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Research Articles

Synthesis, Molecular Docking, and DFT Studies of Some New 2,5-Disubstituted Benzoxazoles as Potential Antimicrobial and Cytotoxic Agents

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Pages 1679-1696 | Received 09 Jun 2020, Accepted 07 Jul 2020, Published online: 06 Aug 2020

References

  • Lynn Peters, Linus Olson, Dung T. K. Khu, Sofia Linnros, Ngai K. Le, Håkan Hanberger, Ngoc T. B. Hoang, Dien M. Tran, and Mattias Larsson, “Multiple Antibiotic Resistance as a Risk Factor for Mortality and Prolonged Hospital Stay: A Cohort Study among Neonatal Intensive Care Patients with Hospital-Acquired Infections Caused by Gram-Negative Bacteria in Vietnam,” PLoS One 14, no. 5 (2019): e0215666.
  • Brad Spellberg, John G. Bartlett, and David N. Gilbert, “The Future of Antibiotics and Resistance,” The New England Journal of Medicine 368, no. 4 (2013): 299–302.
  • Warren Kaplan and Richard Laing, Priority medicines for Europe and the World (Geneva: World Health Organization, 2004).
  • Jessica M. A. Blair, Mark A. Webber, Alison J. Baylay, David O. Ogbolu, and Laura J. V. Piddock, “Molecular Mechanisms of Antibiotic Resistance,” Nature Reviews: Microbiology 13, no. 1 (2015): 42–51.
  • C. Lee Ventola, “The Antibiotic Resistance Crisis: Part 1: Causes and Threats,” P & T: A Peer-Reviewed Journal for Formulary Management 40, no. 4 (2015): 277–83.
  • Kathrin U. Jansen, Charles Knirsch, and Annaliesa S. Anderson, “The Role of Vaccines in Preventing Bacterial Antimicrobial Resistance,” Nature Medicine 24, no. 1 (2018): 10–9.
  • Marisa H. Miceli, José A. Díaz, and Samuel A. Lee, “Emerging Opportunistic Yeast Infections,” The Lancet: Infectious Diseases 11, no. 2 (2011): 142–51.
  • Marie Méan, Oscar Marchetti, and Thierry Calandra, “Bench-to-Bedside Review: Candida Infections in the Intensive Care Unit,” Critical Care 12, no. 1 (2008): 204.
  • David W. Warnock, “Trends in the Epidemiology of Invasive Fungal infections,” Nihon Ishinkin Gakkai Zasshi = Japanese Journal of Medical Mycology 48, no. 1 (2007): 1–12.
  • Michael A. Pfaller, and Daniel J. Diekema, “Epidemiology of Invasive Candidiasis: A Persistent Public Health Problem,” Clinical Microbiology Reviews 20, no. 1 (2007): 133–63.
  • Brad J. Spellberg, Scott G. Filler, and John E. Edwards, Jr, “Current Treatment Strategies for Disseminated Candidiasis,” Clinical Infectious Diseases 42, no. 2 (2006): 244–51.
  • Dimitrios P. Kontoyiannis and Russell E. Lewis, “Antifungal Drug Resistance of Pathogenic Fungi,” The Lancet 359, no. 9312 (2002): 1135–44.
  • Dominique Sanglard and Frank C. Odds, “Resistance of Candida Species to Antifungal Agents: Molecular Mechanisms and Clinical Consequences,” The Lancet: Infectious Diseases 2, no. 2 (2002): 73–85.
  • Joachim Morschhäuser, “The Genetic Basis of Fluconazole Resistance Development in Candida albicans,” Biochimica et Biophysica Acta (BBA) - Molecular Basis of Disease 1587, no. 2–3 (2002): 240–8.
  • S Oğuz Kayaalp, Rasyonel tedavi yönünden tıbbi farmakoloji (Ankara: Hacettepe Taş Kitapçılık Limited Şti., 2005).
  • Hajime Suzuki, Akihiro Asakawa, Haruka Amitani, Norifumi Nakamura, and Akio Inui, “Cancer Cachexia-Pathophysiology and Management,” Journal of Gastroenterology 48, no. 5 (2013): 574–94.
  • Min Wang, Shan Xu, Huajun Lei, Caolin Wang, Zhen Xiao, Shuang Jia, Jia Zhi, Pengwu Zheng, and Wufu Zhu, “Design, Synthesis and Antitumor Activity of Novel Sorafenib Derivatives Bearing Pyrazole Scaffold,” Bioorganic & Medicinal Chemistry 25, no. 20 (2017): 5754–63.
  • J. Ferlay, M. Colombet, I. Soerjomataram, C. Mathers, D. M. Parkin, M. Piñeros, A. Znaor, and F. Bray, “Estimating the Global Cancer Incidence and Mortality in 2018: GLOBOCAN Sources and Methods,” International Journal of Cancer 144, no. 8 (2019): 1941–53.
  • Lindsey A. Torre, Freddie Bray, Rebecca L. Siegel, Jacques Ferlay, Joannie Lortet‐Tieulent, and Ahmedin Jemal, “Global Cancer Statistics, 2012,” CA: A Cancer Journal for Clinicians 65, no. 2 (2015): 87–108.
  • Leon Oehlers, Carolyn L. Mazzitelli, Jennifer S. Brodbelt, Mireya Rodriguez, and Sean Kerwin, “Evaluation of Complexes of DNA Duplexes and Novel Benzoxazoles or Benzimidazoles by Electrospray Ionization Mass Spectrometry,” Journal of the American Society for Mass Spectrometry 15, no. 11 (2004): 1593–603.
  • Richard M. Gale, Calvin E. Higgens, and Marvin M. Hoehn, “Antibiotic A23187 and Process for Preparation Thereof” (US Patent 3,923,823, filed January 17, 1974, and issued December 2, 1975).
  • Kyoichiro Saitoh, Masataka Konishi, and Koji Tomita, “Boxazomycin A and B, New Antibiotics Containing Benzoxazole Nucleus” (US Patent 4,728,612, filed July 25, 1986, and issued March 1, 1988).
  • Devinder Kumar, Melissa R. Jacob, Michael B. Reynolds, and Sean M. Kerwin, “Synthesis and Evaluation of Anticancer Benzoxazoles and Benzimidazoles Related to UK-1,” Bioorganic & Medicinal Chemistry 10, no. 12 (2002): 3997–4004.
  • Shu-Ting Huang, I-Jen Hsei, and Chinpiao Chen, “Synthesis and Anticancer Evaluation of Bis(benzimidazoles), Bis(benzoxazoles), and Benzothiazoles,” Bioorganic & Medicinal Chemistry 14, no. 17 (2006): 6106–19.
  • Samia M. Rida, Fawzia A. Ashour, Soad A. M. El-Hawash, Mona M. ElSemary, Mona H. Badr, and Manal A. Shalaby, “Synthesis of Some Novel Benzoxazole Derivatives as Anticancer, Anti-HIV-1 and Antimicrobial Agents,” European Journal of Medicinal Chemistry 40, no. 9 (2005): 949–59.
  • Meryem Taşcı, Ozlem Temiz-Arpaci, Fatma Kaynak-Onurdag, and Suzan Okten, “Synthesis and Antimicrobial Evaluation of Novel 5-Substituted-2-(p-tert-butylphenyl) Benzoxazoles,” Indian Journal of Chemistry B 57B, no. 03 (2018): 385–9.
  • Abdel‐Ghany A. El‐Helby, Helmy Sakr, Ibrahim H. Eissa, Hamada Abulkhair, Ahmed A. Al‐Karmalawy, and Khaled El‐Adl, “Design, Synthesis, Molecular Docking, and Anticancer Activity of Benzoxazole Derivatives as VEGFR‐2 Inhibitors,” Archiv Der Pharmazie 352, no. 10 (2019): 1900113.
  • Abdelhamid Benazzouz, Thomas Boraud, Pierre Dubédat, Alain Boireau, Jean-Marie Stutzmann, and Christian Gross, “Riluzole Prevents MPTP-Induced Parkinsonism in the Rhesus Monkey: A Pilot Study,” European Journal of Pharmacology 284, no. 3 (1995): 299–307.
  • Yousuke Katsura, Yoshikazu Inoue, Sigetaka Nishino, Masaaki Tomoi, Harunobu Itoh, and Hisashi Takasugi, “Studies on Antiulcer Drugs. III. Synthesis and Antiulcer Activities of Imidazo[1,2-a]pyridinylethylbenzoxazoles and Related Compounds. A Novel Class of Histamine H2-Receptor Antagonists,” Chemical & Pharmaceutical Bulletin 40, no. 6 (1992): 1424–38.
  • Zhuo Wu, Xiao-Lu Bao, Wei-Bo Zhu, Yan-Hui Wang, Nguyen Thi Phuong Anh, Xiao-Feng Wu, Yi-Jia Yan, and Zhi-Long Chen, “Design, Synthesis, and Biological Evaluation of 6-Benzoxazole Benzimidazole Derivatives with Antihypertension Activities,” ACS Medicinal Chemistry Letters 10, no. 1 (2019): 40–3.
  • Mohamed A. Abdelgawad, Rania B. Bakr, Waqas Ahmad, Mohammad M. Al-Sanea, and Heba A. H. Elshemy, “New Pyrimidine-Benzoxazole/Benzimidazole Hybrids: Synthesis, Antioxidant, Cytotoxic Activity, In Vitro Cyclooxygenase and Phospholipase A2-V Inhibition,” Bioorganic Chemistry 92, (2019): 103218.
  • Ming‐Xia Song, Yuping Huang, Shiben Wang, Zeng‐Tao Wang, and Xian‐Qing Deng, “Design, Synthesis, and Evaluation of Anticonvulsant Activities of Benzoxazole Derivatives Containing the 1, 2, 4‐Triazolone Moiety,” Archiv der Pharmazie 352, no. 8 (2019): 1800313.
  • Furkan Ayaz, Ronak Haj Ersan, and Oztekin Algul, “Symmetric Bis-Benzoxazole-Based Chemicals Exerted Anti-Inflammatory Effect on Danger Signal LPS-Stimulated Macrophages,” Monatshefte Für Chemie-Chemical Monthly 150, no. 6 (2019): 1137–46.
  • Diego P. Sangi, Yuri G. Meira, Natália M. Moreira, Thais A. Lopes, Mathias P. Leite, Milton E. Pereira‐Flores, and Elson S. Alvarenga, “Benzoxazoles as Novel Herbicidal Agents,” Pest Management Science 75, no. 1 (2019): 262–9.
  • Ozlem Temiz-Arpaci, Mustafa Arisoy, Duygu Sac, Fatima Doganc, Meryem Tasci, Fatma Sezer Senol, and Ilkay Erdogan Orhan, “Biological Evaluation and Docking Studies of Some Benzoxazole Derivatives as Inhibitors of Acetylcholinesterase and Butyrylcholinesterase,” Zeitschrift Fur Naturforschung C, Journal of Biosciences 71, no. 11–12 (2016): 409–13.
  • Mustafa Arisoy, Ozlem Temiz-Arpaci, Ilkay Yildiz, Fatma Kaynak-Onurdag, Esin Aki, Ismail Yalcin, and Ufuk Abbasoglu, “Synthesis, Antimicrobial Activity and QSAR Studies of 2,5-Disubstituted Benzoxazoles,” SAR and QSAR in Environmental Research 19, no. 5–6 (2008): 589–612.
  • Ozlem Temiz-Arpaci, Aliye Ozdemir, Ismail Yalçin, Ilkay Yildiz, Esin Aki-Sener, and Nurten Altanlar, “Synthesis and Antimicrobial Activity of Some 5-[2-(morpholin-4-yl)acetamido] and/or 5-[2-(4-Substituted piperazin-1-yl)acetamido]-2-(p-substituted phenyl)benzoxazoles,” Archiv Der Pharmazie 338, no. 2–3 (2005): 105–11.
  • Funda Kosova, Özlem Temiz-Arpacı, Ercüment Ölmez, and İbrahim Tuğlu, “The Effects of Benzoxasol Derivate Compounds in Breast Cancer Cells,” Proceedings 1, no. 10 (2017): 1046.
  • CLSI, Performance Standards for Antimicrobial Susceptibility Testing (18th informational supplement, M100-S18, Wayne, PA: CLSI, 2008).
  • CLSI, Approved Standard—6th ed. (Wayne, PA: CLSI; 2006): CLSI document H3-A6.
  • Tim 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.
  • Fen Wang, “Culture of Animal Cells: A Manual of Basic Technique,” In Vitro Cellular & Developmental Biology - Animal 42, no. 5 (2006): 169.
  • Frank A. Barile, In Vitro Methods in Pharmaceutical Research (San Diego: Academic Press, 1997).
  • Katarı́na Horáková, Andrea Sovcíková, Zuzana Seemannová, Dagmar Syrová, Katarı́na Busányová, Zuzana Drobná, and Miroslav Ferencík, “Detection of Drug-Induced, Superoxide-Mediated Cell Damage and Its Prevention by Antioxidants,” Free Radical Biology & Medicine 30, no. 6 (2001): 650–64.
  • LLC Schrödinger, Schrödinger Release 2018-1: Maestro (New York, NY: Schrödinger, LLC, 2018.
  • M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, G. Scalmani, V. Barone, B. Mennucci, G. A. Petersson, et al., Gaussian 09, Revision A. 02 (Gaussian, Inc: Wallingford, CT, 2009, 2015).
  • Tak Roy Dennington, and John M. Millam, GaussView, Version 6 (Shawnee Mission, KS: Semichem Inc., 2016).
  • Molinspiration Cheminformatics, (Bratislava, Slovak Republic: Molinspiration Cheminformatics, 2014).
  • LLC Molsoft, ICM Software Manual, Version (San Diego: LLC Molsoft, 2004).
  • Mustafa Arisoy, Ozlem Temiz-Arpaci, Fatma Kaynak-Onurdag, and Selda Ozgen, “Synthesis and Antimicrobial Activity of Novel Benzoxazoles,” Zeitschrift Fur Naturforschung. C, Journal of Biosciences 67, no. 9–10 (2012): 466–72.
  • Mustafa Arisoy, Ozlem Temiz-Arpaci, Fatma Kaynak-Onurdag, and Selda Ozgen, “Synthesis and Antimicrobial Evaluation of 2-(p-Substituted phenyl)-5-[(4-substituted piperazin-l-yl)acetamido]-benzoxazoles,” Zeitschrift fur Naturforschung. C, Journal of Biosciences 69, no. 9–10 (2014): 368–74.
  • Mustafa Arisoy, Ozlem Temiz-Arpaci, Fatam Kaynak-Onurdag, and Selda Ozgen, “Synthesis of Some Piperazinobenzoxazole Derivatives and Their Antimicrobial Properties,” Indian Journal of Chemistry Section B-Organic Chemistry Including Medicinal Chemistry 55, no. 2 (2016): 240–47.
  • Mustafa Arisoy, Özlem Temiz-Arpaci, Fatma Kaynak-Onurdag, and Selda Ozgen, “Antimycobacterial Properties of Some 2, 5-Disubstituted-Benzoxazole Derivatives,” Ankara Üniversitesi Eczacılık Fakültesi Dergisi 39, no. 2 (2010): 155–62.
  • Francois Denizot and Rita Lang, “Rapid Colorimetric Assay for Cell Growth and Survival: Modifications to the Tetrazolium Dye Procedure Giving Improved Sensitivity and Reliability,” Journal of Immunological Methods 89, no. 2 (1986): 271–77.
  • Ismail Celik, Meryem Erol, Ozlem Temiz Arpaci, Fatma Sezer Senol, and Ilkay Erdogan Orhan, “Evaluation of Activity of Some 2, 5-Disubstituted Benzoxazole Derivatives against Acetylcholinesterase, Butyrylcholinesterase and Tyrosinase: ADME Prediction, DFT and Comparative Molecular Docking Studies,” Polycyclic Aromatic Compounds (2020): 1–12.
  • Mustafa Orhan Puskullu, Ismail Celik, Meryem Erol, Hanifa Fatullayev, Ebru Uzunhisarcikli, and Gulcan Kuyucuklu, “Antimicrobial and Antiproliferative Activity Studies of Some New Quinoline-3-Carbaldehyde Hydrazone Derivatives,” Bioorganic Chemistry 101 (2020): 104014.
  • Meryem Erol, Ismail Celik, Ozlem Temiz-Arpaci, Fatma Kaynak-Onurdag, and Suzan Okten, “Design, Synthesis, Molecular Docking, Density Functional Theory and Antimicrobial Studies of Some Novel Benzoxazole Derivatives as Structural Bioisosteres of Nucleotides,” Journal of Biomolecular Structure and Dynamics 13 (2020): 1–12.
  • Shabir H. Lone, Salman Jameel, Muzzaffar A. Bhat, Rayees A. Lone, Ray J. Butcher, and Khursheed A. Bhat, “Synthesis of an Unusual Quinazoline Alkaloid: Theoretical and Experimental Investigations of Its Structural, Electronic, Molecular and Biological Properties,” RSC Advances 8, no. 15 (2018): 8259–68.
  • Maha S. Almutairi, Azza S. Zakaria, P. Primsa Ignasius, Reem I. Al-Wabli, Isaac Hubert Joe, and Mohamed I. Attia, “Synthesis, Spectroscopic Investigations, DFT Studies, Molecular Docking and Antimicrobial Potential of Certain New Indole-Isatin Molecular Hybrids: Experimental and Theoretical Approaches,” Journal of Molecular Structure 1153, (2018): 333–45.

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