1-(3-Amino-5-tert-butyl-2-hydroxy-phenyl)-ethanone | 100245-20-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-(3-Amino-5-tert-butyl-2-hydroxy-phenyl)-ethanone
• 英文别名: 1-(3-Amino-5-tert-butyl-2-hydroxyphenyl)ethanone
• CAS: 100245-20-3
• 化学式: C₁₂H₁₇NO₂
• 分子量: 207.272
• InChiKey: IIRTVBDDKZSLHE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  63.3
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-(3-Amino-5-tert-butyl-2-hydroxy-phenyl)-ethanone 在 吡啶 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 1.5h， 生成 1H-Tetrazole-5-carboxylic acid (3-acetyl-5-tert-butyl-2-hydroxy-phenyl)-amide
  参考文献：
  名称：

  Synthesis and quantitative structure-activity relationships of antiallergic 2-hydroxy-N-(1H-tetrazol-5-yl)benzamides and N-(2-hydroxyphenyl)-1H-tetrazole-5-carboxamides

  摘要：

  The synthesis and antiallergic activity of a series of 2-hydroxy-N-1H-tetrazol-5-ylbenzamides and isomeric N-(2-hydroxyphenyl)-1H-tetrazole-5-carboxamides is described. A relationship between structure and intravenous antiallergic activity in the rat passive cutaneous anaphylaxis (PCA) test has been established using a Hansch/Free-Wilson model and used to direct studies toward potent derivatives. The contribution of physicochemical properties to activity is discussed. One member of this series, N-(3-acetyl-5-fluoro-2-hydroxyphenyl)-1H-tetrazole-5-carboxamide (3f), which was selected for further evaluation, has an ID50 value of 0.16 mg/kg po and is 130 times more potent than disodium cromoglycate (DSCG) on intravenous administration.

  DOI：

  10.1021/jm00154a019
• 作为产物：
  描述：

  1-(5-叔丁基-2-羟基-3-硝基苯基)乙酮 生成 1-(3-Amino-5-tert-butyl-2-hydroxy-phenyl)-ethanone
  参考文献：
  名称：

  FORD, E.;KNOWLES, PH.;LUNT, E.;MARSHALL, S. M.;PENROSE, A. J.;RAMSDEN, A.+, J. MED. CHEM., 1986, 29, N 4, 538-549

  摘要：

  DOI：

文献信息

• 2-Aminophenol derivatives, methods for their preparation and composition containing the same
  申请人：ONO PHARMACEUTICAL CO., LTD.

  公开号：EP0065874A1

  公开（公告）日：1982-12-01

  2-Aminophenol derivatives of general formula: [wherein R' represents a straight or branched chain alkyl group containing from 1 to 6 carbon atom(s), a group represented by general formula: (wherein R5 represents a hydrogen atom or a straight or branched chain alkyl group containing from 1 to 4 carbon atom(s) and n represents zero or an integer from 1 to 6) or a group represented by general formula: (wherein R6 represents a hydrogen atom, a halogen atom, a straight or branched chain alkyl group containing from 1 to 4 carbon atom(s), a straight or branched chain alkoxyl group containing from 1 to 4 carbon atom(s), a carbamoyl group, an alkoxycarbonyl group containing from 2 to 6 carbon atoms, a carboxyl group, an amino group, a sulfamoyl group or a cyano group and m represents zero or an integer of 1 or 2.), R2 represents a hydroxyl group, a straight or branched chain alkoxyl group containing from 1 to 4 carbon atom(s) or together with R3 an oxo group or a hydroxyimino group. R3 represents a hydrogen atom or together with R2 an oxo group or a hydroxyimino group. R° represents a halogen atom, a straight or branched chain alkyl group containing from 1 to 6 carbon atom(s) or a phenylthio group. With the exclusion of a compound wherein R2 and R3 taken together represent an oxo group, R' represents a methyl group and R4 represents a methyl group.] or their pharmaceutical acceptable acid addition salts which strongly inhibit 5-lipoxygenase specifically, or 5- lipoxygenase and cyclooxygenase at the same time, and are therefore useful as treating agents and preventing agents for diseases which are induced by leukotrienes e.g. allergic tracheal and bronchial diseases or allergic lung diseases, allergic shock and also various allergic inflammations which are induced by prostaglandins, and a process for their preparation and pharmaceutical compositions comprising them as active ingredients.

  通式如下的 2-氨基苯酚衍生物 [其中 R'代表含有 1 至 6 个碳原子的直链或支链烷基，由通式......代表的基团： (其中 R5 代表氢原子或含有 1 至 4 个碳原子的直链或支链烷基，n 代表零或 1 至 6 的整数）或通式：[其中 R6 代表氢原子或含有 1 至 4 个碳原子的直链或支链烷基，n 代表零或 1 至 6 的整数]所代表的基团： (其中 R6 代表氢原子、卤素原子、含 1 至 4 个碳原子的直链或支链烷基、含 1 至 4 个碳原子的直链或支链烷氧基、氨基甲酰基、含 2 至 6 个碳原子的烷氧羰基、羧基、氨基、氨基磺酰基或氰基，m 代表零或 1 或 2 的整数)，R2 代表羟基，R3 代表氢原子，R4 代表卤素原子。R2代表羟基、含有 1 至 4 个碳原子的直链或支链烷氧基，或与 R3 一起代表氧代基团或羟基亚氨基。R3 代表氢原子，或与 R2 一起代表一个氧代基团或羟基亚氨基基团。R° 代表卤素原子、含 1-6 个碳原子的直链或支链烷基或苯硫基。不包括 R2 和 R3 合在一起代表氧代基团、R'代表甲基和 R4 代表甲基的化合物]或其药物可接受的酸加成盐，它们能强烈抑制特定的 5-脂氧合酶，或同时抑制 5-脂氧合酶和环氧合酶，因此可用作白三烯诱导的疾病的治疗剂和预防剂，如过敏性气管炎和肺结核。例如过敏性气管和支气管疾病或过敏性肺部疾病、过敏性休克以及由前列腺素诱发的各种过敏性炎症，以及制备它们的工艺和含有它们作为活性成分的药物组合物。
• Synthesis and quantitative structure-activity relationships of antiallergic 2-hydroxy-N-(1H-tetrazol-5-yl)benzamides and N-(2-hydroxyphenyl)-1H-tetrazole-5-carboxamides
  作者：Roger E. Ford、Phillip Knowles、Edward Lunt、Stuart M. Marshall、Audrey J. Penrose、Christopher A. Ramsden、Anthony J. H. Summers、Joyce L. Walker、Derek E. Wright

  DOI：10.1021/jm00154a019

  日期：1986.4

  The synthesis and antiallergic activity of a series of 2-hydroxy-N-1H-tetrazol-5-ylbenzamides and isomeric N-(2-hydroxyphenyl)-1H-tetrazole-5-carboxamides is described. A relationship between structure and intravenous antiallergic activity in the rat passive cutaneous anaphylaxis (PCA) test has been established using a Hansch/Free-Wilson model and used to direct studies toward potent derivatives. The contribution of physicochemical properties to activity is discussed. One member of this series, N-(3-acetyl-5-fluoro-2-hydroxyphenyl)-1H-tetrazole-5-carboxamide (3f), which was selected for further evaluation, has an ID50 value of 0.16 mg/kg po and is 130 times more potent than disodium cromoglycate (DSCG) on intravenous administration.
• FORD, E.;KNOWLES, PH.;LUNT, E.;MARSHALL, S. M.;PENROSE, A. J.;RAMSDEN, A.+, J. MED. CHEM., 1986, 29, N 4, 538-549
  作者：FORD, E.、KNOWLES, PH.、LUNT, E.、MARSHALL, S. M.、PENROSE, A. J.、RAMSDEN, A.+

  DOI：——

  日期：——