N'-Cycloheptylidene-hydrazinecarbodithioic acid methyl ester | 27268-62-8

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫基化合物
• 英文名称: N'-Cycloheptylidene-hydrazinecarbodithioic acid methyl ester
• 英文别名: methyl N-(cycloheptylideneamino)carbamodithioate
• CAS: 27268-62-8
• 化学式: C₉H₁₆N₂S₂
• 分子量: 216.371
• InChiKey: CKSXLEZCYGRDHY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.93
• 重原子数：
  13.0
• 可旋转键数：
  1.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  24.39
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  N'-Cycloheptylidene-hydrazinecarbodithioic acid methyl ester 、 2-(5-methyl-1-phenyl-1H-pyrazol-4-yl)-2-oxo-N'-phenylacetohydrazonoyl bromide 在 三乙胺 作用下， 以 乙醇 为溶剂， 以68%的产率得到(5-(cycloheptylidenehydrazono)-4-phenyl-4,5-dihydro-1,3,4-thiadiazol-2-yl)(5-methyl-1-phenyl-1H-pyrazol-4-yl)methanone
  参考文献：
  名称：

  2-(5-methyl-1-phenyl-1H-pyrazol-4-yl)-2-oxo-N'-phenylaceto-hydrazonoyl bromide 作为合成新功能化杂环的前体的效用

  摘要：

  摘要 合成了 2-(5-Methyl-1-phenyl-1H-pyrazol-4-yl)-2-oxo-N'-phenylaceto-hydrazonoyl bromide 并作为前驱体合成了一些新的 1,3,4-噻二唑、吡咯并[3,4-c]吡唑和1,2,4-三唑并[4,3-a]嘧啶。讨论了形成产物的机制。此外，所有新合成产物的结构均基于元素分析、光谱数据和替代方法得到确认。图形概要

  DOI：

  10.1080/00397911.2017.1303071
• 作为产物：
  描述：

  环庚酮 在 氢氧化钾 作用下， 以 乙醇 为溶剂， 生成 N'-Cycloheptylidene-hydrazinecarbodithioic acid methyl ester
  参考文献：
  名称：

  Anthoni,U. et al., Acta Chemica Scandinavica (1947), 1970, vol. 24, p. 179 - 188

  摘要：

  DOI：

文献信息

• Reaction with Hydrazonoyl Halides 64: Synthesis of Some New Triazolino[4,3-<i>a</i>]pyrimidines, 1,3,4-Thiadiazoles, and 5-Arylazothiazoles
  作者：Abdou O. Abdelhamid、Abdelgawad A. Fahmi、Basma S. Baaui

  DOI：10.1002/jhet.945

  日期：2012.9

  benzofuran moiety were prepared from the reaction of 2‐(2‐phenylhydrazono)‐1‐(5‐bromobenzofuran‐2‐yl)‐2‐chloroethanone with each of potassium thiocyanate, potassium selenocyanate, alkyl carbodithioate, and pyrmidine‐2‐thione derivatives. All the newly synthesized compounds were confirmed by elemental analysis, spectral data, and alternative route synthesis whenever possible.

  由2-（-）的反应制得2,3-二氢-1,3,4-噻二唑，2,3-二氢-1,3,4-硒代二唑和含苯并呋喃部分的三唑啉并[4,3- a ]嘧啶。 2-苯基肼基）-1-（5-溴苯并呋喃-2-基）-2-氯乙酮与硫氰酸钾，硒氰酸钾，碳二硫代烷基酯和嘧啶-2-硫酮衍生物中的每一种。所有新合成的化合物均通过元素分析，光谱数据和可能的替代路线合成得到确认。
• Utility of<i>Bis-</i>Hydrazonoyl Chlorides as Precursors for Synthesis of New Functionalized<i>Bis</i>-Thiadiazoles as Potent Antimicrobial Agents
  作者：Sobhi M. Gomha、Marwa S. ElGendy、Zeinab A. Muhammad、Abdou O. Abdelhamid、Marwa M. Abdel-Aziz

  DOI：10.1002/jhet.3108

  日期：2018.4

  N′,N″‐([1,1’‐Biphenyl]‐4,4′‐diyl)bis(2‐oxopropanehydrazonoyl chloride) is considered to be the key intermediate for the synthesis of a variety bis‐1,3,4‐thiadiazole derivatives in one step methodology with good yields by reaction of with a series of hydrazinecarbodithioate derivatives 2a–e, 6a,b, and 8a–e. The assigned structures for all the newly synthesized compounds were confirmed on the basis of

  N'，N'' -（[[1,1'-Biphenyl] -4,4'-diyl）bis（2-氧代丙烷肼基氯酰）被认为是合成各种bis -1,3,4的关键中间体-噻二唑衍生物通过一步法与一系列二硫代肼磺酰肼衍生物2a-e，6a，b和8a-e反应，具有良好的收率。在元素分析和光谱数据（红外，核磁共振和质谱）的基础上，确认了所有新合成化合物的指定结构，并讨论了其形成机理。此外，筛选了对十二种选定产品的抗微生物活性，并且通过与所使用的标准杀菌剂和杀真菌剂相比，探索了某些被测化合物的高效力而获得的结果。另外，确定了被测化合物的最小抑制浓度，并且通过探索三种被测化合物对所有被测微生物的高效力而获得的结果。
• 5-(Thiophen-2-yl)-1,3,4-thiadiazole derivatives: synthesis, molecular docking and in vitro cytotoxicity evaluation as potential anticancer agents
  作者：Sobhi Gomha、Mastoura Edrees、Zeinab Muhammad、Ahmed El-Reedy

  DOI：10.2147/dddt.s165276

  日期：——

  Background: Nowadays, cancer is an important public health problem in all countries. Limitations of current chemotherapy for neoplastic diseases such as severe adverse reactions and tumor resistance to the chemotherapeutic drugs have been led to a temptation for focusing on the discovery and development of new compounds with potential anticancer activity. The importance of thiophene and thiadiazole rings as scaffolds present in a wide range of therapeutic agents has been well reported and has driven the synthesis of a large number of novel antitumor agents.Methods: A series of new 1,3,4-thiadiazoles were synthesized by heterocyclization of N-(4nitrophenyl) thiophene-2-carbohydrazonoyl chloride with a variety of hydrazine-carbodithioate derivatives. The mechanisms of these reactions were discussed and the structure of the new products was elucidated via spectral data and elemental analysis. All the new synthesized compounds were investigated for in vitro activities against human hepatocellular carcinoma (HepG-2) and human lung cancer (A-549) cell lines compared with cisplatin standard anticancer drug. Moreover, molecular docking using MOE 2014.09 software was also carried out for the high potent compound 20b with the binding site of dihydrofolate reductase (DHFR, PDB ID (3NU0)).Results: The results showed that compound 20b has promising activities against HepG-2 and A-549 cell lines (IC50 value of 4.37 +/- 0.7 and 8.03 +/- 0.5 mu M, respectively) and the results of molecular docking supported the biological activity with total binding energy equals -1.6 E (Kcal/mol).Conclusion: Overall, we synthesized a new series of 1,3,4-thiadiazoles as potential antitumor agents against HepG-2 and A-549 cell lines.