[(3S,8R,9S,10S,13S,14S)-10,13-dimethyl-17-oxo-1,2,3,4,5,6,7,8,9,11,12,14,15,16-tetradecahydrocyclopenta[a]phenanthren-3-yl] acetate | 95043-80-4

• 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: [(3S,8R,9S,10S,13S,14S)-10,13-dimethyl-17-oxo-1,2,3,4,5,6,7,8,9,11,12,14,15,16-tetradecahydrocyclopenta[a]phenanthren-3-yl] acetate
• CAS: 95043-80-4
• 化学式: C₂₁H₃₂O₃
• 分子量: 332.483
• InChiKey: FDCINQSOYQUNKB-PKIMPSFCSA-N

物化性质

• 熔点：
  157-159 °C
• 沸点：
  424.6±45.0 °C(Predicted)
• 密度：
  1.09±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  24
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  [(3S,8R,9S,10S,13S,14S)-10,13-dimethyl-17-oxo-1,2,3,4,5,6,7,8,9,11,12,14,15,16-tetradecahydrocyclopenta[a]phenanthren-3-yl] acetate 在 sodium tetrahydroborate 、 palladium dichloride 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 1.0h， 以94%的产率得到5α-androstane-3β,17β-diol 3-acetate
  参考文献：
  名称：

  一种新型强效选择性还原剂硼氢化钠-氯化钯系统

  摘要：

  一种新的还原剂，硼氢化钠-氯化钯系统将芳基酮、芳基氯化物和苯甲醇还原成相应的烃。它还以良好的收率将受阻甾体酮还原为醇。

  DOI：

  10.1246/cl.1981.1029

文献信息

• MEDICINAL APPLICATIONS OF BENZOIC ACID HYDRAZONES SYNTHESIZED ON THE BASIS OF STEROIDAL TIGOGENIN
  申请人：Shelar Ashok Ranganath

  公开号：US20110178317A1

  公开（公告）日：2011-07-21

  Novel benzoic acid hydrazones of 5α-androstan-3,17-dione have been prepared on the basis of steroidal tigogenin of the plant Yucca gloriosa . The hydrazones of the General Formula (I), General Formula (II) and General Formula (III) as shown in the accompanying FIGURE of the drawing are synthesized. The hydrazones have shown promising anti-T.B., anti-cancer and anti-HIV activity revealing immense potential as more efficacious, less toxic drugs with fewer undesirable side effects. They could also prove valuable in correcting hormonal abnormalities that cause severe health problems.

  5α-雄甾烷-3,17-二酮的新型苯甲酸肼已经根据植物优格龙胆甾原甙制备。根据图纸中显示的一般式(I)、一般式(II)和一般式(III)，合成了这些肼。这些肼显示出有希望的抗结核、抗癌和抗艾滋病活性，表明它们具有更有效、毒性更小、副作用更少的巨大潜力。它们还可能在纠正引起严重健康问题的激素异常方面具有价值。
• INHIBITORS OF CYP17A1
  申请人：University of Kansas

  公开号：US20160031929A1

  公开（公告）日：2016-02-04

  Compounds according to formula I or II are provided. Such compounds are useful in treating cancers, such as leukemia, colon cancer, breast cancer, or prostate cancer by beneficially inhibiting CYP17A1. Pharmaceutical compositions and methods including the compounds are also provided.

  根据公式I或II提供了化合物。这些化合物对治疗白血病、结肠癌、乳腺癌或前列腺癌等癌症具有用处，通过有益地抑制CYP17A1。还提供了包括这些化合物的药物组合物和方法。
• CYP11B, CYP17, AND/OR CYP21 INHIBITORS
  申请人：Chu Daniel

  公开号：US20130252930A1

  公开（公告）日：2013-09-26

  Provided herein are inhibitors of CYP11B, CYP17, and/or CYP21 enzymes of Formula (Z), (IX), (X), (XI), (XII), (XIII), (XIV), (XV), (XVI), or (XVII). Also described herein are pharmaceutical compositions that include at least one compound described herein and the use of a compound or pharmaceutical composition described herein to treat androgen-dependent diseases, disorders and conditions. Formula (Z)

  本文提供了CYP11B、CYP17和/或CYP21酶的抑制剂，其化学式为(Z)、(IX)、(X)、(XI)、(XII)、(XIII)、(XIV)、(XV)、(XVI)或(XVII)。此外，本文还描述了包括至少一种上述化合物的药物组合物，并使用上述化合物或药物组合物来治疗雄激素依赖性疾病、紊乱和病症。其中化学式(Z)如下：
• ANDROGEN RECEPTOR DOWN-REGULATING AGENTS AND USES THEREOF
  申请人：UNIVERSITY OF MARYLAND EASTERN SHORE

  公开号：US20150361126A1

  公开（公告）日：2015-12-17

  The present disclosure provides the design and synthesis of novel steroidal compounds that cause down-regulation of the androgen receptor (AR), both full length and splice variant. The compounds are potential agents for the treatment of all forms of prostate cancer and other diseases that depend on functional AR.

  本公开说明提供了新型类固醇化合物的设计和合成，这些化合物可以导致雄激素受体（AR）的下调，包括全长和剪切变异体。这些化合物是治疗各种前列腺癌和其他依赖于功能性AR的疾病的潜在药物。
• Evaluation of Mesoporous Silica Nanoparticles as Delivery Vehicles for Novel Hybrid Steroids in Management of Metabolic Syndrome in Mice
  作者：Dina S. El-kady、Mostafa Mabrouk、Soheir Kotob、Mervat Abd-Elhalim、Gamal Elmegeed、Hanan Beheri、Hanaa Ahmed

  DOI：10.21608/ejchem.2021.57952.3295

  日期：2021.5.24

  This approach aimed to address the efficacy of the newly synthesized hybrid steroids modified by sulfurheterogenous rings and loaded on mesoporous silica nanoparticles in manipulating metabolic syndrome induced by high fructose diet. The designed compounds were synthesized by mechanochemical process and then loaded on mesoporous silica nanoparticles as drug delivery vehicles. Thereafter, these compounds were examined for counteracting metabolic syndrome inmice. The synthesized compounds revealed potentiality to prevent body weight gain as indicated by the decreased BMI of the mice fed high fructose diet. The hypolipidemic effect of the designed compounds was evidenced by the reduction of serum cholesterol, triglycerides, LDL-cholesterol and the enhancement of HDL-cholesterol levels. Moreover, the compounds displayed a significant decline in blood glucose and insulin levels. So, they exhibited significant betterment in insulin resistance of the treated mice. Furthermore, the treatment with these compounds improved serum spexin level in metabolic syndrome-challenged mice. Ultimately, the tested compounds demonstrated powerful free radical scavenging activity manifested by lowering MDA, NO and H2O2 serum levels. Conclusively, the newly modified hybrid steroid compounds proved good performance against metabolic syndrome in mice most probably due to their content of sulfur atom, in addition to their loading on mesoporous silica nanoparticles.

  这种方法旨在研究新合成的杂环硫杂环修饰的混合类固醇，以及装载在中孔二氧化硅纳米颗粒上，在处理高果糖饮食引起的代谢综合征方面的功效。设计好的化合物通过机械化学方法合成，然后装载在中孔二氧化硅纳米颗粒上作为药物载体。之后，这些化合物被用于对抗小鼠的代谢综合征。合成后的化合物显示出防止体重增加的潜力，表现为高果糖饮食喂养的小鼠的BMI下降。设计好的化合物的降脂作用表现为血清胆固醇、甘油三酯、低密度脂蛋白胆固醇的降低和高密度脂蛋白胆固醇水平的提高。此外，这些化合物还表现出血糖和胰岛素水平显著下降。因此，它们在治疗小鼠的胰岛素抵抗方面表现出显著的改善。此外，用这些化合物治疗代谢综合征小鼠可提高血清纤溶酶原水平。最终，测试的化合物表现出强大的自由基清除活性，表现为降低MDA、NO和H2O2的血清水平。总之，新合成的杂环类固醇化合物被证明对小鼠的代谢综合征具有良好的疗效，这很可能是因为它们除了装载在中孔二氧化硅纳米颗粒上外，还含有硫原子。