N³-Cyclobutyl-1,1-dioxo-1,4-dihydro-1λ⁶-benzo[1,2,4]thiadiazine-3,7-diamine | 497250-10-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻二嗪
• 英文名称: N³-Cyclobutyl-1,1-dioxo-1,4-dihydro-1λ⁶-benzo[1,2,4]thiadiazine-3,7-diamine
• 英文别名: 3-cyclobutylimino-1,1-dioxo-4H-1lambda6,2,4-benzothiadiazin-7-amine；3-cyclobutylimino-1,1-dioxo-4H-1λ6,2,4-benzothiadiazin-7-amine
• CAS: 497250-10-9
• 化学式: C₁₁H₁₄N₄O₂S
• 分子量: 266.324
• InChiKey: AJJGPEYPBZRNCG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  105
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N³-Cyclobutyl-1,1-dioxo-1,4-dihydro-1λ⁶-benzo[1,2,4]thiadiazine-3,7-diamine 在 三氟化硼乙醚 、 亚硝酸异戊酯 、 盐酸 、 copper(l) chloride 作用下， 以 四氢呋喃 为溶剂， 生成 7-Chloro-3-cyclobutylamino-4H-1,2,4-benzothiadiazine 1,1-dioxide
  参考文献：
  名称：

  Synthesis and evaluation of 7-substituted-3-cyclobutylamino-4H-1,2,4-benzothiadiazine-1,1-dioxide derivatives as KATP channel agonists

  摘要：

  A series of 7-substituted-3-cyclobutylamino-4H-1,2,4-benzothiadiazine-1,1-dioxide derivatives has been synthesized and evaluated as K-ATP channel agonists using the inside-out excised patch clamp technique. The most active compounds were similar to20-fold more potent than diazoxide in opening K-ATP channels. A linear relationship exists between the potency of the compound and the sigma value of the 7-substituent with electron-withdrawing groups exhibiting higher activity. These compounds may be useful in modulating insulin release from pancreatic beta-cells and in diseases associated with hyperinsulinemia. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(02)00617-0
• 作为产物：
  描述：

  3-cyclobutylamino-7-nitro-4H-1,2,4-benzothiadiazine 1,1-dioxide 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 以85%的产率得到N³-Cyclobutyl-1,1-dioxo-1,4-dihydro-1λ⁶-benzo[1,2,4]thiadiazine-3,7-diamine
  参考文献：
  名称：

  Synthesis and evaluation of 7-substituted-3-cyclobutylamino-4H-1,2,4-benzothiadiazine-1,1-dioxide derivatives as KATP channel agonists

  摘要：

  A series of 7-substituted-3-cyclobutylamino-4H-1,2,4-benzothiadiazine-1,1-dioxide derivatives has been synthesized and evaluated as K-ATP channel agonists using the inside-out excised patch clamp technique. The most active compounds were similar to20-fold more potent than diazoxide in opening K-ATP channels. A linear relationship exists between the potency of the compound and the sigma value of the 7-substituent with electron-withdrawing groups exhibiting higher activity. These compounds may be useful in modulating insulin release from pancreatic beta-cells and in diseases associated with hyperinsulinemia. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(02)00617-0

文献信息

• Synthesis and evaluation of 7-substituted-3-cyclobutylamino-4H-1,2,4-benzothiadiazine-1,1-dioxide derivatives as KATP channel agonists
  作者：Andrew J Peat、Claire Townsend、Jennings F Worley, III、Scott H Allen、Dulce Garrido、Robert J Mertz、Jeffrey L Pfohl、Christopher M Terry、Jim F Truax、Robert L Veasey、Stephen A Thomson

  DOI：10.1016/s0960-894x(02)00617-0

  日期：2002.10

  A series of 7-substituted-3-cyclobutylamino-4H-1,2,4-benzothiadiazine-1,1-dioxide derivatives has been synthesized and evaluated as K-ATP channel agonists using the inside-out excised patch clamp technique. The most active compounds were similar to20-fold more potent than diazoxide in opening K-ATP channels. A linear relationship exists between the potency of the compound and the sigma value of the 7-substituent with electron-withdrawing groups exhibiting higher activity. These compounds may be useful in modulating insulin release from pancreatic beta-cells and in diseases associated with hyperinsulinemia. (C) 2002 Elsevier Science Ltd. All rights reserved.