2-methyl-4-phenyl-2H-1,2-benzothiazine-3-carboxylic acid 1,1-dioxide | 1291842-43-7

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: 2-methyl-4-phenyl-2H-1,2-benzothiazine-3-carboxylic acid 1,1-dioxide
• 英文别名: 2-methyl-1,1-dioxo-4-phenyl-1λ6,2-benzothiazine-3-carboxylic acid
• CAS: 1291842-43-7
• 化学式: C₁₆H₁₃NO₄S
• 分子量: 315.35
• InChiKey: DDQWWOKOUSYARL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  83.1
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-methyl-4-phenyl-2H-1,2-benzothiazine-3-carboxylic acid 1,1-dioxide 在 草酰氯 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 N-cyclopropyl-2-methyl-1,1-dioxo-4-phenyl-1lambda6,2-benzothiazine-3-carboxamide
  参考文献：
  名称：

  Discovery of benzothiazine derivatives as novel, orally-active anti-epileptic drug candidates with broad anticonvulsant effect

  摘要：

  In order to develop novel anti-epileptic drugs that are effective for both general and partial seizure, we conducted in vivo screening of our chemical library in the mice MES and sc-PTZ models and found the benzothiazine 1 as lead compound. Optimization of this compound led to the discovery of compound 7b, which showed potent anticonvulsant effect in the MES, scPTZ and rat amygdala kindling models. Since the chemical structure of 7b is different from that of any existing AED, it is suggested that 7b may have unique mechanism of action for relieving both partial and generalized epilepsy. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2015.08.071
• 作为产物：
  描述：

  4-羟基-2-甲基-2H-1,2-苯并噻嗪-3-甲酸乙酯 1,1-二氧化物 在 吡啶 、 potassium phosphate 、 四(三苯基膦)钯 、 水 、 lithium hydroxide 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 二氯甲烷 为溶剂， 生成 2-methyl-4-phenyl-2H-1,2-benzothiazine-3-carboxylic acid 1,1-dioxide
  参考文献：
  名称：

  Discovery of benzothiazine derivatives as novel, orally-active anti-epileptic drug candidates with broad anticonvulsant effect

  摘要：

  In order to develop novel anti-epileptic drugs that are effective for both general and partial seizure, we conducted in vivo screening of our chemical library in the mice MES and sc-PTZ models and found the benzothiazine 1 as lead compound. Optimization of this compound led to the discovery of compound 7b, which showed potent anticonvulsant effect in the MES, scPTZ and rat amygdala kindling models. Since the chemical structure of 7b is different from that of any existing AED, it is suggested that 7b may have unique mechanism of action for relieving both partial and generalized epilepsy. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2015.08.071

文献信息

• Discovery of benzothiazine derivatives as novel, orally-active anti-epileptic drug candidates with broad anticonvulsant effect
  作者：Tomoyuki Tanaka、Nana Yajima、Akihiko Tanitame、Tomoko Kiyoshi、Yoshiki Miura

  DOI：10.1016/j.bmcl.2015.08.071

  日期：2015.10

  In order to develop novel anti-epileptic drugs that are effective for both general and partial seizure, we conducted in vivo screening of our chemical library in the mice MES and sc-PTZ models and found the benzothiazine 1 as lead compound. Optimization of this compound led to the discovery of compound 7b, which showed potent anticonvulsant effect in the MES, scPTZ and rat amygdala kindling models. Since the chemical structure of 7b is different from that of any existing AED, it is suggested that 7b may have unique mechanism of action for relieving both partial and generalized epilepsy. (C) 2015 Elsevier Ltd. All rights reserved.