3-(3,4-dihydroxyphenyl)-(E)-2-propenoic acid heptyl ester

• 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-(3,4-dihydroxyphenyl)-(E)-2-propenoic acid heptyl ester
• 英文别名: heptyl 3-(3,4-dihydroxyphenyl)-2-propenoate；heptyl caffeate；Heptyl-3-(3,4-dihydroxyphenyl)prop-2-enoate；heptyl (E)-3-(3,4-dihydroxyphenyl)prop-2-enoate
• 化学式: C₁₆H₂₂O₄
• 分子量: 278.348
• InChiKey: MVBSOBMQLAJJRB-CSKARUKUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  20
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  66.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  正庚醇 在 哌啶 、 吡啶 作用下， 以 甲苯 为溶剂， 反应 5.0h， 生成 3-(3,4-dihydroxyphenyl)-(E)-2-propenoic acid heptyl ester
  参考文献：
  名称：

  Synthesis and antitumor activity of feruloyl and caffeoyl derivatives

  摘要：

  We developed two efficient protocols for the synthesis of feruloyl and caffeoyl derivatives from commercial vanillin and veratraldehyde. Pharmacological activities were assessed against a panel of human cancer cell lines in vitro. Most synthesized compounds demonstrated attractive cytotoxicity. Several new compounds demonstrated significant antiproliferative and cytotoxic activities against HeLa and Bewo tumor cell lines. In particular, 5-nitro caffeic adamantyl ester showed broad spectrum of tumor inhibition in 10 cell lines, and reduced tumor weight by 36.7% in vivo when administered at a dose of 40 mg kg(-1). (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2014.08.024

文献信息

• Synthesis and Crystal Structure of Heptyl 3-(3,4-dihydroxyphenyl)-2-propenoate
  作者：Chun-nian Xia、Wei-xiao Hu、Wei Zhou、Guo-hong Wang

  DOI：10.1007/s10870-008-9341-y

  日期：2008.8

  The title compound, C16H22O4, synthesized by modified Knoevenagel condensation of protocatechualdehyde with monoheptyl-malonate and recrystallized from benzene, was confirmed by single-crystal X-ray diffraction (CCDC 272827). The compound crystallizes in triclinic space group Pī with cell parameters a = 5.296(3) Å, b = 10.711(13) Å, c = 13.870(4) Å, α = 98.84(7)°, β = 90.97(4)°, γ = 96.77(7)° and Z = 2. The structure is the E isomer and its packing is stabilized by intermolecular O–H···O and C–H···O hydrogen bonds. The title compound, C16H22O4, synthesized by modified Knoevenagel condensation, was confirmed by single-crystal X-ray diffraction showing its structure is in E isomer and its packing is stabilized by hydrogen bonds.

  标题化合物 C16H22O4 是通过原儿茶醛与丙二酸单庚酯的改良克诺文纳格尔缩合反应合成的，并从苯中重结晶，其单晶 X 射线衍射结果（CCDC 272827）证实了该化合物的存在。该化合物在三linic 空间群 Pī 中结晶，晶胞参数 a = 5.296(3) Å, b = 10.711(13) Å, c = 13.870(4) Å, α = 98.该结构为 E 异构体，其堆积通过分子间 O-H-O 和 C-H-O 氢键而稳定。通过改进的克诺文纳格尔缩合反应合成的标题化合物 C16H22O4 经单晶 X 射线衍射证实其结构为 E 异构体，其堆积通过氢键稳定。
• Synthesis, antifungal activity of caffeic acid derivative esters, and their synergism with fluconazole and nystatin against Candida spp.
  作者：Janaína de Cássia Orlandi Sardi、Fernanda Patrícia Gullo、Irlan Almeida Freires、Nayla de Souza Pitangui、Maicon Petrônio Segalla、Ana Marisa Fusco-Almeida、Pedro Luiz Rosalen、Luís Octávio Regasini、Maria José Soares Mendes-Giannini

  DOI：10.1016/j.diagmicrobio.2016.08.002

  日期：2016.12

  We tested the antifungal potential of caffeic acid and 8 of its derivative esters against Candidaalbicans ATCC 90028 and 9 clinical isolatesand carried out a synergism assay with fluconazole and nystatin. Propyl caffeate (C3) showed the best antifungal activity against the tested strains. When in combination, C3 markedly reduced the MIC of fluconazole and nystatin with synergistic effect up to 64-fold

  我们测试了咖啡酸及其8种衍生物对白念珠菌ATCC 90028和9种临床分离株的抗真菌潜力，并与氟康唑和制霉菌素进行了协同试验。咖啡酸丙酯（C3）对测试菌株显示出最佳的抗真菌活性。组合使用时，C3可以显着降低氟康唑和制霉菌素的MIC，协同作用最多可达到64倍。最后，C3对口服角质形成细胞表现出较高的IC50值和选择性指数，表明对这种细胞类型的毒性低，对酵母细胞的选择性低。进一步的研究应证实其抗真菌潜力，可用于开发治疗白色念珠菌感染的联合疗法。
• Antifungal activity of octyl gallate: structural criteria and mode of action
  作者：Isao Kubo、Ping Xiao、Ken'ichi Fujita

  DOI：10.1016/s0960-894x(00)00656-9

  日期：2001.2

  Octyl gallate (3,4,5-trihydroxybenzoate) was found to possess antifungal activity against Saccharomyces cerevisiae and Zygosaccharomyces bailii, in addition to its potent antioxidant activity. Catechol moiety is essential to elicit this activity. The primary fungicidal activity of octyl gallate comes from its ability to act as a nonionic surface-active agent (surfactant). The length of the alkyl chain is not a major contributor but plays an important role in eliciting the activity. (C) 2001 Elsevier Science Ltd. All rights reserved.
• Synthesis of trans-caffeate analogues and their bioactivities against HIV-1 integrase and cancer cell lines
  作者：Chun-nian Xia、Hai-bo Li、Feng liu、Wei-xiao Hu

  DOI：10.1016/j.bmcl.2008.10.046

  日期：2008.12

  Forty caffeate analogues were synthesized via a convenient method starting from vanillin with moderate to good yields. The testing of biological activity of these compounds against HIV-1 integrase indicates that four compounds: bornyl caffeate, bornyl 2-nitrocaffeate, 5-nitrocaffeic acid and 5-nitrocaffeic acid phenethyl ester (5-nitroCAPE) possess a good HIV integrase inhibitory activity, IC50 19.9, 26.8, 25.0 and 13.5 mu M, respectively. Twelve caffeate analogues were tested by MTT assay on growth of human hepatocellular carcinoma BEL-7404, human breast MCF-7 adenocarcinoma, human lung A549 adenocarcinoma and human gastric cancer BCG823 cell lines, respectively. And the best result is IC50 5.5 mu M for CAPE against BEL-7404. (C) 2008 Elsevier Ltd. All rights reserved.
• Hu, Wei-Xiao; Xia, Chun-Nian; Wang, Guo-Hong, Journal of Chemical Research, 2006, # 9, p. 586 - 588
  作者：Hu, Wei-Xiao、Xia, Chun-Nian、Wang, Guo-Hong、Zhou, Wei

  DOI：——

  日期：——