7-chloro-5-iodo-3-methyl-4H-1,2,4-benzothiadiazine 1,1-dioxide | 37148-13-3

• 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: 7-chloro-5-iodo-3-methyl-4H-1,2,4-benzothiadiazine 1,1-dioxide
• 英文别名: 7-chloro-5-iodo-3-methyl-4H-benzo[e][1,2,4]thiadiazine 1,1-dioxide；7-chloro-5-iodo-3-methyl-4H-benzo[e][1,2,4]thiadiazine 1,1-dioxide；124-Benzthiadiazin-11SO2-3ME5I7CL；7-chloro-5-iodo-3-methyl-4H-1λ6,2,4-benzothiadiazine 1,1-dioxide
• CAS: 37148-13-3
• 化学式: C₈H₆ClIN₂O₂S
• 分子量: 356.571
• InChiKey: HZCIDQXNASUMLV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  15
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  66.9
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-氨基苯硼酸 、 7-chloro-5-iodo-3-methyl-4H-1,2,4-benzothiadiazine 1,1-dioxide 在 四(三苯基膦)钯 、 sodium carbonate 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 3.0h， 以51%的产率得到3-(7-chloro-3-methyl-1,1-dioxide-3,4-dihydro-2H-1,2,4-benzothiadiazine-5-yl)aniline
  参考文献：
  名称：

  5-Arylbenzothiadiazine Type Compounds as Positive Allosteric Modulators of AMPA/Kainate Receptors

  摘要：

  The potential therapeutic benefit of compounds able to activate AMPA receptors (AMPAr) has led to the search for new AMPAr positive modulators. On the basis of crystallographic data of the benzothiadiazines binding mode in the S1S2 GluA2 dimer interface, a set of 5-aryl-2,3-dihydrobenzothiadiazine type compounds has been synthesized and tested. Electrophysiological results suggested that 5-heteroaryl substituents on the benzothiadiazine core like 3-furanyl and 3-thiophenyl dramatically enhance the activity as positive modulators of AMPAr with respect to IDRA21 and cyclothiazide. Mouse brain microdialysis studies have suggested that 7-chloro-5-(3-furyl)-3-methyl-3,4-dihydro-2H-1,2,4-benzothiadiazine 1,1-dioxide crosses the blood-brain barrier after intraperitoneal injection. Biological results have been rationalized by a computational docking simulation that it has currently employed to design new AMPAr-positive modulator candidates.

  DOI：

  10.1021/ml200184w
• 作为产物：
  描述：

  2-氨基-5-氯苯磺酰胺 在 一氯化碘 、 溶剂黄146 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 50.0h， 生成 7-chloro-5-iodo-3-methyl-4H-1,2,4-benzothiadiazine 1,1-dioxide
  参考文献：
  名称：

  Derivatives of 1,2,4-benzothiadiazine dioxide, their preparation and use as allosteric modulators of the AMPA receptor

  摘要：

  描述了一种化学式为I的化合物：它被发现是一种令人惊讶且显著有效的AMPA受体异构调节剂，因此特别适用于治疗由谷氨酸能神经递质传递失调引起的记忆认知障碍，如与年龄相关的障碍、焦虑症、进行性神经退行性疾病、抑郁症、精神分裂症、强迫症和躁狂症。

  公开号：

  EP2457906A1

文献信息

• Novel compounds and their use as positive AMPA receptor modulators
  申请人：Neurosearch A/S.

  公开号：US20040043987A1

  公开（公告）日：2004-03-04

  The invention provides novel compounds represented by the general formula 5 compound represented by the formula: 1 wherein the bond represented by the broken line may be a single, a double bond or absent; and if the bond is absent, then the nitrogen is substituted with a hydrogen and R 2 ; X represents SO 2 or C═O or CH 2 ; Y represents —CH(R 4 )—, —N(R 4 )— or —N(R 4 )—CH 2 —, O; and the meaning of R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , and R 8 are as defined in the application The compounds are useful as positive modulators of the AMPA-receptor.

  该发明提供了一种新型化合物，其通式5的化合物如下所示：其中由虚线表示的键可以是单键、双键或不存在；如果键不存在，则氮原子用氢和R2取代；X代表SO2或C═O或CH2；Y代表—CH(R4)—、—N(R4)—或—N(R4)—CH2—、O；R2、R3、R4、R5、R6、R7和R8的含义如申请中所定义。这些化合物可用作AMPA受体的阳性调节剂。
• Derivatives of 1,2,4-benzothiadiazine dioxide, their preparation and use as allosteric modulators of the AMPA receptor
  申请人：Universita'del Salento

  公开号：EP2457906A1

  公开（公告）日：2012-05-30

  A compound of formula I is described: which showed to be surprisingly and significantly effective as an allosteric modulator of the AMPA receptor and is therefore particularly suitable for the treatment of mnemocognitive disorders ascribable to an alteration of glutamatergic neurotransmission, such as age-related disorders, anxiety, progressive neurodegenerative disorders, depressive disorders, schizophrenia, obsessive-compulsive disorders and bipolar disorder.

  描述了一种化学式为I的化合物：它被发现是一种令人惊讶且显著有效的AMPA受体异构调节剂，因此特别适用于治疗由谷氨酸能神经递质传递失调引起的记忆认知障碍，如与年龄相关的障碍、焦虑症、进行性神经退行性疾病、抑郁症、精神分裂症、强迫症和躁狂症。
• .pi.-Substituent constants for the 2H-1,2,4-benzothiadiazine 1,1-dioxide system
  作者：John G. Topliss、Milton D. Yudis

  DOI：10.1021/jm00274a018

  日期：1972.4
• NOVEL COMPOUNDS AND THEIR USE AS POSITIVE AMPA RECEPTOR MODULATORS
  申请人：NEUROSEARCH A/S

  公开号：EP1071426A2

  公开（公告）日：2001-01-31
• US6943159B1
  申请人：——

  公开号：US6943159B1

  公开（公告）日：2005-09-13