3-(4-hydroxy-3-methoxyphenyl)-2-propenoic acid 4-(nitrooxy)butyl ester | 352467-08-4

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: 3-(4-hydroxy-3-methoxyphenyl)-2-propenoic acid 4-(nitrooxy)butyl ester
• 英文别名: NCX 2057；NCX2057；3-[(3-methoxy-4-hydroxy)phenyl]-2-propenoic acid 4-nitrooxybutyl ester；ferulic acid 4-(nitrooxy)butyl ester；4-Nitrooxybutyl 3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate
• CAS: 352467-08-4
• 化学式: C₁₄H₁₇NO₇
• 分子量: 311.291
• InChiKey: ARRUYERCLLVCNV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  22
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  111
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  3-(4-hydroxy-3-methoxyphenyl)-2-propenoic acid 4-(nitrooxy)butyl ester 、 BOC-甘氨酸 在 4-二甲氨基吡啶 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 氯仿 为溶剂， 反应 3.0h， 生成 N-Boc-glycine [2-methoxy-4-[2-propenoyloxy(4-nitrooxybutyl)]]phenyl ester
  参考文献：
  名称：

  [EN] PROSTAGLANDIN DERIVATIVES
  [FR] DERIVES DE PROSTAGLANDINE

  摘要：

  公开号：

  WO2007000641A3
• 作为产物：
  描述：

  ferulic acid 4-(bromo)butyl ester 在 silver nitrate 作用下， 以 乙腈 为溶剂， 以91.7%的产率得到3-(4-hydroxy-3-methoxyphenyl)-2-propenoic acid 4-(nitrooxy)butyl ester
  参考文献：
  名称：

  阿魏酸和咖啡酸衍生物的生物活性评估和构效关系分析

  摘要：

  通过高通量筛选（HTS）方法评估了烷基酯和阿魏酸（FA）和咖啡酸（CA）的NO供体的抗癌活性，并描述了结构与活性之间的关系。与具有相同烷基取代基的FA烷基酯相比，CA烷基酯具有更好的抗癌活性。单硝酸盐和苯基呋喃喃硝酸盐比双硝酸盐更有效。FA的苯磺酰呋喃呋喃硝酸盐，尤其是化合物8b - 8d在抗癌方面表现出更强的活性。

  DOI：

  10.1016/j.bmcl.2012.08.038

文献信息

• WO2007/642
  申请人：——

  公开号：——

  公开（公告）日：——
• Synthesis and crystallographic analysis of new sulfonamides incorporating NO-donating moieties with potent antiglaucoma action
  作者：Francesco Mincione、Francesca Benedini、Stefano Biondi、Alessandro Cecchi、Claudia Temperini、Giuseppe Formicola、Ilaria Pacileo、Andrea Scozzafava、Emanuela Masini、Claudiu T. Supuran

  DOI：10.1016/j.bmcl.2011.04.046

  日期：2011.6

  Several aromatic/heterocyclic sulfonamide scaffolds have been used to synthesize compounds incorporating NO-donating moieties of the nitrate ester type, which have been investigated for the inhibition of five physiologically relevant human carbonic anhydrase (hCA, EC 4.2.1.1) isoforms: hCA I (offtarget), II, IV and XII (antiglaucoma targets) and IX (antitumor target). Some of the new compounds showed effective in vitro inhibition of the target isoforms involved in glaucoma, and the X-ray crystal structure of one of them revealed factors associated with the marked inhibitory activity. In an animal model of ocular hypertension, one of the new compounds was twice more effective than dorzolamide in reducing elevated intraocular pressure characteristic of this disease, anticipating their potential for the treatment of glaucoma. (C) 2011 Elsevier Ltd. All rights reserved.
• [EN] PROSTAGLANDIN DERIVATIVES<br/>[FR] DERIVES DE PROSTAGLANDINE
  申请人：PFIZER

  公开号：WO2007000641A3

  公开（公告）日：2007-03-22
• Biological activity evaluation and structure–activity relationships analysis of ferulic acid and caffeic acid derivatives for anticancer
  作者：Weixia Li、Nianguang Li、Yuping Tang、Baoquan Li、Li Liu、Xu Zhang、Haian Fu、Jin-ao Duan

  DOI：10.1016/j.bmcl.2012.08.038

  日期：2012.10

  The anticancer activities of alkyl esters and NO-donors of ferulic acid (FA) and caffeic acid (CA) were assessed by a high-throughout screening (HTS) method, and the structure–activity relationships were described. CA alkyl esters had better anticancer activities than FA alkyl esters with the same alkyl substituent. Mono-nitrates and phenylfuroxan nitrates were more potent than the dual nitrates.

  通过高通量筛选（HTS）方法评估了烷基酯和阿魏酸（FA）和咖啡酸（CA）的NO供体的抗癌活性，并描述了结构与活性之间的关系。与具有相同烷基取代基的FA烷基酯相比，CA烷基酯具有更好的抗癌活性。单硝酸盐和苯基呋喃喃硝酸盐比双硝酸盐更有效。FA的苯磺酰呋喃呋喃硝酸盐，尤其是化合物8b - 8d在抗癌方面表现出更强的活性。