2-[(1-methyl-1H-tetrazol-5-yl)thio]acetohydrazide | 872473-23-9

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 2-[(1-methyl-1H-tetrazol-5-yl)thio]acetohydrazide
• 英文别名: 2-(1-methyltetrazol-5-yl)sulfanylacetohydrazide
• CAS: 872473-23-9
• 化学式: C₄H₈N₆OS
• mdl: MFCD04062028
• 分子量: 188.213
• InChiKey: LZMQPCBBYNIQKW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.3
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  124
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2-[(1-methyl-1H-tetrazol-5-yl)thio]acetohydrazide 、 2,4-二氯苯乙酮 以 乙醇 为溶剂， 反应 5.0h， 以80%的产率得到N'-(1-(2,4-dichlorophenyl)ethylidene)-2-[(1-methyl-1H-tetrazol-5-yl)thio]acetohydrazide
  参考文献：
  名称：

  某些衍生物作为抗癌新药和抗癌药的合成及生物学评价

  摘要：

  通过2-[（（1-甲基-1 H-四唑-5-基）硫基）]乙酰肼与芳香族醛/酮的亲核加成-消除反应合成了新的衍生物。该化合物在体外针对各种念珠菌进行了测试，并与酮康唑进行了比较。通过umuC和Ames分析评估了最有效的抗候选化合物的基因毒性。还研究了所有化合物对NIH3T3和A549细胞系的细胞毒性作用。化合物8是针对白色念珠菌的最有效的抗真菌衍生物（ATCC-90028），MIC值为0.05 mg / mL。化合物5 由于其对A549细胞系的抑制作用和对NIH3T3细胞的低毒性，因此可以被认为是针对A549癌细胞系的最有希望的抗癌剂。

  DOI：

  10.1016/j.ejmech.2012.10.011
• 作为产物：
  描述：

  ethyl α-[5-(1-methyltetrazolyl)thio]acetate 在 一水合肼 作用下， 以 乙醇 为溶剂， 反应 3.0h， 生成 2-[(1-methyl-1H-tetrazol-5-yl)thio]acetohydrazide
  参考文献：
  名称：

  某些衍生物作为抗癌新药和抗癌药的合成及生物学评价

  摘要：

  通过2-[（（1-甲基-1 H-四唑-5-基）硫基）]乙酰肼与芳香族醛/酮的亲核加成-消除反应合成了新的衍生物。该化合物在体外针对各种念珠菌进行了测试，并与酮康唑进行了比较。通过umuC和Ames分析评估了最有效的抗候选化合物的基因毒性。还研究了所有化合物对NIH3T3和A549细胞系的细胞毒性作用。化合物8是针对白色念珠菌的最有效的抗真菌衍生物（ATCC-90028），MIC值为0.05 mg / mL。化合物5 由于其对A549细胞系的抑制作用和对NIH3T3细胞的低毒性，因此可以被认为是针对A549癌细胞系的最有希望的抗癌剂。

  DOI：

  10.1016/j.ejmech.2012.10.011

文献信息

• 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）。
• 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.