4-methyl-3-oxo-2,3-dihydro-4H-pyrido<4,3-e>-1,2,4-thiadiazine 1,1-dioxide | 174676-45-0

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 4-methyl-3-oxo-2,3-dihydro-4H-pyrido<4,3-e>-1,2,4-thiadiazine 1,1-dioxide
• 英文别名: 4-Methyl-1,1-dioxopyrido[4,3-e][1,2,4]thiadiazin-3-one
• CAS: 174676-45-0
• 化学式: C₇H₇N₃O₃S
• 分子量: 213.217
• InChiKey: IKVUSWZYMDKKFG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.8
• 重原子数：
  14
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  87.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-methyl-3-oxo-2,3-dihydro-4H-pyrido<4,3-e>-1,2,4-thiadiazine 1,1-dioxide 在 吡啶 、 diphosphorus pentasulfide 、 碳酸氢钠 作用下， 以 甲醇 为溶剂， 反应 48.5h， 生成 4-methyl-3-methylsulfanyl-4H-pyrido<4.3-e>-1,2,4-thiadiazine 1,1-dioxide
  参考文献：
  名称：

  3- and 4-Substituted 4H-Pyrido[4,3-e]-1,2,4-thiadiazine 1,1-Dioxides as Potassium Channel Openers:  Synthesis, Pharmacological Evaluation, and Structure−Activity Relationships

  摘要：

  4-N-Subsituted and -unsubstituted 3-alkyl- and 3-(alkylamino)-4H-pyrido[4,3-e]-1,2,4-thiadiazine 1,1-dioxides were synthesized and tested vs diazoxide and selected 3-alkyl- and 3-(alkylamino)-7-chloro-4H-1,2,4-benzothiadiazine 1,1-dioxides as potassium channel openers on pancreatic and vascular tissues. Several 4-N-unsubstituted 3-(alkylamino)pyridothiadiazines and some 3-(alkylamino)-7-chlorobenzothiadiazines were found to be more potent than diazoxide for the inhibition of the insulin-releasing process. Moreover, the 3-(alkylamino)pyridothiadiazines appeared to be more selective for the pancreatic than for the vascular tissue. By means of the pharmacological results obtained on pancreatic B-cells, structure-activity relationships were deduced and a pharmacophoric model for the interaction of these drugs with their receptor site associated to the pancreatic K-ATP channel was proposed. According to their selectivity for the B-cell (endocrine tissue) vs the vascular (smooth muscle tissue) ionic channel, selected 3-(alkylamino)-4H-pyrido[4,3-e]-1,2,4-thiadiazine 1,1-dioxides may serve as pharmacological tools in studying the K-ATP channels (''pancreatic-like'' K-ATP channels) in other tissues.

  DOI：

  10.1021/jm9500582
• 作为产物：
  描述：

  4-(甲基氨基)-3-吡啶磺酰胺 、 尿素 以63%的产率得到4-methyl-3-oxo-2,3-dihydro-4H-pyrido<4,3-e>-1,2,4-thiadiazine 1,1-dioxide
  参考文献：
  名称：

  3- and 4-Substituted 4H-Pyrido[4,3-e]-1,2,4-thiadiazine 1,1-Dioxides as Potassium Channel Openers:  Synthesis, Pharmacological Evaluation, and Structure−Activity Relationships

  摘要：

  4-N-Subsituted and -unsubstituted 3-alkyl- and 3-(alkylamino)-4H-pyrido[4,3-e]-1,2,4-thiadiazine 1,1-dioxides were synthesized and tested vs diazoxide and selected 3-alkyl- and 3-(alkylamino)-7-chloro-4H-1,2,4-benzothiadiazine 1,1-dioxides as potassium channel openers on pancreatic and vascular tissues. Several 4-N-unsubstituted 3-(alkylamino)pyridothiadiazines and some 3-(alkylamino)-7-chlorobenzothiadiazines were found to be more potent than diazoxide for the inhibition of the insulin-releasing process. Moreover, the 3-(alkylamino)pyridothiadiazines appeared to be more selective for the pancreatic than for the vascular tissue. By means of the pharmacological results obtained on pancreatic B-cells, structure-activity relationships were deduced and a pharmacophoric model for the interaction of these drugs with their receptor site associated to the pancreatic K-ATP channel was proposed. According to their selectivity for the B-cell (endocrine tissue) vs the vascular (smooth muscle tissue) ionic channel, selected 3-(alkylamino)-4H-pyrido[4,3-e]-1,2,4-thiadiazine 1,1-dioxides may serve as pharmacological tools in studying the K-ATP channels (''pancreatic-like'' K-ATP channels) in other tissues.

  DOI：

  10.1021/jm9500582

文献信息

• 3- and 4-Substituted 4<i>H</i>-Pyrido[4,3-<i>e</i>]-1,2,4-thiadiazine 1,1-Dioxides as Potassium Channel Openers:  Synthesis, Pharmacological Evaluation, and Structure−Activity Relationships
  作者：Pascal de Tullio、Bernard Pirotte、Philippe Lebrun、Jeanine Fontaine、Léon Dupont、Marie-Hélène Antoine、Raogo Ouedraogo、Smail Khelili、Carine Maggetto、Bernard Masereel、Ousmane Diouf、Tchao Podona、Jacques Delarge

  DOI：10.1021/jm9500582

  日期：1996.1.1

  4-N-Subsituted and -unsubstituted 3-alkyl- and 3-(alkylamino)-4H-pyrido[4,3-e]-1,2,4-thiadiazine 1,1-dioxides were synthesized and tested vs diazoxide and selected 3-alkyl- and 3-(alkylamino)-7-chloro-4H-1,2,4-benzothiadiazine 1,1-dioxides as potassium channel openers on pancreatic and vascular tissues. Several 4-N-unsubstituted 3-(alkylamino)pyridothiadiazines and some 3-(alkylamino)-7-chlorobenzothiadiazines were found to be more potent than diazoxide for the inhibition of the insulin-releasing process. Moreover, the 3-(alkylamino)pyridothiadiazines appeared to be more selective for the pancreatic than for the vascular tissue. By means of the pharmacological results obtained on pancreatic B-cells, structure-activity relationships were deduced and a pharmacophoric model for the interaction of these drugs with their receptor site associated to the pancreatic K-ATP channel was proposed. According to their selectivity for the B-cell (endocrine tissue) vs the vascular (smooth muscle tissue) ionic channel, selected 3-(alkylamino)-4H-pyrido[4,3-e]-1,2,4-thiadiazine 1,1-dioxides may serve as pharmacological tools in studying the K-ATP channels (''pancreatic-like'' K-ATP channels) in other tissues.