3β-hydroxypregn-5-en-20-one hydrazone | 86770-54-9

• 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: 3β-hydroxypregn-5-en-20-one hydrazone
• 英文别名: pregnenolone hydrazone；(-)-3β-Hydroxy-20-hydrazono-pregnen-(5)；(3S,8S,9S,10R,13S,14S,17S)-17-ethanehydrazonoyl-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-ol
• CAS: 86770-54-9
• 化学式: C₂₁H₃₄N₂O
• 分子量: 330.514
• InChiKey: LQOFLKGYBOYGQI-QGVNFLHTSA-N

物化性质

• 沸点：
  480.5±55.0 °C(Predicted)
• 密度：
  1.25±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  24
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  58.6
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3β-hydroxypregn-5-en-20-one hydrazone 在 1,1,2,3-四甲基胍 、 碘 作用下， 以 甲苯 为溶剂， 反应 0.25h， 以80%的产率得到20-iodo-3β-hydroxypregna-5,20-diene
  参考文献：
  名称：

  一种改进的碘乙烯制备方法

  摘要：

  在碱存在下用碘氧化酮可提供乙烯基碘。造成这种情况的三个因素是：（1）没有水；（2）使用强胍碱；（3）反加。

  DOI：

  10.1016/s0040-4039(00)81721-9
• 作为产物：
  描述：

  孕烯醇酮醋酸酯 在 hydrazine hydrate 、 三乙胺 作用下， 以 乙醇 为溶剂， 反应 2.5h， 以89%的产率得到3β-hydroxypregn-5-en-20-one hydrazone
  参考文献：
  名称：

  通过钯催化的氨基羰基化反应合成基于孕烷的新型20-羧酰胺

  摘要：

  由广泛可得的3β-乙酰氧基-pregn-5,16-合成20-羧酰胺基孕烯衍生物，例如3β-乙酰氧基-5α-pregn-20-ene-20-羧酰胺和5α-pregn-20-ene-20-羧酰胺。 Dien-20-one（PDA）使用选择性加氢，肼和碘代烯烃的形成，以及钯催化的氨基羰基化。通过相应的20酮从相应的20-酮衍生物获得的20-碘-20-烯衍生物用作底物。使用各种氮素获得了23种新的20-羧酰胺-亲核试剂，范围从简单的伯胺到α-氨基酸酯。这种方法的新颖之处在于应用轻度，中度或高产率的反应来获得原本难以获得的具有药学重要性的甾族20-羧酰胺。换句话说，代替了例如甾醇或胆酸的酶促或合成降解，使用了基本骨架的功能化（“积累”方法）。

  DOI：

  10.1007/s11696-020-01478-7

文献信息

• Synthesis of N-picolylcarboxamides in aminocarbonylation
  作者：Gábor Mikle、Fanni Bede、László Kollár

  DOI：10.1016/j.tet.2021.132128

  日期：2021.5

  presence of 2-, 3- and 4-picolylamine, as well as secondary amines possessing 1-picolyl substituent. In general, primary picolylamines require less than 2 h to achieve practically complete conversion. The secondary amines proved to be less reactive, requiring 6–24 h depending on the substrate structure. The corresponding carboxamides were isolated in moderate to excellent yields. The synthesis of α,β-unsaturated

  在2-，3-和4-吡啶甲基胺以及具有1-吡啶甲基取代基的仲胺存在下，进行钯催化的碘樟脑和甾体碘代烯烃的氨基羰基化。通常，伯甲基吡啶胺需要少于2小时才能实现几乎完全的转化。仲胺被证明反应性较低，需要6-24小时，具体取决于底物结构。分离出相应的羧酰胺，产率中等至优异。α，β-不饱和羧酰​​胺的合成是基于由可烯醇化的酮合成碘代烯烃底物。
• Amino- and azidocarbonylation of iodoalkenes
  作者：Gábor Mikle、Rita Skoda-Földes、László Kollár

  DOI：10.1016/j.tet.2021.132495

  日期：2021.11

  on the structure of the acyl azides, consecutive hydrolysis toward corresponding primary amides was observed. ‘Direct’ aminocarbonylation of the same iodoalkenes was also carried out by using ammonium carbamate as ammonia source under mild conditions. The α,β-unsaturated primary amides, formed in a chemoselective reaction, were isolated in good to excellent yields.

  碘代烯烃可通过其腙从酮中获得，经过钯催化的叠氮羰基化。根据酰基叠氮化物的结构，观察到连续水解为相应的伯酰胺。在温和条件下，使用氨基甲酸铵作为氨源也可以进行相同碘代烯烃的“直接”氨基羰基化。在化学选择性反应中形成的 α,β-不饱和伯酰胺以良好至极好的产率分离。
• Synthesis of Some Steroidal Derivatives with Side Chain of 20- and 22- Hydrazone Aromatic Heterocycles and their Antiproliferative Activity
  作者：Chunfang Gan、Liang Liu、Jianguo Cui、Zhiping Liu、Haixin Shi、Qifu Lin、Haibing Sheng、Chunhui Yang、Yanmin Huang

  DOI：10.2174/1573406413666161205121039

  日期：2017.5.5

  vitro was evaluated against human HT-29, HeLa, Bel 7404 and SGC 7901 cancer cells by MTT assays. Results: The steroidal compounds with side chain of 20-hydrazone aromatic cycles or heterocycles exhibited distinct cytotoxicity. However, analogues with the side chain of 22-hydrazone resulted in a dramatic decrease of the cytotoxicity. The result of Annexin V assay showed that the 20-hydrazone compounds

  背景：类固醇结构的修饰通常用于改变类固醇在药物化学中的生物活性。一些含有杂环的类固醇对各种癌细胞系表现出明显的细胞毒性，多年来，药物化学家已广泛关注药物发现。 方法：以孕烯醇酮和豆甾醇为原料，通过不同的化学反应，合成了结构侧链为20和22 aromatic的芳香环或杂环的两个系列的类固醇，并通过IR，NMR和HRMS进行了表征。通过MTT分析评估了化合物在体外对人HT-29，HeLa，Bel 7404和SGC 7901癌细胞的抗增殖活性。 结果：具有20 aromatic芳香环或杂环侧链的甾体化合物具有明显的细胞毒性。然而，具有22-侧链的类似物导致细胞毒性的显着降低。Annexin V测定的结果表明20hydr化合物是针对这些癌细胞的有效的凋亡诱导剂。 结论：具有20 aromatic芳香杂环侧链的甾族化合物在体外具有独特的抗增殖活性。然而，具有22-芳族杂环的侧链的化合物降低了该化合物的细胞毒性。
• 孕烯醇酮芳香醛吖嗪甾体化合物及其合成方法 和在制备抗肿瘤药物中的应用
  申请人：广西师范学院

  公开号：CN103254264B

  公开（公告）日：2016-04-06

  一类具有吖嗪结构的孕烯醇酮芳香醛吖嗪甾体化合物，化学结构式如下所示：实验证明本发明的孕烯醇酮芳香醛吖嗪甾体化合物对多种肿瘤细胞株具有明显的抑制作用，可用于制备治疗癌症的药物。
• Synthesis and Evaluation of Pregnane Derivatives as Inhibitors of Human Testicular 17α-Hydroxylase/C_17,20-Lyase^,
  作者：Ji-song Li、Yan Li、Chong Son、Angela M. H. Brodie

  DOI：10.1021/jm960245f

  日期：1996.1.1

  The pregnene derivatives with modifications at the 17,20-side chain and D-ring were synthesized and evaluated as inhibitors of human testicular 17 alpha-hydroxylase/C-17,C-20-lyase. The results demonstrate that compounds which have 20-substituents with moderate to strong dipole properties, such as 20-oxime (3, 20), 20 beta-ol (24, 30), and 20 beta-carboxaldehyde (27), are potent inhibitors of this enzyme complex. The 20-substituents with hydrophobic property were devoid of inhibitory activity, e.g., the dimethylhydrazones 8 and 9. The 16-ene together with 20-oxime (20) showed the most potent inhibition of this enzyme complex, whereas 17(20)-ene modification as in 17(20)-ene-20-carbonitrile (14) did not increase activity in comparison to the 20 beta-carbonitrile (16). The bioisostere of 27 with 20-aza (19) also reduced the inhibitory activity. The results showed that isomeric configurations at the 20-position of some steroidal compounds are important factors which influence the potency of the inhibition significantly (e.g., 20 beta-ols 24 and 30 were 3-5-fold more potent than 20 alpha-ols 23 and 29). As expected, some compounds based on the pregn-5-en-3 beta-ol skeleton, which is similar to the natural substrate of human testicular 17 alpha-hydroxylase/C-17,C-20-lyase in A- and B-rings, showed more potent inhibition than similar compounds which are based on the pregn-4-en-3-one skeleton (e.g., 23-25 compared to 29-31). These results suggest that A- and B-rings make significant contributions to the binding of these steroidal compounds to the 17 alpha-hydroxylase and C-17,C-20-lyase. In comparison to ketoconazole, a nonsteroidal inhibitor of 17 alpha-hydroxylase and C-17,C-20-lyase which has been used in the treatment of prostatic cancer, the steroidal compounds 20, 24, and 27 demonstrate more potent inhibition for this enzyme complex. These inhibitors warrant further investigation in biological systems. The structural features of these compounds may serve as leads in the design of new inhibitors.