5α-cholestane-3β,6α,7β-triol | 202416-16-8

• 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: 5α-cholestane-3β,6α,7β-triol
• 英文别名: 5α-cholestan-3β,6α,7β-triol；cholestane-3β,6α,7β-triol；(10R)-3c.6t.7c-Trihydroxy-10r.13c-dimethyl-17c-((R)-1.5-dimethyl-hexyl)(5tH.8cH.9tH.14tH)-hexadecahydro-1H-cyclopenta[a]phenanthren；3β.6α.7β-Trihydroxy-10.13-dimethyl-17β-((R)-1.5-dimethyl-hexyl)-5α-gonan；5α-Cholestantriol-(3β.6α.7β)；Cholestane-3b,6a,7b-triol；(3S,5S,6R,7R,8S,9S,10R,13R,14S,17R)-10,13-dimethyl-17-[(2R)-6-methylheptan-2-yl]-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthrene-3,6,7-triol
• CAS: 202416-16-8
• 化学式: C₂₇H₄₈O₃
• 分子量: 420.676
• InChiKey: VCEUWUOZLFOWIB-BYOHLECUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7
• 重原子数：
  30
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  60.7
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5α-cholestane-3β,6α,7β-triol 在 sodium hydroxide 、 lithium aluminium tetrahydride 、 硼烷四氢呋喃络合物 、 三氟甲磺酸三甲基硅酯 、 phosphorus pentoxide 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 、 叔丁醇 、 苯 为溶剂， 反应 14.83h， 生成 3α-methoxymethoxy-6α,7β-methylenedioxy-5α,14α-cholestan-15α-ol
  参考文献：
  名称：

  First total synthesis of xestobergsterol A and active structural analogues of the xestobergsterols

  摘要：

  The novel pentacyclic polyhydroxylated sterol, xestobergsterol A la, a strong inhibitor of histamine release from rat mast cells induced by anti-IgE, has been synthesized in 24 steps and good overall yield From stigmasterol 7. The Breslow remote functionalization process has been extended to several more highly functionalized steroid derivatives, especially those with oxygen functionality in the B-ring. The key steps of the synthesis of xestobergsterol A la and its analogues, 7-deoxyxestobergsterol A Id and 16,23-seco-23-deoxyxestobergsterol A 73, are the Breslow remote functionalization of oxygenated steroids and for compounds la and Id, a novel base-catalyzed epimerization-aldol condensation of a dione to give the desired CD-cis ring structure of the xestobergsterols. Thus the known alcohol 75, prepared from stigmasterol 7, was taken to the tetraacetate 107 which was then converted via a Breslow remote functionalization into the alkene aldehyde 114 which was transformed in 5 steps to xestobergsterol A la. Testing of the synthetic materials showed that the two analogues, 7-deoxyxestobergsterol A Ib and 16,23-seco-23-deoxyxestobergsterol A 73, are also potent inhibitors of histamine release with ICS, values (IC50 500 nM and 750 nM, respectively) being only 1015 times less than that of xestobergsterol A itself (50 nM). (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(00)01086-3
• 作为产物：
  描述：

  3β-acetoxy-7α-bromo-5α-cholestan-6-one 在 氢氧化钾 作用下， 生成 5α-cholestane-3β,6α,7β-triol
  参考文献：
  名称：

  Glycol Fission in Rigid Systems. II. The Cholestane-3β,6,7-triols. Existence of a Cyclic Intermediate¹

  摘要：

  DOI：

  10.1021/ja01528a055

文献信息

• An improved and efficient synthesis for IPL576,092 and its analogues
  作者：Jin Liu、Rong Huang、Hongyou Zhu

  DOI：10.1007/s00706-012-0920-4

  日期：2013.7

  AbstractAn improved and efficient preparation of IPL576,092 was developed. The synthetic route involves selective allylic oxidation of ∆5-sterols and subsequent hydroboration–oxidation as the key steps. In addition, two analogues were readily synthesized from commercially available steroidal compounds in two steps in the same way. Graphical abstract

  摘要开发了一种改进的高效IPL576,092的制备方法。合成路线涉及∆ 5-甾醇的选择性烯丙基氧化和随后的硼氢化-氧化作为关键步骤。另外，很容易以相同的方式分两步从商购的甾族化合物合成两种类似物。 图形概要
• Selective Cytotoxicity of Oxysterols through Structural Modulation on Rings A and B. Synthesis, in Vitro Evaluation, and SAR
  作者：João F. S. Carvalho、M. Manuel Cruz Silva、João N. Moreira、Sérgio Simões、M. Luisa Sá e Melo

  DOI：10.1021/jm200803d

  日期：2011.9.22

  Chemically diverse oxysterols were prepared and evaluated for cytotoxicity, aiming to push forward potency and selectivity. They were tested against seven cancer (HT-29, HepG2, A549, PC3, LAMA-84, MCF-7, and SH-SYSY) and two noncancerous cell lines (ARPE-19 and BJ). The influence of the oxidation pattern on rings A and B was studied. Oxygen functionalities on ring B, such as oxo, oxime, acetamide, acetate, and alkoxy, were evaluated. Most oxysterols were cytotoxic in the low micromolar range, with emphasis to the tetrols 14 and 34, the 6 beta methoxy and acetoxy derivatives 21 and 45, and the oxime 28. In general, the oxysterols were more toxic to cancer cells and a set of compounds (9, 14, 21, 28, 45) with very high selectivity was identified. The cytotoxicity of 3 beta-acetates was lower than that of the parent alcohols, although incubation for a longer period rendered them equally cytotoxic, pointing them as potential prodrugs of oxysterols.
• First total synthesis of xestobergsterol A and active structural analogues of the xestobergsterols
  作者：Michael E Jung、Ted W Johnson

  DOI：10.1016/s0040-4020(00)01086-3

  日期：2001.2

  The novel pentacyclic polyhydroxylated sterol, xestobergsterol A la, a strong inhibitor of histamine release from rat mast cells induced by anti-IgE, has been synthesized in 24 steps and good overall yield From stigmasterol 7. The Breslow remote functionalization process has been extended to several more highly functionalized steroid derivatives, especially those with oxygen functionality in the B-ring. The key steps of the synthesis of xestobergsterol A la and its analogues, 7-deoxyxestobergsterol A Id and 16,23-seco-23-deoxyxestobergsterol A 73, are the Breslow remote functionalization of oxygenated steroids and for compounds la and Id, a novel base-catalyzed epimerization-aldol condensation of a dione to give the desired CD-cis ring structure of the xestobergsterols. Thus the known alcohol 75, prepared from stigmasterol 7, was taken to the tetraacetate 107 which was then converted via a Breslow remote functionalization into the alkene aldehyde 114 which was transformed in 5 steps to xestobergsterol A la. Testing of the synthetic materials showed that the two analogues, 7-deoxyxestobergsterol A Ib and 16,23-seco-23-deoxyxestobergsterol A 73, are also potent inhibitors of histamine release with ICS, values (IC50 500 nM and 750 nM, respectively) being only 1015 times less than that of xestobergsterol A itself (50 nM). (C) 2001 Elsevier Science Ltd. All rights reserved.
• Glycol Fission in Rigid Systems. II. The Cholestane-3β,6,7-triols. Existence of a Cyclic Intermediate¹
  作者：S. J. Angyal、R. J. Young

  DOI：10.1021/ja01528a055

  日期：1959.10