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Research Articles

Microwave-Assisted One-Pot Three Component Synthesis of Some Thiazolyl(Hydrazonoethyl)Thiazoles as Potential Anti-Breast Cancer Agents

, , , & ORCID Icon
Pages 7232-7246 | Received 06 Mar 2020, Accepted 20 Oct 2021, Published online: 09 Nov 2021

References

  • R. L. Siegel, K. D. Miller, and A. Jemal, “Cancer Statistics, 2015,” CA: A Cancer Journal for Clinicians 65, no. 1 (2015): 5–29.[pubmedMismatch]
  • P. Yogeeswari, R. Thirumurugan, R. Kavya, J. S. Samuel, J. Stables, and D. Sriram, “3-Chloro-2-Methylphenyl-Substituted Semicarbazones: Synthesis and Anticonvulsant Activity ,” European Journal of Medicinal Chemistry 39, no. 8 (2004): 729–34.
  • R. P. Shank, D. R. Doose, A. J. Streeter, and M. Bialer, “Plasma and Whole Blood Pharmacokinetics Oftopiramate: The Role of Carbonic Anhydrase,” Epilepsy Research 63, no. 2-3 (2005): 103–12.
  • S. M. Gomha, M. M. Edrees, and F. M. A. Altalbawy, “Synthesis and Characterization of Some New Bis-Pyrazolyl-Thiazoles Incorporating the Thiophene Moiety as Potent anti-Tumor Agents,” International Journal of Molecular Sciences 17, no. 9 (2016): 1499–12.
  • J. V. Ragavendran, D. Sriram, S. K. Patel, I. V. Reddy, N. Bharathwajan, J. Stables, and P. Yogeeswari, “Design and Synthesis of Anticonvulsants from a Combined phthalimide-GABA-anilide and hydrazone pharmacophore,” European Journal of Medicinal Chemistry 42, no. 2 (2007): 146–51.
  • R. Thirumurugan, D. Sriram, A. Saxena, J. Stables, and P. Yogeeswari, “2,4-Dimethoxyphenylsemicarbazones with Anticonvulsant Activity against Three Animal Models of Seizures: Synthesis and Pharmacological Evaluation,” Bioorganic & Medicinal Chemistry 14, no. 9 (2006): 3106–12.
  • P. Franchetti, L. Cappellacci, M. Grifantini, A. Barzi, G. Nocentini, H. Yang, A. O'Connor, H. N. Jayaram, C. Carrell, and B. M. Goldstein, “Furanfurin and Thiophenfurin: two Novel Tiazofurin Analogues. Synthesis, Structure, Antitumour Activity, and Interactions with Inosine Monophosphate Dehydrogenase,” Journal of Medicinal Chemistry 38, no. 19 (1995): 3829–37.
  • X. Li, Y. He, C. H. Ruiz, M. Koenig, M. D. Cameron, and T. Vojkovsky, “Characterization of Dasatinib and Its Structural Analogs as CYP3A4 Mechanism-Based Inactivators and the Proposed Bioactivation Pathways,” Drug Metabolism and Disposition: The Biological Fate of Chemicals 37, no. 6 (2009): 1242–50.
  • S. Hu-Lieskovan, S. Mok, B. Homet Moreno, J. Tsoi, L. Robert, L. Goedert, E. M. Pinheiro, R. C. Koya, T. G. Graeber, B. Comin-Anduix, and A. Ribas. Improved Antitumour Activity of Immunotherapy with B-RAF and MEK Inhibitors in BRAF(V600E) Melanoma,” Science Translational Medicine 18, (2015): 279, 279–41.
  • Y. Yao, S. Chen, X. Zhou, L. Xie, and A. Chen, “5-FU and Ixabepilone Modify the microRNA Expression Profiles in MDA-MB-453 Triple-Negative Breast Cancer Cells,” Oncology Letters 7, no. 2 (2014): 541–7.
  • K. H. Altmann, “Epothilone B and Its Analogs – A New Family of Anticancer Agents,” Mini Reviews in Medicinal Chemistry 3, no. 2 (2003): 149–58.
  • A. Aliabadi, F. Shamsa, S. N. Ostad, S. Emami, A. Shafiee, J. Davoodi, and A. Foroumadi, “Synthesis and Biological Evaluation of 2-Phenylthiazole-4-Carboxamide Derivatives as Anticancer Agents,” European Journal of Medicinal Chemistry 45, no. 11 (2010): 5384–9.
  • M. Banimustafa, A. Kheirollahi, M. Safavi, S. Kabudanian Ardestani, H. Aryapour, A. Foroumadi, and S. Emami, “Synthesis and Biological Evaluation of 3-(Trimethoxyphenyl)-2(3H)-Thiazole Thiones as Combretastatin Analogs,” European Journal of Medicinal Chemistry 70, (2013): 692–702.
  • A. Ayati, S. Emami, A. Asadipour, A. Shafiee, and A. Foroumadi, “Recent Applications of 1,3-Thiazole Core Structure in the Identification of New Lead Compounds and Drug Discovery,” European Journal of Medicinal Chemistry 97, (2015): 699–718.
  • D. Das, P. Sikdar, and M. Bairagi, “Recent Developments of 2-Aminothiazoles in Medicinal Chemistry,” European Journal of Medicinal Chemistry 109, (2016): 89–98.
  • M.-Y. Zhao, Y. Yin, X.-W. Yu, C. B. Sangani, S.-F. Wang, A.-M. Lu, L.-F. Yang, P.-C. Lv, M.-G. Jiang, and H.-L. Zhu, “Synthesis, Biological Evaluation and 3D-QSAR Study of Novel 4,5-Dihydro-1H-Pyrazole Thiazole Derivatives as B-RAF(V600E) Inhibitors,” Bioorganic & Medicinal Chemistry 23, no. 1 (2015): 46–54.
  • A. Andreani, S. Burnelli, M. Granaiola, A. Leoni, A. Locatelli, R. Morigi, M. Rambaldi, L. Varoli, N. Calonghi, C. Cappadone, et al. “ew Antitumour Imidazo[2,1-b]Thiazole Guanylhydrazones and Analogues,” Journal of Medicinal Chemistry 51, no. 4 (2008): 809–16.
  • R. M. Mohareb, A. E. Abdallah, and E. A. Ahmed, “Synthesis and Cytotoxicity Evaluation of Thiazole Derivatives Obtained from 2-Amino-4, 5, 6, 7-Tetrahydrobenzo [b] Thiophene-3-Carbonitrile,” Acta Pharmaceutica 67, no. 4 (2017): 495–510.
  • R. M. Mohareb, D. H. Fleita, and O. K. Sakka, “Novel Synthesis of Hydrazide-Hydrazone Derivatives and their Utilization in the Synthesis of Coumarin, Pyridine, Thiazole and Thiophene Derivatives with Antitumor Activity,” Molecules (Basel, Switzerland) 16, no. 1 (2010): 16–27.
  • W. S. Bremner, and M. G. Organ, “Multicomponent Reactions to Form Heterocycles by Microwave-Assisted Continuous Flow Organic Synthesis,” Journal of Combinatorial Chemistry 9, no. 1 (2007): 14–6.
  • T. Murata, M. Murai, Y. Ikeda, K. Miki, and K. Ohe, “ Pd- and Cu-Catalyzed One-pot Multicomponent Synthesis of Hetero α,α'-dimers of Heterocycles,” Organic Letters 14, no. 9 (2012): 2296–9.
  • F. Al-Qalaf, F. Mandani, M. M. Abdelkhalik, and A. A. Bassam, “Synthesis of 5-Substituted 3-Amino-1H-Pyrazole-4-Carbonitriles as Precursors for Microwave Assisted Regiospecific Syntheses of Pyrazolo[1,5-a]Pyrimidines,” Molecules (Basel, Switzerland) 14, no. 1 (2008): 78–88.
  • M. Ezer, L. T. Yildirim, O. Bayro, E. J. Verspohl, and O. B. Dundar, “Synthesis and Antidiabetic Activity of Morpholinothiazolyl-2,4-Thiazolidindione Derivatives,” Journal of Enzyme Inhibition and Medicinal Chemistry 27, no. 3 (2012): 419–27.
  • K. Zhang, J. F. Yan, X. M. Tang, H. P. Liu, L. Fan, G. M. Zhou, and D. C. Yang, “Synthesis of Novel Beta-Aminoalcohols Containing Nabumetone Moiety with Potential Antidiabetic Activity,” Yaoxue Xuebao 46, (2011): 412–21.
  • E. M. H. Abbas, S. M. Gomha, T. A. Farghaly. “Multicomponent reactions for synthesis of bioactive polyheterocyclic ring systems under controlled microwave irradiation”, Arabian J. Chem. 7 (2014): 623–629.
  • J. S. Tarach, “Electronmicroscopic Cytochemical Studies on Lysosomes and Peroxisomes of a Rat Cardiac Muscle in the Experimental Alloxan Diabetes,” Acta Histochemica 62, no. 1 (1978): 32–43.
  • F. M. Abdelrazek, S. M. Gomha, M. E. Shaaban, K. A. Rabee, H. N. El-Shemy, A. M. Abdallah, and Metz, “One-Pot Three-Component Synthesis and Molecular Docking of Some Novel 2-Thiazolyl Pyridines as Potent Antimicrobial Agents,” Mini Reviews in Medicinal Chemistry 19, no. 6 (2019): 527–38.
  • S. M. Gomha, Z. A. Muhammad, M. R. Abdel‐Aziz, H. M. Abdel‐Aziz, H. M. Gaber, and M. M. Elaasser, “One‐Pot Synthesis of New Thiadiazolyl‐Pyridines as Anticancer and Antioxidant Agents,” Journal of Heterocyclic Chemistry 55, no. 2 (2018): 530–6.
  • S. M. Gomha, M. M. Edrees, R. A. Faty, Z. A. Muhammad, and Y. N. Mabkhot, “Microwave-Assisted One Pot Three-Component Synthesis of Some Novel Pyrazole Scaffolds as Potent Anticancer Agents,” Chemistry Central Journal 11, no. 1 (2017): 37.
  • S.M. Gomha, N. A. Kheder, A. O. Abdelhamid, and Y. N. Mabkhot, “One Pot Single Step Synthesis and Biological Evaluation of Some Novel Bis(1,3,4-Thiadiazole) Derivatives as Potential Cytotoxic Agents,” Molecules 21, no. 11 (2016): 1–8.
  • S. M. Gomha, “A Facile One-Pot Synthesis of 6,7,8,9-Tetrahydrobenzo[4,5]Thieno[2,3-d]-1,2,4- Triazolo[4,5-a]Pyrimidin-5-Ones,” Monatshefte Für Chemie – Chemical Monthly 140, no. 2 (2009): 213–20.
  • S. M. Gomha, and F. M. Abdelrazek, “A Facile Three Component-One-Pot Synthesis of Some Novel Tri-Cyclic Hetero-Ring Systems,”Journal of Heterocyclic Chemistry 53no. 6 (2016): 1892–6.
  • S. M. Gomha, and S. M. Riyadh, “Synthesis of Triazolo[4,3-b][1,2,4,5]Tetrazines and Triazolo[3,4-b][1,3,4]Thiadiazines Using Chitosan as Ecofriendly Catalyst under Microwave Irradiation,” Arkivoc 2009, no. 11 (2009): 58–68. xi
  • S. M.Gomha, M. A.Abdallah, M. R.Abd EL-Aziz, and N. Serag, “Eco-Friendly One-Pot Synthesis and Antiviral Evaluation of Pyrazolyl Chalcones and Pyrazolines of Medicinal Interest,” Turkish Journal of Chemistry 40, (2016): 484–98.
  • I. M. Abbas, S. M. Gomha, M. M. Elaasser, and M. A. Bauomi, “Synthesis and Biological Evaluation of New Pyridines Containing Imidazole Moiety as Antimicrobial and Anticancer Agents,” Turkish Journal of Chemistry 39, (2015): 334–46.
  • I. M. Abbas, S. M. Riyadh, M. A. Abdallah, and S. M. Gomha, “A Novel Route to Tetracyclic Fused Tetrazines and Thiadiazines,” Journal of Heterocyclic Chemistry 43, no. 4 (2006): 935–42.
  • P. Makam, P. K. Thakur, and T. Kannan, “In Vitro and in Silico Antimalarial Activity of 2-(2-hydrazinyl)thiazole derivatives,” European Journal of Pharmaceutical Sciences: Official Journal of the European Federation for Pharmaceutical Sciences 52, (2014): 138–45.
  • S. Shawali, and S. M. Gomha, “A New Entry for Short and Regioselective Synthesis of [1,2,4]Triazolo[4,3-b][1,2,4]-Triazin-7(1H)-One,” Advanced Synthesis and Catalysis 342, (2000): 599.
  • S. M. Gomha, M. G. Badrey, and M. M. Edrees, “Heterocyclization of a Bis-Thiosemicarbazone of 2,5-Diacetyl-3,4-Disubstituted-Thieno[2,3-b]Thiophene Bis-Thiosemicarbazones Leading to Bis-Thiazoles and Bis-1,3,4-Thiadiazoles as anti-Breast Cancer Agents,” Journal of Chemical Research 40, no. 2 (2016): 120–5.
  • S. M. Gomha, S. A. Ahmed, and A. O. Abdelhamid, “Synthesis and Cytotoxicity Evaluation of Some Novel Thiazoles, Thiadiazoles, and pyrido[2,3-d][1,2,4]triazolo[4,3-a]pyrimidin-5(1H)-ones Incorporating Triazole Moiety ,” Molecules (Basel, Switzerland) 20, no. 1 (2015): 1357–76.
  • S. M. Gomha, N. A. Kheder, M. R. Abdelaziz, Y. N. Mabkhot, and A. M. Alhajoj, “A Facile Synthesis and Anticancer Activity of Some Novel Thiazoles Carrying 1,3,4‐Thiadiazole Moiety,” Chemistry Central Journal 11, no. 1-9 (2017): 25.
  • S. M. Gomha, A. O. Abdelhamid, O. M. Kandil, S. M. Kandeel, and N. A. Abdelrehem, “Synthesis and Molecular Docking of Some Novel Thiazoles and Thiadiazoles Incorporating Pyranochromene Moiety as Potent Anticancer Agents,” Mini Reviews in Medicinal Chemistry 18, no. 19 (2018): 1670–82. no.
  • A. O. Abdelhamid, S. M. Gomha, N. A. Abdelriheem, and S. M. Kandeel, “Synthesis of New 3-Heteroarylindoles as Potential Anticancer Agents,” Molecules 21, no. 7 (2016): 929–15.
  • S. M. Gomha, S. M. Riyadh, E. A. Mahmmoud, and M. M. Elaasser, “Synthesis and Anticancer Activity of Arylazothiazoles and 1,3,4-Thiadiazoles Using Chitosan-Grafted-Poly(4-Vinylpyridine) as a Novel Copolymer Basic Catalyst,” Chemistry of Heterocyclic Compounds 51, no. 11-12 (2015): 1030–8.

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