3-formyl-4-nitrobenzoic acid | 1092931-93-5

• 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: 3-formyl-4-nitrobenzoic acid
• CAS: 1092931-93-5
• 化学式: C₈H₅NO₅
• 分子量: 195.131
• InChiKey: SPTXSDMRZNPVKQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  100
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-formyl-4-nitrobenzoic acid 在 吡啶 、 咪唑 、 4-二甲氨基吡啶 、 sodium tetrahydroborate 、 palladium 10% on activated carbon 、 氢气 、 caesium carbonate 、 溶剂黄146 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 锌 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 40.0 ℃ 、137.9 kPa 条件下， 反应 25.0h， 生成 (S)-4-(2-(4-(N-(tert-butoxycarbonyl)methylsulfonamido)-3-((tert-butyldimethylsilyloxy)methyl)benzoyloxy)-2-(3-(cyclopropylmethoxy)-4-(difluoromethoxy)phenyl) ethyl)-3,5-dichloropyridine 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：

  3-甲酰基-4-硝基苯甲酸甲酯 在 lithium hydroxide 作用下， 以 四氢呋喃 、 水 为溶剂， 以100%的产率得到3-formyl-4-nitrobenzoic acid
  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

文献信息

• WO2008/152014
  申请人：——

  公开号：——

  公开（公告）日：——
• 3-HETROCYCLYLIDENE-INDOLINONE DERIVATIVES AS INHIBITORS OF SPECIFIC CELL CYCLE KINASES
  申请人：Boehringer Ingelheim International GmbH

  公开号：EP2181108A2

  公开（公告）日：2010-05-05
• NEW COMPOUNDS
  申请人：Engelhardt Harald

  公开号：US20100222331A1

  公开（公告）日：2010-09-02

  The present invention encompasses compounds of general Formula (1) wherein R 2 , R 3 , Q, W, X, Y and Z are defined as in claim 1 , which are suitable for the treatment of diseases characterised by excessive or abnormal cell proliferation, and the use thereof for preparing a medicament having the above-mentioned properties.
• US8207179B2
  申请人：——

  公开号：US8207179B2

  公开（公告）日：2012-06-26
• [EN] NEW COMPOUNDS<br/>[FR] NOUVEAUX COMPOSÉS
  申请人：BOEHRINGER INGELHEIM INT

  公开号：WO2008152014A2

  公开（公告）日：2008-12-18

  [EN] The present invention encompasses compounds of general Formula (I) wherein R2, R3, Q, W, X, Y and Z are defined as in claim 1, which are suitable for the treatment of diseases characterised by excessive or abnormal cell proliferation, and the use thereof for preparing a medicament having the above-mentioned properties.
  [FR] La présente invention concerne des composés représentés par la formule générale (I), dans laquelle R2, R3, Q, W, X, Y et Z désignent des éléments définis dans la revendication 1. Ces composés sont destinés à être utilisés pour le traitement de maladies caractérisées par une prolifération cellulaire excessive ou anormale. L'invention concerne également l'utilisation de ces composés pour la préparation d'un médicament possédant les propriétés décrites ci-dessus.