Dodecanoyl isothiocyanate and N′-(2-cyanoacetyl) dodecanehydrazide as precursors for the synthesis of different heterocyclic compounds with interesting antioxidant and antitumor activity

References

• Kibrom, G.; Girija, S. Reactivity and Diverse Synthetic Applications of Acyl Isothiocyanates. ARKIVOC 2015, 6, 206–245.
   Google Scholar
• Metwally, M. A.; Abdel-Latif, E.; Bondock, S. Thiocarbamoyl Derivatives as Synthons in Heterocyclic Synthesis. J. Sulfur Chem. 2007, 28(4), 431–466. DOI: 10.1080/17415990701397767.
   Google Scholar
• Edman, P. A Method for the Determination of Amino Acid Sequence in Peptides. Arch. Biochem. 1949, 22, 475.
   PubMed Web of Science ®Google Scholar
• Nedolya, N. A.; Trofimov, B. A.; Senning, A. α, β-Unsaturated Isothiocyanates. Sulfur Rep. 1996, 17, 183–395.
   Google Scholar
• Trofimov, B. A. Reactions on Unsaturated Carbanions with Isothiocyanates: A New Avenue to Fundamental Heterocycles. J. Heterocycl. Chem. 1999, 36, 1469–1490.
   Web of Science ®Google Scholar
• Sommen, G. Phenyl Isothiocyanate: A Very Useful Reagent in Heterocyclic Synthesis. Synlett 2004, 7, 1323–1324. DOI: 10.1055/s-2004-825608.
   Web of Science ®Google Scholar
• Mahmoud, R. M.; Ahmed. K. E.; Fatma, S. M.; Mahmoud. F. I.; Sayed. A. S. Synthesis and Reactions of Novel 2,5-disubstituted 1,3,4-Thiazoles. J. Chem. Res. 2013, 11(7), 80–85.
   Web of Science ®Google Scholar
• Fadda, A. A.; Mukhtar, M. M.; Hala, M. R. Utility of Activated Nitriles in the Synthesis of Some New Heterocyclic Compounds. Am. J. Org. Chem. 2012, 2(2), 32–40. DOI: 10.5923/j.ajoc.20120202.06.
   Google Scholar
• Fadda, A. A.; Bondock, Samir.; Rabie, R.; Etman, H. A. Cyanoacetamide Derivatives as Synthons in Heterocyclic Synthesis. Turk. J. Chem. 2008, 32, 259–286.
   Web of Science ®Google Scholar
• Eremeev, A. V.; Piskunova, I. P.; El’kinson, R. S. Synthesis of 2-Amino-1-Azirines and their Reactions with Carboxylic Acids. Khim. Geterotsikl. Soedin. 1985, 9, 1202–1206; Chem. Abstr. 1987, 107, 7016w. DOI: 10.1007/bf00515022.
   Google Scholar
• Elgemeie, G. H.; Elghandour, A. H.; Elzanate, A. M.; Ahmed, S. A. Synthesis of some Novel α-Cyanoketene S,S-Acetals and their Use in Heterocyclic Synthesis. J. Chem. Soc. Perkin Trans. 1997, 21(1), 3285–3290; Chem. Abstr. 1998, 128, 48171v. DOI: 10.1039/a702343j.
   Google Scholar
• Ibrahim, M. K. A.; El-Reedy, A. M.; El-Gharib, M. S. A. Reaction of Aryl Carbamoyl Aryl Hydrazidoyl Chlorides with Activated Nitriles. Commun. Fac. Sci. Univ. Ankra Ser. B Chem. Chem. Eng. 1994, 36(1–2), 45–52; Chem. Abstr. 1995, 123, 198686c. DOI: 10.1501/commub_0000000450.
   Google Scholar
• Ammar, Y. A.; El-Sharief, A. M. Sh.; Al-Sehemi, A. G.; Mohamed, Y. A.; Senussi, M. A.; El-Gaby, M. S. A. Cyano-Acetanilides Intermediates in Heterocyclic Synthesis. Part 2: Preparation of Some Hitherto Unknown Ketene Dithioacetal, Benzoazole and Pyridone Derivatives. J. Chin. Chem. Soc. (Taipei). 2005, 52, 553–558. DOI: 10.1002/jccs.200500081.
   Web of Science ®Google Scholar
• El-Bayouki, K. A. M.; Aly, M. M.; Mohamed, Y. A.; Ba-syouni, W. M.; Abbas, S. Y. Novel 4(3H)-Quinazolinone Containing Biologically Active Thiazole, Pyrazole, 1,3-Dithiazole, Pyridine, Chromene, Pyrazolopyrimidine and Pyranochromene of Expected Biological Activity. World J. Chem. 2009, 4, 161–170. DOI: 10.5155/eurjchem.2.4.455-462.171.
   Google Scholar
• Elgemeie, G. H.; Elghandour, A. H.; Elzanaty, A. M.; Ahmed, A. S. Novel 1,3‐Dithiolan‐2‐ones Using Sodium α‐Cyano-ketene Dithiolates. Synth. Commun. 2006, 36, 755–764. DOI: 10.1002/chin.200633131.
   Web of Science ®Google Scholar
• Dankova, E. F.; Bakulev, V. A.; Grishakov, A. N.; Mokrushin, V. S. New Rearrangement of 5-Amino-1,2,3-Thiadiazole-4-Carbothioamides. Izv. Akad. Nauk. SSSR Ser. Khim. 1988, 5, 1126–1128. DOI: 10.1007/bf00957074.
   Google Scholar
• Huang, W.; Li, J.; Tang, J.; Liu, H.; Shen, J.; Jiang, H. Microwave‐Assisted Synthesis of 2-Amino-Thiophene-3-Carboxylic Derivatives Under Solvent-Free Conditions. Synth. Commun. 2005, 35, 1351–1357.
   Web of Science ®Google Scholar
• Ershov, L. V.; Granik, V. G. Acetals of Lactams and Amides. 45. Synthesis of Condensed 2-Pyridones Based on Activated Amides, Lactams and Lactones. Kim. Geterotsikl. Soedin. 1985, 7, 929–932; Chem. Abstr. 1986, 104, 168389y.
   Google Scholar
• Stetinova, J.; Kada, R.; Lesko, J.; Dandarova, M.; Krublova, M. Synthesis and Spectral Properties of 1-(6-Methoxy-2- Benzothiazolyl)-2-Pyridones. Collect. Czech. Chem. Commun. 1996, 61, 921–929. DOI: 10.1002/chin.199639167.
   Google Scholar
• El Rady, E. A.; Barsy, A. M. A Convenient and Facile Syn-Thesis of Pyridine, Pyridazine, Pyrimido-[4,5-c]Pyridazine, Pyrido[3,4-c]Pyridazine, 1,6-Naphthyridine and Phthalazine Derivatives. J. Heterocycl. Chem. 2006, 43, 243–248. DOI: 10.1002/chin.200631137.
   Web of Science ®Google Scholar
• Ibrahim, S. N.; Abed, M. N.; Kandeel, Z. E. Nitriles in Heterocyclic Synthesis: A New Approach for the Synthesis of Thiazinones. Heterocycles 1984, 22, 1677–1682; Chem. Abstr. 1985, 102, 6351 m. DOI: 10.3987/r-1984-08-1677.
   Web of Science ®Google Scholar
• Ibrahim, M. K. A.; Ramiz, M. M. M.; El-Ghandour, A. H. H. Synthesis of N-(Azolyl)-Alpha-Ketohydrazidoyl Chlorides, Azolotriazole and Azolotriazine Derivatives. J. Chem. Soc. Perkin Trans. 1, 1989, 11(4), 291–6; Chem. Abstr. 1990, 113, 191303k.
   Google Scholar
• Suryakiran, N.; Ramesh, D.; Venkateswarlu, Y. Synthesis of 3-Amino 1H-Pyrazoles Catalyzed by p-Toluene Sulphonic Acid using Polyethylene Glycol-400 as an Efficient and Recyclable Reaction Medium. Green Chem. Lett. Rev. 2007, 1(1), 73–78.
   Web of Science ®Google Scholar
• Rafat, M.; Jonathan, Z.; Abeer, A. M. Uses of 1-Cyanoacetyl-4-phenyl-3-thiosemicarbazide in Heterocyclic Synthesis: Synthesis of Thiazole, Coumarin, and Pyridine Derivatives with Antimicrobial and Antifungal Activities. Phosphorus Sulfur Silicon Relat. Elem. 2007, 182, 1661–1681.
   Web of Science ®Google Scholar
• Larry, T. P.; Michael, M. C.; Florence, O. M. Synthesis of Novel 3,4-Diaryl-5-Aminopyrazoles as Potential Kinase Inhibitors. Tetrahedron 2011, 67, 4601–4611. DOI: 10.1016/j.tet.2011.04.077.
   Web of Science ®Google Scholar
• Kuo, H. M.; Li, S. Y.; Sheu, H. S.; Lai, C. K. Symmetrical Mesogenic 2,5-Bis(6-Naphthalen-2-yl)-1,3,4-Thiadiazoles. Tetrahedron 2012, 68, 7331–7337. DOI: 10.1016/j.tet.2012.06.092.
   Web of Science ®Google Scholar
• Saitoh, M.; Kunitomo, J.; Kimura, E.; Iwashita, H.; Uno, Y.; Onishi, T.; Uchiyama, N.; Kawamoto, T.; Tanaka, T.; Mol, C. D.; Dougan, D. R.; Textor, G. P.; Snell, G. P.; Takizawa, M.; Itoh, F.; Kori, M. 2-{3-[4-(Alkylsulfinyl)phenyl]-1-benzofuran-5-yl}-5-methyl-1,3,4-oxadiazole Derivatives as Novel Inhibitors of Glycogen Synthase Kinase-3β with Good Brain Permeability. J. Med. Chem. 2009, 52, 6270–6286.
   PubMed Web of Science ®Google Scholar
• Kaleta, Z.; Makowski, B. T.; Soos, T.; Dembinski, R. Thionation Using Fluorous Lawesson’s Reagent. Org. Lett. 2006, 8, 1625–1628.
   PubMed Web of Science ®Google Scholar
• Garfunkle, J.; Ezzili, C.; Rayl, T. J.; Hochstatter, D. G.; Hwang, I.; Boger, D. L. Optimization of the Central Heterocycle of α-Ketoheterocycle Inhibitors of Fatty Acid Amide Hydrolase. J. Med. Chem. 2008, 51, 4392–4403. DOI: 10.1021/jm800136b.
   PubMed Web of Science ®Google Scholar
• Yang, H.; Cui-Yun, L.; Xiao-Ming, W.; Yong-Hua, Y.; Hai-Liang, Z. 1,3,4-Thiadiazole: Synthesis, Reactions, and Applications in Medicinal, Agricultural, and Materials Chemistry. Chem. Rev. 2014, 114(10), 5572–5610.
   PubMed Web of Science ®Google Scholar
• Jasmina, D.; Natasa, V.; Gordana, U.; MIJIN, D. Synthesis of 5-(Substituted Phenylazo)-6-Hydroxy-4-Methyl-3-Cyano-2-Pyridones from Ethyl 3-Oxo-2-(Substituted Phenylazo) Butanoates. J. Serb. Chem. Soc. 2011, 76(4), 499–504. DOI: 10.2298/jsc100618044d.
   Web of Science ®Google Scholar
• Mahmoud, R. M.; Sayed, A. S.; Ahmed, K. E.; Fatma, S. M. A.; Mahmoud, F. I. Synthesis and Reactions of Novel 2,5-disubstituted 1,3,4-Thiazoles. Synth. Commun. 2014, 44, 1094–1102. DOI: 10.1080/00397911.2013.846381.
   Web of Science ®Google Scholar
• Ehab, A. L.; Abdel-Galil, M. K. Efficient Synthesis of Some New Functionalized 3-Amino-and 5-Aminopyrazoles Derivatives. Res. Chem. Intermed. 2015, 41, 4555–4567. DOI: 10.1007/s11164-014-1551-7.
   Web of Science ®Google Scholar
• Mosmann, T. Rapid Colorimetric Assay for Cellular Growth and Survival: Application to Proliferation and Cytotoxicity Assays. J. Immunol. Methods. 1983, 65, 55–63. DOI: 10.1016/0022-1759(83)90303-4.
   PubMed Web of Science ®Google Scholar
• Denizot, F.; Lang, R. Rapid Colorimetric Assay for Cell Growth and Survival. Modifications to the Tetrazolium Dye Procedure Giving Improved Sensitivity and Reliability. J. Immunol. Methods. 1986, 22, 271–277. DOI: 10.1016/0022-1759(86)90368-6.
   Web of Science ®Google Scholar
• Thabrew, M. I.; Hughes, R. D.; McFarlane, I. G. Screening of Hepatoprotective Plant Components Using a HepG2 Cell Cytotoxicity Assay. J. Pharm. Pharmacol. 1997, 49(11), 1132–1135. DOI: 10.1111/j.2042-7158.1997.tb06055.x.
   PubMed Web of Science ®Google Scholar
• Lissi, E. A.; Modak, B.; Torres, R.; Escobar, J.; Urzua, A. Total Antioxidant Potential of Resinous Exudates from Heliotropium Species, and a Comparison of the ABTS and DPPH Methods. Free Radic. Res. 1999, 30, 471–477. DOI: 10.1080/10715769900300511.
   PubMed Web of Science ®Google Scholar
• Aeschbach, R.; Loliger, J.; Scott, B. C.; Murcia, A.; Butler, J. Antioxidant Actions of Thymol, Carvacrol, 6-Gingerol, Zingerone and Hydroxytyrosol. Food Chem. Toxicol. 1994, 32, 31–36. DOI: 10.1016/0278-6915(84)90033-4.
   PubMed Web of Science ®Google Scholar
• Chan, T. Y.; Tang, P. L. Characterization of the Antioxidant Effects of Melatonin and Related Indoleamines In Vitro. J. Pineal. Res. 1996, 20, 187–191. DOI: 10.1111/j.1600-079x.1996.tb00257.x.
   PubMed Web of Science ®Google Scholar
• Gutteridge, J.; Rowley, D.; Halliwell, B. Superoxide-Dependent Formation of Hydroxyl Radicals in the Presence of Iron Salts. Detection of free iron in biological systems by using bleomycin-dependent degradation of DNA. Biochem. J. 1981, 99, 263.
   Web of Science ®Google Scholar