(E)-3-(4-fluorophenyl)-1-((3S,8S,9S,10R,13S,14S,17S)-3-hydroxy-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl)prop-2-en-1-one | 1338000-54-6

• 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: (E)-3-(4-fluorophenyl)-1-((3S,8S,9S,10R,13S,14S,17S)-3-hydroxy-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl)prop-2-en-1-one
• 英文别名: (E)-3-(4-fluorophenyl)-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
• CAS: 1338000-54-6
• 化学式: C₂₈H₃₅FO₂
• 分子量: 422.583
• InChiKey: KDTYVBVBHHKSOY-DEZCMFKVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.4
• 重原子数：
  31
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (E)-3-(4-fluorophenyl)-1-((3S,8S,9S,10R,13S,14S,17S)-3-hydroxy-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-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88%的产率得到(E)-3-(4-fluorophenyl)-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：

  反-4-氟肉桂醛 、 孕烯醇酮 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 反应 12.0h， 以88%的产率得到(E)-3-(4-fluorophenyl)-1-((3S,8S,9S,10R,13S,14S,17S)-3-hydroxy-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl)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

• 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。
• OXYSTEROLS AND HEDGEHOG SIGNALING
  申请人：MAX BioPharma, Inc.

  公开号：US20170114089A1

  公开（公告）日：2017-04-27

  Described herein are compounds and pharmaceutical compositions containing such compounds which inhibit Hedgehog signaling. Also described herein are methods for using such Hedgehog signaling inhibitors, alone or in combination with other compounds, for treating diseases or conditions that would benefit from inhibition of Hedgehog signaling.

  本文描述了一些抑制刺猬信号的化合物和含有这些化合物的药物组合物。本文还描述了使用这些刺猬信号抑制剂的方法，单独或与其他化合物结合，用于治疗需要抑制刺猬信号的疾病或病症。
• [EN] OXYSTEROL COMPOUNDS AND USES THEREOF<br/>[FR] COMPOSÉS D'OXYSTÉROL ET LEURS UTILISATIONS
  申请人：MAX BIOPHARMA INC

  公开号：WO2021248049A1

  公开（公告）日：2021-12-09

  Described herein are compounds and pharmaceutical compositions containing such compounds for the modulation of Hedgehog signaling.

  本文描述了一些化合物和含有这些化合物的药物组合物，用于调节Hedgehog信号通路。
• Oxysterols and Hedgehog signaling
  申请人：MAX BIOPHARMA, INC.

  公开号：US10869875B2

  公开（公告）日：2020-12-22

  Described herein are compounds and pharmaceutical compositions containing such compounds which inhibit Hedgehog signaling. Also described herein are methods for using such Hedgehog signaling inhibitors, alone or in combination with other compounds, for treating diseases or conditions that would benefit from inhibition of Hedgehog signaling.

  本文描述了抑制刺猬信号转导的化合物和含有此类化合物的药物组合物。本文还描述了使用此类刺猬信号转导抑制剂（单独使用或与其他化合物联合使用）治疗可从抑制刺猬信号转导中获益的疾病或病症的方法。
• 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.