7-chloro-2-(4-hydroxyphenyl)-3-methoxy-4H-chromen-4-one | 111391-86-7

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 黄酮类化合物
• 英文名称: 7-chloro-2-(4-hydroxyphenyl)-3-methoxy-4H-chromen-4-one
• 英文别名: 7-Chloro-2-(4-hydroxyphenyl)-3-methoxychromen-4-one
• CAS: 111391-86-7
• 化学式: C₁₆H₁₁ClO₄
• 分子量: 302.714
• InChiKey: PZAXKBYPGZOMEQ-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：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  4-苄氧基苯甲醛 在 盐酸 、 sodium hydroxide 、 双氧水 、 potassium carbonate 、 溶剂黄146 作用下， 以 甲醇 、 乙醇 、 丙酮 为溶剂， 反应 139.25h， 生成 7-chloro-2-(4-hydroxyphenyl)-3-methoxy-4H-chromen-4-one
  参考文献：
  名称：

  4'-Hydroxy-3-methoxyflavones with potent antipicornavirus activity

  摘要：

  4'-Hydroxy-3-methoxyflavones are natural compounds with known antiviral activities against picornaviruses such as poliomyelitis and rhinoviruses. In order to establish a structure-activity relationship a series of analogues were synthesized, and their antiviral activities and cytotoxicities were compared with those of flavones from natural origin. The 4'-hydroxyl and 3-methoxyl groups, a substitution in the 5 position and a polysubstituted A ring appeared to be essential requirements for a high activity. The most interesting compound was 4',7-dihydroxy-3-methoxy-5,6-dimethylflavone possessing in vitro TI99 values of > 1000 and > 200 against poliovirus type 1 and rhinovirus type 15, respectively. This compound was also active against other rhinovirus serotypes (2, 9, 14, 29, 39, 41, 59, 63, 70, 85, and 89) tested, having MIC50 values ranging from 0.016 to 0.5-mu-g/mL. Finally in contrast to quercetin it showed to be not mutagenic in concentrations up to 2.5 mg in the Ames test.

  DOI：

  10.1021/jm00106a039

文献信息

• 4'-Hydroxy-3-methoxyflavones with potent antipicornavirus activity
  作者：Nadine De Meyer、Achiel Haemers、Lallan Mishra、Hrishi Kesh Pandey、L. A. C. Pieters、Dirk A. Vanden Berghe、Arnold J. Vlietinck

  DOI：10.1021/jm00106a039

  日期：1991.2

  4'-Hydroxy-3-methoxyflavones are natural compounds with known antiviral activities against picornaviruses such as poliomyelitis and rhinoviruses. In order to establish a structure-activity relationship a series of analogues were synthesized, and their antiviral activities and cytotoxicities were compared with those of flavones from natural origin. The 4'-hydroxyl and 3-methoxyl groups, a substitution in the 5 position and a polysubstituted A ring appeared to be essential requirements for a high activity. The most interesting compound was 4',7-dihydroxy-3-methoxy-5,6-dimethylflavone possessing in vitro TI99 values of > 1000 and > 200 against poliovirus type 1 and rhinovirus type 15, respectively. This compound was also active against other rhinovirus serotypes (2, 9, 14, 29, 39, 41, 59, 63, 70, 85, and 89) tested, having MIC50 values ranging from 0.016 to 0.5-mu-g/mL. Finally in contrast to quercetin it showed to be not mutagenic in concentrations up to 2.5 mg in the Ames test.
• Exploration of Pharmacophore in Chrysosplenol C as Activator in Ventricular Myocyte Contraction
  作者：Eeda Venkateswararao、Min-Jeong Son、Niti Sharma、Manoj Manickam、PullaReddy Boggu、Young Ho Kim、Sun-Hee Woo、Sang-Hun Jung

  DOI：10.1021/acsmedchemlett.5b00043

  日期：2015.7.9

  Chrysosplenol C (4',5,6-trihydroxy-3,3',7-tri-methoxyflavone) isolated from Miliusa balansae has unique structural features as a reversible inotropic agent independent of beta-adrenergic signaling and with selective activation of cardiac myosin ATPase. Hence, a series of chrysosplenol analogues were synthesized and explored for identification of pharmacophore that is essential for the increasing contractility in rat ventricular myocytes. Analogue 7-chloro-2-(3-hydroxypheny1)-3-methoxy-4H-chromen-4-one showed highly potent contractility (54.8% at 10 mu M) through activating cardiac myosin ATPase (38.7% at 10 mu M). Our systematic structure activity relationship study revealed that flavonoid nucleus of chrososplenol C appears to be an essential basic skeleton and hydrophobic substituent at position 7 of chromenone such as methoxy or chloro enhances the activity. Additionally, our ATPase study suggested that these chrysosplenol analogues have selectivity toward cardiac myosin activation. Thus, the novel flavonone with 3-/7-hydrophobic substituent and 3'-hydrogen bonding donor function is a novel scaffold for discovery of a new positive inotropic agent.