methyl 2-(2-hydroxy-phenyl)-benzooxazole-7-carboxylate | 819071-06-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: methyl 2-(2-hydroxy-phenyl)-benzooxazole-7-carboxylate
• 英文别名: Methyl 2-(6-oxocyclohexa-2,4-dien-1-ylidene)-2,3-dihydro-1,3-benzoxazole-7-carboxylate；methyl 2-(2-hydroxyphenyl)-1,3-benzoxazole-7-carboxylate
• CAS: 819071-06-2
• 化学式: C₁₅H₁₁NO₄
• 分子量: 269.257
• InChiKey: MPGCBKITOBODHY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  72.6
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  2-甲氧基苯甲酸甲酯 在 吡啶 、 sodium hydroxide 、 草酰氯 、 对甲苯磺酸 、 N,N-二甲基甲酰胺 作用下， 以 甲醇 、 二氯甲烷 、 xylene 为溶剂， 反应 101.0h， 生成 methyl 2-(2-hydroxy-phenyl)-benzooxazole-7-carboxylate
  参考文献：
  名称：

  Synthesis and anticancer evaluation of bis(benzimidazoles), bis(benzoxazoles), and benzothiazoles

  摘要：

  Four classes of UK-1 analogues were synthesized and their cytotoxicity testing against human A-549, BFTC-905, RD, MES-SA, and HeLa carcinoma cell lines was determined. The results revealed that UK-1 and four of these analogues (15-18) are potent against the cancer cell lines. In particular, compound 16 is more potent than UK-1 against A-549 and HeLa cell lines, and compounds 15, 17, and 18 selectively exhibit potent cytotoxic activity against the BFTV-905 cells (IC50 9.6 PM), A-549 cells (IC50 6.6 mu M), and MES-SA cells (IC50 9.2 mu M),respectively. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2006.05.007

文献信息

• UK-1 analogues: methods of preparation and use
  申请人：Kerwin M. Sean

  公开号：US20050004188A1

  公开（公告）日：2005-01-06

  The present invention includes a number of structural analogues of UK-1. A comparision of the anticancer activity of the UK-1 analogues with their ability to inhibit the growth of methicillin-sensitive and methicillin-resistant Staphylococcus aureus demonstrates that a structurally simplified analogue of UK-1 retains the natural product's selective activity against cancer cells. Structurally conservative changes to UK-1 that diminish Mg 2+ -binding ability may result in a dramatic decrease in cancer cell cytotoxicity. The results may establish a minimum structural pharmacophore as well as a functional role for Mg 2+ -binding in the selective cytotoxicity of UK-1.

  本发明包括多个UK-1的结构类似物。将UK-1类似物的抗癌活性与其抑制甲氧西林敏感和甲氧西林耐药的金黄色葡萄球菌生长的能力进行比较，结果表明UK-1的一个结构简化类似物保留了该天然产物对癌细胞的选择性活性。对UK-1的结构保守性改变可能会降低其与Mg2+结合的能力，从而导致对癌细胞的细胞毒性显著降低。结果可能确定了最小的结构药效团以及Mg2+结合在UK-1的选择性细胞毒性中的功能角色。
• US7294643B2
  申请人：——

  公开号：US7294643B2

  公开（公告）日：2007-11-13