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Research Articles

A Novel of Azo-Thiazole Moiety Alternative for Benzidine-Based Pigments: Design, Synthesis, Characterization, Biological Evaluation, and Molecular Docking Study

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Pages 500-522 | Received 25 Oct 2020, Accepted 30 Nov 2021, Published online: 16 Dec 2021

References

  • K. Chung, S. Chen, T. Y. Wong, and C. Wei, “Effects of Benzidine and Benzidine Analogues on Growth of Bacteria Including Azotobacter vinelandii,” Environmental Toxicology and Chemistry 17, no. 2 (1998): 271–5.
  • D. Hinks, H. S. Freeman, M. Nakpathom, and J. Sokolowska, “Synthesis and Evaluation of Organic Pigments and Intermediates. 1. “Nonmutagenic Benzidine Analogs,” Dyes and Pigments 44, no. 3 (2000): 199–207.
  • E. R. Bandala, M. A. Peláez, A. J. García-López, M. de, J. Salgado, and G. Moeller, “Photocatalytic Decolourisation of Synthetic and Real Textile Wastewater Containing Benzidine-Based Azo Dyes,” Chemical Engineering and Processing: Process Intensification 47, no. 2 (2008): 169–76.
  • S. Satapathi, “Coordination Compounds of Benzidine: A Versatile Family in Coordination Chemistry and Crystal Engineering,” Inorganic Chemistry Communications 56, (2015): 22–34.
  • K.-T. Chung, “Occurrence, Uses, and Carcinogenicity of Arylamines,” Frontiers in Bioscience (Elite Edition) 7, (2015): 322–45.
  • J.-S. Bae, H. S. Freeman, S. H. Warren, and L. D. Claxton, “Evaluation of New 2,2'-Dimethyl-5,5'-Dipropoxybenzidine- and 3,3'-Ddipropoxybenzidine-Based Direct Dye Analogs for Mutagenic Activity by Use of the Salmonella/Mammalian Mutagenicity Assay,” Mutation Research 603, no. 2 (2006): 173–85.
  • Yingli Fu, Yaqin Yu, Shibin Wang, Joseph Kanu, Yueyue You, Yingyu Liu, Yangyu Zhang, Yawen Liu, Bo Li, Yuchun Tao, et al. “Menopausal Age and Chronic Diseases in Elderly Women: A Cross-Sectional Study in Northeast China,” International Journal of Environmental Research and Public Health 13, no. 10 (2016): 936.
  • H. Im, J. Kim, C. Sim, and T. H. Kim, “Crystal Structure of N,N'-Dibenzyl-3,3'-Di-Meth-Oxy-Benzidine ,” Acta Crystallographica. Section E, Crystallographic Communications 74, no. Pt 3 (2018): 271–4.
  • S.-C. Chen, C.-M. Kao, M.-H. Huang, M.-K. Shih, Y.-L. Chen, S.-P. Huang, and T.-Z. Liu, “Assessment of Genotoxicity of Benzidine and Its Structural Analogues to Human Lymphocytes Using Comet Assay,” Toxicological Sciences 72, no. 2 (2003): 283–8.
  • M. A. Hanna, A. A. Al-Sarawy, I. G. Rashed, and F. K. M. Wali, “Novel Symmetrical and Asymmetrical Disaryl Hydrazono Sulphur-Containing Direct Dyes as Possible Alternatives for Benzidine-Based Dyestuffs,” Dyes and Pigments 75, no. 3 (2007): 556–66.
  • Beat J. Brüschweiler, and Cédric Merlot, “Azo Dyes in Clothing Textiles Can Be Cleaved into a Series of Mutagenic Aromatic Amines Which Are Not Regulated Yet,” Regulatory Toxicology and Pharmacology : RTP 88, (2017): 214–26.
  • P. Adris, and K.-T. Chung, “Metabolic Activation of Bladder Procarcinogens, 2-Aminofluorene, 4-Aminobiphenyl, and Benzidine by Pseudomonas aeruginosa and Other Human Endogenous Bacteria,” Toxicology in Vitro: An International Journal Published in Association with BIBRA 20, no. 3 (2006): 367–74.
  • X. Sun, Q.-F. Deng, Z.-F. Liang, Z.-Q. Zhang, L. Zhao, H. Geng, D.-D. Xie, Y. Wang, D.-X. Yu, and C.-Y. Zhong, “Curcumin Reverses Benzidine-Induced Cell Proliferation by Suppressing ERK1/2 Pathway in Human Bladder Cancer T24 Cells,” Experimental and Toxicologic Pathology 68, no. 4 (2016): 215–22.
  • K.-T. Chung, S.-C. Chen, and L. D. Claxton, “Review of the Salmonella Typhimurium Mutagenicity of Benzidine, Benzidine Analogues, and Benzidine-Based Dyes,” Mutation Research 612, no. 1 (2006): 58–76.
  • G. Choudhary, M. J. Citra and F. Llados, “Toxicological profile for benzidine.” Syracuse Research Corporation Under Contract No. 205-1999-00024, U.S. DEPARTMENT OF HEALTH AND HUMAN SERVICES Public Health Service Agency for Toxic Substances and Disease Registry, September 2001.
  • G. Choudhary, “Human Health Perspectives on Environmental Exposure to Benzidine: A Review,”Chemosphere 32, no. 2 (1996): 267–91.
  • M. Nakpathom, D. Hinks, and H. S. Freeman, “Synthesis and Evaluation of Organic Pigments. 4. New Monoarylide and Diarylide Pigments,” Dyes and Pigments 48, no. 2 (2001): 93–106.
  • R. M. Christie, and B. D. Howie, “Potential Alternatives for 3, 3′-Dichlorobenzidine as Tetrazo Components for Diarylide Yellow and Orange Pigments, Part 1: p-Phenylenediamine and Its Derivatives,” Dyes and Pigments 80, no. 2 (2009): 245–53.
  • R. Az, B. Dewald, and D. Schnaitmann, “Pigment Decomposition in Polymers in Applications at Elevated Temperatures,” Dyes and Pigments 15, no. 1 (1991): 1–14.
  • A. El-Shafei, D. Hinks, P. D. Boyle, and H. S. Freeman, “Non-Mutagenic Organic Pigment Intermediates. II. Isomorphous 2, 2′-Dichloro-5, 5′-Dipropoxybenzidine and 2, 2′-Dimethyl-5, 5′-Dipropoxybenzidine,” Acta Crystallographica Section C Crystal Structure Communications 60, no. 8 (2004): o569–o571.
  • O. Hutzinger, “The Handbook of Environmental Chemistry, Volume 3-Part D: Anthropogenic Compounds.” 1986
  • J. E. Ishegbe, K. A. Bello, and A. A. Kogo, “ Synthesis and Application of Direct Dyes Derived from Terephthalic and Isophthalic Acids on Cotton Fabrics,” IOSR Journal of Polymer and Textile Engineering 1, no. 3 (2014): 50–8.
  • K. Wojciechowski, A. Wyrębak, and J. Gumulak, “Direct Dyes Derived from Iso-and Terephthalic Acids,” Dyes and Pigments 56, no. 2 (2003): 99–109.
  • L. A. Al-Mutabagani, F. M. Abdelrazek, S. M. Gomha, A. S. Hebishy, M. S. Abdelfattah, S. M. Hassan, A. R. Sayed, and M. M. Elaasser, “Synthesis and Biological Evaluation of Thiazolyl-Ethylidene Hydrazino-Thiazole Derivatives: A Novel Heterocyclic System,” Applied Sciences 11, no. 19 (2021): 8908.
  • R. M. Kassab, S. M. Gomha, S. A. Al-Hussain, A. S. Abo Dena, M. M. Abdel-Aziz, M. E. A. Zaki, and Z. A. Muhammad, “Synthesis and in-Silico Simulation of Some New Bis-Thiazole Derivatives and Their Preliminary Antimicrobial Profile: Investigation of Hydrazonoyl Chloride Addition to Hydroxy-Functionalized Bis-Carbazones,” Arabian Journal of Chemistry 14, no. 11 (2021): 103396.
  • H. K. Mahmoud, S. M. Gomha, T. A. Farghaly, and H. M. Awad, “Synthesis of Thiazole Linked Imidazo[2,1-b]Thiazoles as Anticancer Agents,” Polycyclic Aromatic Compounds 41, no. 8 (2021): 1608–22.
  • A. R. Sayed, S. M. Gomha, E. A. Taher, Z. A. Muhammad, H. R. El-Seedi, H. M. Gaber, and M. M. Ahmed, “One-Pot Synthesis of Novel Thiazoles as Potential anti-Cancer Agents,” Drug Design, Development and Therapy 14, (2020): 1363–75.
  • Y. A. Ammar, S. M. A. A. El-Hafez, S. A. Hessein, A. M. Ali, A. A. Askar, and A. Ragab, “One-Pot Strategy for Thiazole Tethered 7-Ethoxy Quinoline Hybrids: Synthesis and Potential Antimicrobial Agents as Dihydrofolate Reductase (DHFR) Inhibitors with Molecular Docking Study,” Journal of Molecular Structure 1242, (2021) 130748.
  • S. A. Ibrahim, E. A. Fayed, H. F. Rizk, S. E. Desouky, and A. Ragab, “Hydrazonoyl Bromide Precursors as DHFR Inhibitors for the Synthesis of Bis-Thiazolyl Pyrazole Derivatives; Antimicrobial Activities, Antibiofilm, and Drug Combination Studies against MRSA,” Bioorganic Chemistry 116, (2021): 105339.
  • G. Gong, X. Gao, J. Wang, D. Zhao, and H. S. Freeman, “Trisazo Direct Black Dyes Based on Nonmutagenic 3, 3′-Disubstituted Benzidines,” Dyes and Pigments 53, no. 2 (2002): 109–17.
  • Y. I. El-Gazzar, H. H. Georgey, S. M. El-Messery, H. A. Ewida, G. S. Hassan, M. M. Raafat, M. A. Ewida, and H. I. El-Subbagh, “Synthesis, Biological Evaluation and Molecular Modeling Study of New (1,2,4-Triazole or 1,3,4-Thiadiazole)-Methylthio-Derivatives of Quinazolin-4(3H)-One as DHFR Inhibitors,” Bioorganic Chemistry 72, (2017): 282–92.
  • Ghada S. Hassan, Shahenda M. El-Messery, Fatmah A. M. Al-Omary, Sarah T. Al-Rashood, Marwa I. Shabayek, Yasmin S. Abulfadl, El-Sayed E. Habib, Salwa M. El-Hallouty, Walid Fayad, Khaled M. Mohamed, et al. “Nonclassical Antifolates, Part 4. 5-(2-aminothiazol-4-yl)-4-Phenyl-4H-1,2,4-Triazole-3-Thiols as a New Class of DHFR Inhibitors: Synthesis, Biological Evaluation and Molecular Modeling Study,” European Journal of Medicinal Chemistry 66, (2013): 135–45.
  • P. Gahtori, S. K. Ghosh, P. Parida, A. Prakash, K. Gogoi, H. R. Bhat, and U. P. Singh, “Antimalarial Evaluation and Docking Studies of Hybrid Phenylthiazolyl-1,3,5-Triazine Derivatives: A Novel and Potential Antifolate Lead for Pf-DHFR-TS Inhibition ,” Experimental Parasitology 130, no. 3 (2012): 292–9.
  • A. M. S. El-Sharief, Y. A. Ammar, A. Belal, M. A. M. S. El-Sharief, Y. A. Mohamed, A. B. M. Mehany, G. A. M. Elhag, and A. Ragab, “Design, Synthesis, Molecular Docking and Biological Activity Evaluation of Some Novel Indole Derivatives as Potent Anticancer Active Agents and Apoptosis Inducers,” Bioorganic Chemistry 85, (2019): 399–412.
  • Y. A. Ammar, A. A. Farag, A. M. Ali, S. A. Hessein, A. A. Askar, E. A. Fayed, D. M. Elsisi, and A. Ragab, “Antimicrobial Evaluation of Thiadiazino and Thiazolo Quinoxaline Hybrids as Potential DNA Gyrase Inhibitors; Design, Synthesis, Characterization and Morphological Studies,” Bioorganic Chemistry 99, (2020): 103841.
  • Y. A. Ammar, A. A. Farag, A. M. Ali, A. Ragab, A. A. Askar, D. M. Elsisi, and A. Belal, “Design, Synthesis, Antimicrobial Activity and Molecular Docking Studies of Some Novel di-Substituted Sulfonylquinoxaline Derivatives,” Bioorganic Chemistry 104, (2020): 104164.
  • M. M. S. Wassel, A. Ragab, G. A. M. Elhag Ali, A. B. M. Mehany, and Y. A. Ammar, “Novel Adamantane-Pyrazole and Hydrazone Hybridized: Design, Synthesis, Cytotoxic Evaluation, SAR Study and Molecular Docking Simulation as Carbonic Anhydrase Inhibitors,” Journal of Molecular Structure 1223, (2021): 128966.
  • M. A. El-Borai, H. F. Rizk, S. A. Ibrahim, and A. K. Fares, “An Eco-Friendly Synthesis and Biological Screening of Fused Heterocyclic Compounds Containing a Thiophene Moiety via Gewald Reaction,” Journal of Heterocyclic Chemistry 56, no. 10 (2019): 2787–95.
  • M. A. El-Borai, H. F. Rizk, S. A. Ibrahim, and H. F. El-Sayed, “Microwave Assisted Synthesis of Fused Thiazoles in Multicomponent System and Their in Vitro Antitumor, Antioxidant, and Antimicrobial Activities,” Journal of Heterocyclic Chemistry 54, no. 2 (2017): 1031–41.
  • H. F. Rizk, M. A. Ei-Badawi, S. A. Ibrahim, and M. A. Ei-Borai, “Cyclization of 4, 5‐Diamino Pyrazole Derivatives and Their Antibacterial Activities,” Chinese Journal of Chemistry 29, no. 7 (2011): 1451–9.
  • H.-F. Ji, “Past and Present Research Systems of Green Chemistry,” Organic Chemistry Current Research 4, (2015): 2. 10.4172/2161-0401.C1.008.
  • A. A. Hassan, N. K. Mohamed, A. A. Aly, H. N. Tawfeek, S. Bräse, and M. Nieger, “Synthesis and Structure Confirmation of 2,4-Disubstituted Thiazole and 2,3,4-Trisubstituted Thiazole as Thiazolium Bromide Salts,”Monatshefte Für Chemie – Chemical Monthly 151, no. 7 (2020): 1143–52.
  • G. Ghigo, S. Osella, A. Maranzana, G. Tonachini, "The Mechanism of the Acid-Catalyzed Benzidine Rearrangement of Hydrazobenzene: A Theoretical Study" 2011, no.12 (2011): 2326–233.
  • E. AlTamiemi, S. Khammas, and S. AlKaissi, “Synthesis and Characterization of Some New Morpholine Derivatives,” Baghdad Science Journal 13, no. 2 (2016): 253–65.
  • Ste W. Collier, J. E. Storm, and R. L. Bronaugh, “Reduction of Azo Dyes during in Vitro Percutaneous Absorption,” Toxicology and Applied Pharmacology 118, no. 1 (1993): 73–9.
  • K.-T. Chung, “The Significance of Azo-Reduction in the Mutagenesis and Carcinogenesis of Azo Dyes,” Mutation Research/Reviews in Genetic Toxicology 114, no. 3 (1983): 269–81.
  • R. A. Gladstone, J. M. Jefferies, S. N. Faust, and S. C. Clarke, “Continued Control of Pneumococcal Disease in the UK - The Impact of Vaccination,” Journal of Medical Microbiology 60, no. Pt 1 (2011): 1–8.
  • G. G. Duthie, “Lipid Peroxidation,” European Journal of Clinical Nutrition 47, (1993): 759–64.
  • R. S. Sohal, and R. G. Allen, “Relationship between Oxygen Metabolism, Aging and Development,” Advances in Free Radical Biology & Medicine 2, no. 1 (1986): 117–60.
  • J. V. Anderson, R. D. Palombo, and R. Earl, “Position of the American Dietetic Association: The Role of Nutrition in Health Promotion and Disease Prevention Programs,” Journal of the American Dietetic Association 98, no. 2 (1998): 205–8.
  • M. G. Hertog, E. J. Feskens, P. C. Hollman, M. B. Katan, and D. Kromhout, “Dietary Antioxidant Flavonoids and Risk of Coronary Heart Disease: The Zutphen Elderly Study,” Lancet 342, (1993): 1007–11.
  • J. C. Dekkers, L. J. P. van Doornen, and H. C. G. Kemper, “The Role of Antioxidant Vitamins and Enzymes in the Prevention of Exercise-Induced Muscle Damage,” Sports Medicine 21, (1996): 213–38.
  • G. D. Stoner, and H. Mukhtar, “Polyphenols as Cancer Chemopreventive Agents,” Journal of Cellular Biochemistry 59, no. S22 (1995): 169–80.
  • N. M. Elsayed, and A. Bendich, “Dietary Antioxidants: Potential Effects on Oxidative Products in Cigarette Smoke,” Nutrition Research 21, no. 3 (2001): 551–67.
  • H. F. Rizk, M. A. El-Borai, A. Ragab, and S. A. Ibrahim, “Design, Synthesis, Biological Evaluation and Molecular Docking Study Based on Novel Fused Pyrazolothiazole Scaffold,” Journal of the Iranian Chemical Society 17, no. 10 (2020): 2493–505.
  • A. Z. El-Sonbati, G. G. Mohamed, A. A. El-Bindary, W. M. I. Hassan, M. A. Diab, S. M. Morgan, and A. K. Elkholy, “Supramolecular Structure, Molecular Docking and Thermal Properties of Azo Dye Complexes,” Journal of Molecular Liquids 212, (2015): 487–502.
  • S. Srinivasan, S. K. Sadasivam, S. Gunalan, G. Shanmugam, and G. Kothandan, “Application of Docking and Active Site Analysis for Enzyme Linked Biodegradation of Textile Dyes,” Environmental Pollution (Barking, Essex: 1987) 248, (2019): 599–608.
  • S. T. Al-Rashood, G. S. Hassan, S. M. El-Messery, M. N. Nagi, E.-S E. Habib, F. A. M. Al-Omary, and H. I. El-Subbagh, “Synthesis, Biological Evaluation and Molecular Modeling Study of 2-(1,3,4-Thiadiazolyl-Thio and 4-Methyl-Thiazolyl-Thio)-Quinazolin-4-Ones as a New Class of DHFR Inhibitors,” Bioorganic & Medicinal Chemistry Letters 24, no. 18 (2014): 4557–67.
  • A. S. Hassan, A. A. Askar, A. M. Naglah, A. A. Almehizia, and A. Ragab, “Discovery of New Schiff Bases Tethered Pyrazole Moiety: Design, Synthesis, Biological Evaluation, and Molecular Docking Study as Dual Targeting DHFR/DNA Gyrase Inhibitors with Immunomodulatory Activity” Molecules 25, (2020): 2593.
  • B. W. Lee, and S. D. Lee, “[5,5] Sigmatropic Shift of N-Phenyl-N′-(2-Thiazolyl)Hydrazines and N,N′-Bis(2-Thiazolyl)Hydrazines into 2-Amino-5-(p-Aminophenyl)Thiazoles and 5,5′-Bis(2-Aminothiazole) Derivatives†Dedicated to Professor T. H. Chan on the Occasion of His 60th Birthday,” Tetrahedron Letters 41, no. 20 (2000): 3883–6.
  • G. M. G. Hossain, M. M. Abedin, and S. C. Bachar, “Synthesis and Characterization of N 1 -Phenylhydrazine-1,2- Bis (Carbothioamide) and Its Evaluation for Antimicrobial, Antioxidant, and Brine Shrimp Lethality Bioassay,” Organic Chemistry International 2012, (2012): 1–6.
  • T. G. Pridham, L. A. Lindenfelser, O. L. Shotwell, F. H. Stodola, R. G. Benedict, C. Foley, R. W. Jackson, W. J. Zaumeyer, W. H. Preston, and J. W. Mitchell, “Antibiotics against Plant Disease. 1. Laboratory and Greenhouse Survey,” Journal of Phytopathology 46, (1956): 568–75.
  • W. Brand-Williams, M.-E. Cuvelier, and C. Berset, “Use of a Free Radical Method to Evaluate Antioxidant Activity,” LWT – Food Science and Technology 28, no. 1 (1995): 25–30.
  • Sayed M. Riyadh, Sobhi M. Gomha, Elmahdi A. Mahmmoud, and Mahmoud M. Elaasser, “Synthesis and Anticancer Activities of Thiazoles, 1, 3-Thiazines, and Thiazolidine Using Chitosan-Grafted-Poly (Vinylpyridine) as Basic Catalyst,” Heterocycles 91, no. 6 (2015): 1227–43.
  • T. Mosmann, “Rapid Colorimetric Assay for Cellular Growth and Survival: Application to Proliferation and Cytotoxicity Assays,” Journal of Immunological Methods 65, no. 1–2 (1983): 55–63.
  • E. S. A. E. H. Khattab, A. Ragab, M. A. Abol-Ftouh, and A. A. Elhenawy, “Therapeutic Strategies for Covid-19 Based on Molecular Docking and Dynamic Studies to the ACE-2 Receptors, Furin, and Viral Spike Proteins,” Journal of Biomolecular Structure and Dynamics 39, (2021): 1–19.
  • D. M. Elsisi, A. Ragab, A. A. Elhenawy, A. A. Farag, A. M. Ali, and Y. A. Ammar, “Experimental and Theoretical Investigation for 6-Morpholinosulfonylquinoxalin-2(1H)-One and Its Haydrazone Derivate: Synthesis, Characterization, Tautomerization and Antimicrobial Evaluation,” Journal of Molecular Structure 1247, (2022): 131314.
  • A. S. Hassan, N. M. Morsy, H. M. Awad, and A. Ragab, “Synthesis, Molecular Docking, and in Silico ADME Prediction of Some Fused Pyrazolo[1,5-a]Pyrimidine and Pyrazole Derivatives as Potential Antimicrobial Agents,” Journal of the Iranian Chemical Society. (2021).
  • S. A. Ibrahim, H. F. Rizk, D. S. Aboul-Magd, and A. Ragab, “Design, Synthesis of New Magenta Dyestuffs Based on Thiazole Azomethine Disperse Reactive Dyes with Antibacterial Potential on Both Dyes and Gamma-Irradiated Dyed Fabric,” Dyes and Pigments 193, (2021): 109504.
  • E. A. Fayed, Y. A. Ammar, M. A. Saleh, A. H. Bayoumi, A. Belal, A. B. M. Mehany, and A. Ragab, “Design, Synthesis, Antiproliferative Evaluation, and Molecular Docking Study of New Quinoxaline Derivatives as Apoptotic Inducers and EGFR Inhibitors,” Journal of Molecular Structure 1236, (2021): 130317.
  • S. I. Eissa, A. M. Farrag, S. Y. Abbas, M. F. El Shehry, A. Ragab, E. A. Fayed, and Y. A. Ammar, “Novel Structural Hybrids of Quinoline and Thiazole Moieties: Synthesis and Evaluation of Antibacterial and Antifungal Activities with Molecular Modeling Studies,” Bioorganic Chemistry 110, (2021): 104803.
  • M. A. Salem, A. Ragab, A. A. Askar, A. El-Khalafawy, and A. H. Makhlouf, “One-Pot Synthesis and Molecular Docking of Some New Spiropyranindol-2-One Derivatives as Immunomodulatory Agents and In Vitro Antimicrobial Potential with DNA Gyrase Inhibitor,” European Journal of Medicinal Chemistry 188, (2020): 111977.
  • M. A. Salem, A. Ragab, A. El-Khalafawy, A. H. Makhlouf, A. A. Askar, and Y. A. Ammar, “Design, Synthesis, in Vitro Antimicrobial Evaluation and Molecular Docking Studies of Indol-2-One Tagged with Morpholinosulfonyl Moiety as DNA Gyrase Inhibitors,” Bioorganic Chemistry 96, (2020): 103619.
  • W. D. Alrohily, M. E. Habib, S. M. El-Messery, A. Alqurshi, H. El-Subbagh, and E.-S E. Habib, “Antibacterial, Antibiofilm and Molecular Modeling Study of Some Antitumor Thiazole Based Chalcones as a New Class of DHFR Inhibitors,” Microbial Pathogenesis 136, (2019): 103674.

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