16-formyl-17-chloroandrost-5,16-diene-3β-yl formate | 1470067-88-9

• 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: 16-formyl-17-chloroandrost-5,16-diene-3β-yl formate
• 英文别名: [(3S,8R,9S,10R,13S,14S)-17-chloro-16-formyl-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15-decahydro-1H-cyclopenta[a]phenanthren-3-yl] formate
• CAS: 1470067-88-9
• 化学式: C₂₁H₂₇ClO₃
• 分子量: 362.897
• InChiKey: JMCXQGKLIPPKAT-QWSDNZPMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  25
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  吡唑 、 16-formyl-17-chloroandrost-5,16-diene-3β-yl formate 在 caesium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 生成
  参考文献：
  名称：

  Cytotoxic effect of novel dehydroepiandrosterone derivatives on different cancer cell lines

  摘要：

  The aim of this study was to determine the cytotoxic effect of human cancer cells on three series of novel dehydroepiandrosterone derivatives containing triazole or pyrazole rings at C-17 and an ester moiety at C-3 of the androstane skeleton. The panel cancer cells used in this study were the following: PC-3, MCF-7 and SKLU-1.The results from this study indicated that the steroidal derivatives 4a-4e and 4f-4k showed the highest cytotoxic potency. This difference in this activity could be attributed to the ability of the triazole (three nitrogen atoms) to form stronger hydrogen bonds with the active site of the cell as compared to the pyrazole group having two nitrogen atoms.Compounds 4f-4k having an aromatic ester at C-3 showed an enhanced cytotoxic activity as compared to their aliphatic counterparts 4a-4e. Apparently the electronegative phenyl ring increased the polarity of the molecule, thus increasing the dipole dipole association of the steroidal molecule with the reactive site of the cell. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.02.031
• 作为产物：
  描述：

  醋酸去氢表雄酮 在 sodium hydroxide 、 三氯氧磷 作用下， 以 甲醇 、 氯仿 为溶剂， 反应 10.0h， 生成 16-formyl-17-chloroandrost-5,16-diene-3β-yl formate
  参考文献：
  名称：

  新型脱氢表雄酮苯并咪唑基衍生物作为5α-还原酶同工酶抑制剂。

  摘要：

  5α-R同工酶（1型和2型）在前列腺发育中起重要作用，因为当生理性血清睾丸激素（T）浓度低时，它们负责前列腺内二氢睾丸激素（DHT）的水平。在这项研究中，我们合成了7个在C-17上具有苯并咪唑部分的新型脱氢表雄酮衍生物，并确定了它们对1α和2型5α-还原酶活性的影响。抑制5α-R1活性，而那些在C-3上带有脂环族酯（环丙基，环丁基或环戊基环）或醇基的化合物抑制两种同工酶的活性。在C-3处具有环己基或环庚基酯的衍生物没有抑制活性。在药理实验中 具有C 3-3的具有醇或脂族基团的酯或三个较小的脂环族环之一的酯的衍生物降低了雄性仓鼠胁腹器官的直径，其中环丁酯和环戊基酯显示出更高的作用。除环丁酯和环戊酯外，这些化合物可减轻前列腺和精囊的重量。

  DOI：

  10.3109/14756366.2015.1070843

文献信息

• 一种甾体衍生物及其制备方法和应用、抗肿瘤药物组合物
  申请人：长治学院

  公开号：CN114751954A

  公开（公告）日：2022-07-15

  本发明属于药物合成技术领域，具体涉及一种甾体衍生物及其制备方法和应用、抗肿瘤药物组合物。本发明提供的甾体衍生物具有良好的抗肿瘤细胞增殖活性，在5μM浓度下对癌细胞的抑制率在85％以上，对A549(人肺腺癌细胞)、Hela(子宫颈癌细胞系)、HepG2(人肝癌细胞)三种肿瘤细胞均有很好的细胞毒性，对三种癌细胞的毒性优于顺铂。
• Cytotoxic effect of novel dehydroepiandrosterone derivatives on different cancer cell lines
  作者：Mariana Garrido、Marisa Cabeza、Francisco Cortés、José Gutiérrez、Eugene Bratoeff

  DOI：10.1016/j.ejmech.2013.02.031

  日期：2013.10

  The aim of this study was to determine the cytotoxic effect of human cancer cells on three series of novel dehydroepiandrosterone derivatives containing triazole or pyrazole rings at C-17 and an ester moiety at C-3 of the androstane skeleton. The panel cancer cells used in this study were the following: PC-3, MCF-7 and SKLU-1.The results from this study indicated that the steroidal derivatives 4a-4e and 4f-4k showed the highest cytotoxic potency. This difference in this activity could be attributed to the ability of the triazole (three nitrogen atoms) to form stronger hydrogen bonds with the active site of the cell as compared to the pyrazole group having two nitrogen atoms.Compounds 4f-4k having an aromatic ester at C-3 showed an enhanced cytotoxic activity as compared to their aliphatic counterparts 4a-4e. Apparently the electronegative phenyl ring increased the polarity of the molecule, thus increasing the dipole dipole association of the steroidal molecule with the reactive site of the cell. (C) 2013 Elsevier Masson SAS. All rights reserved.
• Novel dehydroepiandrosterone benzimidazolyl derivatives as 5<b>α</b>-reductase isozymes inhibitors
  作者：Yazmín Arellano、Eugene Bratoeff、Tania Segura、Maria Eugenia Mendoza、Araceli Sánchez-Márquez、Yesica Medina、Yvonne Heuze、Juan Soriano、Marisa Cabeza

  DOI：10.3109/14756366.2015.1070843

  日期：2016.11.1

  5α-reductase types 1 and 2. The derivatives with an aliphatic ester at C-3 of the dehydroepiandrosterone scaffold induced specific inhibition of 5α-R1 activity, whereas those with a cycloaliphatic ester (cyclopropyl, cyclobutyl, or cyclopentyl ring) or an alcohol group at C-3 inhibited the activity of both isozymes. Derivatives with a cyclohexyl or cycloheptyl ester at C-3 showed no inhibitory activity. In pharmacological

  5α-R同工酶（1型和2型）在前列腺发育中起重要作用，因为当生理性血清睾丸激素（T）浓度低时，它们负责前列腺内二氢睾丸激素（DHT）的水平。在这项研究中，我们合成了7个在C-17上具有苯并咪唑部分的新型脱氢表雄酮衍生物，并确定了它们对1α和2型5α-还原酶活性的影响。抑制5α-R1活性，而那些在C-3上带有脂环族酯（环丙基，环丁基或环戊基环）或醇基的化合物抑制两种同工酶的活性。在C-3处具有环己基或环庚基酯的衍生物没有抑制活性。在药理实验中 具有C 3-3的具有醇或脂族基团的酯或三个较小的脂环族环之一的酯的衍生物降低了雄性仓鼠胁腹器官的直径，其中环丁酯和环戊基酯显示出更高的作用。除环丁酯和环戊酯外，这些化合物可减轻前列腺和精囊的重量。