4,6-dicinnamoyl resorcinol | 84422-37-7

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: 4,6-dicinnamoyl resorcinol
• 英文别名: (E)-1-[2,4-dihydroxy-5-[(E)-3-phenylprop-2-enoyl]phenyl]-3-phenyl-prop-2-en-1-one；(E)-1-[2,4-dihydroxy-5-[(E)-3-phenylprop-2-enoyl]phenyl]-3-phenylprop-2-en-1-one
• CAS: 84422-37-7
• 化学式: C₂₄H₁₈O₄
• 分子量: 370.405
• InChiKey: CAAJXTJDBCGUNB-PHEQNACWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  28
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  74.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4,6-dicinnamoyl resorcinol 在 三氯氧磷 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.13h， 以65%的产率得到(E)-1-(4-chloro-7-hydroxy-2-phenyl-2H-chromen-6-yl)-3-phenylprop-2-en-1-one
  参考文献：
  名称：

  Microwave assisted selective synthesis of (E)-1-(4-Chloro-7-hydroxy-2-aryl-2H-chromen-6-yl)-3-arylprop-2-en-1-ones and their antimicrobial activity

  摘要：

  A series of new (E)-1-(4-chloro-7-hydroxy-2-aryl-2H-chromen-6-yl)-3-arylprop-2-en-1-ones (2a-2f) have been synthesized by selective mono cyclization of 4,6-dicinnamoyl resorcinols (1a-1f) using Vilsmeier-Haack reagent under conventional heating and microwave irradiation. The structures of the synthesized compounds have been elucidated by elemental analysis, IR, H-1 NMR, C-13 NMR and Mass spectral data. The synthesized compounds were tested in vitro for antimicrobial activity.

  DOI：

  10.1134/s1070363216040290
• 作为产物：
  描述：

  间苯二酚 在 盐酸 、 potassium hydroxide 、 zinc(II) chloride 作用下， 以 甲醇 、 水 为溶剂， 反应 24.0h， 生成 4,6-dicinnamoyl resorcinol
  参考文献：
  名称：

  Bis-chalcone analogues as potent NO production inhibitors and as cytotoxic agents

  摘要：

  Chalcones have a distinctive 1,3-diarylpropenone skeleton and exert numerous biological effects. Using a one-step Claisen-Schmidt condensation, we synthesized eleven bis-chalcones (3-13) and three acetyl chalcones (14-16) from substituted aldehydes and diacetylresorcinol. The compounds were tested for in vitro cytotoxic activity against four human cancer cell lines (A549, DU145, KB, and KB-VIN) and inhibition of NO production in lipopolysaccharide (LPS)-activated microglial cells. Among them, four compounds (3, 5, 6, and 13) showed significant cytotoxic activity with EC50 values ranging from 1.57 to 514 mu M, and seven compounds (3, 5-8, 10, and 13) displayed potent anti-inflammatory activity by inhibiting NO production with IC50 values ranging from 0.95 to 8.65 mu M. A mechanism of action study of active compounds 6 and 7 discovered that these compounds down-regulated iNOS expression by inhibiting p65 NF-kappa B activation/nuclear translocation due to prevention of ham degradation. Structure-activity relationship (SAR) findings are also discussed. Crown Copyright (C) 2011 Published by Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.10.026

文献信息

• Mohan, Santosh Bala; Pal, Krishan; Murti, V. V. S., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1982, vol. 21, # 8, p. 714 - 717
  作者：Mohan, Santosh Bala、Pal, Krishan、Murti, V. V. S.

  DOI：——

  日期：——
• Anjaneyulu, A. S. R.; Mallavadhani, U. V.; Venkateswarlu, Y., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1982, vol. 21, # 10, p. 963 - 964
  作者：Anjaneyulu, A. S. R.、Mallavadhani, U. V.、Venkateswarlu, Y.

  DOI：——

  日期：——
• Reddy; Ashok; Sarma, Journal of the Indian Chemical Society, 1991, vol. 68, # 4, p. 242 - 243
  作者：Reddy、Ashok、Sarma

  DOI：——

  日期：——
• Reddy, R Jayasimha; Ashok, D; Sarma, P N, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1993, vol. 32, # 3, p. 404 - 406
  作者：Reddy, R Jayasimha、Ashok, D、Sarma, P N

  DOI：——

  日期：——
• Sarma; Sreenivasulu, Journal of the Indian Chemical Society, 1997, vol. 74, # 8, p. 644 - 645
  作者：Sarma、Sreenivasulu

  DOI：——

  日期：——