6,7-dimethoxy-2,3-dihydro-3-<3-(methanesulfonyloxy)propyl>-4H-1,3-benzoxazin-4-one | 128791-64-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并恶嗪类
• 英文名称: 6,7-dimethoxy-2,3-dihydro-3-<3-(methanesulfonyloxy)propyl>-4H-1,3-benzoxazin-4-one
• 英文别名: 2,3-dihydro-6,7-dimethoxy-3-[3-(methanesulfonyloxy)propyl]-4H-1,3-benzoxazin-4-one；3-(6,7-dimethoxy-4-oxo-2H-1,3-benzoxazin-3-yl)propyl methanesulfonate
• CAS: 128791-64-0
• 化学式: C₁₄H₁₉NO₇S
• 分子量: 345.373
• InChiKey: AUQHFRWWBNRJKI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  23
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  99.8
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  6,7-dimethoxy-2,3-dihydro-3-<3-(methanesulfonyloxy)propyl>-4H-1,3-benzoxazin-4-one 在 甲酸 作用下， 反应 0.92h， 生成 2,3-dihydro-6,7-dimethoxy-3-<3-(methyl-3,4-dimethoxyphenethylamino)propyl>-4H-1,3-benzoxazin-4-one
  参考文献：
  名称：

  Synthesis and bradycardic activity of a series of substituted 3-aminoalkyl-2,3-dihydro-4H-1,3-benzoxazin-4-ones as potent antiischemics

  摘要：

  A series of 2,3-dihydro-4H-1,3-benzoxazin-4-ones substituted at the 3-position with an arylalkyaminoalkyl group have been synthesized and their specific bradycardic and antiarrythmic activities evaluated. Bradycardia is optimal when the aromatic rings are substituted with methoxy groups and the side-chain amine is N-methylated. N-Demethylated and 2-alkylated derivatives show the highest antiarrhythmic activity but have little bradycardid action. Most of the compounds described are more potent than Falipamil. Compound lm (F 3226) has been selected for further pharmacological tests and the bradycardic activity has been confirmed when administered orally to anesthetized rats without notable side effects.

  DOI：

  10.1016/0223-5234(93)90027-c
• 作为产物：
  描述：

  2,3-dihydro-6,7-dimethoxy-3-(3-acetoxypropyl)-4H-1,3-benzoxazin-4-one 在 sodium hydroxide 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 0.83h， 生成 6,7-dimethoxy-2,3-dihydro-3-<3-(methanesulfonyloxy)propyl>-4H-1,3-benzoxazin-4-one
  参考文献：
  名称：

  Synthesis and bradycardic activity of a series of substituted 3-aminoalkyl-2,3-dihydro-4H-1,3-benzoxazin-4-ones as potent antiischemics

  摘要：

  A series of 2,3-dihydro-4H-1,3-benzoxazin-4-ones substituted at the 3-position with an arylalkyaminoalkyl group have been synthesized and their specific bradycardic and antiarrythmic activities evaluated. Bradycardia is optimal when the aromatic rings are substituted with methoxy groups and the side-chain amine is N-methylated. N-Demethylated and 2-alkylated derivatives show the highest antiarrhythmic activity but have little bradycardid action. Most of the compounds described are more potent than Falipamil. Compound lm (F 3226) has been selected for further pharmacological tests and the bradycardic activity has been confirmed when administered orally to anesthetized rats without notable side effects.

  DOI：

  10.1016/0223-5234(93)90027-c

文献信息

• 2,3-dihydro-3-arylalkylaminoalkyl-4H-1,3-benzoxazin-4-one derivatives,
  申请人：Pierre Fabre Medicament

  公开号：US05071850A1

  公开（公告）日：1991-12-10

  The invention relates to the new 3-arylalkylaminoalkyl-4H-1,3-benzoxazin-4-one derivatives of general formula ##STR1## in which: R.sub.1, R.sub.2, R.sub.3 and R.sub.4, which may be identical or different, denote a hydrogen, a branched or unbranched lower alkyl group or an alkyloxy, halo, nitro, amino, acylamino or dialkylamino group, and R.sub.1 and R.sub.2 on one hand and R.sub.3, R.sub.4 on the other hand can fuse to give a divalent group and more especially --OCH.sub.2 O--, --OCH.sub.2 CH.sub.2 O-- and --CH.dbd.CH--CH.dbd.CH--; R.sub.5 and R.sub.6, which may be identical or different, denote a hydrogen, a saturated or unsaturated, branched or unbranched alkyl group containing from 1 to 15 carbon atoms or a cycloalkyl group, and R.sub.5 and R.sub.6 can fuse to give a --(CH.sub.2).sub.p -- group with p=2 to 7; R.sub.7 denotes a hydrogen, a saturated or unsaturated, branched or unbranched alkyl group containing from 1 to 15 carbon atoms, a cycloalkyl group, a substituted or unsubstituted aryl and a substituted or unsubstituted arylalkyl; the values of m and n, which may be identical or different, can vary from 1 to 4 inclusive; as well as the therapeutically acceptable organic or inorganic salts of I. The compounds are useful as medicinal products in the treatment of disorders of the cardiovascular system.

  本发明涉及新的3-芳基烷基氨基烷基-4H-1,3-苯并噁嗪-4-酮衍生物，其一般式为##STR1## 其中：R.sub.1、R.sub.2、R.sub.3和R.sub.4可以相同也可以不同，表示氢、支链或直链低碳基或烷氧基、卤素、硝基、氨基、酰胺基或二烷基氨基基团，且R.sub.1和R.sub.2在一侧，R.sub.3和R.sub.4在另一侧可以融合形成二价基团，特别是--OCH.sub.2 O--、--OCH.sub.2 CH.sub.2 O--和--CH.dbd.CH--CH.dbd.CH--；R.sub.5和R.sub.6可以相同也可以不同，表示氢、含1-15个碳原子的饱和或不饱和的支链或直链烷基或环烷基，且R.sub.5和R.sub.6可以融合形成--(CH.sub.2).sub.p--基团，其中p=2到7；R.sub.7表示氢、含1-15个碳原子的饱和或不饱和的支链或直链烷基、环烷基、取代或未取代的芳香基和取代或未取代的芳香基烷基；m和n可以相同也可以不同，其值可以从1到4包括1；以及I的治疗上可接受的有机或无机盐。该化合物可用于治疗心血管系统的疾病。
• US5071850A
  申请人：——

  公开号：US5071850A

  公开（公告）日：1991-12-10
• Synthesis and bradycardic activity of a series of substituted 3-aminoalkyl-2,3-dihydro-4H-1,3-benzoxazin-4-ones as potent antiischemics
  作者：JP Rieu、A Duflos、JC Tristani、JF Patoiseau、J Tisne-Versailles、AM Bessac、R Bonnafous、A Marty、Y Verscheure、DCH Bigg

  DOI：10.1016/0223-5234(93)90027-c

  日期：1993.1

  A series of 2,3-dihydro-4H-1,3-benzoxazin-4-ones substituted at the 3-position with an arylalkyaminoalkyl group have been synthesized and their specific bradycardic and antiarrythmic activities evaluated. Bradycardia is optimal when the aromatic rings are substituted with methoxy groups and the side-chain amine is N-methylated. N-Demethylated and 2-alkylated derivatives show the highest antiarrhythmic activity but have little bradycardid action. Most of the compounds described are more potent than Falipamil. Compound lm (F 3226) has been selected for further pharmacological tests and the bradycardic activity has been confirmed when administered orally to anesthetized rats without notable side effects.