3-(6-bromo-4-oxo-4H-chromen-3-ylmethylene)-1-(2,6-dichlorophenyl)-1,3-dihydroindol-2-one | 1598426-35-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: 3-(6-bromo-4-oxo-4H-chromen-3-ylmethylene)-1-(2,6-dichlorophenyl)-1,3-dihydroindol-2-one
• CAS: 1598426-35-7
• 化学式: C₂₄H₁₂BrCl₂NO₃
• 分子量: 513.174
• InChiKey: DJEBOVUGDRHDPD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.08
• 重原子数：
  31.0
• 可旋转键数：
  2.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  50.52
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  1-(2,6-二氯苯基)-1,3-二氢-2H-吲哚-2-酮 、 6-溴-3-甲酰色酮 反应 0.02h， 以87%的产率得到3-(6-bromo-4-oxo-4H-chromen-3-ylmethylene)-1-(2,6-dichlorophenyl)-1,3-dihydroindol-2-one
  参考文献：
  名称：

  Rational design, synthesis and evaluation of chromone-indole and chromone-pyrazole based conjugates: Identification of a lead for anti-inflammatory drug

  摘要：

  Conjugates of chromone-indole and chromone-pyrazole were screened for cyclooxygenase-2 (COX-2), cyclooxygenase-1 (COX-1) and 5-lipoxygenase (5-LOX) inhibitory activities. Compounds 8 and 9 were identified as preferred inhibitors of COX-2 over the other two enzymes. Their IC50 for COX-2 was 29 nM and 20 nM, respectively and selectivity indices (SI) for COX-2 over COX-1 was 46 and 337. NMR, mass spectral studies and molecular modelling also indicated preferential interactions of compounds 8 and 9 with COX-2. Tested on albino mice against capsaicin induced algesia, compound 8 exhibited analgesic potential comparable to diclofenac. In addition to the biological profile, the desirable physico-chemical properties of these compounds make them promising leads for anti-inflammatory drugs. (C) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2014.03.003

文献信息

• Rational design, synthesis and evaluation of chromone-indole and chromone-pyrazole based conjugates: Identification of a lead for anti-inflammatory drug
  作者：Shaveta、Amrinder Singh、Matinder Kaur、Surbhi Sharma、Rajbir Bhatti、Palwinder Singh

  DOI：10.1016/j.ejmech.2014.03.003

  日期：2014.4

  Conjugates of chromone-indole and chromone-pyrazole were screened for cyclooxygenase-2 (COX-2), cyclooxygenase-1 (COX-1) and 5-lipoxygenase (5-LOX) inhibitory activities. Compounds 8 and 9 were identified as preferred inhibitors of COX-2 over the other two enzymes. Their IC50 for COX-2 was 29 nM and 20 nM, respectively and selectivity indices (SI) for COX-2 over COX-1 was 46 and 337. NMR, mass spectral studies and molecular modelling also indicated preferential interactions of compounds 8 and 9 with COX-2. Tested on albino mice against capsaicin induced algesia, compound 8 exhibited analgesic potential comparable to diclofenac. In addition to the biological profile, the desirable physico-chemical properties of these compounds make them promising leads for anti-inflammatory drugs. (C) 2014 Elsevier Masson SAS. All rights reserved.