Cinnamoyl vanillin

• 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: Cinnamoyl vanillin
• 英文别名: 4-Formyl-2-methoxyphenyl cinnamate；(4-formyl-2-methoxyphenyl) 3-phenylprop-2-enoate
• 化学式: C₁₇H₁₄O₄
• 分子量: 282.296
• InChiKey: HTZRSXRTYZPHGC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  Cinnamoyl vanillin 在 尿素 作用下， 生成 2-methoxy-4-((E)-ureidomethyl)phenyl cinnamate
  参考文献：
  名称：

  STYRYL CARBOXYLATE DERIVATIVES

  摘要：

  提供了一种新型的苯基羧酸酯衍生物，具有治疗免疫性疾病、炎症、肥胖症、高血脂症、高血压、神经系统疾病和糖尿病的活性。

  公开号：

  US20220234987A1
• 作为产物：
  描述：

  肉桂酸 在 氯化亚砜 、 三乙胺 作用下， 以 氯仿 为溶剂， 反应 10.25h， 生成 Cinnamoyl vanillin
  参考文献：
  名称：

  ACYLOXY SUBSTITUTED PHENYL DITHIANE DERIVATIVES

  摘要：

  Para-酰基取代的二氮杂环己烯，其医药配方和制备和使用方法。

  公开号：

  US20220235024A1

文献信息

• Preparation, Spectral Characterization and Anticancer Potential of Cinnamic Esters
  作者：Renan Gonçalves、Iolanda de Farias、Maria Francilene Silva、Cláudia Pessoa、Guilherme Zocolo、Davila Zampieri、Telma Leda de Lemos、Francisco Jose Monte

  DOI：10.21577/0103-5053.20210084

  日期：——

  Cinnamic acid and its derivatives show a remarkable variety of biological activities and are often studied in search of the development of new and highly effective drugs. This work aims to synthesize, characterize and evaluate the cytotoxic activity of esters derived from cinnamic acid. Eighteen esters were synthesized through Steglich’s esterification, of which eleven were not reported in the literature

  肉桂酸及其衍生物具有多种多样的生物活性，经常被用来研究开发新的高效药物。本研究旨在合成、表征和评估肉桂酸衍生酯的细胞毒性活性。通过施特格利希酯化法合成了 18 种酯类化合物，其中 11 种未见文献报道。通过傅立叶变换红外光谱（FTIR）、核磁共振（1H 和 13C NMR）和高分辨质谱（HRMS）数据对所有化合物进行了全面鉴定。利用四种人类肿瘤细胞系评估了所获酯类的细胞毒性活性：通过 3-(4,5-二甲基-2-噻唑基)-2,5-二苯基-2H-四氮唑（MTT）比色法，对 SNB-19（星形细胞瘤）、HCT-116（结肠癌，人类）、PC3（前列腺癌）和 HL60（早幼粒细胞白血病）这四种人类肿瘤细胞系进行了评估。这些研究表明，化合物 3-甲氧基苄基 (E)-3-(4- 甲氧基苯基)丙烯酸酯 (12) 对 HCT-116、PC3 和 SBN-19 细胞的抑制作用最强，在 HCT-116 株系中的半最大抑制浓度 (IC50) 值最低，为 16.2 μM。除了 5-异丙基-2-甲基苯基 (E)-3-(3- 羟基-4-甲氧基苯基)丙烯酸酯（17）（18.6%）和 2-异丙基-5-甲基苯基 (E)-3-(3- 羟基-4-甲氧基苯基)丙烯酸酯（18）（15.5%）之外，其他衍生物的收率都很高（76.6-95%）。
• Design, synthesis and biological evaluation of novel 4-hydroxybenzene acrylic acid derivatives
  作者：Jin-Long Mao、Xiang-Kai Ran、Jing-Zhen Tian、Bo Jiao、Hong-Lei Zhou、Li Chen、Zhen-Guo Wang

  DOI：10.1016/j.bmcl.2010.12.063

  日期：2011.3

  A series of 4-hydroxybenzene acrylic acid derivatives were designed and synthesized based on the ferulic acid of natural active ingredients. The tested compound 5a, 5f and 6a have significant anti-inflammatory activity with suppression rates of 45.29%, 44.75% and 24.11%, respectively, compared with that of indomethacin, and their cardiac toxicity was not observed. The structure-function relationship shows that the p-hydroxyl group on the a-position benzene ring, particularly if acetylated, contributes to the considerable anti-inflammatory activity; that the carboxyl group on the double bond, if esterified, also contributes to the anti-inflammatory activity; that the p-methylsulfonyl group on the other benzene ring, whose introduction is due to the COX-2 selectivity, also contributes to anti-inflammatory activity surprisingly. (C) 2010 Elsevier Ltd. All rights reserved.
• Three-component condensation of Meldrum’s acid with 2-naphthylamine and esters derived from vanillin
  作者：N. G. Kozlov、L. I. Basalaeva

  DOI：10.1134/s1070428006040063

  日期：2006.4

  Three-component condensation of Meldrum's acid (2,2-dimethyl-1,3-dioxane-4,6-dione) with 2-naphthylamine and esters derived from vanillin involves intermediate formation of N-arylmethylidene-2-naphthylamines which are cleaved with Meldrum's acid to give 5-arylmethylidene-2,2-dimethyl-1,3-dioxane4,6-diones and aryimethylideneketenes. Reaction of the latter with 2-naphthylamine leads to formation of 2-methoxy-4-(3-oxo-1,2,3,4-tetrahydrobenzo[f]quinolin-1-yl)phenyl carboxylates.
• STYRYL CARBOXYLATE DERIVATIVES
  申请人：Renovel Innovations, Inc

  公开号：US20220234987A1

  公开（公告）日：2022-07-28

  Novel Styryl Carboxylate derivatives are provided which exhibit activity for the treatment of immunological diseases, inflammation, obesity, hyperlipidemia, hypertension, neurological diseases, and diabetes.

  提供了一种新型的苯基羧酸酯衍生物，具有治疗免疫性疾病、炎症、肥胖症、高血脂症、高血压、神经系统疾病和糖尿病的活性。
• ACYLOXY SUBSTITUTED PHENYL DITHIANE DERIVATIVES
  申请人：Renovel Innovations, Inc

  公开号：US20220235024A1

  公开（公告）日：2022-07-28

  Para-acyl substituted diazacyclohexenes, medical formulations thereof and methods for making and using the same.

  Para-酰基取代的二氮杂环己烯，其医药配方和制备和使用方法。