3β-acetoxyl-5β-hydroxyl-6β-formyl-B-norpregnane | 102854-04-6

• 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-norpregnane
• 英文别名: 3β-Acetoxy-5-hydroxy-6β-formyl-B-nor-pregnanon-(20)
• CAS: 102854-04-6
• 化学式: C₂₃H₃₄O₅
• 分子量: 390.52
• InChiKey: WOSZWIOXIXAYSG-JZKCKYLMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.32
• 重原子数：
  28.0
• 可旋转键数：
  3.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.87
• 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-norpregnane 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 生成 3β,5,20-Trihydroxy-B-bor-5β-pregnan-6β-methanol-3-acetat
  参考文献：
  名称：

  类固醇系列。七。合成6-甲基-B甾族化合物。

  摘要：

  将胆甾烷、孕烷和雄甾烷系列的 3β，5-二羟基-6β-甲酰基-B-去甲-5β-类固醇（IIIa，b，c）用硼氢化钠还原（III），然后对 6-羟甲基进行甲苯磺酰化，再用氢化铝锂处理，转化成相应的 3β，5-二羟基-6β-甲基-B-去甲-5β-类固醇（VIa，d，e）。化合物（VI）被氧化成 3-氧代-5-羟基-6β-甲基-B-去甲-5β-类固醇衍生物（VIIa、b、f），然后脱水成 6ξ-甲基-B-去甲胆甾烷-4-烯-3-酮（VIIIa）、6ξ-甲基-B-去甲孕甾-4-烯-3，20-二酮（VIIIb）和 6ξ-甲基-B-去甲雄甾-4-烯-3，17-二酮（VIIIf）。

  DOI：

  10.1248/cpb.10.439
• 作为产物：
  描述：

  孕烯醇酮醋酸酯 在 aluminum oxide 、 氧气 、 臭氧 作用下， 以 甲醇 、 二氯甲烷 、 苯 为溶剂， 反应 5.5h， 生成 3β-acetoxyl-5β-hydroxyl-6β-formyl-B-norpregnane
  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。
• Tanabe,K. et al., Chemical and pharmaceutical bulletin, 1961, vol. 9, p. 1 - 6
  作者：Tanabe,K. et al.

  DOI：——

  日期：——
• Tanabe,K. et al., Chemical and pharmaceutical bulletin, 1961, vol. 9, p. 12 - 19
  作者：Tanabe,K. et al.

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