2-(2-benzothiazole)-5-methyl-1H-isoindole-1,3(2H)-dione | 1246199-70-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: 2-(2-benzothiazole)-5-methyl-1H-isoindole-1,3(2H)-dione
• 英文别名: 2-benzothiazol-2-yl-5-methyl-isoindole-1,3-dione；2-(1,3-Benzothiazol-2-yl)-5-methylisoindole-1,3-dione
• CAS: 1246199-70-1
• 化学式: C₁₆H₁₀N₂O₂S
• 分子量: 294.334
• InChiKey: GNVDIPJEEFMNJU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  21
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  78.5
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2-氨基苯并噻唑 、 4-甲基苯酐 反应 4.0h， 以76%的产率得到2-(2-benzothiazole)-5-methyl-1H-isoindole-1,3(2H)-dione
  参考文献：
  名称：

  Synthesis and anti-angiogenic activity of benzothiazole, benzimidazole containing phthalimide derivatives

  摘要：

  Benzothiazole and benzimidazole containing phthalimide derivatives (NK037, NK041, NK042, NK0139A and NK0148) have been synthesized and their anti-angiogenic activity was evaluated using ex vivo egg yolk angiogenesis model. A comparative study with pure thalidomide (NKTA) has also been performed to describe the efficacy of these derivatives in blocking angiogenesis. NK037, NK041 and NK042 were equally potent in blocking egg yolk angiogenesis and the anti-angiogenesis effect was higher than NKTA suggesting the efficacy of these three derivatives in blocking angiogenesis when compare to control. Other two derivatives NK0139A and NK0148 showed effect less than NKTA and stronger than control in ex vivo angiogenesis. (c) 2012 Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmcl.2012.10.106

文献信息

• Therapeutic effects of cantharidin analogues without bridging ether oxygen on human hepatocellular carcinoma cells
  作者：Chao-Bin Yeh、Chi-Jung Su、Jin-Ming Hwang、Ming-Chih Chou

  DOI：10.1016/j.ejmech.2010.05.053

  日期：2010.9

  Previous research indicates that cantharidin, norcantharidin and their analogues exhibit anticancer activity due to their inhibition of cancer cell lines such as HL60, HT29 and L1210. The anticancer activities of cantharidin, norcantharidin and their analogues involve the suppression of serine/threonine protein phosphatases (PPs) activity. However, cantharidin is not suitable for cancer therapy because of its high cytotoxicity in vitro (IC(50) = 21 mu M in primary cultured rat hepatocytes). In this study, synthetic cantharidin analogues with a structure of aminothiazole compounds 3-9 and a structure of anhydride compounds 10-12 were screened for anticancer activities and cytotoxic effects on human hepatocellular carcinoma cell (HCC) lines HepG2, Sk-Hep1, and primary cultured rat hepatocytes. Experimental results indicated that compounds 3-9 did not perform as expected with regard to anticancer activity and exhibited lower cytotoxicity. Compound 10 promoted apoptosis in HepG2 (IC(50) = 62 mu M) and SK-Hep1 (IC(50) = 151 mu M) cell lines. Compounds 11 and 12 had anticancer potential similar to that of compound 10. After treatment with compounds 3-12, primary cultured rat hepatocytes exhibited no cytotoxicity (IC(50) > 200 mu M). By investigating the structure activity relationship (SAR) of these analogues as a whole, this study suggests that the anhydride ether oxygen such as in cantharidin, norcantharidin and compounds 10-12 may be correlated with HCC survival suppression. The results further suggest that the elimination of bridging ether oxygen on the ring, such as in compounds 10-12, can decrease cytotoxicity. (C) 2010 Elsevier Masson SAS. All rights reserved.