5-methyl-2H-benzo[e][1,2,4]thiadiazin-3(4H)-one 1,1-dioxide | 71254-64-3

• 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: 5-methyl-2H-benzo[e][1,2,4]thiadiazin-3(4H)-one 1,1-dioxide
• 英文别名: 5-methyl-1,1-dioxo-1,4-dihydro-2H-1λ⁶-benzo[1,2,4]thiadiazin-3-one；5-methyl-3,4-dihydro-2H-1lambda6,2,4-benzothiadiazine-1,1,3-trione；5-methyl-1,1-dioxo-4H-1λ6,2,4-benzothiadiazin-3-one
• CAS: 71254-64-3
• 化学式: C₈H₈N₂O₃S
• 分子量: 212.229
• InChiKey: RISXVHCQQZRPFT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  14
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  83.6
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-methyl-2H-benzo[e][1,2,4]thiadiazin-3(4H)-one 1,1-dioxide 在 硫酸 作用下， 生成 2-氨基-3-甲基苯磺酰胺
  参考文献：
  名称：

  Inhibitors of HCV NS5B polymerase: Synthesis and structure–activity relationships of N-1-benzyl and N-1-[3-methylbutyl]-4-hydroxy-1,8-naphthyridon-3-yl benzothiadiazine analogs containing substituents on the aromatic ring

  摘要：

  A series of non-nucleoside HCV NS5B polymerase inhibitors based on the N-1-benzyl or N-1-[3-methylbutyl]-4-hydroxy-1,8-naphthyridon-3-yl benzothiadiazine core substituted in the D-ring aromatic moiety have been prepared and evaluated. Aromatic substituents extending from position 7 of the D-ring exhibited excellent potency against both genotypes 1a and 1b. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.04.022
• 作为产物：
  描述：

  N-[(2-methylphenyl)carbamoyl]sulfamoyl chloride 在 三氯化铝 作用下， 生成 5-methyl-2H-benzo[e][1,2,4]thiadiazin-3(4H)-one 1,1-dioxide
  参考文献：
  名称：

  Inhibitors of HCV NS5B polymerase: Synthesis and structure–activity relationships of N-1-benzyl and N-1-[3-methylbutyl]-4-hydroxy-1,8-naphthyridon-3-yl benzothiadiazine analogs containing substituents on the aromatic ring

  摘要：

  A series of non-nucleoside HCV NS5B polymerase inhibitors based on the N-1-benzyl or N-1-[3-methylbutyl]-4-hydroxy-1,8-naphthyridon-3-yl benzothiadiazine core substituted in the D-ring aromatic moiety have been prepared and evaluated. Aromatic substituents extending from position 7 of the D-ring exhibited excellent potency against both genotypes 1a and 1b. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.04.022

文献信息

• Benzothiadiazinone-1,1-Dioxide Carbonic Anhydrase Inhibitors Suppress the Growth of Drug-Resistant Mycobacterium tuberculosis Strains
  作者：Silvia Bua、Alessandro Bonardi、Georgiana Ramona Mük、Alessio Nocentini、Paola Gratteri、Claudiu T. Supuran

  DOI：10.3390/ijms25052584

  日期：——

  chemical features of BTD derivatives meet the criteria for a potent inhibition of β-class CA isozymes. BTD derivatives show chemical features meeting the criteria for a potent inhibition of β-class CA isozymes. Specifically, three β-CAs (MtCA1, MtCA2, and MtCA3) were identified in Mycobacterium tuberculosis and their inhibition was shown to exert an antitubercular action. BTDs derivatives 2a-q effectively

  本文探索基于 2H-苯并[e][1,2,4]噻二嗪-3(4H)-酮 1,1-二氧化物 (BTD) 的碳酸酐酶 (CA) 抑制剂作为新型抗分枝杆菌药物。 BTD衍生物的化学特性符合有效抑制β-类CA同工酶的标准。 BTD 衍生物的化学特征符合有效抑制 β 类 CA 同工酶的标准。具体而言，在结核分枝杆菌中鉴定出三种 β-CA（MtCA1、MtCA2 和 MtCA3），并且对它们的抑制显示出抗结核作用。 BTD 衍生物 2a-q 有效抑制分枝杆菌 CA，尤其是 MtCA2 和 MtCA3，Ki 值高达低纳摩尔范围（MtCA3，Ki = 15.1–2250 nM；MtCA2，Ki = 38.1–4480 nM），并且具有显着的选择性比超过脱靶人类 CA I 和 II。进行了计算研究以阐明化合物的结构-活性关系。重要的是，最有效的 MtCA 抑制剂能够有效抑制对利福平和异烟肼（结核病治疗的标准参考药物）耐药的结核分枝杆菌菌株的生长。
• Girard,Y. et al., Journal of the Chemical Society. Perkin transactions I, 1979, p. 1043 - 1047
  作者：Girard,Y. et al.

  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.
• GIRARD Y.; ATKINSON J. G.; ROKACH J., J. CHEM. SOC. PERKIN TRANS., PART 1, 1979, NO 4, 1043-1047
  作者：GIRARD Y.、 ATKINSON J. G.、 ROKACH J.

  DOI：——

  日期：——