[1-(3-Nitro-phenyl)-meth-(E)-ylidene]-(1H-tetrazol-5-yl)-amine | 442851-03-8

• 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: [1-(3-Nitro-phenyl)-meth-(E)-ylidene]-(1H-tetrazol-5-yl)-amine
• CAS: 442851-03-8
• 化学式: C₈H₆N₆O₂
• 分子量: 218.175
• InChiKey: LSSHIVDEMHDEEB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.86
• 重原子数：
  16.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  109.96
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  [1-(3-Nitro-phenyl)-meth-(E)-ylidene]-(1H-tetrazol-5-yl)-amine 在 sodium tetrahydroborate 作用下， 以 乙醇 为溶剂， 反应 15.0h， 生成 3-<(tetrazol-5-ylamino)methyl>nitrobenzene
  参考文献：
  名称：

  Controlled Modification of Acidity in Cholecystokinin B Receptor Antagonists:  N-(1,4-Benzodiazepin-3-yl)-N ‘-[3-(tetrazol-5-ylamino)phenyl]ureas

  摘要：

  The design, synthesis, and biological activity of a novel series of CCK-B receptor antagonists (1) which incorporate a tetrazol-5-ylamino functionality attached to the phenyl ring of the arylurea moiety of L-365,260 are described. In these compounds, the acidity of the tetrazole was gradually modified by utilization of simple conformational constraints, and X-ray crystallographic data were obtained to support the conformational dependence of the pK(a) of the aminotetrazoles. Compounds to emerge from the present work such as 1f and 2c,d are among the highest affinity and, in the case of 1f, most selective (CCK-A/CCK-B, 37 000) antagonists so far reported for this receptor. The C-5-cyclohexyl compound 2c (L-736,380) dose-dependently inhibited gastric acid secretion in anesthetized rats (ID50, 0.064 mg/kg) and er vivo binding of [I-125]CCK-8S in BKTO mice brain membranes (ED(50), 1.7 mg/kg) and is one of the most potent acidic CCK-B receptor antagonists yet described.

  DOI：

  10.1021/jm9506736
• 作为产物：
  描述：

  5-氨基四氮唑 、 间硝基苯甲醛 在 溶剂黄146 作用下， 以 乙醇 为溶剂， 反应 0.67h， 生成 [1-(3-Nitro-phenyl)-meth-(E)-ylidene]-(1H-tetrazol-5-yl)-amine
  参考文献：
  名称：

  Controlled Modification of Acidity in Cholecystokinin B Receptor Antagonists:  N-(1,4-Benzodiazepin-3-yl)-N ‘-[3-(tetrazol-5-ylamino)phenyl]ureas

  摘要：

  The design, synthesis, and biological activity of a novel series of CCK-B receptor antagonists (1) which incorporate a tetrazol-5-ylamino functionality attached to the phenyl ring of the arylurea moiety of L-365,260 are described. In these compounds, the acidity of the tetrazole was gradually modified by utilization of simple conformational constraints, and X-ray crystallographic data were obtained to support the conformational dependence of the pK(a) of the aminotetrazoles. Compounds to emerge from the present work such as 1f and 2c,d are among the highest affinity and, in the case of 1f, most selective (CCK-A/CCK-B, 37 000) antagonists so far reported for this receptor. The C-5-cyclohexyl compound 2c (L-736,380) dose-dependently inhibited gastric acid secretion in anesthetized rats (ID50, 0.064 mg/kg) and er vivo binding of [I-125]CCK-8S in BKTO mice brain membranes (ED(50), 1.7 mg/kg) and is one of the most potent acidic CCK-B receptor antagonists yet described.

  DOI：

  10.1021/jm9506736