3β-acetoxyl-5β-hydroxyl-6β-formyl-B-norandrostane | 14335-56-9

• 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: 3β-acetoxyl-5β-hydroxyl-6β-formyl-B-norandrostane
• 英文别名: 3β-Acetoxy-5-hydroxy-6β-formyl-B-nor-5β-androstanon-(17)
• CAS: 14335-56-9
• 化学式: C₂₁H₃₀O₅
• 分子量: 362.466
• InChiKey: ZXHVFFVPBQRWKC-QOWSYNQHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.68
• 重原子数：
  26.0
• 可旋转键数：
  2.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  80.67
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  3β-acetoxyl-5β-hydroxyl-6β-formyl-B-norandrostane 在 chromium(VI) oxide 、 乙酸酐 、 溶剂黄146 作用下， 生成 3β-acetoxy-B-norandrost-5-en-17-one
  参考文献：
  名称：

  Tanabe,K. et al., Chemical and pharmaceutical bulletin, 1961, vol. 9, p. 12 - 19

  摘要：

  DOI：
• 作为产物：
  描述：

  3β-acetoxyl-5,6-dioxo-5,6-secoandrostane 在 aluminum oxide 作用下， 以 苯 为溶剂， 反应 3.5h， 以84%的产率得到3β-acetoxyl-5β-hydroxyl-6β-formyl-B-norandrostane
  参考文献：
  名称：

  Synthesis and in vitro antiproliferative evaluation of some ring B abeo-sterols

  摘要：

  Using cholesterol, p-sitosterol, dehydroisoandrosterone and pregnenolone as starting materials, a series of 5(6 -> 7)abeo-sterols with different substituted groups and various side chains were synthesized and the antiproliferative activity of these compounds against HeLa, SMMC 7404 and MGC 7901 cells was investigated. The results revealed that the presence of a cholesterol-type side chain was very important for their cytotoxicity, and in particular a thiosemicarbazone at the C-6 position significantly enhanced the antiproliferative activity of these compounds. Although the elimination of 5-hydroxyl has no an obvious effect on their cytotoxic function, removal of the hydroxyl at the C-3 position decreased markedly the antiproliferative activity of the compounds. Some compounds have similar cytotoxic capability as cis-platin does. (C) 2012 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.steroids.2012.05.005

文献信息

• Synthesis of Novel Ring B Abeo-sterol Derivatives and their Antiproliferative Activities
  作者：Chunfang Gan、Lianghua Fan、Yanmin Huang、Zhiping Liu、Jianguo Cui

  DOI：10.2174/1573406411309060008

  日期：2013.7.1

  Using cholesterol, β-sitosterol, dehydroisoandrosterone and pregnenolone as starting materials, a series of 6- hydroximino analogs of ring B abeo-sterols were synthesized and characterized. The antiproliferative activity of analogs was evaluated against SGC 7901 (human gastric carcinoma), HeLa (human cervical carcinoma) and Bel 7404 (human liver carcinoma) cells. The results showed that the presence of a alkyl side chain was very important for their cytotoxicity. However, the presence of 6-hydroximino cannot increase the cytotoxicity of compounds compared with 6-hydroxy group. The information obtained from the studies may be useful for the design of novel chemotherapeutic drugs.

  以胆固醇、β-谷甾醇、脱氢表雄酮和孕烯醇酮为起始原料，合成并表征了一系列环B断裂甾体的6-羟亚氨类似物。评估了这些类似物对SGC 7901（人胃癌）、HeLa（人宫颈癌）和Bel 7404（人肝癌）细胞的抗增殖活性。结果显示，烷基侧链的存在对其细胞毒性至关重要。然而，与6-羟基相比，6-羟亚氨并不能提高化合物的细胞毒性。这些研究获得的信息可能对设计新型化疗药物有所帮助。
• Hydrocyanation. Part IX. Synthesis of β-cyano-aldehydes by conjugate hydrocyanation of allylideneamines followed by hydrolysis
  作者：W. Nagata、M. Yoshioka、T. Okumura、M. Murakami

  DOI：10.1039/j39700002355

  日期：——

  Conjugate hydrocyanation of αβ-unsaturated aldehydes with diethylaluminium cyanide or with hydrogen cyanide and an alkylaluminium was only successful with a substrate having a sterically hindered formyl group. Attempts to desulphurise β-cyano-thiocarboxylates to β-cyano-aldehydes failed. However, allylideneamines (I) carrying a bulky N-alkyl substituent reacted with hydrogen cyanide–alkylaluminium

  αβ-不饱和醛与二乙基铝氰化物或与氰化氢和烷基铝的共轭氢氰化仅在具有空间位阻甲酰基的底物上才能成功。将β-氰基硫代羧酸盐脱硫为β-氰基醛的尝试失败。但是，带有大量N-烷基取代基的烯化亚胺（I）与氰化氢-烷基铝反应生成1，3-二氰基丙胺（II），然后将其水解为β-氰基醛（III），产率很高。作为副产物形成了2-亚氨基吡咯烷（IV）。
• Tanabe,K. et al., Chemical and pharmaceutical bulletin, 1961, vol. 9, p. 1 - 6
  作者：Tanabe,K. et al.

  DOI：——

  日期：——