methyl 2-((E)-3-(3,4-dihydroxyphenyl)acrylamido)benzoate | 1421758-37-3

• 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: methyl 2-((E)-3-(3,4-dihydroxyphenyl)acrylamido)benzoate
• 英文别名: (E)-methyl 2-(3-(3,4-dihydroxyphenyl)acrylamido)benzoate；Methyl 2-((e)-3-(3,4-dihydroxyphenyl)acrylamido)benzoate；methyl 2-[[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]amino]benzoate
• CAS: 1421758-37-3
• 化学式: C₁₇H₁₅NO₅
• 分子量: 313.31
• InChiKey: RLVDRXRKQYHBGF-VQHVLOKHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  95.9
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  methyl 2-((E)-3-(3,4-dihydroxyphenyl)acrylamido)benzoate 在 一水合肼 作用下， 以 正丁醇 为溶剂， 以85%的产率得到2,3-dihydro-2-(3’,4’-dihydroxyphenyl)pyrazolo[5,1-b]quinazolin-9(1H)-one
  参考文献：
  名称：

  Synthesis, anti-inflammatory, and structure antioxidant activity relationship of novel 4-quinazoline

  摘要：

  The practice of medicinal chemistry is devoted to the discovery and development of new agents for treating disease. A new derivative of methyl 2-((E)-3-(3,4-dihydroxyphenyl)acrylamido)benzoate 2 was synthesized by reacting the amino group of methyl anthranilate 1 with caffeic acid in the presence of PCl3. Cyclcondensation of 2 with hydrazine hydrate afforded the corresponding 2,3-dihydro-2-(3,4-dihydroxyphenyl) pyrazolo[5,1-b]quinazolin-9(1H)-one 3. The median lethal doses (LD50s) of compounds 2 and 3 in mice were 1,135 and 495 mg/kg b.w., respectively. The anti-inflammatory, reducing power, chelating activity on Fe2+, free radical-scavenging, and total antioxidant activities were more pronounced in compound 2 compared to compound 3. On the other hand, antipyretic activity was more pronounced in compound 3 compared to compound 2. Antioxidant activity of compounds 2 and 3 increased with increased concentrations. Total antioxidant activity of compounds 2, 3 and both standards decreased in the order of alpha-tocopherol > compound 2 > trolox > BHA > BHT > compound 3. Administration of compounds 2 and 3 orally to the rats at dose of 50, 100, and 150 mg/kg b.w., for 10 days showed non-significant changes in serum level of GOT, GPT, ALP, gamma-GT, and LDH as compared with the control group. In addition, oral administration of the compound 2 at a concentration of 100 and 150 mg/kg b.w. and compound 3 at a concentration of 150 mg/kg b.w. daily to normal rats for 10 days showed a significant increase in liver GSH, GPx, GR, and GST activities and significant decrease in TBARS level. But, administration of diclofenac sodium (30 mg/kg b.w.) orally to the rats daily for 10 days to rats showed significant increase in serum SGOT, SGPT, ALP, gamma-GT, and LDH and significant decrease in liver GSH, GPx, GR, and GST activities. These findings suggest that compounds 2 and 3 exhibited good antioxidant and anti-inflammatory activity and also showed effects on liver enzymes.

  DOI：

  10.1007/s00044-013-0468-9
• 作为产物：
  描述：

  TRANS-咖啡酸 、 邻氨基苯甲酸甲酯 在 三氯化磷 作用下， 以 5,5-dimethyl-1,3-cyclohexadiene 为溶剂， 以77%的产率得到methyl 2-((E)-3-(3,4-dihydroxyphenyl)acrylamido)benzoate
  参考文献：
  名称：

  Mechanism of Antiangiogenic and Antioxidant Activity of Newly Synthesized CAMBA in Ehrlich Ascites Carcinoma-Bearing Mice

  摘要：

  本研究的目的是评估新合成的咖啡酸甲基苯甲酰胺（CAMBA）在EAC负荷小鼠中的抗血管生成活性。计算了CAMBA对Hep-G2肝癌细胞系的IC50值。使用体重为25±5克的成年白化小鼠评估了CAMBA（25和50 mg/k.b.w.）在EAC负荷小鼠中的抗血管生成活性。CAMBA对Hep-G2细胞系的IC50值为52.8μg/mL。将CAMBA每天口服25和50 mg/kg.b.w.浓度给予EAC负荷小鼠30天，结果显示在EAC负荷小鼠中，肿瘤体积和肿瘤重量，ALT，AST，ALP，MMP-2和-9，TNF-α，NOx，TBARs，GSH，CAT，SOD，GPx和VEGF-C基因表达均有显著改善。此外，CAMBA几乎在肝组织结构中使这些效应正常化。我们研究的生化学、组织学和超声检查表明，CAMBA在EAC负荷小鼠中具有抗血管生成活性。

  DOI：

  10.14233/ajchem.2021.23310

文献信息

• Design, synthesis, and evaluation of caffeic acid amides as synergists to sensitize fluconazole-resistant Candida albicans to fluconazole
  作者：Li Dai、Chengxu Zang、Shujuan Tian、Wei Liu、Shanlun Tan、Zhan Cai、Tingjunhong Ni、Maomao An、Ran Li、Yue Gao、Dazhi Zhang、Yuanying Jiang

  DOI：10.1016/j.bmcl.2014.11.022

  日期：2015.1

  A series of caffeic acid amides were designed, synthesized, and their synergistic activity with fluconazole against fluconazole-resistant Candida albicans was evaluated in vitro. The title caffeic acid amides 3-30 except 26 exhibited potent activity, and the subsequent SAR study was conducted. Compound 3, 5, 21, and 34c, at a concentration of 1.0 mu g/ml, decreased the MIC80 of fluconazole from 128.0 mu g/ml to 1.0-0.5 mu g/ml against the fluconazole-resistant C. albicans. This result suggests that the caffeic acid amides, as synergists, can sensitize drug-resistant fungi to fluconazole. The SAR study indicated that the dihydroxyl groups and the amido groups linking to phenyl or heterocyclic rings are the important pharmacophores of the caffeic acid amides. (C) 2014 Elsevier Ltd. All rights reserved.
• Synthesis, anti-inflammatory, and structure antioxidant activity relationship of novel 4-quinazoline
  作者：Mohammed Abdalla Hussein

  DOI：10.1007/s00044-013-0468-9

  日期：2013.10

  The practice of medicinal chemistry is devoted to the discovery and development of new agents for treating disease. A new derivative of methyl 2-((E)-3-(3,4-dihydroxyphenyl)acrylamido)benzoate 2 was synthesized by reacting the amino group of methyl anthranilate 1 with caffeic acid in the presence of PCl3. Cyclcondensation of 2 with hydrazine hydrate afforded the corresponding 2,3-dihydro-2-(3,4-dihydroxyphenyl) pyrazolo[5,1-b]quinazolin-9(1H)-one 3. The median lethal doses (LD50s) of compounds 2 and 3 in mice were 1,135 and 495 mg/kg b.w., respectively. The anti-inflammatory, reducing power, chelating activity on Fe2+, free radical-scavenging, and total antioxidant activities were more pronounced in compound 2 compared to compound 3. On the other hand, antipyretic activity was more pronounced in compound 3 compared to compound 2. Antioxidant activity of compounds 2 and 3 increased with increased concentrations. Total antioxidant activity of compounds 2, 3 and both standards decreased in the order of alpha-tocopherol > compound 2 > trolox > BHA > BHT > compound 3. Administration of compounds 2 and 3 orally to the rats at dose of 50, 100, and 150 mg/kg b.w., for 10 days showed non-significant changes in serum level of GOT, GPT, ALP, gamma-GT, and LDH as compared with the control group. In addition, oral administration of the compound 2 at a concentration of 100 and 150 mg/kg b.w. and compound 3 at a concentration of 150 mg/kg b.w. daily to normal rats for 10 days showed a significant increase in liver GSH, GPx, GR, and GST activities and significant decrease in TBARS level. But, administration of diclofenac sodium (30 mg/kg b.w.) orally to the rats daily for 10 days to rats showed significant increase in serum SGOT, SGPT, ALP, gamma-GT, and LDH and significant decrease in liver GSH, GPx, GR, and GST activities. These findings suggest that compounds 2 and 3 exhibited good antioxidant and anti-inflammatory activity and also showed effects on liver enzymes.
• Mechanism of Antiangiogenic and Antioxidant Activity of Newly Synthesized CAMBA in Ehrlich Ascites Carcinoma-Bearing Mice
  作者：Nada I. Abou-Taleb、Ola A. Elblasy、Esraa A. Elbesoumy、Haidy I. Basuny、Esraa A. Elhamadi、Mohamed S. Nasr eldin、Ahmed A. Emara、Ali A. Ali、Mohamed A. Salem、Fakher M. Ahmed、Mohammed A. Hussein

  DOI：10.14233/ajchem.2021.23310

  日期：——

  The aim of present study was to evaluate antiangiogenic activity of newly synthesized caffeic acid methyl benzoate amide (CAMBA) in EAC-bearing mice. The IC50 value of CAMBA against the Hep-G2 liver carcinoma cell line was calculated. Adult albino mice weighing 25 ± 5 g was used to assess the antiangiogenic activity of CAMBA (25 and 50 mg/k.b.w.) in EAC-bearing mice. IC50 CAMBA against the Hep-G2 cell line equals 52.8 μg/mL. The daily oral administration of CAMBA at concentrations of 25 and 50 mg/kg.b.w. for 30 days to EAC-bearing mice resulted in a significant improvement in tumor volume and tumor weight, ALT, AST, ALP, MMP-2 and -9, TNF-α, NOx, TBARs, GSH, CAT, SOD, GPx and VEGF-C gene expression in EAC-bearing mice. Furthermore, CAMBA almost normalized these effects in liver histoarchitecture. The biochemical, histological and ultrasound examinations of our study suggested that CAMBA have antiangiogenic activity in EAC-bearing mice.

  本研究的目的是评估新合成的咖啡酸甲基苯甲酰胺（CAMBA）在EAC负荷小鼠中的抗血管生成活性。计算了CAMBA对Hep-G2肝癌细胞系的IC50值。使用体重为25±5克的成年白化小鼠评估了CAMBA（25和50 mg/k.b.w.）在EAC负荷小鼠中的抗血管生成活性。CAMBA对Hep-G2细胞系的IC50值为52.8μg/mL。将CAMBA每天口服25和50 mg/kg.b.w.浓度给予EAC负荷小鼠30天，结果显示在EAC负荷小鼠中，肿瘤体积和肿瘤重量，ALT，AST，ALP，MMP-2和-9，TNF-α，NOx，TBARs，GSH，CAT，SOD，GPx和VEGF-C基因表达均有显著改善。此外，CAMBA几乎在肝组织结构中使这些效应正常化。我们研究的生化学、组织学和超声检查表明，CAMBA在EAC负荷小鼠中具有抗血管生成活性。