1-(3-amino-2-hydroxy-5-methoxy-phenyl)-ethanone | 55008-15-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-(3-amino-2-hydroxy-5-methoxy-phenyl)-ethanone
• 英文别名: 1-(3-Amino-2-hydroxy-5-methoxy-phenyl)-aethanon；1-(3-Amino-2-hydroxy-5-methoxyphenyl)ethanone
• CAS: 55008-15-6
• 化学式: C₉H₁₁NO₃
• 分子量: 181.191
• InChiKey: MBXMHYPQLIZLDQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  72.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-(3-amino-2-hydroxy-5-methoxy-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 3'-Acetyl-2'-hydroxy-5'-methoxytetrazol-5-carboxanilid
  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：

  2-Hydroxy-5-methoxy-3-nitro-acetophenon 在 盐酸 、 tin(ll) chloride 作用下， 生成 1-(3-amino-2-hydroxy-5-methoxy-phenyl)-ethanone
  参考文献：
  名称：

  Kasahara, Nippon Kagaku Zasshi, 1958, vol. 79, p. 335,337

  摘要：

  DOI：

文献信息

• PROCESS FOR THE MANUFACTURING OF BETAMIMETICS
  申请人：KRUEGER Thomas

  公开号：US20070088160A1

  公开（公告）日：2007-04-19

  The present invention relates to a process for preparing betamimetics of formula 1, wherein n denotes 1 or 2; R 1 denotes hydrogen, halogen, C 1-4 -alkyl or O—C 1-4 -alkyl; R 2 denotes hydrogen, halogen, C 1-4 -alkyl or O—C 1-4 -alkyl; R 3 denotes hydrogen, C 1-4 -alkyl, OH, halogen, O—C 1-4 -alkyl, O—C 1-4 -alkylene-COOH, O—C 1-4 -alkylene-COO—C 1-4 -alkyl.

  本发明涉及一种制备式1的β-受体激动剂的方法，其中n表示1或2；R1表示氢、卤素、C1-4-烷基或O—C1-4-烷基；R2表示氢、卤素、C1-4-烷基或O—C1-4-烷基；R3表示氢、C1-4-烷基、羟基、卤素、O—C1-4-烷基、O—C1-4-亚烷基-羧基、O—C1-4-亚烷基-COO—C1-4-烷基。
• CLASS OF BIFUNCTIONAL COMPOUNDS WITH QUATERNARY AMMONIUM SALT STRUCTURE
  申请人：Beijing Showby Pharmaceutical Co., Ltd.

  公开号：EP3556435A1

  公开（公告）日：2019-10-23

  The invention provides a class of compounds represented by formula (I), having bifunctional active quaternary ammonium salt structure of a β2-adrenoreceptor agonist and an M receptor antagonist, a pharmaceutically acceptable salt, solvate, and optical isomer thereof. A pharmaceutical composition comprising such a compound with quaternary ammonium salt structure, a method for preparing such a compound with quaternary ammonium salt structure and an intermediate thereof, and uses thereof in treating pulmonary disorders are also provided. The compounds of the invention have high selectivity to the M receptor subtype, and have less adverse reaction and lower toxic and side effects in the treatment of pulmonary diseases such as COPD and asthma.

  本发明提供了一类由式(I)代表的化合物，其具有β2-肾上腺素受体激动剂和M受体拮抗剂的双功能活性季铵盐结构，以及其药学上可接受的盐、溶液和光学异构体。本发明还提供了包含这种具有季铵盐结构的化合物的药物组合物、制备这种具有季铵盐结构的化合物及其中间体的方法，以及其在治疗肺部疾病中的用途。本发明的化合物对 M 受体亚型具有高选择性，在治疗慢性阻塞性肺病和哮喘等肺部疾病时不良反应小，毒副作用低。
• 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：——
• US4442115A
  申请人：——

  公开号：US4442115A

  公开（公告）日：1984-04-10
• US8420809B2
  申请人：——

  公开号：US8420809B2

  公开（公告）日：2013-04-16