3-butyl-4-<<2'-(N-triphenylmethyl)tetrazol-5-yl>biphenyl-4-yl>methyl-2H-1,2,4-benzothiadiazine 1,1-dioxide | 220371-15-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: 3-butyl-4-<<2'-(N-triphenylmethyl)tetrazol-5-yl>biphenyl-4-yl>methyl-2H-1,2,4-benzothiadiazine 1,1-dioxide
• CAS: 220371-15-3
• 化学式: C₄₄H₃₈N₆O₂S
• 分子量: 714.891
• InChiKey: MBTMUPWWIKQWFL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.14
• 重原子数：
  53.0
• 可旋转键数：
  11.0
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  93.34
• 氢给体数：
  0.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  3-butyl-4-<<2'-(N-triphenylmethyl)tetrazol-5-yl>biphenyl-4-yl>methyl-2H-1,2,4-benzothiadiazine 1,1-dioxide 在 盐酸 作用下， 以 四氢呋喃 为溶剂， 反应 4.0h， 以36%的产率得到2-methyl>aminobenzenesulfonamide
  参考文献：
  名称：

  Studies on 1, 2, 4-Benzothiadiazine 1, 1-Dioxide IX.¹Synthesis and Pharmacological Evaluation of 1, 2, 4-Benzothiadiazine 1, 1-Dioxide Biphenyl Tetrazoles as Angiotensin II Antagonists

  摘要：

  AbstractIn the course of our investigations on the development of cardiovascular agents, 3‐butyl‐2‐[2′‐(2H‐tetrazol‐5‐yl)bipheny]‐4‐yl]methyl‐2H‐1, 2, 4‐benzothiadiazine 1, 1‐dioxide (2) was considered as a potential angiotensin II antagonist on the basis of bioisosteric replacement of the quinazoline ring of compound 1 with a 1, 2, 4‐benzothiadiazine 1, 1‐dioxide ring system. Alkylation of 6 with 4 afforded 7 and 8 in 24% and 28% yields, respectively. An attempt to remove the trityl group of compounds 7 and 8 under acidic condition gave the ring opened products 9 and 11 in 28% and 36% yields, respectively. However, compounds 2 and 10 were obtained in 46% and 85% yields when compounds 7 and 8 were refluxed in methanol. Preliminary assays of compounds 9 and 11 against angiotensin II receptors revealed weak activity with IC50 values of 3.6 μM and 5.4 μM, respectively. Compound 10 (IC50 = 87 nM) exhibited stronger binding affinity than compound 2 (IC50 = 750 nM).

  DOI：

  10.1002/jccs.199800121
• 作为产物：
  描述：

  邻氨基苯磺酰胺 在 potassium carbonate 、 对甲苯磺酸 、 potassium iodide 作用下， 以 甲苯 、 乙腈 为溶剂， 反应 168.0h， 生成 3-butyl-4-<<2'-(N-triphenylmethyl)tetrazol-5-yl>biphenyl-4-yl>methyl-2H-1,2,4-benzothiadiazine 1,1-dioxide
  参考文献：
  名称：

  Studies on 1, 2, 4-Benzothiadiazine 1, 1-Dioxide IX.¹Synthesis and Pharmacological Evaluation of 1, 2, 4-Benzothiadiazine 1, 1-Dioxide Biphenyl Tetrazoles as Angiotensin II Antagonists

  摘要：

  AbstractIn the course of our investigations on the development of cardiovascular agents, 3‐butyl‐2‐[2′‐(2H‐tetrazol‐5‐yl)bipheny]‐4‐yl]methyl‐2H‐1, 2, 4‐benzothiadiazine 1, 1‐dioxide (2) was considered as a potential angiotensin II antagonist on the basis of bioisosteric replacement of the quinazoline ring of compound 1 with a 1, 2, 4‐benzothiadiazine 1, 1‐dioxide ring system. Alkylation of 6 with 4 afforded 7 and 8 in 24% and 28% yields, respectively. An attempt to remove the trityl group of compounds 7 and 8 under acidic condition gave the ring opened products 9 and 11 in 28% and 36% yields, respectively. However, compounds 2 and 10 were obtained in 46% and 85% yields when compounds 7 and 8 were refluxed in methanol. Preliminary assays of compounds 9 and 11 against angiotensin II receptors revealed weak activity with IC50 values of 3.6 μM and 5.4 μM, respectively. Compound 10 (IC50 = 87 nM) exhibited stronger binding affinity than compound 2 (IC50 = 750 nM).

  DOI：

  10.1002/jccs.199800121