4-chloromethyl-2-[2-(p-toluenesulfonyl)-hydrazino]-thiazole | 1256585-54-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4-chloromethyl-2-[2-(p-toluenesulfonyl)-hydrazino]-thiazole
• 英文别名: N'-[4-(chloromethyl)-1,3-thiazol-2-yl]-4-methylbenzenesulfonohydrazide
• CAS: 1256585-54-2
• 化学式: C₁₁H₁₂ClN₃O₂S₂
• 分子量: 317.82
• InChiKey: KLEPUAKBOWHJJR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  108
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  4-chloromethyl-2-[2-(p-toluenesulfonyl)-hydrazino]-thiazole 、 乙酸酐 在 吡啶 作用下， 以65.43%的产率得到4-chloromethyl-2-[2-(p-toluenesulfonyl)-N,N'-diacetyl-hydrazino]-thiazole
  参考文献：
  名称：

  Synthesis of some p-toluenesulfonyl-hydrazinothiazoles and hydrazino-bis-thiazoles and their anticancer activity

  摘要：

  A series of novel p-toluenesulfonyl-hydrazinothiazoles and hydrazino-bis-thiazoles derivatives (2a-f,3a-f, and 5-8) were synthesized by initial condensation of p-toluenesulfonylthiosemicarbazide 1 with a series of alpha-halogenocarbonyls in acetone or dimethylformamide (DMF)/acetone, mixture. All our synthesized compounds were submitted for further acylation reaction in the presence of acetic anhydride. The structures of newly synthesized derivatives 2a-f, 3a-f and 5-8 were confirmed by IR, H-1-NMR, EIMS spectral data and elemental analysis. Compounds 2a, 2c, 2d, 2e and 3a showed significant anticancer activities (IC50 < 10 mu M) on both prostate DU-145 and hepatocarcinoma Hep-G2 cancer cell lines. (C) 2010 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2010.08.017
• 作为产物：
  描述：

  1-(p-Toluolsulfonyl)-thiosemicarbazid 、 1,3-二氯丙酮 以 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 24.0h， 以66.23%的产率得到4-chloromethyl-2-[2-(p-toluenesulfonyl)-hydrazino]-thiazole
  参考文献：
  名称：

  Synthesis of some p-toluenesulfonyl-hydrazinothiazoles and hydrazino-bis-thiazoles and their anticancer activity

  摘要：

  A series of novel p-toluenesulfonyl-hydrazinothiazoles and hydrazino-bis-thiazoles derivatives (2a-f,3a-f, and 5-8) were synthesized by initial condensation of p-toluenesulfonylthiosemicarbazide 1 with a series of alpha-halogenocarbonyls in acetone or dimethylformamide (DMF)/acetone, mixture. All our synthesized compounds were submitted for further acylation reaction in the presence of acetic anhydride. The structures of newly synthesized derivatives 2a-f, 3a-f and 5-8 were confirmed by IR, H-1-NMR, EIMS spectral data and elemental analysis. Compounds 2a, 2c, 2d, 2e and 3a showed significant anticancer activities (IC50 < 10 mu M) on both prostate DU-145 and hepatocarcinoma Hep-G2 cancer cell lines. (C) 2010 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2010.08.017

文献信息

• Synthesis of some p-toluenesulfonyl-hydrazinothiazoles and hydrazino-bis-thiazoles and their anticancer activity
  作者：Valentin Zaharia、Adriana Ignat、Nicolae Palibroda、Bathélémy Ngameni、Victor Kuete、Charles N. Fokunang、Marlyse L. Moungang、Bonaventure T. Ngadjui

  DOI：10.1016/j.ejmech.2010.08.017

  日期：2010.11

  A series of novel p-toluenesulfonyl-hydrazinothiazoles and hydrazino-bis-thiazoles derivatives (2a-f,3a-f, and 5-8) were synthesized by initial condensation of p-toluenesulfonylthiosemicarbazide 1 with a series of alpha-halogenocarbonyls in acetone or dimethylformamide (DMF)/acetone, mixture. All our synthesized compounds were submitted for further acylation reaction in the presence of acetic anhydride. The structures of newly synthesized derivatives 2a-f, 3a-f and 5-8 were confirmed by IR, H-1-NMR, EIMS spectral data and elemental analysis. Compounds 2a, 2c, 2d, 2e and 3a showed significant anticancer activities (IC50 < 10 mu M) on both prostate DU-145 and hepatocarcinoma Hep-G2 cancer cell lines. (C) 2010 Elsevier Masson SAS. All rights reserved.