3-(2-aminoethyl)amino-7-chloro-4H-1,2,4-benzothiadiazine 1,1-dioxide monohydrate | 201224-46-6

• 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: 3-(2-aminoethyl)amino-7-chloro-4H-1,2,4-benzothiadiazine 1,1-dioxide monohydrate
• 英文别名: 3-(2-Aminoethyl)amino-7-chloro-4H-1,2,4-benzothiadiazine 1,1-dioxide；2-[(7-chloro-1,1-dioxo-4H-1lambda6,2,4-benzothiadiazin-3-ylidene)amino]ethanamine；2-[(7-chloro-1,1-dioxo-4H-1λ6,2,4-benzothiadiazin-3-ylidene)amino]ethanamine
• CAS: 201224-46-6
• 化学式: C₉H₁₁ClN₄O₂S
• 分子量: 274.731
• InChiKey: WDJRRQZJKQOGQX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.22
• 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：

  乙酸酐 、 3-(2-aminoethyl)amino-7-chloro-4H-1,2,4-benzothiadiazine 1,1-dioxide monohydrate 以87%的产率得到7-chloro-3-(2-acetylaminoethyl)amino-4H-1,2,4-benzothiadiazine 1,1-dioxide
  参考文献：
  名称：

  Effect on insulin release of compounds structurally related to the potassium-channel opener 7-chloro-3-isopropylamino-4H-1,2,4-benzothiadiazine 1,1-dioxide (BPDZ 73): introduction of heteroatoms on the 3-alkylamino side chain of the benzothiadiazine 1,1-dioxide ring

  摘要：

  7-氯-3-吡啶基（烷基）氨基-4H-1,2,4-苯并噻二嗪-1,1-二氧化物和3-烷基氨基-7-氯-4H-1,2,4-苯并噻二嗪-1,1-二氧化物，其侧链在3位含有一个或多个杂原子，已经合成，以寻找新的有效的KATP通道开放剂。通过测量它们对胰岛素释放过程的抑制活性，将这些化合物作为潜在的胰岛B细胞KATP通道开放剂进行了测试。讨论了3位侧链性质对生物活性的影响。

  DOI：

  10.1211/0022357011776216
• 作为产物：
  描述：

  7-chloro-3-thioxo-3,4-dihydro-2H-1,2,4-benzothiadiazine 1,1-dioxide 在 碳酸氢钠 作用下， 以 甲醇 、 水 为溶剂， 生成 3-(2-aminoethyl)amino-7-chloro-4H-1,2,4-benzothiadiazine 1,1-dioxide monohydrate
  参考文献：
  名称：

  Effect on insulin release of compounds structurally related to the potassium-channel opener 7-chloro-3-isopropylamino-4H-1,2,4-benzothiadiazine 1,1-dioxide (BPDZ 73): introduction of heteroatoms on the 3-alkylamino side chain of the benzothiadiazine 1,1-dioxide ring

  摘要：

  7-氯-3-吡啶基（烷基）氨基-4H-1,2,4-苯并噻二嗪-1,1-二氧化物和3-烷基氨基-7-氯-4H-1,2,4-苯并噻二嗪-1,1-二氧化物，其侧链在3位含有一个或多个杂原子，已经合成，以寻找新的有效的KATP通道开放剂。通过测量它们对胰岛素释放过程的抑制活性，将这些化合物作为潜在的胰岛B细胞KATP通道开放剂进行了测试。讨论了3位侧链性质对生物活性的影响。

  DOI：

  10.1211/0022357011776216

文献信息

• Therapeutics for the treatment of glaucoma
  申请人：MAYO FOUNDATION FOR MEDICAL EDUCATION AND RESEARCH

  公开号：US10981951B2

  公开（公告）日：2021-04-20

  The present invention provides benzothiadiazine and chroman derivatives and particularly diazoxide and cromakalim derivatives for use in treating glaucoma, retinopathy, treating age related macular degeneration, treating, stabilizing and/or inhibiting blood and lymph vascularization, and reducing intraocular pressure by administering a pharmaceutically effective amount of a prodrug disposed in an ophthalmically acceptable carrier to the eye, wherein the prodrug specifically modulates a KATP channel to reduce an intraocular pressure.

  本发明提供苯并噻二嗪和色苷衍生物，特别是用于治疗青光眼、视网膜病变、治疗年龄相关性黄斑变性、治疗、稳定和/或抑制血液和淋巴血管生成，并通过向眼睛内给予药学有效量的前药，其中前药特异性调节KATP通道以降低眼内压力。
• NOVEL THERAPEUTICS FOR THE TREATMENT OF GLAUCOMA
  申请人：MAYO FOUNDATION FOR MEDICAL EDUCATION AND RESEARCH

  公开号：US20170002040A1

  公开（公告）日：2017-01-05

  The present invention provides benzothiadiazine and chroman derivatives and particularly diazoxide and cromakalim derivatives for use in treating glaucoma, retinopathy, treating age related macular degeneration, treating, stabilizing and/or inhibiting blood and lymph vascularization, and reducing intraocular pressure by administering a pharmaceutically effective amount of a prodrug disposed in an ophthalmically acceptable carrier to the eye, wherein the prodrug specifically modulates a KATP channel to reduce an intraocular pressure.
• THERAPEUTICS FOR THE TREATMENT OF GLAUCOMA
  申请人：Mayo Foundation for Medical Education and Research

  公开号：US20210040148A1

  公开（公告）日：2021-02-11

  The present invention provides benzothiadiazine and chroman derivatives and particularly diazoxide and cromakalim derivatives for use in treating glaucoma, retinopathy, treating age related macular degeneration, treating, stabilizing and/or inhibiting blood and lymph vascularization, and reducing intraocular pressure by administering a pharmaceutically effective amount of a prodrug disposed in an ophthalmically acceptable carrier to the eye, wherein the prodrug specifically modulates a K ATP channel to reduce an intraocular pressure.
• US6242443B1
  申请人：——

  公开号：US6242443B1

  公开（公告）日：2001-06-05
• Effect on insulin release of compounds structurally related to the potassium-channel opener 7-chloro-3-isopropylamino-4<i>H</i>-1,2,4-benzothiadiazine 1,1-dioxide (BPDZ 73): introduction of heteroatoms on the 3-alkylamino side chain of the benzothiadiazine 1,1-dioxide ring
  作者：S Boverie、M-H Antoine、P de Tullio、F Somers、B Becker、S Sebille、P Lebrun、B Pirotte

  DOI：10.1211/0022357011776216

  日期：2010.2.18

  7-Chloro-3-pyridyl(alkyl)amino-4H-1,2,4-benzothiadiazine 1,1-dioxides and 3-alkylamino-7-chloro-4H-1,2,4-benzothiadiazine 1,1-dioxides containing one or more heteroatoms on the side chain in the 3 position have been synthesized in an attempt to discover new potent KATP-channel openers. The compounds were tested as putative pancreatic B-cells KATP channel openers by measuring their inhibitory activity on the insulin releasing process. The influence on the biological activity of the nature of the side chain in the 3 position is discussed.

  7-氯-3-吡啶基（烷基）氨基-4H-1,2,4-苯并噻二嗪-1,1-二氧化物和3-烷基氨基-7-氯-4H-1,2,4-苯并噻二嗪-1,1-二氧化物，其侧链在3位含有一个或多个杂原子，已经合成，以寻找新的有效的KATP通道开放剂。通过测量它们对胰岛素释放过程的抑制活性，将这些化合物作为潜在的胰岛B细胞KATP通道开放剂进行了测试。讨论了3位侧链性质对生物活性的影响。