2,3-diamino-5-(trifluoromethyl)benzoic acid | 910123-03-4

• 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: 2,3-diamino-5-(trifluoromethyl)benzoic acid
• 英文别名: 2,3-Diamino-5-trifluoromethylbenzoic acid
• CAS: 910123-03-4
• 化学式: C₈H₇F₃N₂O₂
• 分子量: 220.151
• InChiKey: FXYFPIKDVXVKQR-UHFFFAOYSA-N

物化性质

• 沸点：
  362.3±42.0 °C(Predicted)
• 密度：
  1.572±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  89.3
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  2,3-diamino-5-(trifluoromethyl)benzoic acid 在 盐酸 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 N,N-二异丙基乙胺 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 26.0h， 生成 6-trifluoromethyl-3H-benzoimidazole-4-carboxylic acid [3-(lH-tetrazol-5-yl)-phenyl]-amide trifluoroacetate
  参考文献：
  名称：

  Structure-Based Design of Potent and Ligand-Efficient Inhibitors of CTX-M Class A β-Lactamase

  摘要：

  The emergence of CTX-M class A extended-spectrum beta-lactamases poses a serious health threat to the public. We have applied structure-based design to improve the potency of a novel noncovalent tetrazole-containing CTX-M inhibitor (K-i = 21 mu M) more than 200-fold via structural modifications targeting two binding hot spots, a hydrophobic shelf formed by Pro167 and a polar site anchored by Asp240. Functional groups contacting each binding hot spot independently in initial designs were later combined to produce analogues with submicromolar potencies, including 6-trifluoromethyl-3H-benzoimidazole-4-carboxylic acid [3-(1H-tetrazol-5-yl)-phenyl]-amide, which had a K-i value of 89 nM and reduced the MIC of cefotaxime by 64-fold in CTX-M-9 expressing Escherichia coli. The in vitro potency gains were accompanied by improvements in ligand efficiency (from 0.30 to 0.39) and LipE (from 1.37 to 3.86). These new analogues represent the first nM-affinity noncovalent inhibitors of a class A beta-lactamase. Their complex crystal structures provide valuable information about ligand binding for future inhibitor design.

  DOI：

  10.1021/jm2014138
• 作为产物：
  描述：

  2-氯-3-硝基-5-(三氟甲基)苯甲酸 在 ammonium hydroxide 、 palladium 10% on activated carbon 、 氢气 作用下， 以 甲醇 为溶剂， 反应 1.0h， 生成 2,3-diamino-5-(trifluoromethyl)benzoic acid
  参考文献：
  名称：

  [EN] COMPOSITIONS, METHODS OF USE, AND METHODS OF TREATMENT
  [FR] COMPOSITIONS, PROCÉDÉS D'UTILISATION ET PROCÉDÉS DE TRAITEMENT

  摘要：

  本公开的实施例在某一方面涉及β-内酰胺酶抑制剂、包括β-内酰胺酶抑制剂的药物组合物、治疗疾病或病症的方法、使用组合物或药物组合物的治疗方法等。

  公开号：

  WO2013103760A1

文献信息

• [EN] COMPOSITIONS, METHODS OF USE, AND METHODS OF TREATMENT<br/>[FR] COMPOSITIONS, PROCÉDÉS D'UTILISATION ET PROCÉDÉS DE TRAITEMENT
  申请人：UNIV SOUTH FLORIDA

  公开号：WO2013103760A1

  公开（公告）日：2013-07-11

  Embodiments of the present disclosure, in one aspect, relate to a beta-lactamase inhibitor, pharmaceutical compositions including a beta-lactamase inhibitor, methods of treatment of a condition (e.g., infection) or disease, methods of treatment using compositions or pharmaceutical compositions, and the like.

  本公开的实施例在某一方面涉及β-内酰胺酶抑制剂、包括β-内酰胺酶抑制剂的药物组合物、治疗疾病或病症的方法、使用组合物或药物组合物的治疗方法等。
• Benzazole derivatives, compositions, and methods of use as beta-secretase inhibitors
  申请人：Mjalli M.M. Adnan

  公开号：US20060223849A1

  公开（公告）日：2006-10-05

  The present invention is directed to benzazole compounds that inhibit β-site amyloid precursor protein-cleaving enzyme (BACE) and that may be useful in the treatment or prevention of diseases in which BACE is involved, such as Alzheimer's disease. The invention is also directed to pharmaceutical compositions comprising these compounds and the use of these compounds and compositions in the prevention or treatment of such diseases in which BACE is involved.

  本发明涉及一种抑制β-淀粉样前体蛋白剪切酶（BACE）的苯并咪唑化合物，该化合物可用于治疗或预防BACE参与的疾病，如阿尔茨海默病。本发明还涉及包含这些化合物的药物组合物以及在预防或治疗BACE参与的这些疾病中使用这些化合物和组合物的用途。
• Benzazole Derivatives, Compositions, and Methods of Use as Beta-Secretase Inhibitors
  申请人：Mjalli Adnan M.M.

  公开号：US20090326006A1

  公开（公告）日：2009-12-31

  The present invention is directed to benzazole compounds that inhibit β-site amyloid precursor protein-cleaving enzyme (BACE) and that may be useful in the treatment or prevention of diseases in which BACE is involved, such as Alzheimer's disease. The invention is also directed to pharmaceutical compositions comprising these compounds and the use of these compounds and compositions in the prevention or treatment of such diseases in which BACE is involved.

  本发明涉及抑制β位点淀粉样前体蛋白剪切酶（BACE）的苯并唑化合物，可用于治疗或预防BACE参与的疾病，如阿尔茨海默病。本发明还涉及包含这些化合物的药物组合物，以及在预防或治疗BACE参与的这些疾病中使用这些化合物和组合物的用途。
• Benzazole Derivatives, Compositions, and Methods of Use as B-Secretase Inhibitors
  申请人：Mjalli Adnan M.M.

  公开号：US20110065713A1

  公开（公告）日：2011-03-17

  The present invention is directed to benzazole compounds that inhibit β-site amyloid precursor protein-cleaving enzyme (BACE) and that may be useful in the treatment or prevention of diseases in which BACE is involved, such as Alzheimer's disease. The invention is also directed to pharmaceutical compositions comprising these compounds and the use of these compounds and compositions in the prevention or treatment of such diseases in which BACE is involved.

  本发明涉及一种抑制 β-淀粉样前体蛋白裂解酶（BACE）的苯并咪唑化合物，该化合物可能在治疗或预防包括阿尔茨海默病在内的与BACE有关的疾病中有用。本发明还涉及包含这些化合物的药物组合物以及在预防或治疗BACE参与的这类疾病中使用这些化合物和组合物。
• COMPOSITIONS, METHODS OF USE, AND METHODS OF TREATMENT
  申请人：University of South Florida

  公开号：US20140378516A1

  公开（公告）日：2014-12-25

  Embodiments of the present disclosure, in one aspect, relate to a beta-lactamase inhibitor, pharmaceutical compositions including a beta-lactamase inhibitor, methods of treatment of a condition (e.g., infection) or disease, methods of treatment using compositions or pharmaceutical compositions, and the like.

  本公开的实施例在某些方面涉及β-内酰胺酶抑制剂、包括β-内酰胺酶抑制剂的制药组合物、治疗病症（例如感染）或疾病的方法、使用组合物或制药组合物的治疗方法等。