2-羧基阿拉伯糖醇1-磷酸酯 | 965-66-2

• 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
• 中文名称: 2-羧基阿拉伯糖醇1-磷酸酯
• 英文名称: 2α,3α-epoxy-5α-androstan-17β-ol
• 英文别名: 2α,3α-epoxy-17β-hydroxy-5α-androstane；(2α,3α,5α,17β)-2,3-epoxyandrostan-17-ol；(2alpha,3alpha,5alpha,17beta)-2,3-Epoxyandrostan-17-ol；(1S,2S,4R,6S,8S,11R,12S,15S,16S)-2,16-dimethyl-5-oxapentacyclo[9.7.0.02,8.04,6.012,16]octadecan-15-ol
• CAS: 965-66-2
• 化学式: C₁₉H₃₀O₂
• 分子量: 290.446
• InChiKey: ZOAWUHAWUQAFKP-XGRAFVIBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  21
• 可旋转键数：
  0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  32.8
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-羧基阿拉伯糖醇1-磷酸酯 在 manganese(IV) oxide 、 N,N-二甲基乙酰胺 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 1-睾酮
  参考文献：
  名称：

  Klein,U.; Sucrow,W., Chemische Berichte, 1977, vol. 110, p. 994 - 999

  摘要：

  DOI：
• 作为产物：
  描述：

  2α,3α-epoxy-5α-androstan-17-one 在 sodium borohydrid 作用下， 以 甲醇 为溶剂， 生成 2-羧基阿拉伯糖醇1-磷酸酯
  参考文献：
  名称：

  Male contraceptive steroids and methods of use

  摘要：

  本发明的类固醇在口服时被发现可作为男性避孕药物。停止使用本发明的男性避孕类固醇后，男性很快恢复正常生育能力。

  公开号：

  US04297350A1

文献信息

• [EN] 2-(N-SUBSTITUTED PIPERAZINYL) STEROID DERIVATIVES<br/>[FR] DÉRIVÉS DE STÉROÏDES DE TYPE 2-(PIPÉRAZINYLE N-SUBSTITUÉ)
  申请人：UNIV LAVAL

  公开号：WO2010060215A1

  公开（公告）日：2010-06-03

  Novel chemical agents of Formula I are described herein. More specifically, 2-(N-substituted piperazinyl) pregnane and 2-(N-substituted piperazinyl) androstane derivatives exhibiting cytotoxicity on a variety of cancer cell lines are disclosed herein. (I)

  本文描述了化学式I的新型化学试剂。更具体地，本文披露了对多种癌细胞系表现出细胞毒性的2-(N-取代哌嗪基)孕酮和2-(N-取代哌嗪基)雄烷衍生物。 (I)
• 2-(N-Substituted Piperazinyl) Steroid Derivatives
  申请人：Poirier Donald

  公开号：US20110312926A1

  公开（公告）日：2011-12-22

  Novel chemical agents are described herein. More specifically, 2-(N-substituted piperazinyl) pregnane and 2-(N-substituted piperazinyl) androstane derivatives exhibiting cytotoxicity on a variety of cancer cell lines are disclosed herein.

  本文描述了新型化学药剂。更具体地，本文揭示了对多种癌细胞系表现出细胞毒性的2-(N-取代哌嗪基)孕酮和2-(N-取代哌嗪基)雄烷衍生物。
• Chemical synthesis of 2β-amino-5α-androstane-3α,17β-diol N-derivatives and their antiproliferative effect on HL-60 human leukemia cells
  作者：Dominic Thibeault、Jenny Roy、Patrick DeRoy、Donald Poirier

  DOI：10.1016/j.bmc.2008.03.031

  日期：2008.5

  Even though few steroids are used for the treatment of leukemia, 2 beta-(4-methylpiperazinyl)-5 alpha-androstane-3 alpha,17 beta-diol (1) was recently reported for its ability to inhibit the proliferation of human leukemia HL-60 cells. With an efficient procedure that we had developed for the aminolysis of hindered steroidal epoxides, we synthesized a series of 2 beta-amino-5 alpha-androstane-3 alpha,17 beta-diol N-derivatives structurally similar to 1. Hence, the opening of 2,3 alpha-epoxy-5 alpha-androstan-17 beta-diol with primary and secondary amines allowed the synthesis of aminosteroids with diverse length, rami. cation, and functionalization of the 2 beta-side chain. Sixty-four steroid derivatives were tested for their capacity to inhibit the proliferation of HL-60 cells; thus obtaining first structure - activity relationship results. Ten aminosteroids with long alkyl chains (7 - 16 carbons) or bulky groups (diphenyl or adamantyl) have shown antiproliferative activity over 78% at 10 mu M and superior to that of the lead compound. The 3,3-diphenylpropylamino, 4-nonylpiperazinyl and octylamino derivatives of 5 alpha-androstane-3 alpha,17 beta-diol inhibited the HL-60 cell growth with IC(50) of 3.1, 4.2 and 6.4 mu M, respectively. They were also found to induce the HL-60 cell differentiation. (c) 2008 Elsevier Ltd. All rights reserved.
• Fajkos; Sorm, Collection of Czechoslovak Chemical Communications, 1959, vol. 24, p. 3115,3128
  作者：Fajkos、Sorm

  DOI：——

  日期：——
• Fajkos, Collection of Czechoslovak Chemical Communications, 1959, vol. 24, p. 2284,2286
  作者：Fajkos

  DOI：——

  日期：——