used to treat specified clinical disorders such as hyperglycemia and type 2 diabetes. Compounds that can be used in these methods include 4α-fluoro-17α-ethynylandrost-5-ene-3β, 7β,17β-triol, 4α-fluoro-17α-ethynylandrost-5-ene-3β,7α,17β-triol, 4α-fluoro-17α-ethynylandrost-5-ene-3α,7β,17β-triol and 4α-fluoro-17α-ethynylandrost-5-ene-3β,17β-triol-7-one.

  本发明涉及一种用于识别或表征可用于治疗特定临床疾病如高血糖和2型糖尿病的化合物的方法。可用于这些方法的化合物包括4α-氟-17α-乙炔基雄烯-5-烯-3β,7β,17β-三醇，4α-氟-17α-乙炔基雄烯-5-烯-3β,7α,17β-三醇，4α-氟-17α-乙炔基雄烯-5-烯-3α,7β,17β-三醇和4α-氟-17α-乙炔基雄烯-5-烯-3β,17β-三醇-7-酮。
• Drug Identification and Treatment Method
  申请人：Frincke James M.

  公开号：US20080153797A1

  公开（公告）日：2008-06-26

  The invention relates to methods to identify compounds that can treat autoimmune conditions and treat specified clinical disorders such as multiple sclerosis, ulcerative colitis or arthritis. Compounds include 17α-ethynylandrost-5-ene-3β,11β,7α,17β-tetrol, 4α-acetoxy-17α-ethynylandrost-5-ene-3β,7β,17β-triol, 17α-ethynylandrost-5-ene-3β,4β,7α,17β-tetrol, 17α-ethynylandrost-5-ene-3α,4β,7α,17β-tetrol and 17α-ethynylandrost-5-ene-3α,4β,17β-triol-7-one.

  本发明涉及识别可治疗自身免疫疾病和治疗特定临床疾病如多发性硬化症、溃疡性结肠炎或关节炎的化合物的方法。这些化合物包括17α-乙炔基雄烯-5-烯-3β，11β，7α，17β-四醇，4α-乙酰氧基-17α-乙炔基雄烯-5-烯-3β，7β，17β-三醇，17α-乙炔基雄烯-5-烯-3β，4β，7α，17β-四醇，17α-乙炔基雄烯-5-烯-3α，4β，7α，17β-四醇和17α-乙炔基雄烯-5-烯-3α，4β，17β-三醇-7-酮。
• Drug Identification Method
  申请人：Harbor Therapeutics, Inc.

  公开号：US20130164780A1

  公开（公告）日：2013-06-27

  The invention relates to a method to identify compounds exert a transient effect(s) on one or more biological mediators of acute biological responses to acute stimuli or biological insult in subjects exposed to an acute stimulus or biological insult such as systemic exposure to bacterial LPS. The compounds are identified by measuring the effect of the test compound on the mediator of the acute stimulus or biological insult at times when an acute effect(s) to the stimulus or insult is occurring.

  该发明涉及一种方法，用于识别对急性刺激或生物损伤的急性生物反应的一个或多个生物介质产生短暂影响的化合物，这些化合物可以在接受细菌LPS的全身暴露等急性刺激或生物损伤的受试者中被识别。通过测量测试化合物对急性刺激或生物损伤介质的影响，可以在发生刺激或损伤的急性影响时识别化合物。
• STEROID TETROL SOLID STATE FORMS
  申请人：Lewbart Marvin L.

  公开号：US20090143349A1

  公开（公告）日：2009-06-04

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

  本发明涉及雄甾烯-3β、7β、16α、17β-三醇的固态形式、含有或由这种固态形式制备的配方以及使用这种材料调节急性和慢性非生产性炎症。这些配方可用于预防、治疗或延缓与自身免疫有关的疾病，如关节炎、多发性硬化症、溃疡性结肠炎或1型糖尿病。这些配方还可用于预防、治疗或延缓与代谢紊乱有关的疾病，如2型糖尿病。