methyl 2-(cyclopropylmethoxy)-4-(methylsulfonamido)benzoate | 1548870-47-8

• 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: methyl 2-(cyclopropylmethoxy)-4-(methylsulfonamido)benzoate
• 英文别名: Methyl 2-(cyclopropylmethoxy)-4-(methylsulfonamido)benzoate；methyl 2-(cyclopropylmethoxy)-4-(methanesulfonamido)benzoate
• CAS: 1548870-47-8
• 化学式: C₁₃H₁₇NO₅S
• 分子量: 299.348
• InChiKey: UUUXFKWEIRMJNU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  20
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  90.1
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  methyl 2-(cyclopropylmethoxy)-4-(methylsulfonamido)benzoate 在 4-二甲氨基吡啶 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 sodium hydroxide 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 32.0h， 生成 (S)-3,5-dichloro-4-(2-(3-(cyclopropylmethoxy)-4-(difluoromethoxy)phenyl)-2-(2-(cyclopropylmethoxy)-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：

  4-硝基水杨酸 在 吡啶 、 硫酸 、 palladium 10% on activated carbon 、 氢气 、 potassium carbonate 作用下， 以 甲醇 、 二氯甲烷 、 乙腈 为溶剂， 80.0 ℃ 、206.85 kPa 条件下， 反应 137.25h， 生成 methyl 2-(cyclopropylmethoxy)-4-(methylsulfonamido)benzoate
  参考文献：
  名称：

  1-PHENYL-2-PYRIDINYL ALKYL ALCOHOL DERIVATIVES AS PHOSPHODIESTERASE INHIBITORS

  摘要：

  本文描述的化合物（I）的公式是磷酸二酯酶4（PDE4）酶的抑制剂，可用于预防和/或治疗由气道阻塞特征的过敏病状态或呼吸道疾病。

  公开号：

  US20140155391A1

文献信息

• ORGANIC ELECTROLUMINESCENT DEVICE
  申请人：Idemitsu Kosan Co., LT.

  公开号：US20130126849A1

  公开（公告）日：2013-05-23

  An organic electroluminescence device comprising a cathode, an anode and at least one layer comprising a phosphorescent light emitting material and a host material which is sandwiched between the cathode and the anode and further comprising an electron injecting layer which is adhered to the light emitting layer and is capable of transporting electrons, wherein an ionization potential of the host material is 5.9 eV or smaller, and wherein an energy gap of the electron transporting material in the electron injecting layer is smaller than that of the host material in the light emitting layer or wherein a triplet energy of the electron transporting material in the electron injecting layer is smaller than that of the host material in the light emitting layer. It emits phosphorescent light with enhanced efficiency because it comprises a light emitting layer and an electron injecting layer both satisfying specified condition and employs a light emitting layer capable of electron transporting.
• US9944612B2
  申请人：——

  公开号：US9944612B2

  公开（公告）日：2018-04-17
• [EN] 1-PHENYL-2-PYRIDINYL ALKYL ALCOHOL DERIVATIVES AS PHOSPHODIESTERASE INHIBITORS<br/>[FR] DÉRIVÉS D'ALCOOL 1-PHÉNYL-2-PYRIDINYL ALKYLIQUE EN TANT QU'INHIBITEURS DE PHOSPHODIESTÉRASE
  申请人：CHIESI FARMA SPA

  公开号：WO2014086865A1

  公开（公告）日：2014-06-12

  The present invention relates to inhibitors of the phosphodiesterase 4 (PDE4) enzyme. More particularly, the invention relates to 1-phenyl-2-pyridinyl alkyl alcohol derivatives, to processes for the preparation thereof, compositions comprising them, combinations and therapeutic uses thereof.