eugenol

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: eugenol
• 英文别名: 2-Ethyl-4-allyl-phenol；2-Ethyl-4-prop-2-enylphenol
• 化学式: C₁₁H₁₄O
• 分子量: 162.232
• InChiKey: LYBZMEUOPQPABM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  eugenol 在 溶剂黄146 、 sodium hydroxide 作用下， 以 乙醇 、 二氯甲烷 、 水 为溶剂， 反应 24.0h， 生成
  参考文献：
  名称：

  丁香酚及其类似物衍生的 α,β-不饱和酮的合成、杀锥虫和细胞毒活性

  摘要：

  这项工作描述了来自丁香酚和类似物的 α,β-不饱和酮的合成、结构表征、杀锥虫和细胞毒性评价。在合成的化合物中，环戊酸/二氢丁香酚衍生物12在 5.2 nM（比苯并硝唑的效力高 700 倍）时对克氏锥虫的无鞭毛体形式具有活性，并且代表了未来结构优化以降低其毒性的潜在影响。还针对健康人和四种癌细胞系对所有化合物进行了评估，衍生物10对三种癌细胞的活性比多柔比星更强（IC 50值在 2.03-23.51 µM 之间），并且在考虑人体细胞时显示出更高的选择性指数。衍生物14对两种癌细胞也比阿霉素更有效和更具选择性（IC 50值在 4.71–8.86 µM 之间）。

  DOI：

  10.1007/s00044-022-02976-x
• 作为产物：
  描述：

  乙基苯酚 在 sodium hydroxide 、 苄基三丁基溴化铵 作用下， 以 二氯甲烷 为溶剂， 反应 3.5h， 生成 eugenol
  参考文献：
  名称：

  Synthesis, biological evaluation, and preliminary structure-activity considerations of a series of alkylphenols as intravenous anesthetic agents

  摘要：

  Following our discovery of the intravenous (iv) anesthetic activity of 2,6-diethylphenol in mice, a series of alkylphenols was examined in this species and the most active analogues were further evaluated in rabbits. The synthesis of compounds which were not commercially available was accomplished by adaptations of standard ortho-alkylation procedures for phenols. Structure-activity relationships were found to be complex, but, in general, potency and kinetics appeared to be a function of both the lipophilic character and the degree of steric hindrance exerted by ortho substituents. The most interesting compounds were found in the 2,6-dialkyl series, and the greatest potency was associated with 2,6-di-sec-alkyl substitution. In particular, 2,6-diisopropylphenol (ICI 35 868) emerged as a candidate for further development and has subsequently been shown to be an effective iv anesthetic agent in man.

  DOI：

  10.1021/jm00186a013

文献信息

• Antioxidantien für organisches Material
  申请人：CIBA-GEIGY AG

  公开号：EP0174277B1

  公开（公告）日：1988-04-06
• US4691044A
  申请人：——

  公开号：US4691044A

  公开（公告）日：1987-09-01
• [EN] 2-AMINOBENZOXAZOLE DERIVATIVES AND COMBINATORIAL LIBRARIES THEREOF<br/>[FR] DERIVES DE 2-AMINOBENZOXAZOLE ET LEURS BIBLIOTHEQUES COMBINATOIRES
  申请人：LION BIOSCIENCE AG

  公开号：WO2002079753A2

  公开（公告）日：2002-10-10

  The present invention relates to novel 2-aminobenzoxazole derivative compounds of the following formula (I), wherein R1 to R4 and Z have the meanings provided herein. The invention further relates to combinatorial libraries containing two or more such compounds, as well as methods of preparing 2-aminobenzoxazole derivative compounds.
• Synthesis, biological evaluation, and preliminary structure-activity considerations of a series of alkylphenols as intravenous anesthetic agents
  作者：Roger James、John B. Glen

  DOI：10.1021/jm00186a013

  日期：1980.12

  Following our discovery of the intravenous (iv) anesthetic activity of 2,6-diethylphenol in mice, a series of alkylphenols was examined in this species and the most active analogues were further evaluated in rabbits. The synthesis of compounds which were not commercially available was accomplished by adaptations of standard ortho-alkylation procedures for phenols. Structure-activity relationships were found to be complex, but, in general, potency and kinetics appeared to be a function of both the lipophilic character and the degree of steric hindrance exerted by ortho substituents. The most interesting compounds were found in the 2,6-dialkyl series, and the greatest potency was associated with 2,6-di-sec-alkyl substitution. In particular, 2,6-diisopropylphenol (ICI 35 868) emerged as a candidate for further development and has subsequently been shown to be an effective iv anesthetic agent in man.
• Synthesis, trypanocidal and cytotoxic activities of α,β-unsaturated ketones derived from eugenol and analogues
  作者：Rúbia Castro Fernandes Melo Reis、Adriana Cotta Cardoso Reis、Fernanda Karoline Vieira Silva Torchelsen、Marta de Lana、Policarpo Ademar Sales Junior、Geraldo Celio Brandão、Saulo Fehelberg Pinto Braga、Thiago Belarmino de Souza

  DOI：10.1007/s00044-022-02976-x

  日期：2022.12

  This work describes the synthesis, structural characterization, trypanocide and cytotoxic evaluation of α,β-unsaturated ketones derived from eugenol and analogues. Among the synthesized compounds, the cyclopentanonic/dihydroeugenol derivative 12 was active against amastigote forms of Trypanosoma cruzi at 5.2 nM (700 times more potent than benznidazole) and represents a potential hit for future structural

  这项工作描述了来自丁香酚和类似物的 α,β-不饱和酮的合成、结构表征、杀锥虫和细胞毒性评价。在合成的化合物中，环戊酸/二氢丁香酚衍生物12在 5.2 nM（比苯并硝唑的效力高 700 倍）时对克氏锥虫的无鞭毛体形式具有活性，并且代表了未来结构优化以降低其毒性的潜在影响。还针对健康人和四种癌细胞系对所有化合物进行了评估，衍生物10对三种癌细胞的活性比多柔比星更强（IC 50值在 2.03-23.51 µM 之间），并且在考虑人体细胞时显示出更高的选择性指数。衍生物14对两种癌细胞也比阿霉素更有效和更具选择性（IC 50值在 4.71–8.86 µM 之间）。