3β-acetoxyl-5β-hydroxyl-6β-formyl-B-norcholestane | 71592-17-1

• 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-norcholestane
• 英文别名: 6β-Formyl-B-nor-5β-cholestan-(3β,5)-diol-3-acetat；3β-Acetoxy-6β-formyl-B-norcholestan-5β-ol；[(3R,3aR,5aS,5bR,8S,9aR,10R,10aS,10bS)-10-formyl-9a-hydroxy-3a,5b-dimethyl-3-[(2R)-6-methylheptan-2-yl]-2,3,4,5,5a,6,7,8,9,10,10a,10b-dodecahydro-1H-cyclopenta[a]fluoren-8-yl] acetate
• CAS: 71592-17-1
• 化学式: C₂₉H₄₈O₄
• 分子量: 460.698
• InChiKey: GHJRCYRZIVRMJW-VSZHHLKNSA-N

物化性质

• 熔点：
  91-92 °C
• 沸点：
  527.8±40.0 °C(Predicted)
• 密度：
  1.06±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.8
• 重原子数：
  33
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3β-acetoxyl-5β-hydroxyl-6β-formyl-B-norcholestane 在 chromium(VI) oxide 、 lithium aluminium tetrahydride 、 溶剂黄146 作用下， 以 乙醚 为溶剂， 生成 3β-hydroxy-5β-hydroxy-6β-hydroxymethyl-B-norcholestane
  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：

  胆固醇 在 aluminum oxide 、 臭氧 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 、 苯 为溶剂， 反应 2.0h， 生成 3β-acetoxyl-5β-hydroxyl-6β-formyl-B-norcholestane
  参考文献：
  名称：

  B-降胆甾醇氧化衍生物及其合成方法和应用

  摘要：

  本发明提供了一种B‑降胆甾醇氧化衍生物，该化合物的结构式为：其中，R为CH3、CH3CH2CH2、CH3CH2CH2CH2、中的一种。本发明的B‑降胆甾醇氧化衍生物化合物，对人乳腺癌细胞、人乳腺导管癌细胞、人卵巢癌细胞具有显著的抑制肿瘤细胞生长增殖效果，可作为药物中间体或药物应用于不同的药物制造和用途。

  公开号：

  CN109824748A

文献信息

• Synthesis and in vitro antiproliferative evaluation of some novel B-norcholesterols
  作者：Chunfang Gan、Qifu Lin、Jianguo Cui、Jidan Feng、Jinni Guo、Huoying Liao、Yanmin Huang

  DOI：10.1016/j.steroids.2013.10.009

  日期：2014.1

  Some novel B-norcholesterols with different substituted groups were synthesized. The antiproliferative activity of the compounds against cervical carcinoma (HeLa), liver cancer (Bel 7404) and gastric cancer (SGC 7901) cells was assayed. The results revealed that the presence of a 6-alkylthiosemicarbazone or 6-cyano group could enhance the antiproliferative activity of these compounds. The induction

  合成了一些具有不同取代基的新型B-降胆固醇。测定了该化合物对子宫颈癌（HeLa），肝癌（Bel 7404）和胃癌（SGC 7901）细胞的抗增殖活性。结果表明，6-烷基硫代半脲或6-氰基的存在可以增强这些化合物的抗增殖活性。用流式细胞仪检测了化合物6和9对癌细胞凋亡的诱导作用，结果表明该化合物能够有效诱导癌细胞凋亡。该研究为新的抗癌药物的探索提供了理论参考。结果表明，基于其abeo-胆甾烷的化合物6和9可能构成一类新型的抗增殖剂，值得进一步研究。
• 3-乙酰基-5-羟基-B-降胆甾醇-6-（N-甲基）缩氨硫腙、制备方法及其用途
  申请人：广西万德药业有限公司

  公开号：CN110330543A

  公开（公告）日：2019-10-15

  本发明公开了一种3‑乙酰基‑5‑羟基‑B‑降胆甾醇‑6‑(N‑甲基)缩氨硫腙、制备方法及其用途，所述3‑乙酰基‑5‑羟基‑B‑降胆甾醇‑6‑(N‑甲基)缩氨硫腙的结构式如下所示：本发明制得的3‑乙酰基‑5‑羟基‑B‑降胆甾醇‑6‑(N‑甲基)缩氨硫腙对肝癌、肺癌、胃癌、宫颈癌、前列腺癌、结肠癌等多种肿瘤细胞株具有明显的抑制作用，而且毒性低，不易产生耐药性；本发明还提供了该化合物的制备方法和用途，该制备方法简单易行，有利于市场推广应用。
• Synthesis and in Vitro Antiproliferative Evaluation of Some B-norcholesteryl Benzimidazole and Benzothiazole Derivatives
  作者：Jianguo Cui、Binbin Qi、Chunfang Gan、Zhipin Liu、Hu Huang、Qifu Lin、Dandan Zhao、Yanmin Huang

  DOI：10.3390/md13042488

  日期：——

  Taking orostanal (a compound from a Japanese marine sponge, Stelletta hiwasaensis) as a lead compound, some novel B-norcholesteryl benzimidazole and benzothiazole derivatives were synthesized. The antiproliferative activity of the compounds against human cervical carcinoma (HeLa), human lung carcinoma (A549), human liver carcinoma cells (HEPG2) and normal kidney epithelial cells (HEK293T) was assayed. The results revealed that the benzimidazole group was a better substituent than benzothiazole group for increasing the antiproliferative activity of compounds. 2-(3β′-Acetoxy-5β′-hydroxy-6′-B-norcholesteryl)benzimidazole (9b) with the structure of 6-benzimidazole displays the best antiproliferative activity to the cancer cells in all compounds, but is almost inactive to normal kidney epithelial cells (HEK293T). The assay of compound 9b to cancer cell apoptosis by flow cytometry showed that the compound was able to effectively induce cancer cell apoptosis. The research provided a theoretical reference for the exploration of new anti-cancer agents and may be useful for the design of novel chemotherapeutic drugs.

  以日本海洋海绵Stelletta hiwasaensis中的化合物orostanal为先导化合物，合成了一系列新型B-nor胆固醇基苯并咪唑和苯并噻唑衍生物。对这些化合物对人宫颈癌（HeLa）、人肺癌（A549）、人肝癌（HEPG2）细胞和人正常肾上皮细胞（HEK293T）的抗增殖活性进行了检测。结果表明，苯并咪唑类衍生物比苯并噻唑类衍生物具有更好的取代基效应，能更有效地提高化合物的抗增殖活性。其中，具有6-苯并咪唑结构的2-(3β′-乙酸氧基-5β′-羟基-6′-B-nor胆固醇基)苯并咪唑（9b）在所有化合物中对癌细胞显示出最佳的抗增殖活性，但对正常肾上皮细胞（HEK293T）几乎无效。通过流式细胞术检测化合物9b对癌细胞凋亡的影响，结果显示该化合物能够有效诱导癌细胞凋亡。本研究为寻找新型抗癌药物提供了理论参考，并可能对设计新型化疗药物具有指导意义。
• Steroid Series. VII. Synthesis of 6-Methyl-B-norsteroids.
  作者：Rinji Takasaki

  DOI：10.1248/cpb.10.439

  日期：——

  3β, 5-Dihydroxy-6β-formyl-B-nor-5β-steroids (IIIa, b, c) of cholestane, pregnane, and androstane series were converted into the corresponding 3β, 5-dihydroxy-6β-methyl-B-nor-5β-steroids (VIa, d, e) by reduction of (III) with sodium borohydride, followed by tosylation of 6-hydroxymethyl group and subsequent treatment with lithium aluminium hydride. The compounds (VI) were oxidized to 3-oxo-5-hydroxy-6β-methyl-B-nor-5β-steroid derivatives (VIIa, b, f) which were then dehydrated to 6ξ-methyl-B-norcholest-4-en-3-one (VIIIa), 6ξ-methyl-B-norpregn-4-ene-3, 20-dione (VIIIb), and 6ξ-methyl-B-norandrost-4-ene-3, 17-dione (VIIIf).

  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）。
• Synthesis and in vitro antiproliferative evaluation of some ring B abeo-sterols
  作者：Chunfang Gan、Lianghua Fan、Jianguo Cui、Yanmin Huang、Yanxiao Jiao、Wanxin Wei

  DOI：10.1016/j.steroids.2012.05.005

  日期：2012.9

  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.