3-(4-chlorobenzyl)-2H-chromene | 934979-48-3

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 高异黄酮
• 英文名称: 3-(4-chlorobenzyl)-2H-chromene
• 英文别名: 3-[(4-chlorophenyl)methyl]-2H-chromene
• CAS: 934979-48-3
• 化学式: C₁₆H₁₃ClO
• 分子量: 256.732
• InChiKey: HWXPLSPJDIUHNP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  (E)-3-(4-chloro-benzylidene)-chroman-4-one 在 aluminum (III) chloride 、 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 以42%的产率得到(Z)-3-(4-chlorobenzylidene)chroman
  参考文献：
  名称：

  Synthesis and antirhinovirus activity of new 3-benzyl chromene and chroman derivatives

  摘要：

  A series of 3-benzyl chromenes and chromans were synthesized and tested in vitro against human rhinovirus (HRV) 1B and 14, two representative serotypes for rhinovirus group B and A, respectively. All the new compounds, with the exception of 3-benzyl-2H-chromene (3a), showed a potent activity against HRV serotype 1B within micro or submicromolar range (IC(50)s from 0.11 to 6.62 mu M). The low cytotoxicity of all the derivatives resulted in compounds with high therapeutic index (TI). On the contrary, HRV 14 infection was only weakly inhibited by the majority of these compounds. The 3-benzylidenechromans 2b and 2c showed the highest anti-HRV 1B activity (IC50 0.12 and 0.11 mu M, respectively) coupled with remarkable TI (625.00 and 340.91, respectively). Mechanism of action studies on (Z)-3-(4-chlorobenzylidene) chroman (2b) suggest that the new compounds behave as capsid binders and interfere with very early stages of HRV 1B replication, similarly to related flavanoids. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.03.051

文献信息

• Synthesis and antirhinovirus activity of new 3-benzyl chromene and chroman derivatives
  作者：Cinzia Conti、Nicoletta Desideri

  DOI：10.1016/j.bmc.2009.03.051

  日期：2009.5

  A series of 3-benzyl chromenes and chromans were synthesized and tested in vitro against human rhinovirus (HRV) 1B and 14, two representative serotypes for rhinovirus group B and A, respectively. All the new compounds, with the exception of 3-benzyl-2H-chromene (3a), showed a potent activity against HRV serotype 1B within micro or submicromolar range (IC(50)s from 0.11 to 6.62 mu M). The low cytotoxicity of all the derivatives resulted in compounds with high therapeutic index (TI). On the contrary, HRV 14 infection was only weakly inhibited by the majority of these compounds. The 3-benzylidenechromans 2b and 2c showed the highest anti-HRV 1B activity (IC50 0.12 and 0.11 mu M, respectively) coupled with remarkable TI (625.00 and 340.91, respectively). Mechanism of action studies on (Z)-3-(4-chlorobenzylidene) chroman (2b) suggest that the new compounds behave as capsid binders and interfere with very early stages of HRV 1B replication, similarly to related flavanoids. (C) 2009 Elsevier Ltd. All rights reserved.