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LETTER

Ultrasound-assisted green synthesis and antimicrobial assessment of 1,3-thiazoles and 1,3,4-thiadiazines

, , ORCID Icon &
Pages 679-688 | Received 01 Mar 2021, Accepted 05 Oct 2021, Published online: 29 Nov 2021

References

  • Cravotto, G.; Cintas, P. Power Ultrasound in Organic Synthesis: Moving Cavitational Chemistry from Academia to Innovative and Large-Scale Applications. J. Chem. Soc. 2006, 35 (2), 180–196.
  • Muravyova, E.A.; Desenko, S.M.; Musatov, V.I.; Knyazeva, I.V.; Shishkina, S.V.; Shishkin, O.V.; Chebanov, V.A. Ultrasonic-Promoted Three-Component Synthesis of Some Biologically Active 1,2,5,6-Tetrahydropyrimidines. J. Comb. Chem. 2007, 9, 797.
  • Li, J.T.; Yin, Y.; Li, L.; Sun, M.X. A Convenient and Efficient Protocol for the Synthesis of 5-Aryl-1,3-Diphenylpyrazole Catalyzed by Hydrochloric Acid Under Ultrasound Irradiation. Ultrason. Sonochem. 2010, 17, 11.
  • Banaei, A.; Salmanpour, H.; Karimi, S. Ultrasound Irradiation Promoted Synthesis of Bispyrimidine and Bispyrazolines as Selective Adsorbents for the Selective Removal of Ag(I) and Pb(II) from Aqueous Solutions. Monatsh Chem. 2017, 148, 683.
  • Lu, C.W.; Wang, J.J.; Li, F.; Yu, S.J.Y. Efficient Synthesis of 2-Amino-3-Cyano-4H-Pyran Derivatives via a non-Catalytic one-pot Three-Component Reaction. Res. Chem. Intermed. 2018, 44, 1035.
  • Safari, J.; Tavakoli, M.; Ghasemzadeh, M.A. Ultrasound-promoted an Efficient Method for the One-pot Synthesis of Indeno Fused Pyrido[2,3-d]Pyrimidines Catalyzed by H3PW12O40 Functionalized Chitosan@Co3O4 as a Novel and Green Catalyst. J. Organomet. Chem. 2019, 880, 75.
  • Maddila, S.N.; Maddila, S.; Khumalo, M.; Bhaskaruni, S.V.; Jonnalagadda, S.B. An Eco-Friendly Approach for Synthesis of Novel Substituted 4H-Chromenes in Aqueous Ethanol Under Ultra-Sonication with 94% Atom Economy. J. Mol. Struct. 2019, 5, 357.
  • Martins, M.A.P.; Pereira, C.M.P.; Cunico, W.; Moura, S.; Rosa, F.A.; Peres, R.L.; Machado, P.; Zanatta, N.; Bonacorso, H.G. Ultrasound Promoted Synthesis of 5-Hydroxy-5-Trihalomethyl-4,5-Dihydroisoxazoles and β-Enamino Trihalomethyl Ketones in Water. Ultrason. Sonochem. 2006, 13, 364.
  • Rouhani, M.; Ramazani, A.; Joo, S.W. Novel, Fast and Efficient one-pot Sonochemical Synthesis of 2-Aryl-1,3,4-Oxadiazoles. Ultrason. Sonochem. 2014, 21, 262.
  • Sayed, A.R.; Gomha, S.M.; Taher, E.A.; Muhammad, Z.A.; El-Seedi, H.R.; Gaber, H.M.; Ahmed, M.M. One-Pot Synthesis of Novel Thiazoles as Potential Anti-Cancer Agents. Drug. Des. Devel. Ther. 2020, 14, 1363.
  • Gomha, S.M.; Abdelhamid, A.O.; Kandil, O.M.; Kandeel, S.M.; Abdelrehem, N.A. Synthesis and Molecular Docking of Some Novel Thiazoles and Thiadiazoles Incorporating Pyranochromene Moiety as Potent Anticancer Agents. Mini Rev. Med. Chem. 2018, 18, 1670.
  • Gomha, S.M.; Abdel-Aziz, H.M.; Badrey, M.G.; Abdulla, M.M. Efficient Synthesis of Some New 1,3,4-Thiadiazoles and 1,2,4-Triazoles Linked to Pyrazolylcoumarin Ring System as Potent 5α-Reductase Inhibitors. J. Heterocycl. Chem. 2019, 56, 1275.
  • Gomha, S.M.; Abdelhady, H.A.; Hassain, D.Z.H.; Abdelmonsef, A.H.; El-Naggar, M.; Elaasser, M.M.; Mahmoud, H.K. Thiazole-Based Thiosemicarbazones: Synthesis, Cytotoxicity Evaluation and Molecular Docking Study. Drug Des, Devel Ther 2021, 15, 659.
  • Łączkowski, K.Z.; Anusiak, J.; Świtalska, M.; Dzitko, K.; Cytarska, J.; Baranowska-Łączkowska, A.; Plech, T.; Paneth, A.; Wietrzyk, J.; Białczyk, J. Synthesis, Molecular Docking, ctDNA Interaction, DFT Calculation and Evaluation of Antiproliferative and Anti-Toxoplasma Gondii Activities of 2,4-Diaminotriazine-Thiazole Derivatives. Med. Chem. Res. 2018, 27, 1131.
  • Prashanth, T.; Avin, B.R.V.; Thirusangu, P.; Ranganatha, V.L.; Prabhakar, B.T.; Chandra, J.N.N.S.; Khanum, S.A. Synthesis of Coumarin Analogs Appended with Quinoline and Thiazole Moiety and Their Apoptogenic Role Against Murine Ascitic Carcinoma. Biomed. Pharmacother. 2019, 112, 108707.
  • Anuradha, P.S.; Patle, R.; Parameswaran, P.; Jain, A.; Shard, A. Design, Computational Studies, Synthesis and Biological Evaluation of Thiazole-Based Molecules as Anticancer Agents. Eur. J. Pharm. Sci. 2019, 134, 20.
  • Siddiqui, N.; Arya, S.K.; Ahsan, W.; Azad, B. International Journal of Drug Development & Research. October-December 2011. Vol. 3. Issue 4. ISSN 0975-9344| Available Online Http://www. Ijddr. in Covered in Official Product of Elsevier, The Netherlands© 2010 IJDDR. Int J Drug Dev Res 2011, 3 (4), 55.
  • Mohareb, R.M.; Zaki, M.Y.; Abbas, N.S. Synthesis, Anti-Inflammatory and Anti-Ulcer Evaluations of Thiazole, Thiophene, Pyridine and Pyran Derivatives Derived from Androstenedione. Steroids 2015, 98, 80.
  • Eryılmaz, S.; Çelikoğlu, E.T.; İdil, O.; İnkaya, E.; Kozak, Z.; Mısır, E.; Gül, M. Derivatives of Pyridine and Thiazole Hybrid: Synthesis, DFT, Biological Evaluation via Antimicrobial and DNA Cleavage Activity. Bioorg. Chem. 2020, 95, 103476.
  • Meghdadi, S.; Amirnasr, M.; Yavari, E.; Mereiter, K.; Bagheri, M. Synthesis, Characterization, and X-ray Crystal Structures of Copper(I) Halide and Pseudohalide Complexes with 2-(2-Quinolyl)Benzothiazole. Diverse Coordination Geometries and Electrochemical Properties. C. R. Chim 2017, 20 (7), 730.
  • Biernasiuk, A.; Kawczyńska, M.; Berecka-Rycerz, A.; Rosada, B.; Gumieniczek, A.; Malm, A.; Dzitko, K.; Łączkowski, K.Z. Synthesis, Antimicrobial Activity, and Determination of the Lipophilicity of ((Cyclohex-3-Enylmethylene)Hydrazinyl)Thiazole Derivatives. Med. Chem. Res. 2019, 28, 2023.
  • Ansari, A.; Ali, A.; Asif, M.; Rauf, M.A.; Shamsuzzaman, O.M. Facile One-Pot Multicomponent Synthesis and Molecular Docking Studies of Steroidal Oxazole/Thiazole Derivatives with Effective Antimicrobial, Antibiofilm and Hemolytic Properties. Steroids 2018, 134, 22.
  • Ouf, S.A.; Gomha, S.M.; Ewies, M.M.; Sharawy, I.A.A. Synthesis, Characterization, and Antifungal Activity Evaluation of Some Novel Arylazothiazoles. J. Heterocycl. Chem. 2018, 55 (1), 258.
  • Biernasiuk, A.; Kawczyńska, M.; Berecka-Rycerz, A.; Rosada, B.; Gumieniczek, A.; Malm, A.; Dzitko, K.; Łączkowski, K.Z. Synthesis, Antimicrobial Activity, and Determination of the Lipophilicity of ((Cyclohex-3-Enylmethylene)Hydrazinyl)Thiazole Derivatives. Med. Chem. Res. 2019, 28, 2023.
  • Ansari, A.; Ali, A.; Asif, M.; Rauf, M.A.; Shamsuzzaman, O.M. Facile One-Pot Multicomponent Synthesis and Molecular Docking Studies of Steroidal Oxazole/Thiazole Derivatives with Effective Antimicrobial, Antibiofilm and Hemolytic Properties. Steroids 2018, 134, 22.
  • Pricopie, A.-I.; Ionut, I.; Marc, G.; Arseniu, A.-M.; Vlase, L.; Grozav, A.; Gaina, L.I.; Vodnar, D.C.; Pîrnau, A.; Tiperciuc, B.; Oniga, O. Design and Synthesis of Novel 1,3-Thiazole and 2-Hydrazinyl-1,3-Thiazole Derivatives as Anti-Candida Agents: In Vitro Antifungal Screening, Molecular Docking Study, and Spectroscopic Investigation of Their Binding Interaction with Bovine Serum Albumin. Molecules 2019, 24, 3435.
  • Asif, M.; Ali, A.; Zafar, A.; Farhan, M.; Khanam, H.; Hadi, S.M. Microwave-assisted One Pot Synthesis, Characterization, Biological Evaluation and Molecular Docking Studies of Steroidal Thiazoles. J. Photobiol. B Biol. 2017, 166, 104.
  • Abumelha, H.M.A. Synthesis and Antioxidant Assay of New Nicotinonitrile Analogues Clubbed Thiazole, Pyrazole and/or Pyridine Ring Systems. J. Heterocycl. Chem. 2020, 57, 1011.
  • Iqbal, A.M.; Khan, A.Y.; Kalashetti, M.B.; Belavagi, N.S.; Gong, Y.D.; Khazi, I.A.M. Synthesis, Hypoglycemic and Hypolipidemic Activities of Novel Thiazolidinedione Derivatives Containing Thiazole/Triazole/Oxadiazole Ring. Eur. J. Med. Chem. 2012, 53, 308.
  • Paudel, Y.N.; Ali, M.R.; Shah, S.; Adil, M.; Akhtar, M.S.; Wadhwa, R.; Bawa, S.; Sharma, M. 2-[(4-Chlorobenzyl) Amino]-4-Methyl-1,3-Thiazole-5-Carboxylic Acid Exhibits Antidiabetic Potential and Raises Insulin Sensitivity via Amelioration of Oxidative Enzymes and Inflammatory Cytokines in Streptozotocin–induced Diabetic Rats. Biomed. Pharmacother. 2017, 89, 651.
  • Siddiqui, N.; Ahsan, W. Triazole Incorporated Thiazoles as a New Class of Anticonvulsants: Design, Synthesis and in Vivo Screening. Eur. J. Med. Chem. 2010, 45 (4), 1536.
  • Abdel-Aziem, A. Synthesis and Antimicrobial Activity of Some Novel Thiazoles, 1,3,4-Thiadiazines, 1,3,4-Thiadiazoles Incorporating Coumarin Moiety. J. Heterocycl. Chem. 2015, 52, 251.
  • Shubakar, K.; Umesha, K.B.; Srikantamurthy, N. Synthesis and Antimicrobial Evaluation of Novel Derivatives of 1, 3, 4-Thiadiazine Incorporated with Pyrazole-4-Carboxylic Acid Moiety. J. Chethan. Bulgarian Chem. Comm. 2013, 45 (3), 274.
  • Puthiyapurayil, P.; Poojary, B.; Chikkanna, C.; Buridipad, S.K. Synthesis, Spectral Characterization and Biological Evaluation of a Novel Series of 6-Arylsubstituted-3-[2-(4-Substitutedphenyl)Propan-2-yl]-7H-[1,2,4]Triazolo[3,4-b][1,3,4]Thiadiazines. Eur. J. Med. Chem. 2012, 57, 407.
  • Abdel-Aziem, A. Utility of 2-Acetyl Benzofuran for the Synthesis of New Heterocycles as Potential Anticancer Agents. J. Heterocycl. Chem. 2017, 54, 2985.
  • Khan, I.; Zaib, S.; Ibrar, A.; Rama, N.H.; Simpson, J.; Iqbal, J. Synthesis, Crystal Structure and Biological Evaluation of Some Novel 1,2,4-Triazolo[3,4-b]-1,3,4-Thiadiazoles and 1,2,4-Triazolo[3,4-b]-1,3,4-Thiadiazines. Eur. J. Med. Chem. 2014, 78, 167.
  • Abdel-Aziem, A.; Rashdan, H.R.M.; Mohamed Ahmed, E.; Shabaan, S.N. Synthesis and Cytotoxic Activity of Some Novel Benzocoumarin Derivatives Under Solvent Free Conditions. Green Chem. Lett. Rev. 2019, 12 (1), 9.
  • Abdel Aziem, A.N.H.A.R. An Efficient and Simple Synthesis of 2, 3-Dihydro-1, 3, 4-Thiadiazoles, Pyrazoles and Coumarins Containing Benzofuran Moiety Using Both Conventional and Grinding Methods. Int. J. Pharm. Sci. 2015, 7 (1 ), 61–68.
  • Abdel-Aziem, A.; Abdelhamid, A.O. Int. J. Adv. Res. 2013, 1 (9), 717.
  • Zhou, J.; Wu, D.; Gou, D.J. Optimization of the Production of Thiocarbohydrazide Using the Taguchi Method. Chem. Technol. Biotechnol. 2010, 85 (10), 1402.
  • Takahashi, O.; Kirikoshi, R. Intramolecular Cyclization of Aspartic Acid Residues Assisted by Three Water Molecules: A Density Functional Theory Study. Comput. Sci. Discovery 2014, 7, 015005.
  • Asiri, A.M.; Al-Youbi, A.O.; Zayed, M.E.M.; Ng, S.W. 1-Chloro-1-[(4-chlorophenyl)hydrazinylidene]propan-2-one. Acta. Cryst. Sec. E Struct. Rep. 2011, 67 (Pt 8), o1962.
  • Eweiss, N.F.; Osman, A. Synthesis of Heterocycles. Part II. New Routes to Acetylthiadiazolines and Alkylazothiazoles. J. Heterocycl. Chem. 1980, 17, 1713.
  • Abdelhamid, A.O.; El-Shiatey, F.H.H. Reactions with Hydrazidoyl Halides ii [1]: Synthesis and Reactions of 2-Bromothienylglyoxal-2-Phenylhydrazone. Phosphorus Sulfur Silicon Relat. Elem. 1988, 39, 45.
  • Maigali, S.S.; Abd-El-Maksoud, M.A.; El-Hussieny, M.; Soliman, F.M.; Abdel-Aziz, M.S.; Shalaby, E.S.M. Chemistry of Phosphorus Ylides: Part 41 Synthesis of Antimicrobial Agents from the Reaction of Aminoantipyrine, Coumarin- and Quinoline-Carbaldehyde with Phosphacumulene and Phosphaallene Ylides. J. Chem. Res. 2014, 38 (12), 754.
  • Barry, A.L. The Antimicrobial Susceptibility Test, Principle and Practices, 4th ed.; ELBS: London, 1976; p. 180.