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Research Articles

Synthesis, Characterization, and Antimicrobial Evaluation of Some New 1,4-Dihydropyridine Hybrid with 1,3,4-Thiadiazole

ORCID Icon, , , &
Pages 1697-1709 | Received 17 Jan 2020, Accepted 29 Jul 2020, Published online: 17 Aug 2020

References

  • 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.
  • M. A. Abdallah, S. M. Riyadh, I. M. Abbas, and S. M. Gomha, “Synthesis and Biological Activities of 7-Arylazo-7H-Pyrazolo[5,1-c][1,2,4]Triazolo-6(5H)-Ones and 7-Arylhydrazono-7H-[1,2,4] Triazolo[3,4-b][1,3,4]Thiadiazines,” Journal of the Chinese Chemical Society 52, no. 5 (2005): 987–94.
  • S. M. Gomha, H. M. Abdel-Aziz, and K. D. Khalil, “Synthesis and SAR Study of the Novel Thiadiazole-Imidazole Derivatives as a New Anticancer Agents,” Chemical & Pharmaceutical Bulletin 64, no. 9 (2016): 1356–63.
  • S. M. Gomha and H. A. Abdel-Aziz, “Synthesis of New Heterocycles Derived from 3-(3-Methyl-1H-Indol-2-yl)-3-Oxopropanenitrile as Potent Antifungal Agents,” Bulletin of the Korean Chemical Society 33, no. 9 (2012): 2985–90.
  • S. M. Gomha and H. A. Abdel-Aziz, “Synthesis of New Functionalized Derivatives of Indolo[2,3-e][1,2,4]-Triazolo-[4,5-b]-1,2,4-Triazine,” Journal of the Serbian Chemical Society 78, no. 8 (2013): 1119–25.
  • 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 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 xi (2009): 58–68.
  • 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.
  • Taha M. A. Eldebss, Sobhi M. Gomha, Mohamed M. Abdulla, and Reem K. Arafa, “Novel Pyrrole Derivatives as Selective CHK1 Inhibitors: design, Regioselective Synthesis and Molecular Modeling,” MedChemComm 6, no. 5 (2015): 977–87.
  • 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): 1532.
  • Y. N. Mabkhot, A. Barakat, A. M. Al-Majid, S. Alshahrani, S. Yousuf, and M. I. Choudhary, “Synthesis, Reactions and Biological Activity of Some New Bis-Heterocyclic Ring Compounds Containing Sulphur Atom,” Chemistry Central Journal 7, no. 1 (2013): 112.
  • V. Padmavathi, K. Mahesh, D. R. C. V. Subbaiah, D. Deepti, and G. S. Reddy, Arkivoc 10, (2009): 95.
  • K. Nagaraju, N. Harikrishna, V. Rao, and V. Indo, American Journal of Pharmaceutical Sciences 5, (2015): 1604.
  • Y. N. Mabkhot, A. Barakat, A. M. Al-Majid, and M. I. Choudhary, “Synthesis of Thieno[2,3-b]thiophene Containing Bis-Heterocycles-Novel Pharmacophores,” International Journal of Molecular Sciences 14, no. 3 (2013): 5712–22.
  • Juan Á. Bisceglia, María B. García, Rosana Massa, María L. Magri, Mariana Zani, Gabriel O. Gutkind, and Liliana R. Orelli, “Synthesis, Characterization and Biological Activity of Bis(3-Aryl-1-Hexahydropyrimidinyl)Methanes. Novel Heterocyclic Polyamine Derivatives,” Journal of Heterocyclic Chemistry 41, no. 1 (2004): 85–90.
  • H. Liming, L. Xueshu, C. Zhiyuan, and L. Zhaojie, “Synthesis and Biological Activity of Novel Bis-Heterocyclic Compounds Containing 1H-Pyrazole and Thiazole,” Chinese Journal of Chemistry 23, (2003): 1131–4.
  • R. S. Jwad, “Synthesis of Some New Bis-Heterocyclic Derivatives Based on 1, 2, 3-Triazoline and Study Their Antibacterial Activity,” Journal of Al-Nahrain University Science 15, no. 2 (2012): 55–62.
  • T. Godfraid, R. Miller, M. Wibo, and M. “Calcium Antagonism and Calcium Entry Blockade,” Pharmacological Reviews 38, (1986): 321–416.
  • B. Schnell, W. Krenn, K. Faber, and C. O. Kappe, “Synthesis and Reactions of Biginelli-Compounds. Part 23. Chemoenzymatic Syntheses of Enantiomerically Pure 4-Aryl-3,4-Dihydropyrimidin-2(1H )-Ones,” Journal of the Chemical Society, Perkin Transactions 1 1, no. 24 (2000): 4382–9.
  • M. Khoshneviszadeh, N. Edraki, K. Javidnia, A. Alborzi, B. Pourabbas, J. Mardaneh, and R. Mir, “Synthesis and Biological Evaluation of Some New 1,4-Dihydropyridines Containing Different Ester Substitute and Diethyl Carbamoyl Group as Anti-Tubercular Agents,” Bioorganic & Medicinal Chemistry 17, no. 4 (2009): 1579–86.
  • B. Desai, D. Sureja, Y. Naliapara, A. Shah, and A. K. Saxena, “Synthesis and QSAR Studies of 4-Substituted Phenyl-2,6-Dimethyl-3, 5-bis-N-(Substituted Phenyl)Carbamoyl-1,4-Dihydropyridines as Potential Antitubercular Agents,” Bioorganic & Medicinal Chemistry 9, no. 8 (2001): 1993–8.
  • J. G. Breitenbucher, and G. Figliozz, “Solid-Phase Synthesis of 4-Aryl-1,4-Dihydropyridines via the Hantzsch Three Component Condensation,” Tetrahedron Letters 41, no. 22 (2000): 4311–5.
  • N. Razzaghi-Asl, R. Miri, and O. Firuzi, “Assessment of the Cytotoxic Effect of a Series of 1,4-Dihydropyridine Derivatives against Human Cancer Cells,” Iranian Journal of Pharmaceutical Research: IJPR 15, (2016): 413–20.
  • C. E. Sunkel, M. F. de Casa-Juana, L. Santos, M. M. Gómez, M. Villarroya, M. A. González-Morales, J. G. Priego, and M. P. Ortega, “ 4-Alkyl-1,4-Dihydropyridines Derivatives as Specific PAF-Acether Antagonists,” Journal of Medicinal Chemistry 33, no. 12 (1990): 3205–10.
  • Josep M. Tusell, Sonia BarróN, and Joan Serratosa, “Anticonvulsant Activity of Delta-HCH, Calcium Channel Blockers and Calmodulin Antagonists in Seizures Induced by Lindane and Other Convulsant Drugs,” Brain Research 622, no. 1–2 (1993): 99–104.
  • O. Petra, S. Ľubomír, O. Denisa, P. Anna, V. Zuzana, K. Katarína, and M. Stefan, “Antimicrobial Activity of Novel C2-Substituted 1,4-Dihydropyridine Analogues,” Scientia Pharmaceutica 82, (2014): 221.
  • R. Budriesi, P. Ioan, A. Locatelli, S. Cosconati, A. Leoni, M. P. Ugenti, A. Andreani, R. D. Toro, A. Bedini, S. Spampinato, L. Marinelli, et al. “Imidazo[2,1-b]Thiazole System: A Scaffold Endowing Dihydropyridines with Selective Cardiodepressant Activity,” Journal of Medicinal Chemistry 51, no. 6 (2008): 1592–600.
  • S. Rollas, and S. G. Kucukguzel, “Biological Activities of Hydrazone Derivatives,” Molecules (Basel, Switzerland) 12, no. 8 (2007): 1910–39.
  • M. Gokce, S. Utku, and E. Kupeli, “Synthesis and Analgesic and anti-Inflammatory Activities 6-Substituted-3(2H)-Pyridazinone-2-Acetyl-2-(p-Substituted/Nonsubstituted Benzal)Hydrazone Derivatives,” European Journal of Medicinal Chemistry 44, no. 9 (2009): 3760–4.
  • Sevim Rollas, Nehir Gulerman, and Habibe Erdeniz, “Synthesis and Antimicrobial Activity of Some New Hydrazones of 4-Fluorobenzoic Acid Hydrazide and 3-Acetyl-2,5-Disubstituted-1,3,4-Oxadiazolines,” Il Farmaco 57, no. 2 (2002): 171–4.
  • A. Bijev, “New Heterocyclic Hydrazones in the Search for Antitubercular Agents: Synthesis and In Vitro Evaluations,” Letters in Drug Design & Discovery 3, no. 7 (2006): 506–12.
  • G. A. Silva, L. M. M. Costa, F. C. F. Brito, A. L. P. Miranda, E. J. Barreiro, and C. A. M. Fraga, “New Class of Potent Antinociceptive and Antiplatelet 10H-Phenothiazine-1-Acylhydrazone Derivatives,” Bioorganic & Medicinal Chemistry 12, no. 12 (2004): 3149–58.
  • A. R. Todeschini, A. L. P. Miranda, K. C. Silva, S. C. Parrini, and E. J. Barreiro, “Synthesis and Evaluation of Analgesic, anti-Inflammatory and Antiplatelet Properties of New 2-Pyridylarylhydrazone Derivatives,” European Journal of Medicinal Chemistry 33, no. 3 (1998): 189–99.
  • S. M. Gomha, T. A. Farghaly, and A. R. Sayed, “Design, Synthesis, and Characterization of Bis-Thiazoles Based on Bis-Hydrazonoyl Chlorides,” Journal of Heterocyclic Chemistry 54, no. 2 (2017): 1537–42.
  • Sobhi Gomha, Ikhlass Abbas, Mohamed Elneairy, Mahmoud Elaasser, and Bazada Mabrouk, “Synthesis, Molecular Docking and Pharmacological Study of Pyrimido-Thiadiazinones and Its Bis-Derivatives,” Letters in Drug Design & Discovery 14, no. 4 (2017): 434–43.
  • S. M. Gomha, M. M. Edrees, and E. E. El-Arab, “Synthesis and Preliminary In-Vitro Cytotoxic Evaluation of Some Novel Bis-Heterocycles Incorporating Thienothiophene,” Journal of Heterocyclic Chemistry 54, no. 1 (2017): 641–7.
  • Fathy M. Abdelrazek, Sobhi M. Gomha, Peter Metz, and Mohamed M. Abdalla, “Synthesis of Some Novel 1,4-Phenylene-Bis-Thiazolyl Derivatives and Their anti-Hypertensive α-Blocking Activity Screening,” Journal of Heterocyclic Chemistry 54, no. 1 (2017): 618–23.
  • A. R. Sayed, S. M. Gomha, and T. A. Farghaly, “Synthesis and Characterization of Bis-Imidazoles, Bis-Triazoles, Bis-Thiadiazoles and Bis-Thiazoles from Novel Bis-Hydrazonoyl Dichlorides,” Journal of Heterocyclic Chemistry 53, no. 1 (2016): 255–63.
  • 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, F. M. Abdelrazek, A. H. Abdelrahman, and P. Metz, “Synthesis of Some Novel Thiazole, Thiadiazole and 1,4-Phenylene-Bis-Thiazole Derivatives,” Heterocycles 92, no. 5 (2016): 954–67.
  • S. M. Gomha, S. M. Riyadh, and M. M. Abdalla, “Solvent-Drop Grinding Method: Efficient Synthesis, DPPH Radical Scavenging and anti-Diabetic Activities of Chalcones, Bis-Chalcones, Azolines, and Bis-Azolines,” Current Organic Synthesis 12, no. 2 (2015): 220–8.
  • Sayed M. Riyadh, Sobhi M. Gomha, Khaled D. Khalil, and Ali M. El-Zanaty, “A Facile Green Synthesis and anti-Cancer Activity of Bis-Arylhydrazononitriles, Triazolo[5,1-c][1,2,4]Triazine, and 1,3,4-Thiadiazoline,” Heterocycles 87, no. 5 (2013): 1109–20.
  • 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.
  • S. M. Gomha, T. A. Farghaly, E. M. Abbas, H. Nadia, and T. Alqurashi, “Terephthalaldehyde: An Effecient Key Precursor for Novel Synthesis of Some Interesting Bis-Thiazoles and Bis-Triazolopyrimidinones,” Journal of Heterocyclic Chemistry 55, no. 3 (2018): 750–5.
  • B. Kherodiya, P. Prajapat, M. Kumawat, and G. L. Talesara, “Synthesis and Antimicrobial Evaluation of Bis Imidazolidinone Assembled Dihydropyridine Ethoxyphthalimide Derivatives,” Iranian Journal of Organic Chemistry 7, (2015): 1661–8.
  • M. A. Pfaller, L. Burmeister, M. S. Bartlett, and M. G. Rinaldi, “Multicenter Evaluation of Four Methods of Yeast Inoculum Preparation,” Journal of Clinical Microbiology 26, no. 8 (1988): 1437–41.
  • CLSI; Clinical and Laboratory Standards Institute, Twentieth informational supplement. M100-S22. Wayne, PA, 2012.
  • National Committee for Clinical Laboratory Standards, NCCLS Document M38‐A; Wayne, PA, 2002.
  • A. Klančnik, S. Piskernik, B. Jeršek, and S. S. Možina, “Evaluation of Diffusion and Dilution Methods to Determine the Antibacterial Activity of Plant Extracts,” Journal of Microbiological Methods 81, no. 2 (2010): 121–6.

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