215
Views
16
CrossRef citations to date
0
Altmetric
Original Articles

Utility of thiophene-2-carbonyl isothiocyanate as a precursor for the synthesis of 1,2,4-triazole, 1,3,4-oxadiazole and 1,3,4-thiadiazole derivatives with evaluation of their antitumor and antimicrobial activities

ORCID Icon, &
Pages 630-636 | Received 24 Jan 2018, Accepted 22 May 2018, Published online: 30 Oct 2018

References

  • Drobnica, L.; Kristian, P.; Augustin, J. A. The Chemistry of Cyanates and Their Thio Derivatives, Patai, S. Ed; John Wiley & Sons: New York, 1977; Vol. 2, 1003–1221.
  • Sharma, S. Isothiocyanates in Heterocyclic Synthesis. Sulfur. Rep. 1989, 8, 327–454.
  • Mukerjee, A. K.; Ashare, R. Isothiocyanates in the Chemistry of Heterocycles. Chem. Rev. 1991, 91, 1–24.
  • Bedane, K. G.; Singh, G. S. Reactivity and Diverse Synthetic Applications of Acyl Isothiocyanates. ARKIVOC. 2015, 2015, 206–245.
  • Sommen, G. Phenyl Isothiocyanate: A Very Useful Reagent in Heterocyclic Synthesis. Synlett. 2004, 7, 1323–1324.
  • Hantzsch, A.; Weber, J. H. Berichtigung. Ber. Dtsch. Chem. Ges. 1887, 20, 3132–3336.
  • Hemdan, M. M.; Fahmy, A. F.; Ali, N. F.; Hegazi, E.; Abd-Elhaleem, A. Synthesis of Some New Heterocycles Derived from Phenylacetyl Isothiocyanate. Chin. J. Chem. 2008, 26, 388–391.
  • Hemdan, M. M.; Fahmy, A. F.; El- Sayed, A. A. Synthesis and Antimicrobial Study of 1,2,4-Triazole, Quinazoline and Benzothiazole Derivatives from 1-Naphthoylisothiocyanate. J. Chem. Res. 2010, 34, 219–221.
  • Hemdan, M. M.; Abou Elmagd, W. S. I.; Samy, S. S.; Youssef, A. S. A. Dodecanoyl Thiosemicarbazide Derivatives as Useful Synthons in the Synthesis of 1,2,4-Triazole, 1,3,4-Thiadiazole, and 1,3-Benzothiazole Derivatives. Synth. Comm. 2016, 46, 710–718.
  • Hemdan, M. M.; El-Bordany, E. A. Use of Dodecanoyl Isothiocyanate as Building Block in Synthesis of Target Benzothiazine, Quinazoline, Benzothiazole and Thiourea Derivatives. Chem. Pap. 2016, 70, 1117–1125.
  • Hemdan, M. M.; El-Sayed, A. A. Use of Phthalimidoacetyl Isothiocyanate as a Scaffold in the Synthesis of Target Heterocyclic Systems, and Their Antimicrobial Assessment. Chem. Pharm. Bull. 2016, 64, 483–489.
  • Galabov, A. S.; Galabov, B. S.; Neykova, N. A. Structure-Activity Relationship of Diphenylthiourea Antivirals. J. Med. Chem. 1980, 23, 1048–1051.
  • Rollas, S.; Buyuktimkinand, S.; Cevikbas, A. N-[4-(3H-1,3,4-Oxadiazoline-2-Thion-5-Yl)Phenyl]-N′-Substituted Thioureas: Synthesis and Antimicrobiological Activities. Arch. Pharmaz. 1991, 324, 189–190.
  • Sriram, D.; Yogeeswari, P.; Thirumurugan, R.; Pavana, R. K. Discovery of New Antitubercular Oxazolyl Thiosemicarbazones. J. Med. Chem. 2006, 49, 3448–3450.
  • García, C. C.; Brousse, B. N.; Carlucci, M. J.; Moglioni, A. G.; Alho, M. M.; Moltrasio, G. Y.; D'Accorso, N. B.; Damonte, E. B. Inhibitory Effect of Thiosemicarbazone Derivatives on Junin Virus Replication in-Vitro. Antivir. Chem. Chemother. 2003, 14, 99–105.
  • Klayman, D. L.; Scovill, J. P.; Bruce, J.; Bartosevich, J. F. 2-Acetylpyridine Thiosemicarbazones Derivatives of Acetylisoquinoline as Potential Antimalarial Agents. J. Med. Chem. 1984, 27, 84–87.
  • Jalilian, A. R.; Yousefnia, H.; Shafaii, K.; Novinrouz, A.; Rajamand, A. A. Preparation and Biodistribution Studies of a Radiogallium-Acetyl Acetonate Bis (Thiosemicarbazone) Complex in Tumor-Bearing Rodents. Iran. J. Pharm. Res. 2012, 11, 523–531.
  • Maia, P. I. S.; Nguyen, H. H.; Ponader, D.; Hagenbach, A.; Bergemann, S.; Gust, R.; Deflon, V. M.; Abram, U. Neutral Gold Complexes with Tridentate SNS Thiosemicarbazide Ligands. Inorg. Chem. 2012, 51, 1604–1613.
  • Novaković, S. B.; Bogdanović, G. A.; Fraisse, B.; Ghermani, N. E.; Bouhmaida, N.; Spasojević-de Biré, A. Topological Features of Both Electron Density and Electrostatic Potential in the Bis(Thiosemi- Carbazide)Zinc(II) Dinitrate Complex. J. Phys. Chem. A. 2007, 111, 13492–13505.
  • Mobinikhaledi, A.; Foroughifar, N.; Kalhor, M.; Ebrahimi, S.; Bodaghi Fard, M. A. Synthesis of Some Symmetrical Novel Bis-Thiosemi- Carbazides, 1,2,4-Triazoles, 1,3,4-Thiadiazoles and Their Derivatives. Phosphorus Sulfur Silicon Relat. Elem. 2010, 186, 67–73.
  • Dolman, S. J.; Gosselin, F.; O'Shea, P. D.; Davies, I. W. Superior Reactivity of Thiosemicarbazides in the Synthesis of 2-Amino-1,3,4-Oxadiazoles. J. Org. Chem. 2006, 71, 9548–9551.
  • Singh, S. P.; Parmar, S. S.; Raman, K.; Stenberg, V. I. Chemistry and Biological Activity of Thiazolidinones. Chem. Rev. 1981, 81, 175–203.
  • Mosmann, T.; Immunol, J. Rapid Colorimetric Assay for Cellular Growth and Survival: application to Proliferation and Cytotoxicity Assays. Methods. 1983, 65, 55–63.
  • Denizot, F.; Lang, R. J. Rapid Colorimetric Assay for Cell Growth and Survival. Modifications to the Tetrazolium Dye Procedure Giving Improved Sensitivity and Reliability. Immunol. Methods. 1986, 89, 271–277.
  • Stylianakis, A.; Kolocouris, N.; Kolocouris, G.; Fytas, G. B.; Foscolos, E.; Padalko, J.; Neyts, D.; Clerq, E. Spiro[Pyrrolidine-2,2′-Adamantanes]: Synthesis, anti-Influenza Virus Activity and Conformational Properties. Bioorg. Med. Chem. Lett. 2003, 13, 1699–1703.

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.