3-(furan-2-yl)-1-(preg-5-en-3β-ol-17-yl)prop-2- en-1-one

• 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: 3-(furan-2-yl)-1-(preg-5-en-3β-ol-17-yl)prop-2- en-1-one
• 英文别名: (2E)-3-(furan-2-yl)-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)prop-2-en-1-one；21-((E)-furfurylidene)-3β-hydroxy-pregn-5-en-20-one；21-((E)-Furfuryliden)-3β-hydroxy-pregn-5-en-20-on；(E)-3-(furan-2-yl)-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]prop-2-en-1-one
• 化学式: C₂₆H₃₄O₃
• 分子量: 394.554
• InChiKey: NZXSUNGFHDUJQY-LIIPZQNNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  29
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  50.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-(furan-2-yl)-1-(preg-5-en-3β-ol-17-yl)prop-2- en-1-one 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以82%的产率得到(E)-3-(furan-2-yl)-1-[(1S,2R,5S,7R,9S,11S,12S,15S,16S)-5-hydroxy-2,16-dimethyl-8-oxapentacyclo[9.7.0.02,7.07,9.012,16]octadecan-15-yl]prop-2-en-1-one
  参考文献：
  名称：

  Synthesis and biological evaluation of 21-arylidenepregnenolone derivatives as neuroprotective agents

  摘要：

  A series of 21-arylidenepregnenolone derivatives and their corresponding epoxides were synthesized. The neuroprotective effects of these steroidal compounds against amyloid-beta(5-35)(A beta(25-35))- and hydrogen peroxide (H2O2)-induced neurotoxicity in PC12 cells, and oxygen-glucose deprivation (OGD)-induced neurotoxicity in SH-SY5Y cells were evaluated. The bioassay results indicated that several 3b-pregn-21-benzylidene-20-one derivatives displayed potent in vitro neuroprotective effects in different screening models, for example, compounds 2b, 3a, 3b, and 3s showing significant activities against A beta(25-35)-induced neurotoxicity in PC12 cells, 2b showing significant activities against H2O2-induced neurotoxicity in PC12 cells, and 2g, 3b, and 3e showing potent protection against OGD insult. The results suggested that introduction of an arylidene group into steroidal nucleus played an important role in neuroprotective activity, while the formation of epoxy group at C-5,6 could be also important for the neuroprotective activity in some degree. The pharmacological data reported here are helpful for the design of novel steroidal neuroprotective candidates. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.01.103
• 作为产物：
  描述：

  糠醛 、 孕烯醇酮醋酸酯 在 sodium hydroxide 作用下， 以 乙醇 、 水 为溶剂， 反应 24.0h， 以74%的产率得到3-(furan-2-yl)-1-(preg-5-en-3β-ol-17-yl)prop-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。
• Manufacture of derivatives of etiocholenic acid
  申请人：JOSEPH ROSS WALTER CHARLES

  公开号：US02470903A1

  公开（公告）日：1949-05-24
• 21-furfurylidene and 21-thenylidene derivatives of progesterone and 19-norprogestersone
  申请人：SEARLE &

  公开号：US02862924A1

  公开（公告）日：1958-12-02
• 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.
• Synthesis and biological evaluation of 21-arylidenepregnenolone derivatives as neuroprotective agents
  作者：Cheng-Shi Jiang、Xian-Jun Guo、Jing-Xu Gong、Ting-Ting Zhu、Hai-Yan Zhang、Yue-Wei Guo

  DOI：10.1016/j.bmcl.2012.01.103

  日期：2012.3

  A series of 21-arylidenepregnenolone derivatives and their corresponding epoxides were synthesized. The neuroprotective effects of these steroidal compounds against amyloid-beta(5-35)(A beta(25-35))- and hydrogen peroxide (H2O2)-induced neurotoxicity in PC12 cells, and oxygen-glucose deprivation (OGD)-induced neurotoxicity in SH-SY5Y cells were evaluated. The bioassay results indicated that several 3b-pregn-21-benzylidene-20-one derivatives displayed potent in vitro neuroprotective effects in different screening models, for example, compounds 2b, 3a, 3b, and 3s showing significant activities against A beta(25-35)-induced neurotoxicity in PC12 cells, 2b showing significant activities against H2O2-induced neurotoxicity in PC12 cells, and 2g, 3b, and 3e showing potent protection against OGD insult. The results suggested that introduction of an arylidene group into steroidal nucleus played an important role in neuroprotective activity, while the formation of epoxy group at C-5,6 could be also important for the neuroprotective activity in some degree. The pharmacological data reported here are helpful for the design of novel steroidal neuroprotective candidates. (C) 2012 Elsevier Ltd. All rights reserved.