6-chloro-3-[(1E,3E)-4-phenylbuta-1,3-dienyl]-4H-chromen-4-one | 1251862-36-8

• 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: 6-chloro-3-[(1E,3E)-4-phenylbuta-1,3-dienyl]-4H-chromen-4-one
• 英文别名: 6-chloro-3-[(1E,3E)-4-phenylbuta-1,3-dienyl]chromen-4-one
• CAS: 1251862-36-8
• 化学式: C₁₉H₁₃ClO₂
• 分子量: 308.764
• InChiKey: RSMDNHXDVZVDBH-KBXRYBNXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  反-苯乙烯乙酸 、 6-氯-3-甲酰基色酮 在 吡啶 、 potassium tert-butylate 作用下， 以69%的产率得到6-chloro-3-[(1E,3E)-4-phenylbuta-1,3-dienyl]-4H-chromen-4-one
  参考文献：
  名称：

  New 4H-chromen-4-one and 2H-chromene derivatives as anti-picornavirus capsid-binders

  摘要：

  Substituted (E)-3-styryl-4H-chromen-4-ones 1a-d, 3-[(1E,3E)-4-phenylbuta-1,3-dienyl]-4H-chromen-4-ones 2a-d, (E)-3-styryl-2H-chromenes 3a-d and 3-[(1E, 3E)-4-phenylbuta-1,3-dienyl]-2H-chromenes 4a-d were designed and synthesized to improve the anti-picornavirus activity of previously tested analogues. The new compounds were evaluated in vitro against human rhinovirus (HRV) serotypes 1B and 14 and enterovirus (EV) 71. All the compounds interfered with the replication of picornaviruses, although considerable differences were observed in the sensitivity of viruses to each compound. Generally, both HRVs were more susceptible than EV71 and their sensitivity was dependent upon the linker chain length as well as upon the oxidation state of the heterocyclic ring. (E)-3-Styryl-2H-chromene (3a) emerged as the most effective inhibitor of both HRVs showing IC50 values of 0.20 mu M and 1.38 mu M towards serotype 1B and 14, respectively. The potent activity was also coupled with low cytotoxicity resulting in high therapeutic indexes (250 and 36, respectively). Mechanism of action studies indicated that 3a, like structurally related compounds, behaves as a capsid binder interfering with the early stages of rhinovirus infection, probably at the adsorption and/or uncoating level. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.06.103

文献信息

• New 4H-chromen-4-one and 2H-chromene derivatives as anti-picornavirus capsid-binders
  作者：Cinzia Conti、Nicoletta Desideri

  DOI：10.1016/j.bmc.2010.06.103

  日期：2010.9

  Substituted (E)-3-styryl-4H-chromen-4-ones 1a-d, 3-[(1E,3E)-4-phenylbuta-1,3-dienyl]-4H-chromen-4-ones 2a-d, (E)-3-styryl-2H-chromenes 3a-d and 3-[(1E, 3E)-4-phenylbuta-1,3-dienyl]-2H-chromenes 4a-d were designed and synthesized to improve the anti-picornavirus activity of previously tested analogues. The new compounds were evaluated in vitro against human rhinovirus (HRV) serotypes 1B and 14 and enterovirus (EV) 71. All the compounds interfered with the replication of picornaviruses, although considerable differences were observed in the sensitivity of viruses to each compound. Generally, both HRVs were more susceptible than EV71 and their sensitivity was dependent upon the linker chain length as well as upon the oxidation state of the heterocyclic ring. (E)-3-Styryl-2H-chromene (3a) emerged as the most effective inhibitor of both HRVs showing IC50 values of 0.20 mu M and 1.38 mu M towards serotype 1B and 14, respectively. The potent activity was also coupled with low cytotoxicity resulting in high therapeutic indexes (250 and 36, respectively). Mechanism of action studies indicated that 3a, like structurally related compounds, behaves as a capsid binder interfering with the early stages of rhinovirus infection, probably at the adsorption and/or uncoating level. (C) 2010 Elsevier Ltd. All rights reserved.