(2E,2'E)-1,1'-[4,6-dihydroxy-1,3-phenylene]bis(3-(furan-2-yl)prop-2-en-1-one) | 115540-51-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: (2E,2'E)-1,1'-[4,6-dihydroxy-1,3-phenylene]bis(3-(furan-2-yl)prop-2-en-1-one)
• 英文别名: 4,6-di(2-furfurylcinnamoyl)resorcinol；(E)-3-(furan-2-yl)-1-[5-[(E)-3-(furan-2-yl)prop-2-enoyl]-2,4-dihydroxyphenyl]prop-2-en-1-one
• CAS: 115540-51-7
• 化学式: C₂₀H₁₄O₆
• 分子量: 350.328
• InChiKey: MCLWASDUFLZLDF-KQQUZDAGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  26
• 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：
  101
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (2E,2'E)-1,1'-[4,6-dihydroxy-1,3-phenylene]bis(3-(furan-2-yl)prop-2-en-1-one) 在 溴 作用下， 以 氯仿 为溶剂， 生成 2,3-dibromo-1-[5-[2,3-dibromo-3-(furan-2-yl)propanoyl]-2,4-dihydroxyphenyl]-3-(furan-2-yl)propan-1-one
  参考文献：
  名称：

  Reddy; Ashok; Sarma, Journal of the Indian Chemical Society, 1991, vol. 68, # 4, p. 242 - 243

  摘要：

  DOI：
• 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 (2E,2'E)-1,1'-[4,6-dihydroxy-1,3-phenylene]bis(3-(furan-2-yl)prop-2-en-1-one)
  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

• 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：——
• A Facile Synthesis of 3,7-Diphenyl-4,6-Distyryl-2,8-Dioxo-2H,8H-Benzo[1,2-b:5,4-b′]dipyrans and Their Antifeedant Activity
  作者：B. Sreenivasulu、P. N. Sarma

  DOI：10.1080/00397919708003383

  日期：1997.7

  The synthesis, characterisation and antifeedant activity of some new dicoumarins prepared from 4,6-diacetyl resorcinol has been reported.
• Ashok, D.; Sarma, P. N., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1987, vol. 26, # 1-12, p. 900 - 902
  作者：Ashok, D.、Sarma, P. N.

  DOI：——

  日期：——
• Ashok; Sarasija; Jeyanthi, Indian Journal of Heterocyclic Chemistry, 2016, vol. 25, # 3-4, p. 231 - 235
  作者：Ashok、Sarasija、Jeyanthi、Shravani、Sudershan

  DOI：——

  日期：——
• Reddy, S. Purushotham; Sreenivasulu, B.; Sarma, P. N., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1995, vol. 34, # 7, p. 658 - 659
  作者：Reddy, S. Purushotham、Sreenivasulu, B.、Sarma, P. N.

  DOI：——

  日期：——