7-氯-4-甲基-2H-1,2,4-苯并噻二嗪-3(4H)-酮-1,1-二氧化物 | 5790-71-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻二嗪
• 中文名称: 7-氯-4-甲基-2H-1,2,4-苯并噻二嗪-3(4H)-酮-1,1-二氧化物
• 中文别名: 2-乙基-N,N-二(丙-2-炔-1-基)苯胺
• 英文名称: 7-chloro-4-methyl-2H-benzo[e][1,2,4]thiadiazin-3(4H)-one 1,1-dioxide
• 英文别名: 7-chloro-4-methyl-1,1-dioxo-1,4-dihydro-2H-1λ⁶-benzo[1,2,4]thiadiazin-3-one；7-Chlor-4-methyl-3-oxo-2,3-dihydro-4H-1,2,4-benzothiadiazin-1,1-dioxid；7-Chlor-4-methyl-3-oxo-2,3-dihydro-4H-1.2.4-benzothiadiazin-1.1-dioxid；7-Chlor-4-methyl-3-oxodihydro-1,2,4-benzothiadiazin-1,1-dioxid；7-Chloro-4-methyl-2H-1,2,4-benzothiadiazin-3(4H)-on-1,1-dioxide；7-chloro-4-methyl-1,1-dioxo-1λ6,2,4-benzothiadiazin-3-one
• CAS: 5790-71-6
• 化学式: C₈H₇ClN₂O₃S
• 分子量: 246.674
• InChiKey: JIJQUHAXUWATKU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 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：
  74.9
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  7-氯-4-甲基-2H-1,2,4-苯并噻二嗪-3(4H)-酮-1,1-二氧化物 在 五氯化磷 作用下， 反应 0.5h， 生成 3,7-二氯-4-甲基-4H-1,2,4-苯并噻二嗪1,1-二氧化物
  参考文献：
  名称：

  Anti-tubercular agents. Part 3. Benzothiadiazine as a novel scaffold for anti-Mycobacterium activity

  摘要：

  In an effort to develop new and more effective therapies to treat tuberculosis, a series of benzothiadiazine 1,1-dioxide derivatives were synthesized and their in vitro activity against Mycobacterium tuberculosis, Mycobacterium avium and Mycobacterium intracellulare was evaluated. One of the compounds, 8c, exhibited potent anti-tubercular activity, particularly for the resistant strains and thus prompted us to investigate its in vivo profile. However, the in vivo testing in a mouse model of tuberculosis infection did not show significant anti-tubercular activity, probably because of its poor bioavailability. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.08.063
• 作为产物：
  描述：

  4-氯-N-甲基苯胺 在 三氯化铝 作用下， 以 硝基甲烷 为溶剂， 反应 1.0h， 生成 7-氯-4-甲基-2H-1,2,4-苯并噻二嗪-3(4H)-酮-1,1-二氧化物
  参考文献：
  名称：

  Anti-tubercular agents. Part 3. Benzothiadiazine as a novel scaffold for anti-Mycobacterium activity

  摘要：

  In an effort to develop new and more effective therapies to treat tuberculosis, a series of benzothiadiazine 1,1-dioxide derivatives were synthesized and their in vitro activity against Mycobacterium tuberculosis, Mycobacterium avium and Mycobacterium intracellulare was evaluated. One of the compounds, 8c, exhibited potent anti-tubercular activity, particularly for the resistant strains and thus prompted us to investigate its in vivo profile. However, the in vivo testing in a mouse model of tuberculosis infection did not show significant anti-tubercular activity, probably because of its poor bioavailability. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.08.063

文献信息

• Di Bella; Albasini; Monzani, Farmaco, Edizione Scientifica, 1974, vol. 29, # 6, p. 424 - 433
  作者：Di Bella、Albasini、Monzani、Rinaldi

  DOI：——

  日期：——
• Raffa,L.; Pecorari,P., Farmaco, Edizione Scientifica, 1966, vol. 21, p. 16 - 29
  作者：Raffa,L.、Pecorari,P.

  DOI：——

  日期：——
• “A Sweet Combination”: Developing Saccharin and Acesulfame K Structures for Selectively Targeting the Tumor-Associated Carbonic Anhydrases IX and XII
  作者：Silvia Bua、Carrie Lomelino、Akilah B. Murray、Sameh M. Osman、Zeid A. ALOthman、Murat Bozdag、Hatem A. Abdel-Aziz、Wagdy M. Eldehna、Robert McKenna、Alessio Nocentini、Claudiu T. Supuran

  DOI：10.1021/acs.jmedchem.9b01669

  日期：2020.1.9

  The sweeteners saccharin (SAC) and acesulfame K (ACE) recently entered the topic of anticancer human carbonic anhydrase (CA, EC 4.2.1.1) inhibitors, as they showed to selectively inhibit the tumor-associated CAs IX/XII over ubiquitous CAs. A drug design strategy is here reported, which took SAC and ACE as leads and produced a series of 2H-benzo [e][1,2,4]thiadiazin-3(4H)-one-1,1-dioxides (BTD). Many derivatives showed greater potency (K(I)s-CA IX 19.1-408.5 nM) and selectivity (II/IX SI 2-76) than the leads (K(I)s-CA IX 103, 2400 nM; II/IX-SI 56, >4) against CA IX/XII over off-target isoforms. A thorough X-ray crystallographic study depicted their binding mode to both CA II and IX-mimic. The most representative BTDs were characterized in vitro for their antitumor activity against A549, PC-3, and HCT-116 cancer cell lines both in normoxia and hypoxia. The two most effective compounds were assayed for their effect on several apoptosis markers, identifying promising leads for the development of new anticancer drugs.
• RAFFA; DI BELLA; MONZANI, Farmaco, Edizione Scientifica, 1962, vol. 17, p. 548 - 555
  作者：RAFFA、DI BELLA、MONZANI

  DOI：——

  日期：——
• Di Bella; Rinaldi; Fabio, Farmaco, Edizione Scientifica, 1973, vol. 28, # 10, p. 777 - 783
  作者：Di Bella、Rinaldi、Fabio、Manicardi

  DOI：——

  日期：——