2,3-dihydro-1H-imidazo<1,2-b><1,2,4>benzothiadiazine 5,5-dioxide | 65998-70-1

• 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: 2,3-dihydro-1H-imidazo<1,2-b><1,2,4>benzothiadiazine 5,5-dioxide
• 英文别名: 3,10-dihydro-2H-imidazo[1,2-b][1,2,4]benzothiadiazine 5,5-dioxide
• CAS: 65998-70-1
• 化学式: C₉H₉N₃O₂S
• 分子量: 223.255
• InChiKey: POTZGOPWLBYTGR-UHFFFAOYSA-N

物化性质

• 沸点：
  418.6±28.0 °C(Predicted)
• 密度：
  1.68±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  15
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  70.2
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2,3-dihydro-1H-imidazo<1,2-b><1,2,4>benzothiadiazine 5,5-dioxide 在 potassium iodide 作用下， 以 六甲基磷酰三胺 为溶剂， 生成 2,4-Dihydro-1H-imidazo<2,1-c><1,2,4>benzothiadiazine 5,5-dioxide
  参考文献：
  名称：

  Friary,R.; Gold,E.H., Heterocycles, 1977, vol. 7, p. 765 - 771

  摘要：

  DOI：
• 作为产物：
  描述：

  1-(2-nitrophenylsulfonyl)-2-methylthio-2-imidazolidine 生成 2,3-dihydro-1H-imidazo<1,2-b><1,2,4>benzothiadiazine 5,5-dioxide
  参考文献：
  名称：

  Friary,R.; Gold,E.H., Heterocycles, 1977, vol. 7, p. 765 - 771

  摘要：

  DOI：

文献信息

• 1,2,4 Benzothiadiazine 1,1-dioxide. V: 1 synthesis of built-in hydroxuguanidine tricycles as potential anticancer agents
  作者：Ji-Wang Chern、Jiann-Gwo Rong

  DOI：10.1016/0040-4039(91)80654-o

  日期：1991.6

  Two representative built in hydroxyguanidine tricycles, 10-N-hydroxy-2,3-dihydroimidazol [1,2-][1,2,4]benzothiadiazine 5,5-dioxide (a) and 11-N-hydroxy-2,3-dihydro-4H-pyrimido-[l,2-c] [l,2,4]benzothiadiazine 6,6-dioxide (b), were obtained in 78% and 30% yields, respectively by a treatment of 1-(2-nitrobenzenesulfonyl)-2-benzylthio-2-imidazolidine and -4,5-dihydro-6H-pyrimidine with zinc in acetic acid

  内置的两个典型的羟基胍三环化合物10 - N-羟基-2,3-二氢咪唑[1,2- ] [1,2,4]苯并噻二嗪5,5-二氧化物（a）和11 - N-羟基-2,3通过1 - （- ）的处理，分别以78％和30％的产率获得-二氢-4 H-嘧啶基-[ 1，2- c ] [1，2，4]苯并噻二嗪6，6-二氧化物（b）。在冰冷却下于乙酸中将2-硝基苯磺酰基）-2-苄硫基-2-咪唑烷和-4,5-二氢-6 H-嘧啶与乙酸在锌中冷却30分钟。
• Unexpected Heteroannulation and Chlorination of Benzothiadiazine Derivatives Mediated by DDQ
  作者：Nicolas Lebegue、Valerie Verones、Nathalie Flouquet、Amaury Farce、Pascal Berthelot

  DOI：10.1055/s-0033-1340249

  日期：——

  Abstract In the course of studies directed toward the synthesis of new tubulin polymerization inhibitors, several benzothiadiazine derivatives were prepared. The oxidative dehydrogenation reaction with DDQ unexpectedly led to heteroannulation and chlorination of the benzothiadiazine tricycles. A rationale for their formation is proposed. In the course of studies directed toward the synthesis of new

  摘要 在针对合成新的微管蛋白聚合抑制剂的研究过程中，制备了几种苯并噻二嗪衍生物。与DDQ的氧化脱氢反应出乎意料地导致了苯并噻二嗪三环的杂环化和氯化反应。提出了形成它们的理由。 在针对合成新的微管蛋白聚合抑制剂的研究过程中，制备了几种苯并噻二嗪衍生物。与DDQ的氧化脱氢反应出乎意料地导致了苯并噻二嗪三环的杂环化和氯化反应。提出了形成它们的理由。
• Synthesis and Biological Evaluation of <i>N</i>-[2-(4-Hydroxyphenylamino)-pyridin-3-yl]-4-methoxy-benzenesulfonamide (ABT-751) Tricyclic Analogues as Antimitotic and Antivascular Agents with Potent in Vivo Antitumor Activity
  作者：Zacharie Segaoula、Julien Leclercq、Valérie Verones、Nathalie Flouquet、Marie Lecoeur、Lionel Ach、Nicolas Renault、Amélie Barczyk、Patricia Melnyk、Pascal Berthelot、Xavier Thuru、Nicolas Lebegue

  DOI：10.1021/acs.jmedchem.6b00847

  日期：2016.9.22

  Benzopyridothiadiazepine (2a) and benzopyridooxathiazepine (2b) were modified to produce tricyclic quinazolinone 15-18 or benzothiadiazine 26-27 derivatives. These compounds were evaluated in cytotoxicity and tubulin inhibition assays and led to potent inhibitors of tubulin polymerization. N-[2(4-Methoxyphenyl)ethyl]-1,2-dihydro-pyrimidino[2,1-b]quinazolin-6-one (16a) exhibited the best in vitro cytotoxic activity (GI50 10-66.9 nM) against the NCI 60 human tumor cell line and significant potency against tubulin assembly (IC50 0.812 mu M). In mechanism studies, 16a was shown to block cell cycle in G2/M phase and to disrupt microtubule formation and displayed good antivascular properties as inhibition of cell migration, invasion, and endothelial tube formation. Compound 16a was evaluated in C57BL/6 mouse melanoma B16F10 xenograft model to validate its antitumor activity, in comparison with reference ABT-751 (1). Compound 16a displayed strong in vivo antitumor and antivascular activities at a dose of 5 mg/kg without obvious toxicity, whereas 1 needed a 10-fold higher concentration to reach similar effects.
• Studies on 1,2,4-Benzothiadiazine 1,1-Dioxides VII and Quinazolinones IV: Synthesis of Novel Built-In Hydroxyguanidine Tricycles as Potential Anticancer Agents
  作者：Ji-Wang Chern、Yen-Chywan Liaw、Chien-Shu Chen、Jiann-Gwo Rong、Chien-Lin Huang、Chao-Han Chan、Andrew H.-J. Wang

  DOI：10.3987/com-92-6285

  日期：——

  Two representative built-in hydroxyguanidine tricycles containing 1,2,4-benzothiadiazine 1,1-dioxides (3) and quinazolinones (4) were prepared by reductive cyclization of 1-(2-nitrophenyl-sulfonyl)-2-benzylthio-2-imidazoline (9a), 1-(2-nitrophenylsulfonyl)-2-benzylthio-1,4,5,6-tetrahydropyrimidine (9b), 1-(2-nitrobenzoyl)-2-benzylthio-2-imidazolidine (10a) and 1-(2-nitrobenzoyl)-2-benzyl-thio-1,4,5,6-tetrahydropyrimidine hydrobromide respectively (10b) with zinc dust in acetic acid under ice-cooling. 2,10-Dihydro-10-hydroxy-3H-imidazo[1,2-b][1,2,4]benzothiadiazine 5,5-dioxide (3a) and 2,3,4,11-tetrahydro-11-hydroxypyrimido[1,2-b][1,2,4]benzothiadiazine 6,6-dioxide (3b) were found to be active against solid tumor cell lines such as KB, Colo 205, HeLa, and Hepa-2.