5-amino-N-(β-phenethyl)salicylamide | 327037-09-2

• 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: 5-amino-N-(β-phenethyl)salicylamide
• 英文别名: 5-amino-2-hydroxy-N-(2-phenylethyl)benzamide
• CAS: 327037-09-2
• 化学式: C₁₅H₁₆N₂O₂
• 分子量: 256.304
• InChiKey: VDUZBTVQWIPOJT-UHFFFAOYSA-N

物化性质

• 熔点：
  190-191 °C
• 沸点：
  496.1±45.0 °C(Predicted)
• 密度：
  1.234±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  75.4
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-amino-N-(β-phenethyl)salicylamide 在 sodium cyanoborohydride 作用下， 以 甲醇 、 苯 为溶剂， 反应 26.5h， 生成 5-(2,5-Dihydroxy-benzylamino)-2-hydroxy-N-phenethyl-benzamide
  参考文献：
  名称：

  Design, Synthesis, and Biological Evaluation of a Series of Lavendustin A Analogues That Inhibit EGFR and Syk Tyrosine Kinases, as Well as Tubulin Polymerization

  摘要：

  A series of N-alkylamide analogues of the lavendustin A pharmacophore were synthesized and tested for inhibition of the epidermal growth factor receptor (EGFR) protein tyrosine kinase and the nonreceptor protein tyrosine kinase Syk. Although several compounds in the series were effective inhibitors of both kinases, it seemed questionable whether their inhibitory effects on these kinases were responsible for the cytotoxic properties observed in a variety of human cancer cell cultures. Accordingly, a COMPARE analysis of the cytotoxicity profile of the most cytotoxic member of the series was performed, and the results indicated that its cytotoxicity profile was similar to that of antitubulin agents. This mechanism of action was supported by demonstrating that most compounds in the series were moderately effective as inhibitors of tubulin polymerization. This suggests that the lavendustin A analogues reported here, as well as some of the previously reported lavendustin A analogues, may be acting as cytotoxic agents by a mechanism involving the inhibition of tubulin polymerization.

  DOI：

  10.1021/jm000387g
• 作为产物：
  描述：

  5-氨基水杨酸 在 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 、 三氟乙酸 作用下， 以 1,4-二氧六环 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 98.0h， 生成 5-amino-N-(β-phenethyl)salicylamide
  参考文献：
  名称：

  Design, Synthesis, and Biological Evaluation of a Series of Lavendustin A Analogues That Inhibit EGFR and Syk Tyrosine Kinases, as Well as Tubulin Polymerization

  摘要：

  A series of N-alkylamide analogues of the lavendustin A pharmacophore were synthesized and tested for inhibition of the epidermal growth factor receptor (EGFR) protein tyrosine kinase and the nonreceptor protein tyrosine kinase Syk. Although several compounds in the series were effective inhibitors of both kinases, it seemed questionable whether their inhibitory effects on these kinases were responsible for the cytotoxic properties observed in a variety of human cancer cell cultures. Accordingly, a COMPARE analysis of the cytotoxicity profile of the most cytotoxic member of the series was performed, and the results indicated that its cytotoxicity profile was similar to that of antitubulin agents. This mechanism of action was supported by demonstrating that most compounds in the series were moderately effective as inhibitors of tubulin polymerization. This suggests that the lavendustin A analogues reported here, as well as some of the previously reported lavendustin A analogues, may be acting as cytotoxic agents by a mechanism involving the inhibition of tubulin polymerization.

  DOI：

  10.1021/jm000387g

文献信息

• Compounds for Inhibiting Copper-Containing Amine Oxidases and Uses Thereof
  申请人：Clauzel Marti Luc

  公开号：US20070066646A1

  公开（公告）日：2007-03-22

  This invention is directed to inhibitors of copper-containing amine oxidases (E.C. 1.4.3.6) including semicarbazide-sensitive amine oxidase (SSAO; also known as vascular adhesion protein-1, VAP-1), and their therapeutic use in inflammatory diseases, diabetes and its associated complications, atherosclerosis, neurodegenerative diseases, obesity, hypertension and cancer.

  这项发明涉及铜含量胺氧化酶（E.C. 1.4.3.6）的抑制剂，包括半胱氨酸敏感胺氧化酶（SSAO；也称为血管粘附蛋白-1，VAP-1），以及它们在炎症性疾病、糖尿病及其相关并发症、动脉粥样硬化、神经退行性疾病、肥胖症、高血压和癌症中的治疗用途。
• PROCESS FOR DYEING IN THE PRESENCE OF OXIDATION BASES COMPRISING AT LEAST ONE SULFONIC, SULFONAMIDE, SULFONE, AMID OR ACID GROUP AND A METAL CATALYST, DEVICE AND READY-TO-USE COMPOSITION
  申请人：L'OREAL

  公开号：US20160143826A1

  公开（公告）日：2016-05-26

  The present invention relates to a process for dyeing human keratin fibres, in which use is made of one or more metal catalysts and a composition (A) comprising: (a) at least 10% by weight of one or more fatty substances, (b) one or more oxidation bases of formula (I) or (II), the addition salts thereof, solvates thereof and mixtures thereof: Formula (I), Formula (II) (c) one or more chemical oxidizing agents other than atmospheric oxygen. The invention also relates to a multi-compartment device and to a composition comprising all of the above-mentioned ingredients.
• US9872822B2
  申请人：——

  公开号：US9872822B2

  公开（公告）日：2018-01-23
• Design, Synthesis, and Biological Evaluation of a Series of Lavendustin A Analogues That Inhibit EGFR and Syk Tyrosine Kinases, as Well as Tubulin Polymerization
  作者：Fanrong Mu、Stephanie L. Coffing、David J. Riese、Robert L. Geahlen、Pascal Verdier-Pinard、Ernest Hamel、Jill Johnson、Mark Cushman

  DOI：10.1021/jm000387g

  日期：2001.2.1

  A series of N-alkylamide analogues of the lavendustin A pharmacophore were synthesized and tested for inhibition of the epidermal growth factor receptor (EGFR) protein tyrosine kinase and the nonreceptor protein tyrosine kinase Syk. Although several compounds in the series were effective inhibitors of both kinases, it seemed questionable whether their inhibitory effects on these kinases were responsible for the cytotoxic properties observed in a variety of human cancer cell cultures. Accordingly, a COMPARE analysis of the cytotoxicity profile of the most cytotoxic member of the series was performed, and the results indicated that its cytotoxicity profile was similar to that of antitubulin agents. This mechanism of action was supported by demonstrating that most compounds in the series were moderately effective as inhibitors of tubulin polymerization. This suggests that the lavendustin A analogues reported here, as well as some of the previously reported lavendustin A analogues, may be acting as cytotoxic agents by a mechanism involving the inhibition of tubulin polymerization.