(21E)-3β-hydroxy-21-(4'-bromobenzylidene)pregn-5-en-20-one | 1365727-61-2

• 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: (21E)-3β-hydroxy-21-(4'-bromobenzylidene)pregn-5-en-20-one
• 英文别名: 3-(4-bromophenyl)-1-(preg-5-en-3β-ol-17-yl)-prop-2-en-1-one；(21E)-3β-hydroxy-21-(p-bromobenzylidene)pregn-5-en-20-one；(E)-3-(4-bromophenyl)-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: 1365727-61-2
• 化学式: C₂₈H₃₅BrO₂
• 分子量: 483.489
• InChiKey: CBFAVJFARBSJEA-DEZCMFKVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  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：
  0.61
• 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：

  (21E)-3β-hydroxy-21-(4'-bromobenzylidene)pregn-5-en-20-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80%的产率得到(E)-3-(4-bromophenyl)-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：

  孕烯醇酮醋酸酯 、 对溴苯甲醛 在 sodium hydroxide 作用下， 以 乙醇 、 水 为溶剂， 反应 24.0h， 以76%的产率得到(21E)-3β-hydroxy-21-(4'-bromobenzylidene)pregn-5-en-20-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

• Synthesis of D-ring-substituted (5′R)- and (5′S)-17β-pyrazolinylandrostene epimers and comparison of their potential anticancer activities
  作者：Zoltán Iványi、Nikoletta Szabó、Judit Huber、János Wölfling、István Zupkó、Mihály Szécsi、Tibor Wittmann、Gyula Schneider

  DOI：10.1016/j.steroids.2012.02.001

  日期：2012.4

  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.
• Efficient synthesis of novel antiproliferative steroidal spirooxindoles via the [3+2] cycloaddition reactions of azomethine ylides
  作者：Bin Yu、Xiao-Nan Sun、Xiao-Jing Shi、Ping-Ping Qi、Yi-Chao Zheng、De-Quan Yu、Hong-Min Liu

  DOI：10.1016/j.steroids.2015.08.003

  日期：2015.10

  A series of novel steroidal spirooxindoles 3a-h were synthesized from pregnenolone in a high regioselective manner using the 1,3-dipolar cycloaddition as the key step. This protocol resulted in the formation of two C-C bonds, one C-N bond and the creation of one pyrrolidine ring and three contiguous stereocenters in a single operation. Biological evaluation showed that these synthesized steroidal spirooxindoles exhibited moderate to good antiproliferative activity against the tested cell lines and some of them were more potent than 5-FU. Among them, compounds 3e and 3f displayed the best antiproliferative activity against MCF-7 cells with the IC50 values of 4.0 and 3.9 mu M, respectively. Flow cytometry analysis demonstrated that compound 3d caused the cellular apoptosis and cell cycle arrest at G2/M phase in a concentration-dependent manner. Docking results indicated that compound 3d fitted well into the MDM2 active site 1RV1 by interacting with Lys94 and Thr101 residues. (C) 2015 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.
• Synthesis, In Vitro Anti-HIV Activity, Cytotoxicity, and Computational Studies of Some New Steroids and Their Pyrazoline and Oxime Analogues
  作者：Wasfi A. Al-Masoudi、Najim A. Al-Masoudi、Bahjat A. Saeed、Rainer Winter、Christophe Pannecouque

  DOI：10.1134/s1068162020050039

  日期：2020.9

  respectively. Analogously, treatment of 3-((4-bromophenyl)-1-(preg-5-en-3β-ol-17-yl)prop-2-en-1-one with hydroxylamine afforded the Z/E isomers of 3-(4-bromophenyl)-1-(preg-5-en-3β-ol-17-yl)prop-2-en-1-one oxime. The new compounds were assayed against HIV-1 and HIV-2 in MT-4 cells. Compounds 3-(thiophene-2-yl)-1-(preg-5-en-3β-ol-17-yl)prop-2-en-1-one and 1-O-acetyl-(5-(4-bromophenyl)-3-(preg-5-en-3β-ol-17-yl)-4

  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