(1-phenyl-1H-tetrazol-5-ylthiol)acetic acid hydrazide | 13980-80-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: (1-phenyl-1H-tetrazol-5-ylthiol)acetic acid hydrazide
• 英文别名: 2-[(1-phenyl-1H-tetrazol-5-yl)-thio]acetohydrazide；2-[(1-phenyl-1H-tetrazol-5-yl)thio]acetohydrazide；(1-phenyltetrazol-5-ylthio)acetohydrazide；2-(1-phenyl-1H-tetrazol-5-ylsulfanyl)-acetic acid hydrazide；(1-Phenyl-tetrazolyl-(5)-mercapto)-essigsaeurehydrazid；2-[(1-Phenyl-1H-1,2,3,4-tetrazol-5-YL)sulfanyl]acetohydrazide；2-(1-phenyltetrazol-5-yl)sulfanylacetohydrazide
• CAS: 13980-80-8
• 化学式: C₉H₁₀N₆OS
• mdl: MFCD00631305
• 分子量: 250.284
• InChiKey: VICAGCCAGCMBGC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.111
• 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：

  (1-phenyl-1H-tetrazol-5-ylthiol)acetic acid hydrazide 在 盐酸 、 sodium nitrite 作用下， 以 溶剂黄146 为溶剂， 反应 0.5h， 生成 [(1-phenyl-1H-tetrazol-5-yl)thio]-acetyl azide
  参考文献：
  名称：

  1-取代-4-苯基-1、4-二氢-5H-四唑-5-硫酮和（1-苯基-1H-四唑-5-基）硫代乙酰衍生物的高效合成

  摘要：

  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

  DOI：

  10.1002/hc.20353
• 作为产物：
  描述：

  1-苯基-5-巯基四氮唑 在 potassium carbonate 、 一水合肼 作用下， 以 乙醇 、 丙酮 为溶剂， 反应 13.0h， 生成 (1-phenyl-1H-tetrazol-5-ylthiol)acetic acid hydrazide
  参考文献：
  名称：

  Synthesis and Evaluation of Tetrazole-BasedHydrazone Derivatives Bearing a Pyridine Moiety as Antimicrobial Agents

  摘要：

  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）。

  DOI：

  10.2174/1570180812666150309235217

文献信息

• 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.
• Synthesis and bioactivity of 5-(1-aryl-1H-tetrazol-5-ylsulfanylmethyl)-N-xylopyranosyl-1,3,4-oxa(thia)diazol-2-amines
  作者：Yao-Wu He、Ling-Hua Cao、Jian-Bin Zhang、Duo-Zhi Wang、Haji Akber Aisa

  DOI：10.1016/j.carres.2011.01.010

  日期：2011.4

  A series of new N'-[N-(2,3,4-tri-O-acetyl-beta-D-xylopyranosyl)thiocarbamoyl]-2-[(1-aryl-1H-tetrazol-5-yl) sulfanyl]acetohydrazides 5a-5e were synthesized rapidly in high yields from 2-(1-aryl-1H-tetrazol-5-ylsulfanyl)acetohydrazides 3a-3e and 2,3,4-tri-O-acetyl-beta-D-xylopyranosyl isothiocyanate 4, then 5a-5e were converted to a series of new 5-(1-aryl-1H-tetrazol-5-ylsulfanylmethyl)-N-(2,3,4-tri-O-acetyl-beta-D-xylopyranosyl)-1,3,4-oxadiazole-2-amines 6a-6e and 5-(1-aryl-1H-tetrazol-5-ylsulfanylmethyl)-N-(2,3,4-tri-O-acetyl-beta-D-xylopyranosyl)-1,3,4-thiadiazole-2-amines 7a-7e, respectively under mercuric acetate/alcohol system or acetic anhydride/phosphoric acid system, then deacetylated in the solution of CH3ONa/CH3OH. All of the novel compounds were characterized by IR. H-1 NMR, C-13 NMR, MS and elemental analysis. The structures of compounds 2e, 3e, 5a and 5c have been determined by X-ray diffraction analysis. Some of the synthesized compounds displayed PTP1B inhibition and microorganism inhibition. (C) 2011 Elsevier Ltd. All rights reserved.
• Neidlein,R.; Tauber,J., Chemische Berichte, 1967, vol. 100, # 3, p. 736 - 740
  作者：Neidlein,R.、Tauber,J.

  DOI：——

  日期：——
• Waisser, Karel; Vanzura, Jiri; Hrabalek, Alexandr, Collection of Czechoslovak Chemical Communications, 1991, vol. 56, # 11.1, p. 2389 - 2394
  作者：Waisser, Karel、Vanzura, Jiri、Hrabalek, Alexandr、Vinsova, Jarmila、Gresak, Stefan、et al.

  DOI：——

  日期：——
• The Synthesis of 1-(1-Phenyl-1<i>H</i>-tetrazole-5-ylthiol)-acetyl-4-aroyl-thiosemicarbazides and 2-Aroylamino-5- (1-phenyl-1<i>H</i>-tetrazole-5-ylthiolmethylene)- 1,3,4-thiadiazoles
  作者：Tai-Bao Wei、Man-Lin Li、Qi Lin、Hong Liu、You-Ming Zhang

  DOI：10.1080/10426500500366434

  日期：2006.6.1

  A series of 1-(1-phenyl-H-1-tetrazole-5-ylthiol)acetyl-4-aroylthiosemicarbazides were synthesized in good to excellent yields under phase transfer catalytic conditions. By the cyclization of compounds 3a-i in concentrated H2SO4 at 0 degrees C,2-aroylamino-5-(1-phenyl-H-1-tetrazole-5-ylthiolmethylene)-1,3,4-thiadiazoles were obtained in high yields. The structures of the products were established by elemental analysis, IR, H-1 NMR, and C-13 NMR.