(E)-3-[(E)-3-(4-chlorophenyl)allylidene]chroman-4-one | 1351524-13-4

• 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: (E)-3-[(E)-3-(4-chlorophenyl)allylidene]chroman-4-one
• 英文别名: (3E)-3-[(E)-3-(4-chlorophenyl)prop-2-enylidene]chromen-4-one
• CAS: 1351524-13-4
• 化学式: C₁₈H₁₃ClO₂
• 分子量: 296.753
• InChiKey: PTXOCWLNFFHCOV-ORRXZRLISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 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：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (E)-3-[(E)-3-(4-chlorophenyl)allylidene]chroman-4-one 在 aluminum (III) chloride 、 lithium aluminium tetrahydride 、 palladium 10% on activated carbon 作用下， 以 1,4-二氧六环 、 乙醚 为溶剂， 20.0 ℃ 、275.8 kPa 条件下， 反应 4.0h， 生成 3-[3-(4-chlorophenyl)propyl]chroman
  参考文献：
  名称：

  3-苯基烷基-2H-色烯和-色氨酸作为新型鼻病毒感染抑制剂。

  摘要：

  在我们研究抗鼻炎病毒色烯和苯并二氢吡喃衍生物的构效关系后，我们设计并合成了两个系列的新的3-苯基烷基-2H-色烯和-苯并二氢吡喃，在两个循环之间带有不同大小的脂肪族连接链。在HeLa细胞培养物中评估了新化合物对人鼻病毒（HRV）血清型1B和14感染的细胞毒性和抗病毒活性。大多数测试化合物以微摩尔或亚微摩尔浓度干扰HRV1B的繁殖，而HRV14较不敏感。选择3- [3-（4-氯苯基）丙基]苯并二氢吡喃（9c）是因为它对两种血清型均具有有效的活性（对HRV1B和14的IC50分别为0.48μM和1.36μM），并具有较高的抗药性，因此被选作初步的作用机理研究。选择性（分别为SI = 206.18和73.26）。

  DOI：

  10.1016/j.bmc.2017.02.012
• 作为产物：
  描述：

  2,3-二氢苯并吡喃-4-酮 、 4-氯肉桂醛 在 磷酸 作用下， 反应 4.0h， 以83%的产率得到(E)-3-[(E)-3-(4-chlorophenyl)allylidene]chroman-4-one
  参考文献：
  名称：

  Design, synthesis and in vitro evaluation of novel chroman-4-one, chroman, and 2H-chromene derivatives as human rhinovirus capsid-binding inhibitors

  摘要：

  As part of an effort to generate broad-spectrum inhibitors of rhinovirus replication, novel series of (E)-3-[(E)-3-phenylallylidene]chroman-4-ones 1a-e, (E)-3-(3-phenylprop-2-yn-1-ylidene)chroman-4-ones 2a and 2b, (Z)-3-[(E)-3-phenylallylidene]chromans 3a-e, and (E)-3-(3-phenylprop-1-en-1-yl)-2H-chromenes 4a-d were designed and synthesized. All the compounds were tested in vitro for their efficacy against infection by human rhinovirus (HRV) 1B and 14, two representative serotypes for rhinovirus group B and A, respectively. Most of the analogues were found to be potent and selective inhibitors of both HRVs, although HRV 1B was generally more susceptible than HRV 14. Mechanism of action studies of (E)-6-chloro-3-(3-phenylprop-1-en-1-yl)-2H-chromene 4b, the most potent compound on HRV 1B infection, suggested that 4b behaves as a capsid-binder probably acting at the uncoating level. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.10.060

文献信息

• Design, synthesis and in vitro evaluation of novel chroman-4-one, chroman, and 2H-chromene derivatives as human rhinovirus capsid-binding inhibitors
  作者：Cinzia Conti、Luca Proietti Monaco、Nicoletta Desideri

  DOI：10.1016/j.bmc.2011.10.060

  日期：2011.12

  As part of an effort to generate broad-spectrum inhibitors of rhinovirus replication, novel series of (E)-3-[(E)-3-phenylallylidene]chroman-4-ones 1a-e, (E)-3-(3-phenylprop-2-yn-1-ylidene)chroman-4-ones 2a and 2b, (Z)-3-[(E)-3-phenylallylidene]chromans 3a-e, and (E)-3-(3-phenylprop-1-en-1-yl)-2H-chromenes 4a-d were designed and synthesized. All the compounds were tested in vitro for their efficacy against infection by human rhinovirus (HRV) 1B and 14, two representative serotypes for rhinovirus group B and A, respectively. Most of the analogues were found to be potent and selective inhibitors of both HRVs, although HRV 1B was generally more susceptible than HRV 14. Mechanism of action studies of (E)-6-chloro-3-(3-phenylprop-1-en-1-yl)-2H-chromene 4b, the most potent compound on HRV 1B infection, suggested that 4b behaves as a capsid-binder probably acting at the uncoating level. (C) 2011 Elsevier Ltd. All rights reserved.
• 3-Phenylalkyl-2 H -chromenes and -chromans as novel rhinovirus infection inhibitors
  作者：Cinzia Conti、Luca Proietti Monaco、Nicoletta Desideri

  DOI：10.1016/j.bmc.2017.02.012

  日期：2017.4

  less susceptible. 3-[3-(4-Chlorophenyl)propyl]chroman (9c) was selected for preliminary mechanism of action studies due to its potent activity against both serotypes (IC50 of 0.48μM and 1.36μM towards HRV1B and 14, respectively) coupled with high selectivity (SI=206.18 and 73.26, respectively). Results of time of addition/removal studies suggest that 9c, similarly to related derivatives, behaves as a capsid

  在我们研究抗鼻炎病毒色烯和苯并二氢吡喃衍生物的构效关系后，我们设计并合成了两个系列的新的3-苯基烷基-2H-色烯和-苯并二氢吡喃，在两个循环之间带有不同大小的脂肪族连接链。在HeLa细胞培养物中评估了新化合物对人鼻病毒（HRV）血清型1B和14感染的细胞毒性和抗病毒活性。大多数测试化合物以微摩尔或亚微摩尔浓度干扰HRV1B的繁殖，而HRV14较不敏感。选择3- [3-（4-氯苯基）丙基]苯并二氢吡喃（9c）是因为它对两种血清型均具有有效的活性（对HRV1B和14的IC50分别为0.48μM和1.36μM），并具有较高的抗药性，因此被选作初步的作用机理研究。选择性（分别为SI = 206.18和73.26）。