(2E)-1-((10R,13S)-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-3(β)-hydroxy-10,13-dimethyl-1H-cyclopenta[α]phenanthren-17(β)-yl)-3-p-tolylprop-2-en-1-one | 1338000-52-4

• 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: (2E)-1-((10R,13S)-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-3(β)-hydroxy-10,13-dimethyl-1H-cyclopenta[α]phenanthren-17(β)-yl)-3-p-tolylprop-2-en-1-one
• 英文别名: 3-(4-methylphenyl)-1-(preg-5-en-3β-ol-17-yl)- prop-2-en-1-one；(2E)-1-((10R,13S)-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-3(β)-hydroxy-10,13-dimethyl-1H-cyclopenta[a]phenanthren-17(β)-yl)-3-p-tolylprop-2-en-1-one；(E)-1-[(3S,8S,9S,10R,13S,14S,17S)-3-hydroxy-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl]-3-(4-methylphenyl)prop-2-en-1-one
• CAS: 1338000-52-4
• 化学式: C₂₉H₃₈O₂
• 分子量: 418.62
• InChiKey: JIYKWXRVIJVKGV-OROKFEPCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.7
• 重原子数：
  31
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (2E)-1-((10R,13S)-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-3(β)-hydroxy-10,13-dimethyl-1H-cyclopenta[α]phenanthren-17(β)-yl)-3-p-tolylprop-2-en-1-one 在 盐酸羟胺 作用下， 以 乙醇 为溶剂， 反应 2.0h， 以90%的产率得到(2E)-1-((10R,13S)-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-3-hydroxy-10,13-dimethyl-1H-cyclopenta[α]phenanthren-17-yl)-3-p-methylphenylprop-2-en-1-hydroxyimine
  参考文献：
  名称：

  Benzylidine pregnenolones and their oximes as potential anticancer agents: Synthesis and biological evaluation

  摘要：

  The present study reveals the anticancer activity of benzylidine pregnenolones and their oxime derivatives. The synthesis of the analogs of both series is very simple and involves aldol condensation in the first step followed by nucleophillic addition of hydroxylamine across carbonyl in the second step. Quantitative yields of more than 80% are obtained in both the steps. All the compounds were tested for their cytotoxic activities against a panel of six human cancer cell lines. Amongst all the compounds of both the series screened for their cytotoxic actvity, compound 3e, 3f and 4e are very potent especially against HCT-15 and MCF-7 cancer cell lines. (C) 2014 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.steroids.2014.03.010
• 作为产物：
  描述：

  孕烯醇酮醋酸酯 、 对甲基苯甲醛 在 sodium hydroxide 作用下， 以 乙醇 、 水 为溶剂， 反应 24.0h， 以84%的产率得到(2E)-1-((10R,13S)-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-3(β)-hydroxy-10,13-dimethyl-1H-cyclopenta[α]phenanthren-17(β)-yl)-3-p-tolylprop-2-en-1-one
  参考文献：
  名称：

  一些新型类固醇及其吡唑啉和肟的类似物的合成，体外抗HIV活性，细胞毒性和计算研究

  摘要：

  摘要— 迫切需要设计和开发用于治疗HIV感染的新的更安全的药物，该药物通过开发新的非核苷类逆转录酶抑制剂（NNRTIs）来对抗目前耐药的病毒株。合成了一系列孕烯醇酮类似物3-（（芳基）-1-（5-pregnen-3β-ol-17-yl）prop-2-en-1-ones。进一步处理3-（（4 -溴，4-，三氟甲基或4-甲基苯基）-1-（preg-5-en-3β-ol-17-基）丙-2-烯-1-酮与硫代氨基脲在乙醇KOH中或在肼中的水合肼得到5-（4-溴-，4-三氟甲基或4-甲基苯基）-3-（preg-5-en-3β-ol-17-yl）-4,5-二氢-1 H-吡唑啉-1-碳硫酰胺和1- O-乙酰基-（5-（4-溴苯基）-3-（preg-5-en-3β-ol-17-yl）-4,5-二氢-1 H-吡唑啉。类似地，用羟胺处理3-（（4-溴苯基）-1-（preg-5-en-3β-ol-17-基）丙-2-烯-1-酮得到3-的Z

  DOI：

  10.1134/s1068162020050039

文献信息

• Steroidal pyrazolines and pyrazoles as potential 5α-reductase inhibitors: Synthesis and biological evaluation
  作者：Abid H. Banday、Shameem A. Shameem、Salika Jeelani

  DOI：10.1016/j.steroids.2014.09.004

  日期：2014.12

  Taking pregnenolone as the starting material, two series of pyrazolinyl and pyrazolyl pregnenolones were synthesized through different routes. The synthesis of the analogs of both series is multistep and proceeds in good overall yields. While the key step in the synthesis of pyrazolinyl pregnenolones is the heterocyclization of benzylidine derivatives (3) in presence of hydrazine hydrate, it is the

  以孕烯醇酮为起始原料，通过不同途径合成了两个系列的吡唑啉基和吡唑基孕烯醇酮。两个系列的类似物的合成是多步的，并且以良好的总产率进行。吡唑啉基孕烯醇酮合成的关键步骤是在水合肼存在下苄基衍生物（3）的杂环化反应，但它是3β-羟基-21-羟甲基亚甲基pregn-5-en-3β-ol-20-的缩合反应（ 5）与苯肼合成吡唑基衍生物。测试了两个系列的化合物的5α-还原酶抑制活性。在筛选出具有5α-还原酶抑制活性的所有化合物中，发现化合物4b，4c和6b的活性最高。
• Synthesis, pharmacological evaluation and Molecular modelling studies of pregnenolone derivatives as inhibitors of human dihydrofolate reductase
  作者：Muhammad Bilal Tufail、Muhammad Aamir Javed、Muhammad Ikram、Mater H. Mahnashi、Bandar A. Alyami、Yahya S. Alqahtani、Abdul Sadiq、Umer Rashid

  DOI：10.1016/j.steroids.2021.108801

  日期：2021.4

  In current study, we synthesized chalcone derivatives (13a-c) via base-catalyzed Claisen-Schmidt condensation reaction. We further treated diamino compounds with synthesized chalcones to produce 3,4-dihydropyrimidin-2(1H)-one (18a-c), 3,4-dihydropyrimidin-2(1H)-thione (19a-c) and 2-aminopyrimidine (20a-c) derivatives of pregnenolone by cyclization reaction. Cell viability test of synthesized steroidal

  在当前的研究中，我们通过碱催化的Claisen-Schmidt缩合反应合成了查尔酮衍生物（13a-c）。我们用合成的查耳酮进一步处理了二氨基化合物，以产生3,4-dihydropyrimidin-2（1H）-one（18a-c），3,4-dihydropyrimidin-2-2（1H）-硫酮（19a-c）和2-aminopyrimidine（ 20a-c）孕烯醇酮的衍生物通过环化反应。使用（4,5-二甲基噻唑-2- yl）-2,5-二苯基溴化四氮唑（MTT），测定。进一步评估化合物对重组人DHFR（rhDHFR）的抑制潜力。所有化合物均显示出从低微摩尔到亚微摩尔范围的活性。IC50值为180 nM的化合物20b成为对抗rhDHFR的最有效化合物。还通过对接模拟研究了新合成的孕烯醇酮衍生物与hDHFR和雌激素受体α（ERα）的相互作用。hDHFR抑制的总体结果表明，这些类似物可以进一步优化和开发为有效的抗癌药。
• Synthesis and antimicrobial studies of chalconyl pregnenolones
  作者：Abid H. Banday、M. Iqbal Zargar、Bashir A. Ganaie

  DOI：10.1016/j.steroids.2011.07.001

  日期：2011.11

  An efficient and facile synthesis of 17-chalconyl derivatives of pregnenolone and their evaluation as antimicrobial agents against various microbial strains is reported. The scheme involves the transformation of the starting pregnenolone acetate into pregnenolone, conversion of pregnenolone to the corresponding chalcone derivatives. The compounds 3a-3j showed significant antimicrobial activity against all microbial strains used for testing. (C) 2011 Elsevier Inc. All rights reserved.