2-sulfonamido-6-(4'-methylphenyl)imidazo[2,1-b]-1,3,4-thiadiazole | 63775-37-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 2-sulfonamido-6-(4'-methylphenyl)imidazo[2,1-b]-1,3,4-thiadiazole
• 英文别名: 6-p-tolyl-imidazo[2,1-b][1,3,4]thiadiazole-2-sulfonic acid amide；6-(4-Methylphenyl)imidazo[2,1-b][1,3,4]thiadiazole-2-sulfonamide
• CAS: 63775-37-1
• 化学式: C₁₁H₁₀N₄O₂S₂
• 分子量: 294.358
• InChiKey: DFFSLCOEJXWSCY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  127
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2-sulfonamido-6-(4'-methylphenyl)imidazo[2,1-b]-1,3,4-thiadiazole 以 乙醇 为溶剂， 反应 0.5h， 生成 N'-[5-[(E)-(carbamimidoylhydrazono)methyl]-6-(p-tolyl)imidazo[2,1-b][1,3,4]thiadiazol-2-yl]sulfonyl-N,N-dimethyl-formamidine
  参考文献：
  名称：

  Synthesis and antibacterial activity of some 5-guanylhydrazone/thiocyanato-6-arylimidazo[2,1-b]-1,3,4-thiadiazole-2-sulfonamide derivatives†

  摘要：

  6-Arylimidazo[2,1-b]-1,3,4-thiadiazole-2-sulfonamides 3 on Vilsmeier-Haak reaction produced 5-formyl-6-arylimidazo[2, 1-b]1,3,3-thiadiazole-2-[N-(dimethylaminomethino)]sulfonamides 4, while 3 on treatment with potassium thiocyanate in the presence of bromine in acetic acid produced 5-thiocyanato-2-sulfonamides 6. Interaction of 4 with aminoguanidine hydrochloride in ethanol produced the corresponding 5-guanylhydrazone derivatives 5. Compounds 5 and 6 showed a high degree of antibacterial activity against both Escherichia coli and Staphylococcus aureus comparable to that of sulfamethoxazole and Norfloxacin. However, they were found to show moderate activity against Salmonella typhi, Pseudomonas aeruginosa and Pneumococci. (C) 2000 Editions scientifiques et medicales Elsevier SAS.

  DOI：

  10.1016/s0223-5234(00)00166-5
• 作为产物：
  描述：

  5-氨基-1,3,4-噻二唑-2-磺酰胺 、 2-溴-4'-甲基苯乙酮 以 乙醇 为溶剂， 反应 12.0h， 以51%的产率得到2-sulfonamido-6-(4'-methylphenyl)imidazo[2,1-b]-1,3,4-thiadiazole
  参考文献：
  名称：

  一系列2-磺酰胺基/三氟甲基-6-取代的咪唑并[2,1-b] -1,3,4-噻二唑衍生物的合成及抗结核活性。

  摘要：

  一系列的2-磺酰胺基/三氟甲基-6-（4'-取代的芳基/杂芳基）咪唑并[2,1-b] -1,3,4-噻二唑衍生物（II）已通过2-氨基- 5-磺酰胺基/三氟甲基-1,3,4-噻二唑和适当的α-卤代芳基/杂芳基酮。为了研究这些取代基对生物活性的影响，还合成了5-溴（III），5-硫氰酸根（IV），5-甘氨酰hydr（V）衍生物。这些化合物的结构通过IR，（1）H NMR，（13）C NMR，质量和HRMS确定。使用放射BACTEC和肉汤稀释测定方法评估所选化合物对结核分枝杆菌H37Rv菌株的初步体外抗结核活性。结果表明，化合物5、7、8 10和12在MIC> 6.25 microg / mL时表现出中等至良好的抗结核活性，抑制百分比分别为29、43、58、31和41。化合物18的MIC为20微克/毫升。

  DOI：

  10.1016/j.bmc.2004.07.060

文献信息

• Imidazo [2,1-b]-1,3,4-thiadiazole suflonamides
  申请人：Jaquith B. James

  公开号：US20050069492A1

  公开（公告）日：2005-03-31

  This invention relates to compounds of Formula (I) and the use of compounds of Formula (I) as neuroprotective agents in the treatment of neuronal disorders of the central and peripheral nervous systems.

  本发明涉及公式（I）的化合物以及在治疗中枢和周围神经系统的神经元疾病中使用公式（I）化合物作为神经保护剂的用途。
• Imidazo[2,1-b]-1,3,4-thiadiazole sulfonamides
  申请人：Jaquith B. James

  公开号：US20070088059A1

  公开（公告）日：2007-04-19

  This invention relates to compounds of Formula I and the use of compounds of Formula I as neuroprotective agents in the treatment of neuronal disorders of the central and peripheral nervous systems. Formula I:

  本发明涉及I式化合物及其在治疗中枢和周围神经系统神经元疾病中作为神经保护剂的应用。I式：
• IMIDAZO [2,1,-b]-1,3,4-THIADIAZOLE SULFONAMIDES
  申请人：JAQUITH James B.

  公开号：US20090042953A1

  公开（公告）日：2009-02-12

  This invention relates to compounds of Formula I and the use of compounds of Formula I as neuroprotective agents in the treatment of neuronal disorders of the central and peripheral nervous systems. Formula I:

  本发明涉及公式I化合物及其作为神经保护剂用于治疗中枢和外周神经系统的神经元疾病的用途。公式I：
• RADIOACTIVE IMIDAZOTHIADIAZOLE DERIVATIVE COMPOUND
  申请人：Nihon Medi-Physics Co., Ltd

  公开号：EP3845541A1

  公开（公告）日：2021-07-07

  The present invention provides a radiolabeled compound represented by the following formula (1), which is a radioactive imidazothiadiazole derivative compound having an affinity for CA-IX, or a salt thereof. wherein n is an integer of 1 to 4, and L represents a radionuclide or a mono- to tetravalent group containing a radionuclide.

  本发明提供了由下式（1）表示的放射性标记化合物，它是一种对 CA-IX 具有亲和力的放射性咪唑噻二唑衍生物化合物或其盐。 其中 n 为 1 至 4 的整数，L 代表放射性核素或含有放射性核素的单价至四价基团。
• Cerebrovasodilatation through selective inhibition of the enzyme carbonic anhydrase. 2. Imidazo[2,1-b]thiadiazole and imidazo[2,1-b]thiazolesulfonamides
  作者：Ian T. Barnish、Peter E. Cross、Roger P. Dickinson、Brian Gadsby、Michael J. Parry、Michael J. Randall、Ian W. Sinclair

  DOI：10.1021/jm00176a003

  日期：1980.2

  A series of imidazo[2,1-b]thiadiazole and imidazo[2,1-b]thiazolesulfonamide carbonic anhydrase inhibitors is described and their anticonvulsant activities are listed. Many of the compounds have the same degree of ionization as acetazolamide and methazolamide, but their higher lipophilicity means that they are more able to penetrate into the central nervous system. One compound, 6-tert-butyl-2-sulfamoylimidazo[2,1-b]-1,3,4-thiadiazole (8, UK-15,454) had an anticonvulsant ED50 of 2.6 mg/kg when administered orally to mice. 8 selectively increased cerebral blood flow in animals without producing a high level of metabolic acidosis.