7-Methoxy-8-[2-(4-methylphenyl)sulfonyl-3-[4-(trifluoromethyl)phenyl]-3,4-dihydropyrazol-5-yl]chromen-2-one | 1426962-24-4

• 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: 7-Methoxy-8-[2-(4-methylphenyl)sulfonyl-3-[4-(trifluoromethyl)phenyl]-3,4-dihydropyrazol-5-yl]chromen-2-one
• 英文别名: 7-methoxy-8-[2-(4-methylphenyl)sulfonyl-3-[4-(trifluoromethyl)phenyl]-3,4-dihydropyrazol-5-yl]chromen-2-one
• CAS: 1426962-24-4
• 化学式: C₂₇H₂₁F₃N₂O₅S
• 分子量: 542.535
• InChiKey: LSOCORHURLDSNY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  38
• 可旋转键数：
  5
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  93.6
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为产物：
  描述：

  7-乙酰氧基香豆素 在 aluminum (III) chloride 、 sodium hydroxide 作用下， 以 乙醇 、 丙酮 为溶剂， 反应 61.0h， 生成 7-Methoxy-8-[2-(4-methylphenyl)sulfonyl-3-[4-(trifluoromethyl)phenyl]-3,4-dihydropyrazol-5-yl]chromen-2-one
  参考文献：
  名称：

  Synthesis and biological evaluation of novel coumarin–pyrazoline hybrids endowed with phenylsulfonyl moiety as antitumor agents

  摘要：

  Two groups of coumarin pyrazoline hybrids were synthesized. The target compounds were obtained by cyclization of the coumarin chalcones with various substituted hydrazines to produce the corresponding pyrazolines through 1,4-addition on alpha,beta-unsaturated carbonyl system. Selected compounds were investigated for their anticancer activity toward 60 cancer cell lines according to US NCI protocol where breast cancer MCF7 and colon cancer HCT-116 were the most susceptible to the influence of compounds 7d, 8c and 9c. Encouraged by this, all final compounds were screened against colorectal cell line HCT-116. The tested compounds exhibited high potency with IC50 ranging from 0.01 mu M to 2.8 mu M. Moreover, compound 9c which possessed the highest cytotoxicity proved to have weak enzyme inhibitory activity against PI3K (p110 alpha/p85 alpha). (C) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.12.004

文献信息

• Synthesis and biological evaluation of novel coumarin–pyrazoline hybrids endowed with phenylsulfonyl moiety as antitumor agents
  作者：Kamilia M. Amin、Amal A.M. Eissa、Sahar M. Abou-Seri、Fadi M. Awadallah、Ghaneya S. Hassan

  DOI：10.1016/j.ejmech.2012.12.004

  日期：2013.2

  Two groups of coumarin pyrazoline hybrids were synthesized. The target compounds were obtained by cyclization of the coumarin chalcones with various substituted hydrazines to produce the corresponding pyrazolines through 1,4-addition on alpha,beta-unsaturated carbonyl system. Selected compounds were investigated for their anticancer activity toward 60 cancer cell lines according to US NCI protocol where breast cancer MCF7 and colon cancer HCT-116 were the most susceptible to the influence of compounds 7d, 8c and 9c. Encouraged by this, all final compounds were screened against colorectal cell line HCT-116. The tested compounds exhibited high potency with IC50 ranging from 0.01 mu M to 2.8 mu M. Moreover, compound 9c which possessed the highest cytotoxicity proved to have weak enzyme inhibitory activity against PI3K (p110 alpha/p85 alpha). (C) 2012 Elsevier Masson SAS. All rights reserved.