2-(((5-mercapto-1,3,4-thiadiazol-2-yl)imino)methyl)phenol | 94527-22-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 2-(((5-mercapto-1,3,4-thiadiazol-2-yl)imino)methyl)phenol
• 英文别名: 2-salicylideneimino-5-mercapto-1,3,4-thiadiazole；2-(2-hydroxybenzylideneamino)-5-mercapto-1,3,4-thiadiazole；2-((5-Mercapto-1,3,4-thiadiazol-2-ylimino)methyl)phenol；5-[(2-hydroxyphenyl)methylideneamino]-3H-1,3,4-thiadiazole-2-thione
• CAS: 94527-22-7
• 化学式: C₉H₇N₃OS₂
• 分子量: 237.306
• InChiKey: IALAVJLXFRTJRB-UHFFFAOYSA-N

物化性质

• 熔点：
  244-246 °C
• 沸点：
  391.8±44.0 °C(Predicted)
• 密度：
  1.53±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  114
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(((5-mercapto-1,3,4-thiadiazol-2-yl)imino)methyl)phenol 、 2-氯甲基-5-苯基-1,3,4-噁二唑 在 potassium carbonate 作用下， 以 丙酮 为溶剂， 以51.5%的产率得到2-[[5-[(5-Phenyl-1,3,4-oxadiazol-2-yl)methylsulfanyl]-1,3,4-thiadiazol-2-yl]iminomethyl]phenol
  参考文献：
  名称：

  Synthesis and antitumor activities of novel hybrid molecules containing 1,3,4-oxadiazole and 1,3,4-thiadiazole bearing Schiff base moiety

  摘要：

  A series of novel hybrid molecules containing 1,3,4-oxadiazole and 1,3,4-thiadiazole bearing Schiff base moiety were designed, synthesized and evaluated for their in vitro antitumor activities against SMMC-7721, MCF-7 and A549 human tumor cell lines by CCK-8 assay. The bioassay results demonstrated that most of the tested compounds showed potent antitumor activities, and some compounds exhibited stronger effects than positive control 5-fluorouracil (5-FU) against various cell lines. Among these compounds, compound 8d showed the best inhibitory effect against SMMC-7721 cells, with IC50 value of 2.84 mu M. Compounds 8k and 8n displayed highly effective antitumor activities against MCF-7 cells, with IC50 values of 4.56 and 4.25 mu M, respectively. Compounds 8a and 8n exhibited significant antiproliferative activity against A549 cells, with IC50 values of 4.11 and 4.13 mu M, respectively. The pharmacological results suggest that the substituents of phenyl ring on the 1,3,4-oxadiazole are vital for modulating antiproliferative activities against various tumor cell lines. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2014.09.086
• 作为产物：
  描述：

  水杨醛 、 2-氨基-5-巯基-1,3,4-噻二唑 以 乙醇 为溶剂， 生成 2-(((5-mercapto-1,3,4-thiadiazol-2-yl)imino)methyl)phenol
  参考文献：
  名称：

  一些新型5-Arylmethylideneamino-1,3,4-Thiadiazole-2-Ylthioacetanilide衍生物的合成及生物活性

  摘要：

  摘要 5-芳基亚甲基氨基-2-巯基-1,3,4-噻二唑与氯乙酰苯胺在固相作用下S-烷基化合成了5-芳基亚甲基氨基-1,3,4-噻二唑-2-基硫基乙酰胺衍生物。在碳酸钾存在下使用聚乙二醇-400 (PEG-400) 催化剂进行液相转移催化。研究了一些标题化合物的植物生长调节活性。发现它们在低浓度下显着增强根伸长。[本文有补充材料。转至出版商在线版的磷、硫和硅及相关元素，查看以下免费补充文件：附加图和表]。图形概要

  DOI：

  10.1080/10426507.2013.787995

文献信息

• Molecular docking studies and biological evaluation of 1,3,4-thiadiazole derivatives bearing Schiff base moieties as tyrosinase inhibitors
  作者：Junyuan Tang、Jinbing Liu、Fengyan Wu

  DOI：10.1016/j.bioorg.2016.09.007

  日期：2016.12

  1,3,4-Thiadiazole derivatives bearing Schiff base moieties were designed, synthesized, and their tyrosinase inhibitory activities were evaluated. Some compounds displayed potent tyrosinase inhibitory activities, especially, 4-(((5-mercapto-1,3,4-thiadiazol-2-yl)-imino)methyl)-2-methoxy-phenol (14) exhibited superior inhibitory effect to the other compounds with an IC50 value of 0.036 μM. The structure–activity

  设计，合成了带有席夫碱部分的1,3,4-噻二唑衍生物，并评估了它们对酪氨酸酶的抑制活性。一些化合物显示出强效的酪氨酸酶抑制活性，尤其是4-（（（5-mercapto-1,3,4-thiadiazol-2-yl）-imino）methyl）-2-methoxy-phenol（14）表现出优异的抑制作用。其他化合物的IC 50值为0.036μM。初步讨论了结构-活性关系（SARs），对接研究表明化合物14对蘑菇酪氨酸酶具有很强的结合亲和力。羟基可能是活性基团。抑制动力学研究表明，化合物（13和14）通过充当非竞争性抑制剂来抑制酪氨酸酶。化合物14的LD 50值为5000mg / kg。
• SYNTHESIS OF SOME NOVEL AND BIOLOGICALLY ACTIVE SCHIFF BASES BEARING A 1,3,4-THIADIAZOLE MOIETY UNDER ACIDIC AND PTC CONDITIONS
  作者：A MOBINIKHALEDI、M JABBARPOUR、A HAMTA

  DOI：10.4067/s0717-97072011000300020

  日期：——

  The synthesis of some new Schiff bases bearing a 1,3,4-thiadiazole moiety, 3a-1, by reaction of 2-amino-5-mercapto-1,3,4-thiadiazole with aromatic aldehydes under acidic and phase transfer catalyst (PTC) conditions was studied. The structure of all the Schiff bases was characterized using FT-IR and NMR spectroscopy, and elemental analyses. The antibacterial activity of these compounds was investigated against Staphylococcus aureus (RTCC, 1885), and Escherichia coli (ATCC, 35922).
• Satpathy, K. C.; Jal, B. B.; Mishra, R., Indian Journal of Chemistry, Section A: Inorganic, Physical, Theoretical and Analytical, 1984, vol. 23, # 11, p. 959 - 961
  作者：Satpathy, K. C.、Jal, B. B.、Mishra, R.

  DOI：——

  日期：——