3-Guanidinomethyl-benzoic acid | 199535-03-0

• 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-Guanidinomethyl-benzoic acid
• 英文别名: 3-[(diaminomethylideneamino)methyl]benzoic acid
• CAS: 199535-03-0
• 化学式: C₉H₁₁N₃O₂
• 分子量: 193.205
• InChiKey: TXDDMDVTPDDPIM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  102
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  氨基亚氨基甲烷磺酸 、 3-(氨甲基)苯甲酸 在 sodium hydroxide 、 碳酸氢钠 作用下， 反应 16.0h， 以58%的产率得到3-Guanidinomethyl-benzoic acid
  参考文献：
  名称：

  Design and Synthesis of Benzoic Acid Derivatives as Influenza Neuraminidase Inhibitors Using Structure-Based Drug Design

  摘要：

  A series of 94 benzoic acid derivatives was synthesized and tested for its ability to inhibit influenza neuraminidase. The enzyme-inhibitor complex structure was determined by X-ray crystallographic analysis for compounds which inhibited the enzyme. The most potent compound tested in vitro, 5 (4-(acetylamino)-3-guanidinobenzoic acid), had an IC50 = 2.5 x 10(-6) M against N9 neuraminidase. Compound 5 was oriented in the active site of the neuraminidase ina manner that was not predicted from the reported active site binding of GANA (4) with neuraminidase. In a mouse model of influenza, 5 did not protect the mice from weight loss due to the influenza virus when dosed intranasally.

  DOI：

  10.1021/jm970479e

文献信息

• [EN] IMIDAZO[4,5-c] RING COMPOUNDS CONTAINING GUANIDINE SUBSTITUTED BENZAMIDE GROUPS<br/>[FR] COMPOSÉS COMPRENANT UN CYCLE IMIDAZO[4,5-C] CONTENANT DES GROUPES BENZAMIDE À SUBSTITUTION GUANIDINE
  申请人：3M INNOVATIVE PROPERTIES CO

  公开号：WO2018160552A1

  公开（公告）日：2018-09-07

  lmidazo[4,5-c] ring compounds of formula I, (particularly imidazo4,5-c]quinolines, 6,7,8,9-tetrahydroimidazo[4,5-c]quinolines, imidazo[4,5- c]naphthyridines, and 6,7,8,9-tetrahydroimidazo[4,5-c]naphthyridine compounds) having a guanidine substituted benzamide that is attached at the N-l position by a linking group, pharmaceutical compositions containing the compounds, and methods of making the compounds are disclosed. Methods of use of the compounds as immune response modifiers, for inducing cytokine biosynthesis in animals and in the treatment of diseases including viral and neoplastic diseases are also disclosed.

  lmidazo[4,5-c]环化合物的化学式I（特别是咪唑[4,5-c]喹啉，6,7,8,9-四氢咪唑[4,5-c]喹啉，咪唑[4,5-c]萘啉和6,7,8,9-四氢咪唑[4,5-c]萘啉化合物），具有一种通过连接基团连接到N-1位置的胍基取代苯甲酰胺，包含这些化合物的药物组合物以及制备这些化合物的方法已被披露。还披露了将这些化合物用作免疫应答调节剂，用于诱导动物体内细胞因子生物合成以及用于治疗包括病毒性和肿瘤性疾病在内的疾病的方法。
• Imidazo[4,5-c] ring compounds containing guanidine substituted benzamide groups
  申请人：3M INNOVATIVE PROPERTIES COMPANY

  公开号：US10766896B2

  公开（公告）日：2020-09-08

  Imidazo[4,5-c] ring compounds of formula I, (particularly imidazo4,5-c]quinolines, 6,7,8,9-tetrahydroimidazo[4,5-c]quinolines, imidazo[4,5-c]naphthyridines, and 6,7,8,9-tetrahydroimidazo[4,5-c]naphthyridine compounds) having a guanidine substituted benzamide that is attached at the N−1 position by a linking group, pharmaceutical compositions containing the compounds, and methods of making the compounds are disclosed. Methods of use of the compounds as immune response modifiers, for inducing cytokine biosynthesis in animals and in the treatment of diseases including viral and neoplastic diseases are also disclosed.

  式 I 的咪唑并[4,5-c]环化合物（特别是咪唑并[4,5-c]喹啉类、6,7,8,9-四氢咪唑并[4,5-c]喹啉类、咪唑并[4,5-c]萘啶类和 6,7,8,9- 四氢咪唑并[4、5-c]萘啶化合物）、含有这些化合物的药物组合物以及制造这些化合物的方法。还公开了将这些化合物用作免疫反应调节剂、诱导动物体内细胞因子的生物合成以及治疗包括病毒性和肿瘤性疾病在内的疾病的方法。
• IMIDAZO[4,5-C]RING COMPOUNDS CONTAINING GUANIDINE SUBSTITUTED BENZAMIDE GROUPS
  申请人：3M Innovative Properties Company

  公开号：EP3589631B1

  公开（公告）日：2021-07-21
• Imidazo[4,5-c] Ring Compounds Containing Guanidine Substituted Benzamide Groups
  申请人：3M INNOVATIVE PROPERTIES COMPANY

  公开号：US20200087298A1

  公开（公告）日：2020-03-19

  Imidazo[4,5-c] ring compounds of formula I, (particularly imidazo4,5-c]quinolines, 6,7,8,9-tetrahydroimidazo[4,5-c]quinolines, imidazo[4,5-c]naphthyridines, and 6,7,8,9-tetrahydroimidazo[4,5-c]naphthyridine compounds) having a guanidine substituted benzamide that is attached at the N−1 position by a linking group, pharmaceutical compositions containing the compounds, and methods of making the compounds are disclosed. Methods of use of the compounds as immune response modifiers, for inducing cytokine biosynthesis in animals and in the treatment of diseases including viral and neoplastic diseases are also disclosed.
• Design and Synthesis of Benzoic Acid Derivatives as Influenza Neuraminidase Inhibitors Using Structure-Based Drug Design
  作者：Pooran Chand、Yarlagadda S. Babu、Shanta Bantia、Naiming Chu、L. Brent Cole、Pravin L. Kotian、W. Graeme Laver、John A. Montgomery、Ved P. Pathak、Sandra L. Petty、David P. Shrout、David A. Walsh、Gerald M. Walsh

  DOI：10.1021/jm970479e

  日期：1997.12.1

  A series of 94 benzoic acid derivatives was synthesized and tested for its ability to inhibit influenza neuraminidase. The enzyme-inhibitor complex structure was determined by X-ray crystallographic analysis for compounds which inhibited the enzyme. The most potent compound tested in vitro, 5 (4-(acetylamino)-3-guanidinobenzoic acid), had an IC50 = 2.5 x 10(-6) M against N9 neuraminidase. Compound 5 was oriented in the active site of the neuraminidase ina manner that was not predicted from the reported active site binding of GANA (4) with neuraminidase. In a mouse model of influenza, 5 did not protect the mice from weight loss due to the influenza virus when dosed intranasally.