N-[4-(dimethylamino)butyl]-4-hydroxy-2-methyl-2H-1,2-benzothiazine-3-carboxamide 1,1-dioxide | 439254-53-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻嗪类
• 英文名称: N-[4-(dimethylamino)butyl]-4-hydroxy-2-methyl-2H-1,2-benzothiazine-3-carboxamide 1,1-dioxide
• 英文别名: N-[4-(dimethylamino)-butyl]-4-hydroxy-2-methyl-1,1-dioxo-2H-1,2-benzothiazine-3-carboxamide；N-[4-(dimethylamino)butyl]-4-hydroxy-2-methyl-1,1-dioxo-1lambda6,2-benzothiazine-3-carboxamide；N-[4-(dimethylamino)butyl]-4-hydroxy-2-methyl-1,1-dioxo-1λ6,2-benzothiazine-3-carboxamide
• CAS: 439254-53-2
• 化学式: C₁₆H₂₃N₃O₄S
• 分子量: 353.442
• InChiKey: HEYDSZDLMXSTEQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  98.3
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  N-[4-(dimethylamino)butyl]-4-hydroxy-2-methyl-2H-1,2-benzothiazine-3-carboxamide 1,1-dioxide 、 碘甲烷 以 丙酮 为溶剂， 反应 2.0h， 以72%的产率得到[4-(4-hydroxy-2-methyl-2H-1,2-benzothiazine-1,1-dioxide-3-carboxamido)butyl]trimethyl ammonium iodide
  参考文献：
  名称：

  New quaternary ammonium oxicam derivatives: synthesis and in vitro antiosteoarthritis evaluation

  摘要：

  A series of new oxicam derivatives bearing a quaternary ammonium (QA) moiety was synthesized and evaluated in vitro for antiosteoarthritis properties. Propyltrimethyl ammonium 3 and propyldie-thylmethyl ammonium 11 stimulated aggrecan expression and mitigated the inhibitory action of IL-1. QA derivative 3 also increased TGF-beta 2 and type II receptor expression. These results suggest that such derivatives may not only inhibit the osteoarthritis degradation process but also stimulate its regeneration. QA derivatives 3 and 11 offer potential for developing new therapeutic approaches to osteoarthritis treatment. (C) 2009 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2009.09.026
• 作为产物：
  描述：

  甲基物 、 4-二甲基氨基丁胺 以 5,5-dimethyl-1,3-cyclohexadiene 为溶剂， 反应 24.0h， 以18%的产率得到N-[4-(dimethylamino)butyl]-4-hydroxy-2-methyl-2H-1,2-benzothiazine-3-carboxamide 1,1-dioxide
  参考文献：
  名称：

  New quaternary ammonium oxicam derivatives: synthesis and in vitro antiosteoarthritis evaluation

  摘要：

  A series of new oxicam derivatives bearing a quaternary ammonium (QA) moiety was synthesized and evaluated in vitro for antiosteoarthritis properties. Propyltrimethyl ammonium 3 and propyldie-thylmethyl ammonium 11 stimulated aggrecan expression and mitigated the inhibitory action of IL-1. QA derivative 3 also increased TGF-beta 2 and type II receptor expression. These results suggest that such derivatives may not only inhibit the osteoarthritis degradation process but also stimulate its regeneration. QA derivatives 3 and 11 offer potential for developing new therapeutic approaches to osteoarthritis treatment. (C) 2009 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2009.09.026

文献信息

• 1,1-dioxo-2h-1,2-benzothiazine-3-carboxamide derivatives,method for preparing same and pharmaceutical compositions comprising same
  申请人：——

  公开号：US20040063696A1

  公开（公告）日：2004-04-01

  1 wherein: represents a single or double bond, R 1 represents a hydrogen atom or a hydroxy, alkoxy, acyloxy, alkylsulphonyloxy, arylsulphonyloxy or arylalkoxy group, R 2 represents a hydrogen atom or an alkyl group, R 3 and R4, which may be identical or different, each represent a hydrogen atom, a halogen atom or an alkyl, hydroxy or alkoxy group, Ak represents an alkylene chain, R 5 , R6 and R 7 , which may be identical or different, each represent an alkyl group, or R 5 , R6 and R 7 , taken together with the nitrogen atom carrying them, form a saturated or unsaturated nitrogen-containing heterocycle, X represents a halogen atom, and its optical isomers when they exist. Medicaments.

  其中：表示一个单键或双键，R1表示一个氢原子或一个羟基，烷氧基，酰氧基，烷基磺酰氧基，芳基磺酰氧基或芳基烷氧基，R2表示一个氢原子或一个烷基，R3和R4，可以相同也可以不同，分别表示一个氢原子，一个卤原子或一个烷基，羟基或烷氧基，Ak表示一个烷基链，R5，R6和R7，可以相同也可以不同，分别表示一个烷基，或者R5，R6和R7，与携带它们的氮原子一起形成一个饱和或不饱和的含氮杂环，X表示一个卤原子，及其存在时的光学异构体。药物。
• DERIVES DE 1, 1-DIOXO-2H-1, 2-BENZOTHIAZINE-3-CARBOXAMIDES, LEUR PROCEDE DE PREPARATION ET LES COMPOSITIONS PHARMACEUTIQUES QUI LES CONTIENNENT
  申请人：Les Laboratoires Servier

  公开号：EP1343774A1

  公开（公告）日：2003-09-17
• [EN] 1,1-DIOXO-2H-1, 2-BENZOTHIAZINE-3-CARBOXAMIDE DERIVATIVES, METHOD FOR PREPARING SAME AND PHARMACEUTICAL COMPOSITIONS COMPRISING SAME<br/>[FR] DERIVES DE 1, 1-DIOXO-2H-1, 2-BENZOTHIAZINE-3-CARBOXAMIDES, LEUR PROCEDE DE PREPARATION ET LES COMPOSITIONS PHARMACEUTIQUES QUI LES CONTIENNENT
  申请人：SERVIER LAB

  公开号：WO2002050049A1

  公开（公告）日：2002-06-27

  Formule (I) dans laquelle: (a) représente une liaison simple ou double, R1 représente un atome d'hydrogène ou un groupement hydroxy, alkoxy, acyloxy, alkylsulfonyloxy, arylsulfonyloxy ou arylalkoxy, R2 représent un atome d'hydrogène ou un groupement alkyle, R3 et R4, identiques ou différents, représentent chacun un atome d'hydrogène, d'halogène ou un groupement alkyle, hydroxy ou alkoxy, Ak représente une chaîne alkylène, R5, R6 et R7, identiques ou différents, représentent chacun un groupement alkyle, ou bien R5, R6 et R7, pris ensemble avec l'atome d'azote qui les porte, forment un hétérocycle azoté saturé ou insaturé, X représente un atome d'halogène, ainsi que ses isomères optiques lorsqu'ils existent.
• New quaternary ammonium oxicam derivatives: synthesis and in vitro antiosteoarthritis evaluation
  作者：Aurélien Vidal、Jean-Michel Chezal、Emmanuelle Mounetou

  DOI：10.1016/j.ejmech.2009.09.026

  日期：2010.1

  A series of new oxicam derivatives bearing a quaternary ammonium (QA) moiety was synthesized and evaluated in vitro for antiosteoarthritis properties. Propyltrimethyl ammonium 3 and propyldie-thylmethyl ammonium 11 stimulated aggrecan expression and mitigated the inhibitory action of IL-1. QA derivative 3 also increased TGF-beta 2 and type II receptor expression. These results suggest that such derivatives may not only inhibit the osteoarthritis degradation process but also stimulate its regeneration. QA derivatives 3 and 11 offer potential for developing new therapeutic approaches to osteoarthritis treatment. (C) 2009 Elsevier Masson SAS. All rights reserved.