E-1-(4-hydroxy-3-(morpholin-4-ylmethyl)phenyl)-3-(2-pyridinyl)prop-2-en-1-one | 1064288-12-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: E-1-(4-hydroxy-3-(morpholin-4-ylmethyl)phenyl)-3-(2-pyridinyl)prop-2-en-1-one
• 英文别名: (E)-1-[4-hydroxy-3-(morpholin-4-ylmethyl)phenyl]-3-pyridin-2-ylprop-2-en-1-one
• CAS: 1064288-12-5
• 化学式: C₁₉H₂₀N₂O₃
• 分子量: 324.379
• InChiKey: IFBTVAUNEZQYBE-FNORWQNLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  62.7
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  对羟基苯乙酮 在 sodium hydroxide 作用下， 以 乙腈 为溶剂， 反应 48.5h， 生成 E-1-(4-hydroxy-3-(morpholin-4-ylmethyl)phenyl)-3-(2-pyridinyl)prop-2-en-1-one
  参考文献：
  名称：

  1-(3-Aminomethyl-4-hydroxyphenyl)-3-pyridinyl-2-propen-1-ones: A novel group of tumour-selective cytotoxins

  摘要：

  Two series of 1-(3-aminomethyl-4-hydroxyphenyl)-3-pyridinyl-2-propen-1-ones, designed as novel cytotoxins, were synthesized. The compounds had low CC50 values in the micromolar range against HL-60 promyelocytic leukemic cells and HSC-2, HSC-3 and HSC-4 oral squamous cell carcinomas. The CC 50 values of these compounds were higher towards non-malignant HGF (gingival fibroblasts), HPC (pulp cells), and HPLF (periodontal ligament fibroblasts) cells, which reveals the tumour-selectivity of these enones. A representative compound 4c caused cleavage of PARP1 in HSC-2 cells but not in HGF cells, which may be a contributing factor to the tumour-selectivity.

  DOI：

  10.3109/14756366.2012.700927

文献信息

• Design, synthesis, and biological evaluation of Mannich bases of heterocyclic chalcone analogs as cytotoxic agents
  作者：M. Vijaya Bhaskar Reddy、Chung-Ren Su、Wen-Fei Chiou、Yi-Nan Liu、Rosemary Yin-Hwa Chen、Kenneth F. Bastow、Kuo-Hsiung Lee、Tian-Shung Wu

  DOI：10.1016/j.bmc.2008.06.018

  日期：2008.8

  The chalcone skeleton (1,3-diphenyl-2-propen-1-one) is a unique template that is associated with various biological activities. We synthesized Mannich bases of heterocyclic chalcones (9-47) using a one-step Claisen-Schmidt condensation of heterocyclic aldehydes with Mannich bases of acetophenones, and tested the target compounds for cytotoxicity against three human cancer cell lines (prostate, PC-3; breast, MCF-7; nasopharynx, KB) and a multi-drug resistant subline (KB-VIN). Out of the 39 chalcones synthesized, 31 compounds showed potent activity against at least one cell line with IC50 values ranging from 0.03 to 3.80 mu g/mL. Structure-activity relationships (SAR) are also discussed. (C) 2008 Elsevier Ltd. All rights reserved.
• 1-(3-Aminomethyl-4-hydroxyphenyl)-3-pyridinyl-2-propen-1-ones: A novel group of tumour-selective cytotoxins
  作者：Sinan Bilginer、Halise Inci Gul、Ebru Mete、Umashankar Das、Hiroshi Sakagami、Naoki Umemura、Jonathan Richard Dimmock

  DOI：10.3109/14756366.2012.700927

  日期：2013.10.1

  Two series of 1-(3-aminomethyl-4-hydroxyphenyl)-3-pyridinyl-2-propen-1-ones, designed as novel cytotoxins, were synthesized. The compounds had low CC50 values in the micromolar range against HL-60 promyelocytic leukemic cells and HSC-2, HSC-3 and HSC-4 oral squamous cell carcinomas. The CC 50 values of these compounds were higher towards non-malignant HGF (gingival fibroblasts), HPC (pulp cells), and HPLF (periodontal ligament fibroblasts) cells, which reveals the tumour-selectivity of these enones. A representative compound 4c caused cleavage of PARP1 in HSC-2 cells but not in HGF cells, which may be a contributing factor to the tumour-selectivity.