tert-butyl 2-(5-chloro-2-oxoindolin-3-ylidene)hydrazinecarboxylate

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: tert-butyl 2-(5-chloro-2-oxoindolin-3-ylidene)hydrazinecarboxylate
• 英文别名: tert-butyl N-[(5-chloro-2-oxoindol-3-yl)amino]carbamate
• 化学式: C₁₃H₁₄ClN₃O₃
• 分子量: 295.725
• InChiKey: APUUSKGGUJUXSY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.52
• 重原子数：
  20.0
• 可旋转键数：
  1.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  79.79
• 氢给体数：
  2.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  tert-butyl 2-(5-chloro-2-oxoindolin-3-ylidene)hydrazinecarboxylate 在 劳森试剂 作用下， 以 5,5-dimethyl-1,3-cyclohexadiene 为溶剂， 以87%的产率得到tert-butyl 2-(5-chloro-2-thioxoindolin-3-ylidene)hydrazinecarboxylate
  参考文献：
  名称：

  The new facile and straightforward method for the synthesis of 4 H -1,2,3-thiadiazolo[5,4- b ]indoles and determination of their antiproliferative activity

  摘要：

  A series of 4H-1,2,3-thiadiazolo[5,4-b]indoles were synthesized by novel tandem of oxidative cyclization of 3-alkoxycarbonylhydrazonoindoline-2-thiones, 1,5-H-shift and elimination of tert-butoxy(ethoxy) carbonyl group. The simple method for their modifications by the reactions with electrophilic agents were elaborated and as a result of the synthetic investigation a number of N-alkyl-, N-acyl- and N-sulfonyl-4H-1,2,3-thiadiazolo[5,4-b]indoles were prepared in good yields. Preliminary biological tests for the three examples of synthesized compounds with different substituents at the nitrogen atom indole ring have shown that the biological behavior of the investigated 1,2,3-thiadiazolo[5,4-b]indoles is substantially directed by this structural fragment. (C) 2015 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2015.11.011
• 作为产物：
  描述：

  肼基甲酸叔丁酯 、 5-氯靛红 以 乙醇 为溶剂， 以83%的产率得到tert-butyl 2-(5-chloro-2-oxoindolin-3-ylidene)hydrazinecarboxylate
  参考文献：
  名称：

  The new facile and straightforward method for the synthesis of 4 H -1,2,3-thiadiazolo[5,4- b ]indoles and determination of their antiproliferative activity

  摘要：

  A series of 4H-1,2,3-thiadiazolo[5,4-b]indoles were synthesized by novel tandem of oxidative cyclization of 3-alkoxycarbonylhydrazonoindoline-2-thiones, 1,5-H-shift and elimination of tert-butoxy(ethoxy) carbonyl group. The simple method for their modifications by the reactions with electrophilic agents were elaborated and as a result of the synthetic investigation a number of N-alkyl-, N-acyl- and N-sulfonyl-4H-1,2,3-thiadiazolo[5,4-b]indoles were prepared in good yields. Preliminary biological tests for the three examples of synthesized compounds with different substituents at the nitrogen atom indole ring have shown that the biological behavior of the investigated 1,2,3-thiadiazolo[5,4-b]indoles is substantially directed by this structural fragment. (C) 2015 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2015.11.011

文献信息

• The new facile and straightforward method for the synthesis of 4 H -1,2,3-thiadiazolo[5,4- b ]indoles and determination of their antiproliferative activity
  作者：Nataliya P. Belskaya、Kseniya I. Lugovik、Vasiliy A. Bakulev、Jenny Bauer、Igor Kitanovic、Pavlo Holenya、Maksim Zakhartsev、Stefan Wölfl

  DOI：10.1016/j.ejmech.2015.11.011

  日期：2016.1

  A series of 4H-1,2,3-thiadiazolo[5,4-b]indoles were synthesized by novel tandem of oxidative cyclization of 3-alkoxycarbonylhydrazonoindoline-2-thiones, 1,5-H-shift and elimination of tert-butoxy(ethoxy) carbonyl group. The simple method for their modifications by the reactions with electrophilic agents were elaborated and as a result of the synthetic investigation a number of N-alkyl-, N-acyl- and N-sulfonyl-4H-1,2,3-thiadiazolo[5,4-b]indoles were prepared in good yields. Preliminary biological tests for the three examples of synthesized compounds with different substituents at the nitrogen atom indole ring have shown that the biological behavior of the investigated 1,2,3-thiadiazolo[5,4-b]indoles is substantially directed by this structural fragment. (C) 2015 Elsevier Masson SAS. All rights reserved.