6-bromo-4-(4-iodophenoxymethyl)chromen-2-one | 1574356-01-6

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 香豆素及其衍生物
• 英文名称: 6-bromo-4-(4-iodophenoxymethyl)chromen-2-one
• 英文别名: 6-Bromo-4-[(4-iodophenoxy)methyl]chromen-2-one；6-bromo-4-[(4-iodophenoxy)methyl]chromen-2-one
• CAS: 1574356-01-6
• 化学式: C₁₆H₁₀BrIO₃
• 分子量: 457.062
• InChiKey: YTIYQVMHQWQWRN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  6-bromo-4-(bromomethyl)-2H-chromen-2-one 、 4-碘苯酚 在 potassium carbonate 作用下， 以 丙酮 为溶剂， 反应 24.5h， 以66%的产率得到6-bromo-4-(4-iodophenoxymethyl)chromen-2-one
  参考文献：
  名称：

  Synthesis, structure–activity relationship of iodinated-4-aryloxymethyl-coumarins as potential anti-cancer and anti-mycobacterial agents

  摘要：

  A series of new iodinated-4-aryloxymethylcoumarins 6, 8 and 10 have been obtained from the reaction of various 4-bromomethylcoumarins 4 with 2-iodophenol 5, 3-iodophenol 7 and 4-iodophenol 9 respectively. All the title compounds were screened for anticancer activity against two cancer cell lines (MDA-MB human adenocarcinoma mammary gland and A-549 human lung carcinoma) and two mycobacterial strains (Mycobacterium tuberculosis H-37 RV and Mycobacterium phlei). The SAR results indicate that nine compounds are potent, among these 10h and 10i having chlorine are most effective. This is the first report assigning in vitro anti-mycobacterial, anticancer and structure activity relationship for this new class of iodinated-4-aryloxymethyl-coumarins. (C) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.12.061

文献信息

• Synthesis, structure–activity relationship of iodinated-4-aryloxymethyl-coumarins as potential anti-cancer and anti-mycobacterial agents
  作者：Mahantesha Basanagouda、Vishwanath B. Jambagi、Nivedita N. Barigidad、Sandeep S. Laxmeshwar、Venkatesh Devaru、Narayanachar

  DOI：10.1016/j.ejmech.2013.12.061

  日期：2014.3

  A series of new iodinated-4-aryloxymethylcoumarins 6, 8 and 10 have been obtained from the reaction of various 4-bromomethylcoumarins 4 with 2-iodophenol 5, 3-iodophenol 7 and 4-iodophenol 9 respectively. All the title compounds were screened for anticancer activity against two cancer cell lines (MDA-MB human adenocarcinoma mammary gland and A-549 human lung carcinoma) and two mycobacterial strains (Mycobacterium tuberculosis H-37 RV and Mycobacterium phlei). The SAR results indicate that nine compounds are potent, among these 10h and 10i having chlorine are most effective. This is the first report assigning in vitro anti-mycobacterial, anticancer and structure activity relationship for this new class of iodinated-4-aryloxymethyl-coumarins. (C) 2014 Elsevier Masson SAS. All rights reserved.