1-[(4-methylphenyl)sulfonyl]-5-oxo-2,3,4,5-tetrahydro-1H-1-benzazepine-4-carbonitrile | 105895-94-1

• 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-[(4-methylphenyl)sulfonyl]-5-oxo-2,3,4,5-tetrahydro-1H-1-benzazepine-4-carbonitrile
• 英文别名: 5-hydroxy-1-tosyl-2,3-dihydro-1H-benzazepine-4-carbonitrile；2,3-Dihydro-5-hydroxy-1-[(4-methylphenyl)sulfonyl]-1H-1-benzazepine-4-carbonitrile；5-hydroxy-1-(4-methylphenyl)sulfonyl-2,3-dihydro-1-benzazepine-4-carbonitrile
• CAS: 105895-94-1
• 化学式: C₁₈H₁₆N₂O₃S
• 分子量: 340.403
• InChiKey: JQFVFEABZLBADO-UHFFFAOYSA-N

物化性质

• 熔点：
  154-155 °C(Solv: ethanol (64-17-5))
• 沸点：
  550.9±60.0 °C(Predicted)
• 密度：
  1.42±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  24
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  89.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1-[(4-methylphenyl)sulfonyl]-5-oxo-2,3,4,5-tetrahydro-1H-1-benzazepine-4-carbonitrile 在 盐酸 、 三氯氧磷 作用下， 以 氯仿 、 溶剂黄146 为溶剂， 反应 95.5h， 生成 4-(2-hydroxyethylamino)-6,7-dihydro-5H-pyrimido<5,4-d><1>benzazepine
  参考文献：
  名称：

  Polycyclic N-Hetero Compounds. XXI. Synthesis of Novel Ring System, 4H-Imidazo[1',2':1,6]pyrimido[5,4-d][1]benzazepine as B-Homo-6,11,13,15-tetraazastereoidal Analogue

  摘要：

  DOI：

  10.3987/r-1986-01-0143
• 作为产物：
  描述：

  2-(4-甲基苯磺酰胺基)苯甲酸甲酯 在 sodium hydride 、 potassium carbonate 、 potassium iodide 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 168.0h， 生成 1-[(4-methylphenyl)sulfonyl]-5-oxo-2,3,4,5-tetrahydro-1H-1-benzazepine-4-carbonitrile
  参考文献：
  名称：

  Polycyclic N-Hetero Compounds. XXI. Synthesis of Novel Ring System, 4H-Imidazo[1',2':1,6]pyrimido[5,4-d][1]benzazepine as B-Homo-6,11,13,15-tetraazastereoidal Analogue

  摘要：

  DOI：

  10.3987/r-1986-01-0143

文献信息

• Theoretical studies, synthesis, and biological activity of 1-[(4-methylphenyl)sulfonyl]-5-oxo-2,3,4,5-tetrahydro-1H-1-benzazepine-4-carbonitrile (C9) as a non-peptide antagonist of the arginine vasopressin V1a and V2 receptors
  作者：M. Citlalli Contreras-Romo、José Correa-Basurto、Itzia Padilla-Martínez、Marlet Martínez-Archundia、Federico Martínez-Ramos、Magdalena J. Ślusarz、Gilberto López-Pérez、Andrés Quintanar-Stephano

  DOI：10.1007/s00044-013-0739-5

  日期：2014.3

  In this work, the synthesis of 1-[(4-methylphenyl)sulfonyl]-5-oxo-2,3,4,5-tetrahydro-1H-1-benzazepine-4-carbonitrile (C9) and the study of its biological activity as a new putative antagonist of vasopressin receptors are described. The chemical identification of the compound C9 was confirmed using H-1 and C-13 nuclear magnetic resonance. This compound contains a moiety core similar to those of vaptans; therefore, we decided to study the compound's binding on vasopressin receptors (V1aR and V2R), whose models were built, refined by molecular dynamics simulations, and validated through docking studies. The biological effects of C9 on vascular smooth muscle (VSM) contractility and aquaresis were also tested. Rat aortic rings were used to test the inhibitory effect of C9 (0.0, 5.9, 59, and 590 mu M) on AVP-induced VSM contraction (10 mu M). The inhibition of the antidiuretic effect of vasopressin (50 mu U/kg) by C9 (100 mu g/kg) was determined using a water load test in rats. The results showed that C9 inhibits aortic rings' contraction in a concentration-dependent manner, whereas C9 exhibited an aquaretic effect on urine flow. Docking studies showed that C9 reaches the vaptan binding site via the V1a and V2 receptors, which explains the similarity in their biological effects. The results indicate that C9 functions as an antagonist on both V1aR and V2R.
• HIROTA, TAKASHI;FUKUMOTO, MASAMI;SASAKI, KENJI;NAMBA, TETSUTO;HAYAKAWA, S+, HETEROCYCLES, 1986, 24, N 1, 143-154
  作者：HIROTA, TAKASHI、FUKUMOTO, MASAMI、SASAKI, KENJI、NAMBA, TETSUTO、HAYAKAWA, S+

  DOI：——

  日期：——
• Polycyclic N-Hetero Compounds. XXI. Synthesis of Novel Ring System, 4H-Imidazo[1',2':1,6]pyrimido[5,4-d][1]benzazepine as B-Homo-6,11,13,15-tetraazastereoidal Analogue
  作者：Takashi Hirota、Masami Fukukoto、Kenji Sasaki、Tetsuo Namba、Shohei Hayakawa

  DOI：10.3987/r-1986-01-0143

  日期：——