(4H-[1,2,4]Triazol-3-ylsulfanyl)-acetic acid ethyl ester | 307545-28-4

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: (4H-[1,2,4]Triazol-3-ylsulfanyl)-acetic acid ethyl ester
• 英文别名: ethyl 2-(1H-1,2,4-triazol-5-ylsulfanyl)acetate
• CAS: 307545-28-4
• 化学式: C₆H₉N₃O₂S
• mdl: MFCD00463052
• 分子量: 187.222
• InChiKey: KWRBZESLGXYFOV-UHFFFAOYSA-N

物化性质

• 熔点：
  55-57 °C(Solv: hexane (110-54-3); benzene (71-43-2))
• 沸点：
  350.9±44.0 °C(Predicted)
• 密度：
  1.34±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  12
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  93.2
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (4H-[1,2,4]Triazol-3-ylsulfanyl)-acetic acid ethyl ester 在 四乙基氟化铵水合物 作用下， 以 乙二醇二甲醚 为溶剂， 以2%的产率得到Fluoro-[(4H-[1,2,4]triazol-3-ylsulfanyl)]-acetic acid ethyl ester
  参考文献：
  名称：

  有机化合物的电解部分氟化。47. 2-噻二唑基，2-恶二唑基和2-三唑基硫化物的高度区域选择性阳极单氟化。

  摘要：

  DOI：

  10.1021/jo010300e
• 作为产物：
  描述：

  溴乙酸乙酯 、 3-巯基-1,2,4-三氮唑 在 potassium carbonate 作用下， 以 乙腈 为溶剂， 生成 (4H-[1,2,4]Triazol-3-ylsulfanyl)-acetic acid ethyl ester
  参考文献：
  名称：

  Unique Azolyl Acylhydrazonyl Hybridization of Aloe Emodins to Access Potential Antibacterial Agents

  摘要：

  A 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.

  DOI：

  10.1002/cjoc.202400160

文献信息

• Synthesis and Preliminary Biological Properties Assessment of Novel 2-S-, 4-, 5-Substituted and Bicyclic Derivatives of 6-Methylpyrimidine-4-ol
  作者：Aleksandr P. Yengoyan、Zhermen A. Azaryan、Vergush A. Pivazyan、Emma A. Ghazaryan、Rafael A. Tamazyan、Armen G. Ayvazyan

  DOI：10.2174/1570178616666190411110415

  日期：2020.1.7

  and 4-aminotriazolylpyrimidines were synthesized from the quaternary ammonium salt of pyrimidine and 4-chloro-substituted 2-thiomethyl-6-methylpyrimidine, respectively. The reaction of potassium salt of 1-methyl-6-oxo-1,6-dihydropyridazin-3-ole with ethyl 2-chloro-3-oxobutanoate and subsequent treatment with thiourea led to 6-((4-hydroxy-2-mercapto-6-methylpyrimidin-5-yl)oxy)-2- methylpyridazin-3 (2H)-one

  通过可获得和有效的方法合成了一系列新颖的2-S-，4-，5-取代的和双环的6-甲基嘧啶-4-醇衍生物，包括分子中的吡唑，1,2,4-三唑和哒嗪部分。硫吡唑基衍生物获自2-巯基-6-甲基嘧啶-4-醇。分别由嘧啶和4-氯取代的2-硫代甲基-6-甲基嘧啶的季铵盐合成4-三唑基和4-氨基三唑基嘧啶。1-甲基-6-氧代-1,6-二氢哒嗪-3-烯烃的钾盐与2-氯-3-氧代丁酸乙酯的反应，然后用硫脲处理，得到6-（（4-羟基-2-巯基） -6-甲基嘧啶-5-基）氧基）-2-甲基哒嗪-3（2H）-。后者与3-氯戊烷-2,4-二酮的反应产物进行杂环化，得到了嘧啶的目标双环衍生物。合成的化合物对植物生长显示出明显的刺激作用。与异生长素相比，它们的生长刺激活性在60-93％的范围内。
• Synthesis of novel 1,3-substituted 1<i>H</i>-[1,2,4]-triazole-3-thiol derivatives
  作者：Karine A. Eliazyan、Lusya V. Shahbazyan、Vergine A. Pivazyan、Emma A. Ghazaryan、Aleksandr P. Yengoyan

  DOI：10.1002/hc.20565

  日期：——

  By means of regioselective S-alkylation of 1H-1,2,4-triazole-3-thiol (1), a series of S-substituted derivatives 2a-j were synthesized. In certain conditions, the reaction of 2 with arylsulfochlorides, arylisocyanates, and quaternary ammonium salts of azines corresponding compounds were obtained 1-arylsulfonyl- (3a-d), 1-arylcarbonamido- (4a,b), and 1-azinyl-1,2,4- (6a-p) triazoles. Structures of compounds

  通过1H-1,2,4-三唑-3-硫醇(1)的区域选择性S-烷基化，合成了一系列S-取代的衍生物2a-j。在一定条件下，2与芳基磺酰氯、芳基异氰酸酯和吖嗪类季铵盐反应得到1-芳基磺酰基-(3a-d)、1-芳基碳酰氨基-(4a,b)和1-吖嗪基-1， 2,4- (6a-p) 三唑。化合物的结构由 1 H NMR 和元素分析证实。© 2010 Wiley Periodicals, Inc. 杂原子化学 20:405–410, 2009; 在线发表于 Wiley InterScience (www.interscience.wiley.com)。DOI 10.1002/hc.20565
• Insecticidal compositions
  申请人：IMPERIAL CHEMICAL INDUSTRIES PLC

  公开号：EP0369613A1

  公开（公告）日：1990-05-23

  The invention provides an aphicidal composition suitable for use as a concentrate for the preparation of a foliar spray, characterised in that the composition is a slow-release emulsifiable concentrate comprising, as active ingredient, an aphicide selected from the group of aphicides consisting of pirimicarb, dimethoate, demeton-S-­methyl, heptenophos, 1-(dimethylcarbamoyl)-3-t-butyl-­5-carboethoxymethyl-thio-1H-1,2,4-triazole, acephate, tefluthrin, chlorpyrifos, monocrotophos, fenitrothion, methomyl, oxydemeton-methyl, omethoate, pirimiphos-methyl, pirimiphos-ethyl, triazophos, profenofos, permethrin, cypermethrin, lambda-­cyhalothrin, menazon and phosalone, a carrier solvent and a polymeric substance which is more soluble in the carrier solvent than in water. The invention also provides processes for the preparation of the compositions and a method for their use in preventing or combating aphid infestations of plants.

  本发明提供了一种杀蚜组合物，适合用作制备叶面喷洒剂的浓缩物，其特征在于该组合物是一种缓释乳油，其活性成分包括选自以下杀蚜剂组的杀蚜剂：吡蚜酮、乐果、甲霜灵、七氟磷、1-(二甲基氨基甲酰基)-3-叔丁基-5-羧乙氧基甲基-硫-1H-1,2,4-三唑、乙酰甲胺磷、氟氯氰菊酯、氯氟氰菊酯、氯氟氰菊酯、氯氟氰菊酯、氯氟氰菊酯、1-(二甲基氨基甲酰基)-3-叔丁基-5-甲氧羰基甲基硫-1H-1,2,4-三唑、乙酰甲胺磷、氟氯氰菊酯、毒死蜱、久效磷、杀螟硫磷、灭多威、甲基氧化乐果、氧化乐果、甲基吡蚜酮、乙基吡蚜酮、三氯杀螨醇、一种载体溶剂和一种在载体溶剂中的溶解度大于在水中的溶解度的聚合物质。本发明还提供了制备这些组合物的工艺及其用于预防或防治植物蚜虫害的方法。
• Synthesis and antimicrobial activity of N-[(α-methyl)benzylidene]-(3-substituted-1,2,4-triazol-5-yl-thio)acetohydrazides
  作者：Seyhan Ersan、Sultan Nacak、Rukiye Berkem

  DOI：10.1016/s0014-827x(98)00095-0

  日期：1998.12

  In this study 18 new hydrazones have been synthesized by reacting ortho- or para-substituted acetophenones with (3-substituted-1,2,4-triazol-5-yl-thio)acetohydrazide in ethanol. The prepared compounds were tested for antimicrobial activity. The prepared compounds exhibited only poor activity against Gram (+) and Gram (-) bacteria with the minimal inhibitory concentration (MIC) > or = 400 micrograms/ml. Moderate activity was observed against Candida species with MIC in the range 100-400 micrograms/ml.