ethyl 2-[(5-methyl-1,3,4-thiadiazol-2-yl)thio]acetate | 64145-09-1

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: ethyl 2-[(5-methyl-1,3,4-thiadiazol-2-yl)thio]acetate
• 英文别名: Ethyl 2-((5-methyl-1,3,4-thiadiazol-2-yl)thio)acetate；ethyl 2-[(5-methyl-1,3,4-thiadiazol-2-yl)sulfanyl]acetate
• CAS: 64145-09-1
• 化学式: C₇H₁₀N₂O₂S₂
• mdl: MFCD03856386
• 分子量: 218.301
• InChiKey: HCXLALXMJKCJFX-UHFFFAOYSA-N

物化性质

• 沸点：
  334.1±44.0 °C(Predicted)
• 密度：
  1.32±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  13
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.571
• 拓扑面积：
  106
• 氢给体数：
  0
• 氢受体数：
  6

安全信息

• 海关编码：
  2934999090

反应信息

• 作为反应物：
  描述：

  ethyl 2-[(5-methyl-1,3,4-thiadiazol-2-yl)thio]acetate 在 氢氧化钾 、 一水合肼 作用下， 以 乙醇 为溶剂， 生成 5-[1-(5'-methyl-1',3',4'-thiadiazol-2'ylthio)methyl]-4-amino-3-mercapto-1,2,4-s-triazole
  参考文献：
  名称：

  Kidwai, Mozaahir; Kumar, Parven, Journal of Chemical Research - Part S, 1996, # 5, p. 254 - 255

  摘要：

  DOI：
• 作为产物：
  描述：

  溴乙酸乙酯 、 2-巯基-5-甲基-1,3,4-噻二唑 在 potassium carbonate 作用下， 以 丙酮 为溶剂， 以86 %的产率得到ethyl 2-[(5-methyl-1,3,4-thiadiazol-2-yl)thio]acetate
  参考文献：
  名称：

  新型恶二唑-噻二唑衍生物：合成、生物学评价和计算机研究

  摘要：

  在寻找新的抗癌药物的过程中，我们合成了一系列新的噻二唑-恶二唑杂化噻唑衍生物。最终化合物 (5a–5i) 通过 1H NMR、13C NMR 和...进行分析

  DOI：

  10.1080/07391102.2023.2247087

文献信息

• Arylbiguanides in Heterocyclization Reactions
  作者：D. V. Kryl’skii、Kh. S. Shikhaliev、A. S. Shestakov、M. M. Liberman

  DOI：10.1007/s11176-005-0218-x

  日期：2005.2

  The reactions of arylbiguanides with acetyacetone derivatives were used to obtain N-(pyrimidin-2-yl)-N′-arylguanidines, and the reactions with acetoacetic ester derivatives (depending on the structure of the keto esters), N-aryl-N′-(4-oxo-3,4-dihydropyrimidin-2-yl)guanidines or 2-amino-4-arylamino-6-aryl(heteryl)-sulfanylmethylene-1,3,5-triazines. The N-aryl-N′-heterylguanidines formed by the reactions with anhydrides, acyl halides, and aryl isocyanates give rise to the corresponding triaza derivatives.

  芳基双胍与乙酰丙酮衍生物反应得到N-(嘧啶-2-基)-N'-芳基胍，与乙酰乙酸酯衍生物(取决于酮酯的结构)、N-芳基-N'反应-(4-氧代-3,4-二氢嘧啶-2-基)胍或2-氨基-4-芳基氨基-6-芳基(杂基)-硫酰亚甲基-1,3,5-三嗪。通过与酸酐、酰卤和芳基异氰酸酯反应形成的N-芳基-N'-杂基胍产生相应的三氮杂衍生物。
• Synthesis of thiadiazole derivatives bearing hydrazone moieties and evaluation of their pharmacological effects on anxiety, depression, and nociception parameters in mice
  作者：Özgür Devrim Can、Mehlika Dilek Altıntop、Ümide Demir Özkay、Umut İrfan Üçel、Bürge Doğruer、Zafer Asım Kaplancıklı

  DOI：10.1007/s12272-012-0410-6

  日期：2012.4

  Novel thiadiazole derivatives bearing hydrazone moieties were synthesized through the reaction of 2-[(5-methyl-1,3,4-thiadiazol-2-yl)thio)]acetohydrazide with aldehydes/ketones. The chemical structures of the compounds were elucidated by 1H-NMR, 13C-NMR, MS-FAB spectral data, and elemental analyses. Behavioral effects of the test compounds in mice were examined by hole-board, activity cage, tail suspension and modified forced swimming tests (MFST). Antinociceptive activities were evaluated using the hot-plate and tail-clip methods. Results of the experiments indicated that the test compounds did not significantly change the exploratory behaviors or locomotor activities of animals in the hole-board and activity cage tests, respectively. Administration of the reference drug fluoxetine (10 mg/kg) and compounds 3a, 3b, 3c, 3j, 3k, and 3l significantly shortened the immobility times of animals in the tail suspension and MFST tests, indicating the antidepressant-like effects of these derivatives. Morphine (10 mg/kg) and compounds 3a, 3b, 3c, 3d, 3e, 3j, 3k, and 3l increased the reaction times of mice in both the hot-plate and tail-clip tests, indicating the antinociceptive effects of these compounds. To the best of our knowledge, this is the first study of central nervous system activities of chemical compounds carrying thiadiazole and hydrazone moieties together on their structures.

  通过 2-[(5-甲基-1,3,4-噻二唑-2-基)硫代)]乙酰肼与醛/酮反应，合成了带有腙分子的新型噻二唑衍生物。化合物的化学结构通过 1H-NMR、13C-NMR、MS-FAB 光谱数据和元素分析得以阐明。通过孔板试验、活动笼试验、尾悬挂试验和改良强迫游泳试验（MFST）考察了受试化合物对小鼠行为的影响。热板法和夹尾法评估了抗痛觉活性。实验结果表明，在孔板试验和活动笼试验中，受试化合物没有明显改变动物的探索行为或运动活动。给参考药物氟西汀（10 毫克/千克）和化合物 3a、3b、3c、3j、3k 和 3l 服用后，动物在悬尾试验和 MFST 试验中的不动时间明显缩短，这表明这些衍生物具有抗抑郁样作用。吗啡（10 毫克/千克）和化合物 3a、3b、3c、3d、3e、3j、3k 和 3l 增加了小鼠在热板试验和夹尾试验中的反应时间，表明这些化合物具有抗痛觉作用。据我们所知，这是首次对结构中同时含有噻二唑和腙的化合物的中枢神经系统活性进行研究。
• Synthesis and biological evaluation of thiazoline derivatives as new antimicrobial and anticancer agents
  作者：Mehlika Dilek Altıntop、Zafer Asım Kaplancıklı、Gülşen Akalın Çiftçi、Rasime Demirel

  DOI：10.1016/j.ejmech.2013.12.060

  日期：2014.3

  N'-(3,4-Diarylthiazol-2(3H)-ylidene)-2-(arylthio)acetohydrazides were synthesized and evaluated for their antimicrobial activity and cytotoxicity against NIH/3T3 cells. Compound 22 bearing 1-phenyl-1H-tetrazole and p-chlorophenyl moieties was found to be the most promising antibacterial agent against Pseudomonas aeruginosa, whereas compound 23 bearing 1-phenyl-1H-tetrazole and p-bromophenyl moieties was the most promising antifungal agent against Candida albicans. The most effective derivatives were also evaluated for their cytotoxicity against C6 glioma cells. The results indicated that compound 17 bearing 1-phenyl-1H-tetrazole and nonsubstituted phenyl moieties (IC50 = 8.3 +/- 2.6 mu g/mL) was more effective than cisplatin (IC50 = 13.7 +/- 1.2 mu g/mL) against C6 glioma cells. Compound 17 also exhibited DNA synthesis inhibitory activity on C6 cells. Furthermore, compound 17 showed low toxicity to NIH/3T3 cells (IC50 = 416.7 +/- 28.9 mu g/mL). (C) 2014 Elsevier Masson SAS. All rights reserved.
• Unique Azolyl Acylhydrazonyl Hybridization of Aloe Emodins to Access Potential Antibacterial Agents
  作者：Yi‐Xin Wang、Zhao Deng、Aisha Bibi、Bo Fang、Cheng‐He Zhou

  DOI：10.1002/cjoc.202400160

  日期：2024.8

  Comprehensive SummaryA type of unique azole‐hybridized acylhydrazonyl aloe emodins (AAEs) were developed as new antibacterial agents for combating bacterial infections. Some target AAEs showed strong antibacterial activities, especially, tetrazolylthioether AAE 27a exhibited broad antibacterial spectrum with 16—256 folds and 8—64 folds more active antibacterial efficacy than the reference drugs aloe emodin and norfloxacin, respectively. Tetrazolylthioether AAE 27a also gave low hemolysis and cytotoxicity, as well as favorable bioavailability. Preliminary mechanism explorations revealed that tetrazolylthioether AAE 27a could cause bacterial membrane depolarization and damage the cell membrane, resulting in nucleic acid leakage. Moreover, compound 27a could intercalate into DNA to impede its replication and form supramolecular 27a‐DNA gyrase complex to disturb the function of DNA gyrase. These findings would provide valuable insights for the further exploration of azolyl acylhydrazonyl aloe emodins as new potential antibacterial candidates.