16β-hydroxycholesterol | 30270-29-2

• 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
• 英文名称: 16β-hydroxycholesterol
• 英文别名: Cholest-5-ene-3beta,16beta-diol；(3S,8S,9S,10R,13S,14S,16S,17R)-10,13-dimethyl-17-[(2R)-6-methylheptan-2-yl]-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthrene-3,16-diol
• CAS: 30270-29-2
• 化学式: C₂₇H₄₆O₂
• 分子量: 402.661
• InChiKey: IXRAQYMAEVFORF-LBQSOJHBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.2
• 重原子数：
  29
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  16β-hydroxycholesterol 在 chromium(VI) oxide 、 sodium acetate 、 溶剂黄146 作用下， 生成 16-ketocholesterol
  参考文献：
  名称：

  Stereospecific introduction of tritium in the 16α or 16β position of cholesterol

  摘要：

  用KB3 H4还原胆固醇-5-烯-3β-醇-16-酮，获得了[16α-3H]-胆固醇-5-烯-3β, 16β-二醇和[16β-3H]-胆固醇-5-烯-3β, 16α-二醇的混合物，随后分别分离并转化为[16β-3H]-胆固醇-5-烯-3β-醇和[16α-3H]-胆固醇-5-烯-3β-醇。

  DOI：

  10.1002/jlcr.2580140506
• 作为产物：
  描述：

  薯蓣皂素 在 吡啶 、 盐酸 、 lithium aluminium tetrahydride 、 锌 作用下， 以 四氢呋喃 、 乙醇 、 水 为溶剂， 生成 16β-hydroxycholesterol
  参考文献：
  名称：

  结核分枝杆菌甾体抑制剂的合成

  摘要：

  胆固醇的氧化衍生物已被证明可以抑制 () 的生长。这些化合物的抑菌活性归因于它们对 CYP125A1 和 CYP142A1 的抑制，这两种代谢关键细胞色素 P450 会引发甾醇侧链的降解。在这里，我们合成并表征了 28 种胆固醇衍生物的广泛库，以开发此类抑制剂的结构-活性关系。评估了候选化合物的 MIC 毒性以及与 CYP125A1 和 CYP142A1 的结合研究

  DOI：

  10.1016/j.jsbmb.2024.106479

文献信息

• Conversion of ruscogenin into 1α- and 1β hydroxycholesterol derivatives
  作者：M. Noam、I. Tamir、E. Breuer、R. Mechoulam

  DOI：10.1016/s0040-4020(01)92435-4

  日期：1981.1

  and 3, and mesylation of position 16 followed by LAH reduction. The utility of the shift reagent Eu(dpm)3 to determine the structures of the products was studied. It was shown that the shifts induced are characteristic of the position and orientation of the OH groups, and can facilitate the elucidation of the structures of hydroxylated steroids.

  对ruscogenin（1）的化学性质进行了研究，因为它的结构特征使其可以用作1-羟基维​​生素D类似物的潜在原料。芸香皂苷元被氧化成1-氧代衍生物2，其被还原成芸香苷元（1）和1-表皮环氧菌素（3）的混合物。既1和3通过克莱门森还原转化成相应的四元醇12和21，将其进一步还原成三醇15和25和二醇16和24通过连续的处理与p -甲苯磺酰氯和LAH。通过位置1和3的选择性苯甲酰化，以及位置16的甲磺酸化，然后LAH还原，将三醇15还原为二醇20。研究了转化试剂Eu（dpm）3在确定产物结构方面的用途。结果表明，引起的移位是OH基团的位置和取向的特征，并且可以促进阐明羟基化类固醇的结构。
• Meiosis regulating compounds
  申请人：——

  公开号：US20020013302A1

  公开（公告）日：2002-01-31

  Sterol derivative compounds, structurally related to natural compounds which can be extracted from bull testes and from human follicular fluid, useful for regulating meiosis in oocytes and in male germ cells. Some of these compounds are useful in the treatment of infertility, whereas other compounds are useful as contraceptives.

  甾醇衍生物化合物，结构上与可以从公牛睾丸和人类卵泡液中提取的天然化合物相关，对调节卵母细胞和男性生殖细胞中的减数分裂有用。其中一些化合物对治疗不孕症有用，而其他化合物则可用作避孕药。
• Short synthesis of 16β-hydroxy-5α-cholestane-3,6-dione a novel cytotoxic marine oxysterol
  作者：Mickaël Denancé、Michèle Guyot、Mohammad Samadi

  DOI：10.1016/j.steroids.2006.03.002

  日期：2006.7

  The first and short synthesis of 16beta-hydroxy-5alpha-cholestane-3,6-dione 1 a metabolite from marine algae, has been achieved in six steps from readily available diosgenin 5. Selective deoxygenation of primary alcohol of triol 6 has been accomplished in one step using Et(3)SiH and catalytic amount of B(C(6)F(5))(3) to produce compound 9 in high yield. Oxidation of 11 with PCC, allowed the introduction

  从易得的薯os皂苷元5分六步完成了从海藻中代谢产物16beta-hydroxy-5alpha-cholestane-3,6-dione 1 a的首次和短期合成。第一步，使用Et（3）SiH和催化量的B（C（6）F（5））（3）以高收率生产化合物9。用PCC氧化11可以引入3,6-烯二酮官能团，进一步的催化加氢和脱保护得到3,6-二酮类固醇1。
• [EN] THERAPEUTIC COMPOUNDS<br/>[FR] COMPOSÉS THÉRAPEUTIQUES
  申请人：UNIV IOWA RES FOUND

  公开号：WO2017100153A1

  公开（公告）日：2017-06-15

  The invention provides compounds of formula (I): and salts thereof, wherein R1, R2, R3, B, X, Y, and Z have any of the values defined herein. The invention also provides pharmaceutical compositions comprising a compound of formula (I) or a pharmaceutically acceptable salt thereof, processes for preparing compounds of formula (I) and salts thereof, intermediates useful for preparing compounds of formula (I) and salts thereof, and therapeutic methods for treating cancer using a compound of formula (I) or a pharmaceutically acceptable salt thereof.

  该发明提供了化合物的结构式（I）及其盐，其中R1、R2、R3、B、X、Y和Z具有本文中定义的任何值。该发明还提供了包括化合物的结构式（I）或其药学上可接受的盐的药物组合物，制备化合物的结构式（I）及其盐的方法，用于制备化合物的结构式（I）及其盐的中间体，以及使用化合物的结构式（I）或其药学上可接受的盐治疗癌症的治疗方法。
• Synthesis and evaluation of new 6-hydroximinosteroid analogs as cytotoxic agents
  作者：Javier Poza、Miriam Rega、Vanessa Paz、Beatriz Alonso、Jaime Rodríguez、Nélida Salvador、Antonio Fernández、Carlos Jiménez

  DOI：10.1016/j.bmc.2007.05.003

  日期：2007.7

  Taking into account the structural requirements for cytotoxicity, several new hydroximinosteroid derivatives have been prepared and evaluated for their cytotoxic activity against A-549, HI 16, PSN1, and T98G cultured tumor cell lines in order to obtain further information on the potential pharmacophoric core of this type of compound. The influence of the oxygenated position in the A ring, the presence of an additional oxygenated position at C-7 and C-16, and a fluorinated position at C-5 were considered in order to study the structure-activity relationships. The results reveal the importance of oxygenated positions in the A ring (e.g., 4,5-epoxide showed an IC50 value against HCT-116 under micromolar level) for an increase in cytotoxic activity in this type of compound. Furthermore, they showed an important selectivity toward colon tumor line (HCT-116). (c) 2007 Elsevier Ltd. All rights reserved.