(3-Methoxy-4-nitrophenyl)-(5,6,7,8-tetrahydrothieno[3,2-b]azepin-4-yl)methanone | 190276-75-6

• 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-Methoxy-4-nitrophenyl)-(5,6,7,8-tetrahydrothieno[3,2-b]azepin-4-yl)methanone
• 英文别名: (3-methoxy-4-nitrophenyl)-(5,6,7,8-tetrahydrothieno[3,2-b]azepin-4-yl)methanone
• CAS: 190276-75-6
• 化学式: C₁₆H₁₆N₂O₄S
• 分子量: 332.38
• InChiKey: LLSMWOWQOMIIOV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  23
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  104
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (3-Methoxy-4-nitrophenyl)-(5,6,7,8-tetrahydrothieno[3,2-b]azepin-4-yl)methanone 在 palladium on activated charcoal 氢氧化钾 、 氢气 、 三溴化硼 、 potassium carbonate 、 三乙胺 、 potassium iodide 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 7.0h， 生成 [2-[(Biphenyl-2-carbonyl)-amino]-5-(5,6,7,8-tetrahydro-thieno[3,2-b]azepine-4-carbonyl)-phenoxy]-acetic acid
  参考文献：
  名称：

  Synthesis and Structure−Activity Relationships of 5,6,7,8-Tetrahydro-4H-thieno[3,2-b]azepine Derivatives:  Novel Arginine Vasopressin Antagonists

  摘要：

  A variety of novel heterocyclic compounds having thienoazepine, pyrroloazepine, furoazepine, and thienodiazepine skeletons were synthesized, most of which exhibited potent antagonism of [H-3]-AVP specific binding in assays using rat liver (V1), rat kidney (V2), human platelet plasma membranes, and recombinant human CHO cells (V2), as well as antagonizing AVP-induced hypertension in rats (V1, intravenous) and showing a diuretic effect in rats (V2, oral). By detailed studies of the structure-activity relationships of these compounds, the thienoazepine derivative 1 was found to be a very potent combined V1 and V2 antagonist. After further pharmacological and toxicological evaluation as well as physical properties, the hydrochloride 2 (JTV-605) of compound 1 was selected for clinical studies as a potent AVP antagonist with a long duration of action.

  DOI：

  10.1021/jm030287l
• 作为产物：
  描述：

  3-甲氧基-4-硝基苯甲酸 在 lithium aluminium tetrahydride 、 氯化亚砜 作用下， 以 氯仿 、 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 生成 (3-Methoxy-4-nitrophenyl)-(5,6,7,8-tetrahydrothieno[3,2-b]azepin-4-yl)methanone
  参考文献：
  名称：

  Regioselective Synthesis of Several Heterocyclic Fused Azepines Using Diisobutylaluminum Hydride

  摘要：

  5,6,7,8-Tetrahydrothieno[3,2-b]azepine,5,6,7,8-tetrahydro-1H-furo[3,- 2b]azepine, and 1,4,5,6,7,8-hexahydropyrrolo [3,2-b]azepine were synthesized by the ring expansion reaction of heterocyclic fused cyclohexanone oximes with diisobutylaluminum hydride (DIBAH). The mechanism of the reaction was different from that of Beckmann rearrangement.

  DOI：

  10.3987/com-98-8104