methyl 2-(1-(naphthalen-2-yl)ethylidene)hydrazine-1-carbodithioate | 26158-32-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: methyl 2-(1-(naphthalen-2-yl)ethylidene)hydrazine-1-carbodithioate
• 英文别名: Methyl 3-{1-(2-naphthyl)}ethylidenedithio-carbazate；methyl N-(1-naphthalen-2-ylethylideneamino)carbamodithioate
• CAS: 26158-32-7
• 化学式: C₁₄H₁₄N₂S₂
• 分子量: 274.411
• InChiKey: GNCUNYABYLLJGI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  81.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  methyl 2-(1-(naphthalen-2-yl)ethylidene)hydrazine-1-carbodithioate 、 2-(2-phenylhydrazono)-2-chloro-N-phenylacetamide 在 三乙胺 作用下， 以 乙醇 为溶剂， 反应 1.0h， 以72%的产率得到
  参考文献：
  名称：

  Zohdi, Hussein F.; Rateb, Nora M.; Sallam, Mohamed M. M., Journal of Chemical Research, Miniprint, 1998, # 12, p. 3329 - 3347

  摘要：

  DOI：

文献信息

• Reactions with Hydrazonoyl Halides XXX: Synthesis of Some 2,3-Dihydro-1,3,4-Thiadiazoles and Unsymmetrical Azines Containing Benzothiazole Moiety
  作者：Abdou O. Abdelhamid、Nora M. Rateb、Kamal M. Dawood

  DOI：10.1080/10426500008082403

  日期：2000.1.1

  to give 2,3-dihydro-1,3,4-thiadiazoles in good yields. In contrast, hydrazonoyl bromides react with each of phenylthiourea (19a), phenylthiosemicarbazide (19b), and benzoylthiosemicarbazide (19c) afforded 5-arylazothiazole 22–24(a-c) derivatives, respectively. Structures of the new compounds were elucidated on the basis of elemental analyses, spectral data, and alternative methods of synthesis whenever

  摘要 C-苯并噻唑酰-N-芳基腙酰溴化物 1a,b 与 2-噻唑基氰基亚甲基碳二硫代甲酯 (2)、碳二硫代烷基酯 8-10 和硫代氨基甲酸甲酯 14a-c 在三乙胺存在下反应，得到 2,3 -二氢-1,3,4-噻二唑，收率良好。相比之下，腙酰溴分别与苯基硫脲 (19a)、苯基氨基硫脲 (19b) 和苯甲酰氨基脲 (19c) 反应，分别得到 5-芳基偶氮噻唑 22-24(ac) 衍生物。新化合物的结构是在元素分析、光谱数据和其他可能的合成方法的基础上阐明的。
• One Pot Single Step Synthesis and Biological Evaluation of Some Novel Bis(1,3,4-thiadiazole) Derivatives as Potential Cytotoxic Agents
  作者：Sobhi Gomha、Nabila Kheder、Abdou Abdelhamid、Yahia Mabkhot

  DOI：10.3390/molecules21111532

  日期：——

  A novel series of bis(1,3,4-thiadiazole) derivatives were synthesized in one step methodology with good yields by condensation reaction between bis-hydrazonoyl chloride 1 and various reagents. The structures of the prepared compounds were confirmed by spectral data (IR, NMR, and MS), and elemental analysis. The anticancer activity against human breast carcinoma (MCF-7) cancer cell lines was evaluated

  通过双腙酰氯 1 与各种试剂的缩合反应，在一步方法中合成了一系列新型双 (1,3,4-噻二唑) 衍生物，收率良好。通过光谱数据（IR、NMR 和 MS）和元素分析确认了制备的化合物的结构。在 MTT 测定中评估了对人乳腺癌 (MCF-7) 癌细胞系的抗癌活性。结果表明，双噻二唑衍生物5c、d、7b、c和9c比标准药物伊马替尼具有更高的抗肿瘤活性。
• 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.