3-氯-6-甲氧基-1,2-苯并异噻唑 | 103486-07-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻唑类
• 中文名称: 3-氯-6-甲氧基-1,2-苯并异噻唑
• 英文名称: 3-chloro-6-methoxy-1,2-benzisothiazole
• 英文别名: 3-chloro-6-methoxy-1,2-benzothiazole
• CAS: 103486-07-3
• 化学式: C₈H₆ClNOS
• 分子量: 199.661
• InChiKey: KRKWNQCJSABKNP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  50.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-氯-6-甲氧基-1,2-苯并异噻唑 在 盐酸 、 正丁基锂 作用下， 反应 0.25h， 生成 6-Methoxy-3-piperazin-1-yl-benzo[d]isothiazole; hydrochloride
  参考文献：
  名称：

  Synthesis and biological activity of the putative metabolites of the atypical antipsychotic agent tiospirone

  摘要：

  Putative oxidative metabolites of the lead antipsychotic agent tiospirone (1) were synthesized to assist in the identification of the authentic metabolic products found in human urine samples. Thus far, six authentic metabolites have been correlated to the synthetic species. 4a The putative metabolites were further examined in vitro to assess their central nervous system therapeutic potential. SAR analysis of these derivatives indicates that hydroxyl substitution, particularly in the azaspirodecanedione region of the molecule, diminishes the dopamine D-2 affinity of the species without significantly altering the serotonin type-1A and type-2 interactions. In addition, an increase in alpha-1-adrenergic affinity appears to be linked to the attenuation of effects at the dopamine receptors. The biological profile of the 6-hydroxytiospirone metabolite 42 was exemplary in these respects and the in vivo actions of this compound suggest potent antipsychotic potential with a minimal liability for extrapyramidal side effects (EPS). While compound 42 has been unambiguously characterized as an actual human metabolite of tiospirone, the role of 42 in the observed antipsychotic activity of the parent drug, if any, has not yet been determined.

  DOI：

  10.1021/jm00115a024
• 作为产物：
  描述：

  6-methoxybenzisothiazol-3(2H)-one 在 三氯氧磷 作用下， 以60 %的产率得到3-氯-6-甲氧基-1,2-苯并异噻唑
  参考文献：
  名称：

  Ynamides 与 1,2-苯并异噻唑环化构建 1,4-苯并硫氮杂卓和 3-氨基异喹啉

  摘要：

  已开发出 ynamides 和 1,2-苯并异噻唑之间两种不同的 TMSOTf 催化环化反应。通过应用不同的热力学控制条件可以轻松切换反应方向。在室温下，ynamides与1,2-苯并异噻唑发生[5 + 2]环化反应，得到1,4-苯并硫氮杂卓类化合物，而在加热条件下，脱硫环化反应顺利进行，得到3-氨基异喹啉。这两个方案在温和的反应条件下以高效率和广泛的底物范围提供了生物学上重要的 1,4-苯并硫氮杂卓和 3-氨基异喹啉。

  DOI：

  10.1021/acs.orglett.4c00247

文献信息

• [EN] NEW COMPOUNDS INHIBITORS OF THE YAP/TAZ-TEAD INTERACTION AND THEIR USE IN THE TREATMENT OF MALIGNANT MESOTHELIOMA<br/>[FR] NOUVEAUX COMPOSÉS INHIBITEURS DE L'INTERACTION YAP/TAZ-TEAD ET LEUR UTILISATION DANS LE TRAITEMENT DU MÉSOTHÉLIOME MALIN
  申请人：INVENTIVA

  公开号：WO2017064277A1

  公开（公告）日：2017-04-20

  The invention relates to compounds of formula (I) wherein R1, R2, R3, R4, R5 and R6 are as defined in the description. The compounds of formula (I) are inhibitors of the YAP/TAZ-TEAD interaction.

  该发明涉及公式（I）中的化合物，其中R1、R2、R3、R4、R5和R6如描述中所定义。公式（I）中的化合物是YAP/TAZ-TEAD相互作用的抑制剂。
• METHOD FOR PRODUCING 3-HALO-1,2-BENZISOTHIAZOLES
  申请人：Sakaue Shigeki

  公开号：US20130005983A1

  公开（公告）日：2013-01-03

  A method for producing a 3-halo-1,2-benzisothiazole represented by the general formula (2): wherein R 1 is a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, an alkoxycarbonyl group having 2 to 5 carbon atoms, a nitro group or a halogen atom, and X is a halogen atom, the method characterized by reacting a 1,2-benzisothiazol-3-one represented by the general formula (1): wherein R 1 is the same group as the R 1 defined in the above general formula (2), with a thionyl halide in a polar solvent. The 3-halo-1,2-benzisothiazole obtainable according to the method of the present invention is suitably used as production raw materials and the like for a medicament and the like.

  一种制备3-卤代-1,2-苯并异噻唑的方法，其化学式表示为（2）：其中R1是氢原子，具有1至4个碳原子的烷基，具有1至4个碳原子的烷氧基，具有2至5个碳原子的烷氧羰基，硝基或卤素原子，X是卤素原子，该方法的特征在于将一种化学式表示为（1）的1,2-苯并异噻唑-3-酮：其中R1是与上述化学式（2）中定义的R1相同的基团，在极性溶剂中与硫酰卤反应。根据本发明的方法获得的3-卤代-1,2-苯并异噻唑适用于作为药物等的生产原料等。
• Method for producing 3-halo-1,2-benzisothiazoles
  申请人：Sakaue Shigeki

  公开号：US08664404B2

  公开（公告）日：2014-03-04

  A method for producing a 3-halo-1,2-benzisothiazole represented by the general formula (2): wherein R1 is a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, an alkoxycarbonyl group having 2 to 5 carbon atoms, a nitro group or a halogen atom, and X is a halogen atom, the method characterized by reacting a 1,2-benzisothiazol-3-one represented by the general formula (1): wherein R1 is the same group as the R1 defined in the above general formula (2), with a thionyl halide in a polar solvent. The 3-halo-1,2-benzisothiazole obtainable according to the method of the present invention is suitably used as production raw materials and the like for a medicament and the like.

  一种生产一种由通式（2）表示的3-卤代-1,2-苯并异噻唑的方法： 其中R1是氢原子，具有1至4个碳原子的烷基，具有1至4个碳原子的烷氧基，具有2至5个碳原子的烷氧羰基，硝基或卤原子，X是卤原子，其特征在于将由通式（1）表示的1,2-苯并异噻唑-3-酮： 其中R1是与上述通式（2）中定义的R1相同的基团，与硫酰卤在极性溶剂中反应。根据本发明方法获得的3-卤代-1,2-苯并异噻唑适用于作为药物等的生产原料等。
• PROCESSES FOR PRODUCING ISOTHIAZOLE DERIVATIVES
  申请人：SUMITOMO SEIKA CHEMICALS CO., LTD.

  公开号：EP0805151A1

  公开（公告）日：1997-11-05

  A method for producing a 1,2-benzisothiazole characterized by treating a 2-(alkylthio)benzaldehyde oxime with a halogen compound; a method for producing a 3-halo-1,2-benzisothiazole characterized by treating a 1,2-benzisothiazole with a halogenating agent; and a method for producing a 1-(1,2-benzisothiazol-3-yl)piperazine characterized by reacting the obtained 3-halo-1,2-benzisothiazoles with a piperazine. By the method of the present invention, 1,2-benzisothiazoles and 3-halo-1,2-benzisothiazoles, which are useful as intermediates for pharmaceutical compositions such as psychotropic agents, and 1-(1,2-benzisothiazole-3-yl)piperazines synthesized therefrom can be obtained in a high yield without using expensive starting materials by shorter and simpler process than conventional methods.

  一种生产1,2-苯并异噻唑的方法，其特征在于用卤素化合物处理2-(烷硫基)苯甲醛肟；一种生产3-卤代-1,2-苯并异噻唑的方法，其特征在于用卤化剂处理1,2-苯并异噻唑；以及一种生产1-(1,2-苯并异噻唑-3-基)哌嗪的方法，其特征在于使得到的3-卤代-1,2-苯并异噻唑与哌嗪反应。通过本发明的方法，可以不使用昂贵的起始原料，通过比传统方法更短和更简单的过程，高产率地获得1,2-苯并异噻唑和3-卤代-1,2-苯并异噻唑，以及由其合成的1-(1,2-苯并异噻唑-3-基)哌嗪。
• ——
  作者：SMITH D. W.、 YEVICH J. P.

  DOI：——

  日期：——