7-chloro-2,3-dihydro-3-oxo-4H-1,2,4-benzothiadiazine | 5800-59-9

• 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-2,3-dihydro-3-oxo-4H-1,2,4-benzothiadiazine
• 英文别名: 7-chloro-3-oxo-3,4-dihydro-2H-1,2,4-benzothiadiazine 1,1-dioxide；7-Chlor-3,4-dihydro-3-oxo-2H-1,2,4-benzothiadiazin-1,1-dioxid；7-chloro-2H-benzo[e][1,2,4]thiadiazin-3(4H)-one 1,1-dioxide；7-chloro-2H-1,2,4-benzothiadiazin-3(4H)-one 1,1-dioxide；7-chloro-1,1-dioxo-1,4-dihydro-2H-1λ⁶-benzo[1,2,4]thiadiazin-3-one；7-chloro-3,4-dihydro-3-oxo-2H-1,2,4-benzothiadiazine 1,1-dioxide；7-chloro-1,1-dioxo-4H-1λ6,2,4-benzothiadiazin-3-one
• CAS: 5800-59-9
• 化学式: C₇H₅ClN₂O₃S
• 分子量: 232.647
• InChiKey: SDCJBUKXFVQVKG-UHFFFAOYSA-N

物化性质

• 熔点：
  314-315 °C
• 密度：
  1.622±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  14
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  83.6
• 氢给体数：
  2
• 氢受体数：
  3

安全信息

• 海关编码：
  2933990090

反应信息

• 作为反应物：
  描述：

  7-chloro-2,3-dihydro-3-oxo-4H-1,2,4-benzothiadiazine 在 硫酸 作用下， 以 水 为溶剂， 反应 8.0h， 生成 氯甲苯噻嗪
  参考文献：
  名称：

  Khelili, Smail; Faury, Gilles; Nicolle, Edwige, Medicinal Chemistry Research, 2003, vol. 12, # 9, p. 457 - 470

  摘要：

  DOI：
• 作为产物：
  描述：

  7-chloro-1,1-dioxo-1,4-dihydro-2H-1λ⁶-benzo[1,2,4]thiadiazin-3-one; sodium salt 在 sodium hydroxide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 7-chloro-2,3-dihydro-3-oxo-4H-1,2,4-benzothiadiazine
  参考文献：
  名称：

  Raffa,L.; Pecorari,P., Farmaco, Edizione Scientifica, 1966, vol. 21, p. 16 - 29

  摘要：

  DOI：

文献信息

• [EN] BENZOTHIADIAZINE COMPOUNDS<br/>[FR] COMPOSÉS BENZOTHIADIAZINE
  申请人：GLAXOSMITHKLINE IP DEV LTD

  公开号：WO2017098421A1

  公开（公告）日：2017-06-15

  The invention is directed to substituted benzothiadiazine derivatives. Specifically, the invention is directed to compounds according to Formula (I):wherein R, R1, R2, R3, R4 and R5 are as defined herein. The compounds of the invention are inhibitors of CD73 and can be useful in the treatment of cancer, pre-cancerous syndromes and diseases associated with CD73 inhibition, such as AIDS, autoimmune diseases, infections, atherosclerosis, and ischemia-reperfusion injury. Accordingly, the invention is further directed to pharmaceutical compositions comprising a compound of the invention. The invention is still further directed to methods of inhibiting CD73 activity and treatment of disorders associated therewith using a compound of the invention or a pharmaceutical composition comprising a compound of the invention.

  本发明涉及取代苯并噻二嗪衍生物。具体而言，本发明涉及式(I)化合物：其中R、R1、R2、R3、R4和R5定义如下。本发明的化合物是CD73的抑制剂，可用于治疗癌症、前癌综合症和与CD73抑制相关的疾病，如艾滋病、自身免疫病、感染、动脉粥样硬化和缺血-再灌注损伤。因此，本发明进一步涉及包含本发明化合物的药物组合物。本发明更进一步的涉及使用本发明化合物或包含本发明化合物的药物组合物抑制CD73活性和治疗相关疾病的方法。
• 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。
• Impact of the Nature of the Substituent at the 3-Position of 4<i>H</i>-1,2,4-Benzothiadiazine 1,1-Dioxides on Their Opening Activity toward ATP-Sensitive Potassium Channels
  作者：Bernard Pirotte、Pascal de Tullio、Stéphane Boverie、Catherine Michaux、Philippe Lebrun

  DOI：10.1021/jm200100c

  日期：2011.5.12

  The synthesis of diversely substituted 3-isopropoxy-, 3-isopropylsulfanyl-, 3-isopropylsulfinyl-, and 3-isobutyl-4H-1,2,4-benzothiadiazine 1,1-dioxides is described. Their activity on pancreatic β-cells (inhibitory effect on the insulin releasing process) and on vascular and uterine smooth muscle tissues (myorelaxant effects) was compared to that of previously reported KATP channel openers belonging

  描述了不同取代的3-异丙氧基-，3-异丙基硫烷基- ，3-异丙基亚磺酰基-和3-异丁基-4 H -1,2,4-苯并噻二嗪1,1-二氧化物的合成。将其对胰腺β细胞的活性（对胰岛素释放过程的抑制作用）以及对血管和子宫平滑肌组织的活性（对髓鞘松弛的作用）与先前报道的属于3-isopropylamino-4 H -1的K ATP通道开放剂进行了比较， 2,4-苯并噻二嗪1,1-二氧化物。本研究旨在评估O，S，S（= O）等位取代3-烷基氨基-4 H -1,2,4-苯并噻二嗪1,1-二氧化物的NH基团对生物活性的影响或CH 2团体。通过比较带有相同取代基的化合物，在胰腺β细胞上观察到的效价排名如下：3-异丙基氨基> 3-异丁基> 3-异丙氧基> 3-异丙基硫烷基> 3-异丙基亚磺酰基取代的4 H -1,2,4 -苯并噻二嗪1,1-二氧化物（NH> CH 2 > O> S> S（= O））。分子模型研
• Design, synthesis, and SAR of cis-1,2-diaminocyclohexane derivatives as potent factor Xa inhibitors. Part II: Exploration of 6–6 fused rings as alternative S1 moieties
  作者：Kenji Yoshikawa、Shozo Kobayashi、Yumi Nakamoto、Noriyasu Haginoya、Satoshi Komoriya、Toshiharu Yoshino、Tsutomu Nagata、Akiyoshi Mochizuki、Kengo Watanabe、Makoto Suzuki

  DOI：10.1016/j.bmc.2009.10.024

  日期：2009.12.15

  derivatives possessing a 6–6 fused ring for the S1 moiety were synthesized as novel factor Xa (fXa) inhibitors. The synthesis, structure–activity relationship (SAR), and physicochemical properties are reported herein, together with the discovery of compound 45c, which has potent anti-fXa activity, good physicochemical properties and pharmacokinetic (PK) profiles, including a reduced negative food effect

  合成了一系列具有S1部分6-6稠合环的顺式-1,2-二氨基环己烷衍生物，作为新颖的Xa因子（fXa）抑制剂。本文报道了合成，结构-活性关系（SAR）和理化性质，并发现了具有强大的抗fXa活性，良好的理化性质和药代动力学（PK）的化合物45c，包括降低的不良食物效应。
• [EN] HALOGENATED BENZOTHIADIAZINES FOR THE TREATMENT OF CANCER<br/>[FR] BENZOTHIADIAZINES HALOGÉNÉES POUR LE TRAITEMENT DU CANCER
  申请人：UNIV NEBRASKA

  公开号：WO2021236818A1

  公开（公告）日：2021-11-25

  Provided herein are compounds and methods for modulating the mitochondrial respiratory complex II (CII) and vascular endothelial growth factor (VEGF) pathways. More particularly, provided are inhibitors of the mitochondrial respiratory complex II (CII) and vascular endothelial growth factor (VEGF) pathways and the uses of such inhibitors in regulating diseases and disorders, e.g., to treat cancer.

  本文提供了一些化合物和方法，用于调节线粒体呼吸链复合物II（CII）和血管内皮生长因子（VEGF）通路。更具体地，提供了线粒体呼吸链复合物II（CII）和血管内皮生长因子（VEGF）通路的抑制剂，以及这些抑制剂在调节疾病和紊乱方面的用途，例如治疗癌症。