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Research Articles

Synthesis, Antimicrobial Evaluation and Molecular Docking of New Functionalized Bis(1,3,4-Thiadiazole) and Bis(Thiazole) Derivatives

, ORCID Icon & ORCID Icon
Pages 2029-2041 | Received 01 Nov 2019, Accepted 20 Dec 2019, Published online: 08 Jan 2020

References

  • A. S. Shawali, “A Review on Bis-Hydrazonoyl Halides: Recent Advances in Their Synthesis and Their Diverse Synthetic Applications Leading to Bis-Heterocycles of Biological Interest,” Journal of Advanced Research 7, no. 6 (2016): 873–907.
  • S. M. Gomha, N. A. Kheder, A. O. Abdelhamid, and Y. 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): 1532–40.
  • 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.
  • S. M. Gomha, M. S. ElGendy, Z. A. Muhammad, A. O. Abdelhamid, and M. M. Abdel-Aziz, “Utility of Bis-Hydrazonoyl Chlorides as Precursors for Synthesis of New Functionalized Bis-Thiadiazoles as Potent Antimicrobial Agents,” Journal of Heterocyclic Chemistry 55, no. 4 (2018): 844–51.
  • A. M. Farag, A. S. Shawali, M. S. Algharib, and K. M. Dawood, “One-Step Synthesis of Novel 2,2′-bi(4,5-Dihydro-1,3,4-Thiadiazole) and 2,3-Disubstituted 1,4-Benzothiazine Derivatives,” Tetrahedron 50 (1994): 5091–8.
  • K. M. Dawood, M. A. Raslan, and A. M. Farag, “Synthesis of 3, 3′-bi-1,2,4-Triazolo [4,5-a]-Benzimidazole, 5,5′-bi-1,3,4-Thiadiazole, and Thiazolo[3,2-a]Benzimidazole Derivatives,” Synthetic Communications 33, no. 23 (2003): 4079–86.
  • K. M. Dawood, and N. M. Elwan, “Synthesis of 3, 3′-Bipyrazole, 5,5′-bi-1,3,4-Thiadiazole and Fused Azole Systems via Bishydrazonoyl Chlorides,” Journal of Chemical Research 4 (2004): 264–6.
  • K. M. Dawood, T. M. Eldebss, H. S. El-Zahabi, M. H. Yousef, and P. Metz, “Synthesis of Some New Pyrazole-Based 1, 3-Thiazoles and 1, 3, 4-Thiadiazoles as Anticancer Agents,” European Journal of Medicinal Chemistry 70 (2013): 740–9.
  • K. M. Dawood, and T. A. Farghaly, “Thiadiazole Inhibitors: A Patent Review,” Expert Opinion on Therapeutic Patents 27, no. 4 (2017): 477–505.
  • N. Kushwaha, S. K. S. Kushwaha, and A. K. Rai, “Biological Activities of Thiadiazole Derivatives: A Review. Inter,” Journal of Chemical Research 4 (2012): 517–31.
  • S. M. Gomha, Z. A. Muhammad, H. M. Gaber, and M. M. Amin, “Synthesis of Some Novel Heterocycles Bearing Thiadiazoles as Potent anti-Inflammatory and Analgesic Agents,” Journal of Heterocyclic Chemistry 54, no. 5 (2017): 2708–16.
  • K. Singh, G. Mishra, and K. Jyoti, “Review on Biological Activities of 1,3,4-Thiadiazole Derivatives,” Journal of Applied Pharmaceutical Science 1 (2011): 44–9.
  • N. Siddiqui, P. Ahuja, W. Ahsan, S. N. Pandeya, and M. S. Alam, “Thiadiazoles: Progress Report on Biological Activities,” Journal of Chemical and Pharmaceutical Research 1 (2009): 19–30.
  • S. M. Gomha, K. D. Khalil, A. M. El-Zanate, and S. M. Riyadh, “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 (2013): 1109–20.
  • S. Haider, M. S. Alam, and H. Hami, “1,3,4-Thiadiazoles: A Potent Multi Targeted Pharmacological Scaffold,” European Journal of Medicinal Chemistry 92 (2015): 156–77.
  • 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.
  • X.-H. Liu, Y.-X. Shi, Y. Ma, C.-Y. Zhang, W.-L. Dong, L. Pan, B.-L. Wang, B.-J. Li, and Z.-M. Li, “Synthesis Antifungal Activities and 3D-QSAR Study of N-(5-Substituted-1,3,4-Thiadiazol-2-yl)Cyclopropane Carboxamides,” European Journal of Medicinal Chemistry 44, no. 7 (2009): 2782–6.
  • M. K. Abdel-Hamid, A. A. Abdel-Hafez, N. A. El-Koussi, N. M. Mahfouz, A. Innocenti, and C. T. Supuran, “Design, Synthesis, and Docking Studies of New 1,3,4-Thiadiazole-2-Thione Derivatives with Carbonic Anhydrase Inhibitory Activity,” Bioorganic & Medicinal Chemistry 15, no. 22 (2007): 6975–84.
  • J. Matysiak, “Biological and Pharmacological Activities of 1,3,4-Thiadiazole Based Compounds,” Mini-Reviews in Medicinal Chemistry 15, no. 9 (2015): 762–75.
  • C. T. Supuran, and B. W. Clare, “Carbonic Anhydrase Inhibitors–Part 57: Quantum Chemical QSAR of a Group of 1,3,4-Thiadiazole and 1,3,4-Thiadiazoline Disulfonamides with Carbonic Anhydrase Inhibitory Properties,” European Journal of Medicinal Chemistry 34, no. 1 (1999): 41–50.
  • J. F. Adediji, S. A. Ahmed, and A. Lawal, “Ligation of Cadmium (II) Complex by 2, 5-Diamino-1, 3, 4-Thiadiazole and Their Biological Activity,” Ife Journal of Science 16 (2014): 11–8.
  • K. N. Thimmaiah, G. T. Chandrappa, W. D. Lloyd, and C. Párkányi, “Synthesis and Structural Investigation of Biologically Active Complexes of 4-Acetyl-2-(Acetylamino)-5-dimethyl-Δ2-1,3,4-Thiadiazole with Zn (II), Hg (II), Cd (II) and Cu (II),” Inorganica Chimica Acta 107, no. 1 (1985): 1–4. ‏
  • T. T. Qin, J. Li, H. Q. Luo, M. Li, and N. B. Li, “Corrosion Inhibition of Copper by 2,5-Dimercapto-1,3,4-Thiadiazole Monolayer in Acidic Solution,” Corrosion Science 53, no. 3 (2011): 1072–8. ‏
  • W. Xue, W. Ma, X. Xu, T. Li, X. Zhou, and P. Wang, “Synthesis and Properties of Thiadiazole Lubricant Additives,” Industrial Lubrication and Tribology 69, no. 6 (2017): 891–6.
  • W. C. Patt, H. W. Hamilton, M. D. Taylor, M. J. Ryan, D. G. Taylor, C. J. C. Connolly, A. M. Doherty, S. R. Klutchko, and I. Sircar, “Sircar, I. Structure-Activity Relationships of a Series of 2-Amino-4-Thiazole-Containing Renin Inhibitors,” Journal of Medicinal Chemistry 35, no. 14 (1992): 2562–72. ‏
  • R. N. Sharma, F. P. Xavier, K. K. Vasu, S. C. Chaturvedi, and S. S. Pancholi, “Synthesis of 4-Benzyl-1,3-Thiazole Derivatives as Potential anti-Inflammatory Agents: An Analogue-Based Drug Design Approach,” Journal of Enzyme Inhibition and Medicinal Chemistry .24, no. 3 (2009): 890–7. ‏
  • J. C. Jaen, L. D. Wise, B. W. Caprathe, H. Tecle, S. Bergmeier, C. C. Humblet, T. G. Heffner, L. T. Meltzer, and T. A. Pugsley, “4-(1,2,5,6-Tetrahydro-1-Alkyl-3-Pyridinyl)-2-Thiazolamines: A Novel Class of Compounds with Central Dopamine Agonist Properties,” Journal of Medicinal Chemistry 33, no. 1 (1990): 311–7. ‏
  • K. Tsuji, and H. Ishikawa, “Synthesis and anti-Pseudomonal Activity of New 2-Isocephems with a Dihydroxypyridone Moiety at C-7,” Bioorganic & Medicinal Chemistry Letters 4, no. 13 (1994): 1601–6. ‏
  • F. W. Bell, A. S. Cantrell, M. Hoegberg, S. R. Jaskunas, N. G. Johansson, C. L. Jordan, M. D. Kinnick, P. Lind, and J. M. Morin, “Phenethylthiazolethiourea (PETT) Compounds, a New Class of HIV-1 Reverse Transcriptase Inhibitors. 1. Synthesis and Basic Structure-Activity Relationship Studies of PETT Analogs,” Journal of Medicinal Chemistry 38, no. 25 (1995): 4929–36. ‏
  • J. Rudolph, H. Theis, R. Hanke, R. Endermann, L. Johannsen, and F. U. Geschke, “Seco-Cyclothialidines: New Concise Synthesis, Inhibitory Activity toward Bacterial and Human DNA Topoisomerases, and Antibacterial Properties,” Journal of Medicinal Chemistry 44, no. 4 (2001): 619–26. ‏
  • E. Gürsoy, and N. U. Güzeldemirci, “Synthesis and Primary Cytotoxicity Evaluation of New Imidazo[2,1-b]Thiazole Derivatives,” European Journal of Medicinal Chemistry 42, no. 3 (2007): 320–6. ‏
  • A. K. Jain, S. Sharma, A. Vaidya, V. Ravichandran, and R. K. Agrawal, “1,3,4‐Thiadiazole and Its Derivatives: A Review on Recent Progress in Biological Activities,” Chemical Biology & Drug Design 81, no. 5 (2013): 557–76.
  • A. R. Sayed, S. S. Al-Shihry, and M. A. A. Gomaa, “Synthesis and Characterization of Novel Heterocycles Based on Tetrazine and Hydrazonoyl Halides,” European Journal of Chemistry 5, no. 2 (2014): 267–71.
  • 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): 112–21.
  • S. Shafi, M. Mahboob Alam, N. Mulakayala, C. Mulakayala, G. Vanaja, A. M. Kalle, R. Pallu, and M. S. Alam, “Synthesis of Novel 2-Mercapto Benzothiazole and 1, 2, 3-Triazole Based Bis-Heterocycles: Their anti-Inflammatory and anti-Nociceptive Activities,” European Journal of Medicinal Chemistry 49 (2012): 324–33.
  • V. Padmavathi, K. Mahesh, D. R. C. V. Subbaiah, D. Deepti, and G. S. Reddy, “Synthesis and Biological Activity of a New Class of Sulfone Linked Bis(Heterocycles),”Arkivoc 10 (2009): 95–208.
  • J. Á. Bisceglia, M. B. García, R. Massa, M. L. Magri, M. Zani, G. O. Gutkind, and L. 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.
  • A. H. M. Elwahy, and A. A. Abbas, “Bis(β-Difunctional) Compounds: Versatile Starting Materials for Novel Bis(Heterocycles,” Synthetic Communications 30, no. 16 (2000) :2903–21.
  • A. A. Abbas, M. A. A. Elneairy, and Y. N. Mabkhot, “Versatile Starting Materials for Novel 1,ω-Bis(Pyridin-4-Ylphenoxy)Alkanes, and Their Corresponding Bis(Thieno[2,3-b]Pyridin-4-Ylphenoxy) Derivatives,” Journal of Chemical Research 2001, no. 4 (2001): 124–6; Journal of Chemical Research (M) (2001): 411–27.
  • A. A. Abbas, “Bis(Enaminones): Key Intermediates for Novel α,ω-Bis(Pyrazolylphenoxy), Bis(Pyranylphenoxy), and Bis(Benzo[b]Furanylphenoxy) Alkanes,” Journal of Heterocyclic Chemistry 46, no. 2 (2009): 340–6.
  • A. H. M. Elwahy, and A. A. Abbas, “Synthesis of New Benzo-Substituted Macrocyclic Ligands Containing Pyridine or Triazole as Subcyclic Units,” Tetrahedron 56, no. 6 (2000): 885–95.
  • 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.
  • 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.
  • 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, M. A. El-Hashash, M. M. Edrees, and E. E. El-Arab, “Synthesis, Characterization and Molecular Docking of Novel Bis-Thiazolylthienothiophene Derivatives as Promising Cytotoxic Antitumor Drug,” Journal of Heterocyclic Chemistry 54, no. 5 (2017): 2686–95.
  • S. M. Cutfield, E. J. Dodson, B. F. Anderson, P. C. Moody, C. J. Marshall, P. A. Sullivan, and J. F. Cutfield, “The Crystal Structure of a Major Secreted Aspartic Proteinase from Candida albicans in Complexes with Two Inhibitors,” Structure 3, no. 11 (1995): 1261–71.
  • W. H. Miller, M. A. Seefeld, K. A. Newlander, I. N. Uzinskas, W. J. Burgess, D. A. Heerding, C. C. Yuan, M. S. Head, D. J. Payne, S. F. Rittenhouse, et al. “Discovery of Aminopyridine-Based Inhibitors of Bacterial Enoyl-ACP Reductase (FabI),” Journal of Medicinal Chemistry 45, no. 15 (2002): 3246–56.
  • Y. A. Ibrahim, A. H. M. Elwahy, and A. A. Abbas, “New Synthesis of Macrocyclic Crown-Formazans from Pyruvic Acid Derivatives,” Tetrahedron 50 (1994): 11489–98.
  • M. K. Mahapatra, U. Kulandaivelu, P. Saiko, G. Graser, T. Szekeres, G. Andrei, R. Snoeck, J. Balzarini, and V. Jayaprakash, “Methyl-2-Arylidene Hydrazinecarbodithioates: Synthesis and Biological Activity,”Chemical Papers 67 (2013): 650–6.
  • D. L. Klayman, J. F. Bartosevich, T. S. Griffin, C. J. Mason, and J. P. Scovill, “2-Acetylpyridine Thiosemicarbazones. 1. A New Class of Potential Antimalarial Agents,” Journal of Medicinal Chemistry 22, no. 7 (1979): 855–62.
  • S. M. Gomha, M. M. Edrees, Z. A. Muhammad, and A. A. El-Reedy, “5-(Thiophen-2-yl)-1,3,4-Thiadiazole Derivatives: Synthesis, Molecular Docking and in-Vitro Cytotoxicity Evaluation as Potential Anticancer Agents,” Drug Design, Development and Therapy 12 (2018): 1511–23.
  • F. M. Abdelrazek, S. M. Gomha, P. Metz, and M. 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. Smania, Jr, F. D. Monache, E. D. F. A. Smania, and R. S. Cuneo, “Antibacterial Activity of Steroidal Compounds Isolated from Ganoderma applanatum (Pers.) Pat. (Aphyllophoromycetideae) Fruit Body,” International Journal of Medicinal Mushrooms 1, no. 4 (1999): 325–30.

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