2-甲氧基-4-[(甲基磺酰基)氨基]-苯甲酸甲酯 | 620612-15-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 2-甲氧基-4-[(甲基磺酰基)氨基]-苯甲酸甲酯
• 英文名称: 4-methanesulfonylamino-2-methoxybenzoic acid methyl ester
• 英文别名: methyl 2-methoxy-4-(methylsulfonamido)benzoate；Methyl 2-methoxy-4-[(methylsulfonyl)amino]benzoate；methyl 4-(methanesulfonamido)-2-methoxybenzoate
• CAS: 620612-15-9
• 化学式: C₁₀H₁₃NO₅S
• 分子量: 259.283
• InChiKey: UGQNIPSTEHXMQA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  90.1
• 氢给体数：
  1
• 氢受体数：
  6

安全信息

• 海关编码：
  2935009090

反应信息

• 作为反应物：
  描述：

  2-甲氧基-4-[(甲基磺酰基)氨基]-苯甲酸甲酯 在 盐酸 、 4-二甲氨基吡啶 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 lithium hydroxide 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 乙酸乙酯 为溶剂， 反应 32.0h， 生成 (S)-3,5-dichloro-4-(2-(3-(cyclopropylmethoxy)-4-(difluoromethoxy)phenyl)-2-(2-methoxy-4-(methylsulfonamido)-benzoyloxy)ethyl)pyridine 1-oxide
  参考文献：
  名称：

  Novel Class of Benzoic Acid Ester Derivatives as Potent PDE4 Inhibitors for Inhaled Administration in the Treatment of Respiratory Diseases

  摘要：

  The first steps in the selection process of a new anti-inflammatory drug for the inhaled treatment of asthma and chronic obstructive pulmonary disease are herein described. A series of novel ester derivatives of 1-(3-(cyclopropylmethoxy)-4-(difluoromethoxy)phenyl)-2-(3,5-di-chloropyriclin-4-yl) ethanol have been synthesized and evaluated for inhibitory activity toward cAMP-specific phosphodiesterase-4 (PDE4). In particular, esters of variously substituted benzoic acids were extensively explored, and structural modification of the alcoholic and benzoic moieties were performed to maximize the inhibitory potency. Several compounds with high activity in cell-free and cell-based assays were obtained. Through the evaluation of opportune in vitro ADME properties, a potential candidate suitable for inhaled administration in respiratory diseases was identified and tested in an in vivo model of pulmonary inflammation, proving its efficacy.

  DOI：

  10.1021/jm401549m
• 作为产物：
  描述：

  2-甲氧基-4-氨基苯甲酸甲酯 、 甲基磺酰氯 在 吡啶 作用下， 以 氯仿 为溶剂， 反应 5.0h， 以95%的产率得到2-甲氧基-4-[(甲基磺酰基)氨基]-苯甲酸甲酯
  参考文献：
  名称：

  Synthesis and Crystallographic Studies of New Acridinic Esters and Amides: An Efficient Synthetic Route to 4-Methyl Functionalized Acridines

  摘要：

  In order to open a new way in antitumor drugs research, an efficient synthetic route to mono functional 4-substitued acridine derivatives has been developed on the basis of direct electrophilic substitution of acridine. This method leads to a wide range of simple acridinic patterns that can be linked to various side chains. We present here the synthesis of two new families of acridine ester and amide derivatives, obtained from acridinic alcohol and amine respectively, with high yields. Some crystallographic aspects of one representative compound of each family are discussed.

  DOI：

  10.3987/com-03-9778

文献信息

• Synthesis and Crystallographic Studies of New Acridinic Esters and Amides: An Efficient Synthetic Route to 4-Methyl Functionalized Acridines
  作者：Julien Chiron、Jean-Pierre Galy

  DOI：10.3987/com-03-9778

  日期：——

  In order to open a new way in antitumor drugs research, an efficient synthetic route to mono functional 4-substitued acridine derivatives has been developed on the basis of direct electrophilic substitution of acridine. This method leads to a wide range of simple acridinic patterns that can be linked to various side chains. We present here the synthesis of two new families of acridine ester and amide derivatives, obtained from acridinic alcohol and amine respectively, with high yields. Some crystallographic aspects of one representative compound of each family are discussed.
• Novel Class of Benzoic Acid Ester Derivatives as Potent PDE4 Inhibitors for Inhaled Administration in the Treatment of Respiratory Diseases
  作者：Elisabetta Armani、Gabriele Amari、Andrea Rizzi、Renato De Fanti、Eleonora Ghidini、Carmelida Capaldi、Laura Carzaniga、Paola Caruso、Matilde Guala、Ilaria Peretto、Elena La Porta、Pier T. Bolzoni、Fabrizio Facchinetti、Chiara Carnini、Nadia Moretto、Riccardo Patacchini、Franco Bassani、Valentina Cenacchi、Roberta Volta、Francesco Amadei、Silvia Capacchi、Maurizio Delcanale、Paola Puccini、Silvia Catinella、Maurizio Civelli、Gino Villetti

  DOI：10.1021/jm401549m

  日期：2014.2.13

  The first steps in the selection process of a new anti-inflammatory drug for the inhaled treatment of asthma and chronic obstructive pulmonary disease are herein described. A series of novel ester derivatives of 1-(3-(cyclopropylmethoxy)-4-(difluoromethoxy)phenyl)-2-(3,5-di-chloropyriclin-4-yl) ethanol have been synthesized and evaluated for inhibitory activity toward cAMP-specific phosphodiesterase-4 (PDE4). In particular, esters of variously substituted benzoic acids were extensively explored, and structural modification of the alcoholic and benzoic moieties were performed to maximize the inhibitory potency. Several compounds with high activity in cell-free and cell-based assays were obtained. Through the evaluation of opportune in vitro ADME properties, a potential candidate suitable for inhaled administration in respiratory diseases was identified and tested in an in vivo model of pulmonary inflammation, proving its efficacy.