3-(4-chlorobenzyl)-chroman-4-one | 76285-74-0

• 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)-chroman-4-one
• 英文别名: 3-(4-chlorobenzyl)chroman-4-one；3-(p-chlorobenzyl)-4-chromanone；3-[(4-chlorophenyl)methyl]-2,3-dihydrochromen-4-one
• CAS: 76285-74-0
• 化学式: C₁₆H₁₃ClO₂
• 分子量: 272.731
• InChiKey: YJFXWVMIPDREFG-UHFFFAOYSA-N

物化性质

• 沸点：
  418.1±34.0 °C(Predicted)
• 密度：
  1.274±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.19
• 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：

  3-(4-chlorobenzyl)-chroman-4-one 在 aluminum (III) chloride 、 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 以72%的产率得到3-(4-chlorobenzyl)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
• 作为产物：
  描述：

  3-苯氧基丙腈 在 palladium on activated charcoal 盐酸 、 氢气 作用下， 以 乙醇 、 乙酸乙酯 为溶剂， 反应 1.5h， 生成 3-(4-chlorobenzyl)-chroman-4-one
  参考文献：
  名称：

  Sangwan, Naresh K.; Rastogi, Shri Nivas, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1980, vol. 19, # 6, p. 500 - 503

  摘要：

  DOI：

文献信息

• Synthesis, anticancer, structural, and computational docking studies of 3-benzylchroman-4-one derivatives
  作者：Lalitha Simon、Abdul Ajees Abdul Salam、S. Madan Kumar、T. Shilpa、K.K. Srinivasan、K. Byrappa

  DOI：10.1016/j.bmcl.2017.10.026

  日期：2017.12

  exhibited moderate activity against HeLa cells (IC50 = 42.8 µM). The molecular structures of 3h and 3i were solved by single crystal X-ray crystallographic technique. Additionally, the molecular docking studies between the tumour suppressor protein p53 with the lead compound 3h, which exhibited better anticancer activity against HeLa cells was examined.

  合成了一系列的3-苄基苯并吡喃-4-酮，并通过MTT法筛选了其抗癌活性。针对两种癌细胞系BT549（人类乳腺癌），HeLa（人类宫颈癌）和一种非癌细胞系vero（正常肾脏上皮细胞）对化合物进行了评估。发现3b是对抗BT549细胞（IC 50  = 20.1 µM）最活跃的分子，而3h是对抗HeLa细胞（IC 50  = 20.45 µM）最活跃的分子。3b还显示出对HeLa细胞的中等活性（IC 50  = 42.8 µM）。3h和3i的分子结构通过单晶X射线晶体学技术解决。此外，检查了在肿瘤抑制蛋白p53与先导化合物3h之间的分子对接研究，该化合物对HeLa细胞表现出更好的抗癌活性。
• Sangwan, Naresh K.; Rastogi, Shri Nivas, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1980, vol. <B> 19, # 6, p. 500 - 503
  作者：Sangwan, Naresh K.、Rastogi, Shri Nivas

  DOI：——

  日期：——
• 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.