(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-(4-methoxyphenyl)prop-2-en-1-one | 1246397-34-1

• 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-(4-methoxyphenyl)prop-2-en-1-one
• 英文别名: (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-(4-methoxy phenyl)prop-2-en-1-one；(21E)-3β-hydroxy-21-(p-methoxybenzylidene)pregn-5-en-20-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-methoxyphenyl)prop-2-en-1-one
• CAS: 1246397-34-1
• 化学式: C₂₉H₃₈O₃
• 分子量: 434.619
• InChiKey: PEGAPZRVEJMUDP-DKJWFPIDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.3
• 重原子数：
  32
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

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-(4-methoxyphenyl)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85%的产率得到(E)-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]-3-(4-methoxyphenyl)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：

  4-甲氧基肉桂醛 、 孕烯醇酮 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 反应 12.0h， 以99%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-(4-methoxyphenyl)prop-2-en-1-one
  参考文献：
  名称：

  Synthesis of D-ring-substituted (5′R)- and (5′S)-17β-pyrazolinylandrostene epimers and comparison of their potential anticancer activities

  摘要：

  Various steroidal benzylidenes were synthetized from pregnenolone with benzaldehyde and p-substituted benzaldehydes. The resulting 17 beta-chalconyl derivatives of pregnenolone were reacted with hydrazine hydrate in acetic acid solution. Regardless of the starting material, the ring-closure reaction afforded (in contrast with the literature data) a mixture of two steroidal pyrazoline epimers. The epimers were critical isomer pairs, which could be separated only in their acetylated form; their structures were investigated by NMR techniques. The in vitro inhibition of rat testicular C-17,C-20-lyase activity and the antiproliferative effects on four human cancer cell lines were measured, and the results obtained from the two epimer series were compared. (C) 2012 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.steroids.2012.02.001

文献信息

• Neighboring Heteroatom Effect Unique to Aqueous Aldol Reactions of Water-Insoluble Substrates
  作者：Bo Li、Chunbao Li

  DOI：10.1021/jo500213b

  日期：2014.3.7

  In the aqueous aldol condensations, Li2CO3 was an efficient catalyst, and therefore base-liable groups such as epoxides, esters, and silyl groups could survive. For heteroaromatic ethanones, the aqueous aldol reactions were accomplished without PTC to give β-hydroxyketones in good yields. The water-mediated condensations of aldosyl hemiacetals with aromatic ketones led to a new carbohydrate-derived

  在Li +存在下和在水存在或不存在PTC的情况下，进行酮和醛的反应以生成醛醇产物。已经证明了水性反应相对于有机溶剂介导的反应的几个优点，包括更高的产率，更短的反应时间，更简单的纯化以及更好的官能团耐受性。在水中已经实现了一些在有机溶剂中不发生的反应。成功归因于相邻的杂原子效应。在水性羟醛缩合中，Li 2 CO 3硫醇是一种有效的催化剂，因此可与碱结合的基团（例如环氧化物，酯和甲硅烷基）可以幸免。对于杂芳族乙酮，在没有PTC的情况下完成了水性醛醇缩合反应，以良好的收率得到了β-羟基酮。水介导的醛基半缩醛与芳香族酮的缩合导致定量产率的新的碳水化合物衍生骨架。在某种程度上，这项研究扩大了醛醇缩合和反应的适用性。
• 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。
• Benzylidine pregnenolones and their oximes as potential anticancer agents: Synthesis and biological evaluation
  作者：Abid H. Banday、S.M.M. Akram、Shameem A. Shameem

  DOI：10.1016/j.steroids.2014.03.010

  日期：2014.6

  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.
• 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.