ethyl 2-(1-phenyl-1H-tetrazol-5-ylthio)acetate | 13980-78-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: ethyl 2-(1-phenyl-1H-tetrazol-5-ylthio)acetate
• 英文别名: Ethyl 2-(1-phenyltetrazol-5-yl)sulfanylacetate
• CAS: 13980-78-4
• 化学式: C₁₁H₁₂N₄O₂S
• mdl: MFCD00186053
• 分子量: 264.308
• InChiKey: ZZEPFFJCNRUHDM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  18
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.272
• 拓扑面积：
  95.2
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  ethyl 2-(1-phenyl-1H-tetrazol-5-ylthio)acetate 在 ammonium heptamolybdate 、 双氧水 作用下， 以 乙醇 为溶剂， 反应 75.0h， 以4.70 g的产率得到ethyl (1-phenyl-1H-tetrazol-5-ylsulfonyl)acetate
  参考文献：
  名称：

  乙酸乙酯（苯并噻唑-2-基磺酰基）乙酸乙酯：用于从醛类中立体选择性合成α，β-不饱和酯的新试剂。

  摘要：

  标题试剂在温和的反应条件下（DBU，CH（2）Cl（2），rt或-78℃）与醛一起进行改性的Julia烯化反应，生成α，β-不饱和酯；具有显着链支化元素的芳基醛和脂族醛可产生具有高立体选择性的反烯烃产物（E：Z最高> 98：2），而直链脂族醛则优先产生顺式产物（Z：E最高92：8）。

  DOI：

  10.1039/b500713e
• 作为产物：
  描述：

  1-苯基-5-巯基四氮唑 在 18-冠醚-6 、 水 、 potassium hydroxide 作用下， 以 二甲基亚砜 为溶剂， 反应 24.0h， 生成 ethyl 2-(1-phenyl-1H-tetrazol-5-ylthio)acetate
  参考文献：
  名称：

  Synthesis, antibacterial and QSAR evaluation of 5-oxo and 5-thio derivatives of 1,4-disubstituted tetrazoles

  摘要：

  A series of 1,4-disubstituted tetrazol-5-ones 3a, 5, 7, 12, 13 and 1,4-disubstituted tetrazol-5-thiones 3b, 9, 10 was synthesized and fully characterized by IR, MS, H-1 NMR and C-13 NMR. The series was evaluated for in vitro antibacterial activity against four Gram negative (Escherichia coli, Proteus mirabilis, Klebsiella pneumonia, and Pseudomonas aeruginosa) and three Gram positive (Staphylococcus aureus, Enterococcus faecalis, and Bacillus subtilis) bacteria. The zone of inhibition was measured using the well-diffusion assay, and in vitro minimum inhibitory concentration (MIC) was determined by microbroth dilution assay. MIC values indicate that compounds exhibited a varied range (0.2-37 mu g/mL) of antibacterial activity against the tested bacterial strains. Statistically significant QSAR models were developed by the simple linear regression analysis for the correlation of MIC with computed descriptors. The concluded cross validated regression factors are 0.953 and 0.986 for E. coli, and S. aureus, respectively. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2015.04.070

文献信息

• Efficient synthesis of 1-substituted-4-phenyl-1, 4-dihydro-5H-tetrazole-5-thione and (1-phenyl-1H-tetrazol-5-yl)thioacetyl derivatives
  作者：Walid Fathalla、Ibrahim A. I. Ali

  DOI：10.1002/hc.20353

  日期：2007.8

  A new and convenient synthesis of a variety of N- and S-substituted tetrazoles has been developed via azide and Mannich reaction methods. Compounds were characterized by elemental analysis, MALDI MS, and 1H NMR data. © 2007 Wiley Periodicals, Inc. Heteroatom Chem 18:637–643, 2007; Published online in Wiley InterScience (www.interscience.wiley.com). DOI 10.1002/hc.20353

  已经通过叠氮化物和曼尼希反应方法开发了一种新的、方便的合成各种 N 和 S 取代的四唑。通过元素分析、MALDI MS 和 1 H NMR 数据表征化合物。© 2007 Wiley Periodicals, Inc. 杂原子化学 18:637–643, 2007; 在线发表于 Wiley InterScience (www.interscience.wiley.com)。DOI 10.1002/hc.20353
• 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 and Evaluation of Tetrazole-BasedHydrazone Derivatives Bearing a Pyridine Moiety as Antimicrobial Agents
  作者：Ahmet Ozdemir、Mehlika Dilek Altıntop、Belgin Sever、Zerrin Canturk、Zafer Asım Kaplancıkl

  DOI：10.2174/1570180812666150309235217

  日期：2015.7.30

  2-[(1-Methyl-1H-tetrazol-5-yl)thio]-N'-[(aryl)methylidene/ethylidene]acetohydrazides were synthesized and investigatedin vitroagainst pathogenic bacteriaand Candidaspecies for their antimicrobial activityusing CLSI broth microdilution method. MTT assay was also carried out to evaluate their cytotoxic effects on NIH/3T3 mouse embryonic fibroblast cell lines.2-((1-Phenyl-1H-tetrazol-5-yl)thio)-N'-(1-(pyridin-3-yl)ethylidene)acetohydrazide can be considered as the most promising antibacterial agent againstEnterococcusfaecalis (ATCC 29212) with a MIC value of 100 µg/mL when compared with chloramphenicol (MIC= 200 µg/mL) and low toxicity against NIH/3T3 cells(IC50500µg/mL).

  合成了 2-[(1-甲基-1H-四唑-5-基)硫]-N'-[(芳基)亚甲基/亚乙基]乙酰肼，并采用 CLSI 肉汤微稀释法对其抗菌活性进行了体外研究。此外，还进行了 MTT 试验，以评估它们对 NIH/3T3 小鼠胚胎成纤维细胞系的细胞毒性作用。(2-((1-苯基-1H-四唑-5-基)硫基)-N'-(1-(吡啶-3-基)亚乙基)乙酰肼可被视为最有希望抗Enterococcusfaecalis（ATCC 29212）的抗菌剂，与氯霉素（MIC= 200 µg/mL）相比，其 MIC 值为 100 µg/mL，对 NIH/3T3 细胞的毒性较低（IC50500 µg/mL）。
• Electrolytic partial fluorination of organic compounds
  作者：Bakenova Zagipa、Hirokatsu Nagura、Toshio Fuchigami

  DOI：10.1016/j.jfluchem.2007.07.013

  日期：2007.10

  Anodic fluorination of five-membered nitrogen-containing heterocyclic sulfides like tetrazolyl sulfides was comparatively studied. The anodic fluorination of tetrazolyl sulfides having α-electron-withdrawing groups was successfully carried out to provide α-monofluorinated tetrazolyl derivatives in moderate yields. This is in sharp contrast to the low efficient anodic fluorination of triazolyl sulfides

  比较研究了五元含氮杂环硫化物（如四唑基硫化物）的阳极氟化。具有α-吸电子基团的四唑基硫化物的阳极氟化已成功进行，从而以中等收率提供了α-单氟化四唑基衍生物。这与三唑基硫化物的低效率阳极氟化形成鲜明对比。因此，发现阳极氟化的效率受到起始杂环硫化物的杂环基的碱性的很大影响。
• 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.