2-amino-1,3,4-thiadiazino[6,5-b]indole | 943642-52-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 2-amino-1,3,4-thiadiazino[6,5-b]indole
• 英文别名: [1,3,4]thiadiazino[6,5-b]indol-3-amine
• CAS: 943642-52-2
• 化学式: C₉H₆N₄S
• 分子量: 202.239
• InChiKey: RYMBIHQOKNBZCE-UHFFFAOYSA-N

物化性质

• 熔点：
  230 °C(Solvent: Methanol)
• 沸点：
  408.2±28.0 °C(Predicted)
• 密度：
  1.72±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.77
• 重原子数：
  14.0
• 可旋转键数：
  0.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  64.69
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  2-amino-1,3,4-thiadiazino[6,5-b]indole 在 溶剂黄146 、 zinc(II) chloride 作用下， 以 甲醇 为溶剂， 生成 2-[2-(4-N,N-dimethylphenyl)-4-thiazolidinon-3-yl]-1,3,4-thiadiazino[6,5-b]indole
  参考文献：
  名称：

  Panwar, Hemant; Verma; Srivastava, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2006, vol. 45, # 9, p. 2099 - 2104

  摘要：

  DOI：
• 作为产物：
  描述：

  2,3-吲哚二酮 3-硫代缩氨基脲 在 硫酸 作用下， 以 乙醇 为溶剂， 反应 8.0h， 以45.4%的产率得到2-amino-1,3,4-thiadiazino[6,5-b]indole
  参考文献：
  名称：

  4-噻唑烷酮和1-硫杂3,4,9-三氮杂芴共轭物：合成，表征和抗菌筛选

  摘要：

  一些新的4-噻唑烷酮衍生物是通过将isatin / 5-氯异丁嗪与硫代氨基脲缩合而合成的，得到硫代氨基脲，然后将其环化形成相应的thia-3,4,9-三氮杂-芴-2-基胺。使它们与取代的醛反应以得到相应的席夫碱，将其在氯化锌存在下使用巯基乙酸环化以获得4-噻唑烷酮衍生物。所有合成的化合物都通过光谱（IR，MS和NMR）和元素分析进行​​了表征。将化合物筛选它们对革兰氏阳性菌的抗菌活性（枯草芽孢杆菌，金黄色葡萄球菌，短小芽孢杆菌和中号。藤黄微球菌），革兰氏阴性细菌（铜绿假单胞菌，大肠杆菌和荧光假单胞菌）以及通过琼脂扩散法对黑曲霉和产黄青霉的抗真菌活性。这些化合物的最小抑菌浓度也通过试管稀释法确定。发现所有化合物的抗微生物效力是浓度依赖性的。两种化合物-2-甲基-3-（1-硫杂-3，4，9-三氮杂芴-2-基）-噻唑烷丁-4-酮（7aI）和2-萘-1-基-3-（1 -thia-3，4，9-三氮杂

  DOI：

  10.1007/s00044-012-0200-1

文献信息

• Synthesis, Characterization and in vitro Antitubercular Evaluation of Some Schiff Bases of Substituted Indoles and their Inclusion Complexes with b-Cyclodextrin
  作者：Pramoda Kumar Das、Rabinarayana Sahu、Prakasini Satapathy、Dasarathi Dash、Bamakanta Garnaik

  DOI：10.14233/ajchem.2018.20986

  日期：——

  Indole derivatives are best known for their biological importance as bactericides and fungicides which encouraged us to synthesize some Schiff bases of substituted indoles i.e. 2(([1,3,4]thiadiazino[6,5-b]indol-3-ylimino)methyl)substituted phenols. The synthesized compounds are found to exhibit antitubercular activities. With a view to enhance solubility induced potential anti tubercular activities, these synthesized compounds are encapsulated with b-cyclodextrin. Through elemental and spectral (UV, IR, 1H NMR) characterization, the architecture of the compounds and their inclusion complexes are confirmed. They are also screened for in vitro antitubercular activities by using rifampicin as the reference standard. The synthesized compounds exhibited good antitubercular activity but their inclusion complexes exhibited profound antitubercular activities as compared to their respective compounds.

  吲哚衍生物因其作为杀菌剂和杀真菌剂的生物学重要性而闻名，这促使我们合成了一些取代吲哚的希夫碱，即2(([1,3,4]噻二唑并[6,5-b]吲哚-3-亚氨基)甲基)取代苯酚。所合成的化合物显示出抗结核活性。为了提高溶解性并诱导潜在的抗结核活性，这些合成的化合物被包封在β-环糊精中。通过元素分析和光谱（UV、IR、1H NMR）表征，确认了化合物的结构及其包合物。这些化合物还通过使用利福平作为参考标准进行了体外抗结核活性筛选。所合成的化合物表现出良好的抗结核活性，但它们的包合物相比各自的化合物显示出更显著的抗结核活性。
• A Comparative Study of Inclusion Complexes of Orthosubstituted [Arylidenamino]-1,3,4- thiadiazino[6,5b] Indole Derivatives
  作者：Sunakar Panda、Jagat Krushna Tripathy

  DOI：10.1155/2012/156346

  日期：——

  Some[Arylidenamino]-1,3,4-thiadiazino[6,5b] indoles have been synthesized starting from indole-2,3-dione, thiosemicarbazide and aromatic aldehydes with activating and deactivating groups. Inclusion complexes of these compounds have been prepared with β-cyclodextrin so as increase the solubility and bioaccessibility. Thermodynamic properties like change in free energy, change in enthalpy, change in entropy and stability constant of the inclusion complexes have been determined to know whether the inclusion complex formation is thermodynamically allowed or not. The compounds and their inclusion complexes are also screened againt S.aureus and E.coli.to know the antibacterial activity change after inclusion complex formation The antioxidant activities are also studied.

  [Arylidenamino]-1,3,4-噻二唑并[6,5b]吲哚类化合物已经合成，起始原料为吲哚-2,3-二酮、硫脲半胱氨酸和带有活化和去活化基团的芳香醛。这些化合物的包含复合物已经与β-环糊精制备，以增加其溶解度和生物可及性。已经确定了包含复合物的热力学性质，如自由能变化、焓变化、熵变化和稳定常数，以确定包含复合物形成是否在热力学上允许。这些化合物及其包含复合物也已经对金黄色葡萄球菌和大肠杆菌进行了筛选，以了解包含复合物形成后的抗菌活性变化。此外，还研究了这些化合物的抗氧化活性。
• Study of Mesoionic Compounds: Synthesis and Pharmacological Evaluation of Several 2-[{(4-Substituted-1-sulphonyl) Sydnon-3-yl}]-1,3,4-thiadiazino(6,5-b)indoles as Antimicrobial, Insecticidal and Antihelmintic Agents
  作者：Ranjana Dubey、Nidhi Chaudhary、Ravindra Kumar、Hament Panwar

  DOI：10.13005/ojc/300134

  日期：2014.3.30
• Synthesis of new substituted azetidinoyl and thiazolidinoyl-1,3,4-thiadiazino (6,5-b) indoles as promising anti-inflammatory agents
  作者：Sudhir Kumar Bhati、Ashok Kumar

  DOI：10.1016/j.ejmech.2007.10.012

  日期：2008.11

  Various N-(5-[(arylmethylene)amino]-1,3,4-thiadiazol-2-yl}methyl) [1,3,4] thiadiazino[6,5-b]indol-3-amine (6a-6h), 2-aryl-3-5-[[1,3,4] thiadiazino[6,5- b]indol-3-ylamino}methyl]-1,3,4-thiadiazol-2-yl}-1,3-thiazolidin-4-one (7a-7h), and 3-chloro-4-aryl-l-5-[[1,3,4]thiadiazino[6,5-b]indol-3-ylamino]methyl]- 1,3,4-thiadiazol-2-yl}azetidin-2-one (8a-8h) have been synthesized in the present study. The structure of these newly synthesized compounds were confirmed by their analytical and spectral data. These compounds were also evaluated for their anti-inflammatory, ulcerogenic and analgesic activities. Compound 8g has shown most active anti-inflammatory and analgesic activities with better ulcerogenic activity than phenylbutazone, while this compound was found to be associated with lesser degree of anti-inflammatory and analgesic activities as compared to indomethacin. (C) 2007 Elsevier Masson SAS. All rights reserved.
• Panda, Sunakar; Tripathy, Jagat Krushna, Asian Journal of Chemistry, 2011, vol. 23, # 4, p. 1631 - 1635
  作者：Panda, Sunakar、Tripathy, Jagat Krushna

  DOI：——

  日期：——