((S)-N-(triphenylmethyl)aziridine)-2-hydrazide

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: ((S)-N-(triphenylmethyl)aziridine)-2-hydrazide
• 英文别名: (2S)-1-tritylaziridine-2-carbohydrazide
• 化学式: C₂₂H₂₁N₃O
• 分子量: 343.428
• InChiKey: JTEPYNMZOMXNHE-JINQPTGOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  26
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  58.1
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  ((S)-N-(triphenylmethyl)aziridine)-2-hydrazide 、 异氰酸正丁酯 以 二氯甲烷 为溶剂， 反应 1.0h， 以98%的产率得到1-butyl-3-[[(2S)-1-tritylaziridine-2-carbonyl]amino]urea
  参考文献：
  名称：

  Synthesis and evaluation of the catalytic properties of semicarbazides derived from N-triphenylmethyl-aziridine-2-carbohydrazides

  摘要：

  A straightforward synthesis of a series of new catalysts derived from N-triphenylmethyl-aziridine-2-carbohydrazides is described. The new compounds have been tested for the enantioselective addition of diethyl- and phenylethynylzinc to aryl and alkyl aldehydes, which afforded the corresponding chiral alcohols in high chemical yields (up to 92%) and with excellent ee's of approximately 90%. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2013.09.006
• 作为产物：
  描述：

  (S)-(-)-1-三苯甲基-2-氮丙啶羧酸甲酯 在 一水合肼 作用下， 以 二氯甲烷 为溶剂， 反应 16.0h， 以90%的产率得到((S)-N-(triphenylmethyl)aziridine)-2-hydrazide
  参考文献：
  名称：

  Synthesis and evaluation of the catalytic properties of semicarbazides derived from N-triphenylmethyl-aziridine-2-carbohydrazides

  摘要：

  A straightforward synthesis of a series of new catalysts derived from N-triphenylmethyl-aziridine-2-carbohydrazides is described. The new compounds have been tested for the enantioselective addition of diethyl- and phenylethynylzinc to aryl and alkyl aldehydes, which afforded the corresponding chiral alcohols in high chemical yields (up to 92%) and with excellent ee's of approximately 90%. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2013.09.006

文献信息

• Autophagy Inhibition with Chloroquine Increased Pro-Apoptotic Potential of New Aziridine-Hydrazide Hydrazone Derivatives against Glioblastoma Cells
  作者：Monika Witusik-Perkowska、Pola Głowacka、Adam M. Pieczonka、Ewa Świderska、Agnieszka Pudlarz、Michał Rachwalski、Julia Szymańska、Magdalena Zakrzewska、Dariusz J. Jaskólski、Janusz Szemraj

  DOI：10.3390/cells12141906

  日期：——

  significant increase in apoptosis triggered by the tested compounds, as well as temozolomide. The new aziridine–hydrazide hydrazone derivatives, which present cytotoxic potential against glioblastoma cells comparable to or even higher than that of temozolomide, show promising results and, thus, should be further investigated as antineoplastic agents. Moreover, our findings suggest that the combination

  由于治疗引起的不良副作用（例如促存活自噬或细胞衰老）而导致肿瘤治疗逃避，是最终导致肿瘤休眠和复发的关键耐药机制之一。胶质母细胞瘤是中枢神经系统最常见且几乎无法治愈的肿瘤。因此，已经研究了新的治疗方式，以找到比目前采用的基于替莫唑胺的标准更有效的解决方案。本研究检查了新合成的氮丙啶-酰肼腙衍生物化合物，以确定它们在体外对胶质母细胞瘤细胞的抗肿瘤潜力。尽管我们的研究结果清楚地表明了它们的促凋亡活性，但细胞毒性作用似乎被治疗诱导的自噬所阻断，在替莫唑胺作用的情况下也检测到了这种现象。添加自噬抑制剂氯喹会导致测试化合物以及替莫唑胺引发的细胞凋亡显着增加。新的氮丙啶-酰肼腙衍生物对胶质母细胞瘤细胞的细胞毒性潜力与替莫唑胺相当甚至更高，显示出有希望的结果，因此应该作为抗肿瘤药物进行进一步研究。此外，我们的研究结果表明，凋亡诱导剂与自噬抑制剂的组合可以优化化疗效率，并且添加自噬抑制剂应被视为一种可选的辅
• Synthesis and evaluation of the catalytic properties of semicarbazides derived from N-triphenylmethyl-aziridine-2-carbohydrazides
  作者：Stanisław Leśniak、Adam M. Pieczonka、Szymon Jarzyński、Katarzyna Justyna、Michał Rachwalski

  DOI：10.1016/j.tetasy.2013.09.006

  日期：2013.10

  A straightforward synthesis of a series of new catalysts derived from N-triphenylmethyl-aziridine-2-carbohydrazides is described. The new compounds have been tested for the enantioselective addition of diethyl- and phenylethynylzinc to aryl and alkyl aldehydes, which afforded the corresponding chiral alcohols in high chemical yields (up to 92%) and with excellent ee's of approximately 90%. (C) 2013 Elsevier Ltd. All rights reserved.