N-(6-chlorobenzothiazol-2-yl)-2-hydrazinylacetamide | 1620996-28-2

• 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: N-(6-chlorobenzothiazol-2-yl)-2-hydrazinylacetamide
• CAS: 1620996-28-2
• 化学式: C₉H₉ClN₄OS
• 分子量: 256.716
• InChiKey: HTSVUXODZAOUFO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.35
• 重原子数：
  16.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  80.04
• 氢给体数：
  3.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  N-(6-chlorobenzothiazol-2-yl)-2-hydrazinylacetamide 、 乙氧基亚甲基丙二腈 在 potassium carbonate 作用下， 以 乙醇 为溶剂， 反应 8.0h， 以49%的产率得到2-(5-amino-4-cyano-1H-pyrazol-1-yl)-N-(6-chlorobenzothiazol-2-yl)acetamide
  参考文献：
  名称：

  Synthesis and in vitro antitumor activity of new series of benzothiazole and pyrimido[2,1-b]benzothiazole derivatives

  摘要：

  New series of benzothiazole and pyrimido[2,1-b]benzothiazole derivatives were synthesized and characterized by analytical and spectrometrical methods (IR, HRMS, H-1 and C-13 NMR). Nineteen of the synthesized compounds were selected by the National Cancer Institute (NCI), USA, to be screened for their antitumor activity at a single dose (10 mu M) against a panel of 60 cancer cell lines. The most active compounds, 4, 6, 10, 14, 17 and 20 were selected for further evaluation at five dose level screening. Compounds 17 (GI(50) = 0.44 mu M, TGI = 1.2 mu M and LC50 MG-MID = 6.6 mu M) and 4 (GI(50) = 0.77 mu M, TGI = 2.08 mu M and LC50 MG-MID = 11.74 mu M) were proved to be the most active members in this study. 3D and 2D pharmacophoric maps for the structural features of both compounds were studied. (C) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2014.07.097
• 作为产物：
  描述：

  2-chloro-N-(6-chlorobenzo[d]thiazol-2-yl)acetamide 在 一水合肼 作用下， 以 乙醇 为溶剂， 生成 N-(6-chlorobenzothiazol-2-yl)-2-hydrazinylacetamide
  参考文献：
  名称：

  Synthesis and in vitro antitumor activity of new series of benzothiazole and pyrimido[2,1-b]benzothiazole derivatives

  摘要：

  New series of benzothiazole and pyrimido[2,1-b]benzothiazole derivatives were synthesized and characterized by analytical and spectrometrical methods (IR, HRMS, H-1 and C-13 NMR). Nineteen of the synthesized compounds were selected by the National Cancer Institute (NCI), USA, to be screened for their antitumor activity at a single dose (10 mu M) against a panel of 60 cancer cell lines. The most active compounds, 4, 6, 10, 14, 17 and 20 were selected for further evaluation at five dose level screening. Compounds 17 (GI(50) = 0.44 mu M, TGI = 1.2 mu M and LC50 MG-MID = 6.6 mu M) and 4 (GI(50) = 0.77 mu M, TGI = 2.08 mu M and LC50 MG-MID = 11.74 mu M) were proved to be the most active members in this study. 3D and 2D pharmacophoric maps for the structural features of both compounds were studied. (C) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2014.07.097

文献信息

• Structure-based drug design and biological evaluation of 2-acetamidobenzothiazole derivative as EGFR kinase inhibitor
  作者：Moustafa T. Gabr、Nadia S. El-Gohary、Eman R. El-Bendary、Mohamed M. El-Kerdawy

  DOI：10.3109/14756366.2014.887707

  日期：2015.1.2

  EGFR tyrosine kinase has been reported mainly in 40-80% of non-small lung cancers, in addition to colon and breast cancers. In this study, we illustrate the synthesis of a highly potent antitumor agent. The synthesized compound 4 was screened at NCI, USA, for antitumor activity against non-small lung cancer, colon cancer and breast cancer cell lines. Results indicated that this compound is more potent antitumor agent compared to erlotinib against all tested cell lines except breast cancer (MDA-MB-468) cell line. In addition, it was tested initially at a single dose concentration of 100 mu M over 11 different kinases. At this concentration, 94.45% inhibition of the enzymatic activity of EGFR kinase was observed, while the inhibition in activity was below 55% in all other kinases. Compound 4 was further tested in a 10-dose IC50 mode and showed IC50 value of 0.239 mu M for EGFR kinase. In vivo acute toxicity of this compound was also tested.