271
Views
6
CrossRef citations to date
0
Altmetric
Research Articles

Docking, Synthesis, Antifungal and Cytotoxic Activities of Some Novel Substituted 4H-Benzoxazin-3-one

, , , , , , , , & show all
Pages 347-367 | Received 17 Sep 2018, Accepted 14 Feb 2019, Published online: 11 May 2019

References

  • V. S. Dinakaran, B. Bomma, and K. K. Srinivasan, “Fused Pyrimidines: The Heterocycle of Diverse Biological and Pharmacological Significance,” Der Pharma Chem 4, no. 1 (2012): 255–65.
  • P. Martins, J. Jesus, S. Santos, L. R. Raposo, C. Roma-Rodrigues, P. V. Baptista, and A. R. Fernandes, “Heterocyclic Anticancer Compounds: recent Advances and the Paradigm Shift towards the Use of Nanomedicine’s Tool Box,” Molecules 20, no. 9 (2015): 16852–91.
  • E. Vitaku, D. T. Smith, and J. T. Njardarson, “Analysis of the Structural Diversity, substitution Patterns, and Frequency of Nitrogen Heterocycles among US FDA Approved Pharmaceuticals: Miniperspective,” Journal of Medicinal Chemistry 57, no. 24 (2014): 10257–74.
  • K. Shen, Y. Fu, J.-N. Li, L. Liu, and Q.-X. Guo, “What Are the pKa Values of C–H Bonds in Aromatic Heterocyclic Compounds in DMSO?,” Tetrahedron 63, no. 7 (2007): 1568–76. doi: https://doi.org/10.1016/j.tet.2006.12.032.
  • P. Arora, V. Arora, H. Lamba, and D. Wadhwa, “Importance of Heterocyclic Chemistry: A Review,” International Journal of Pharmaceutical Sciences and Research 3, no. 9 (2012): 2947.
  • L.-j. Meng, H. Zuo, B. Vijaykumar, G. Dupati, K.-M. Choi, K. Jang, Y.-J. Yoon, and D.-S. Shin, “Microwave Synthesis of Chiral N-Benzyl-2-methyl-2H-benzo [b][1, 4] oxazin/thiazin-3 (4H)-Ones via Smiles Rearrangement and Their Biological Evaluation,” Bulletin of the Korean Chemical Society 34, no. 2 (2013): 585.
  • M. Tanaka, Y. Oshima, H. Aoki, and H. Hakusui, “Determination of a New Fluoroquinolone Antimicrobial Agent,(S)-10-[(S)-(8-amino-6-azaspiro [3, 4] octan-6-yl]-9-fluoro-2, 3-dihydro-3-methyl-7-oxo-7H-pyrido [1, 2, 3-de [1, 4] Benzoxazine-6-carboxylic Acid Hemihydrate, DV-7751a, in Human Serum and Urine Using Solid-phase Extraction and High-performance Liquid Chromatography with Fluorescence Detection,” Journal of Chromatography B: Biomedical Sciences and Applications 664, no. 2 (1995): 401–7.
  • S. Alper-Hayta, E. Akı-Sener, B. Tekiner-Gulbas, I. Yıldız, O. Temiz-Arpacı, I. Yalcın, and N. Altanlar, “Synthesis, antimicrobial Activity and QSARs of New Benzoxazine-3-Ones,” European Journal of Medicinal Chemistry 41, no. 12 (2006): 1398–404. doi: https://doi.org/10.1016/j.ejmech.2006.06.011.
  • R. Fringuelli, N. Giacchè, L. Milanese, E. Cenci, A. Macchiarulo, A. Vecchiarelli, G. Costantino, and F. Schiaffella, “Bulky 1, 4-benzoxazine Derivatives with Antifungal Activity,” Bioorganic & Medicinal Chemistry 17, no. 11 (2009): 3838–46.
  • A. Macchiarulo, G. Costantino, D. Fringuelli, A. Vecchiarelli, F. Schiaffella, and R. Fringuelli, “1, 4-Benzothiazine and 1, 4-benzoxazine Imidazole Derivatives with Antifungal Activity: A Docking Study,” Bioorganic & Medicinal Chemistry 10, no. 11 (2002): 3415–23.
  • X. Li, N. Liu, H. Zhang, S. E. Knudson, R. A. Slayden, and P. J. Tonge, “Synthesis and SAR Studies of 1, 4-benzoxazine MenB Inhibitors: novel Antibacterial Agents against Mycobacterium tuberculosis,” Bioorganic & Medicinal Chemistry Letters 20, no. 21 (2010): 6306–9.
  • G. N. Kumar, N. S. Subramanian, M. R. Devi, P. Harathi, N. S. Latha, G. Thapaswini, and N. Ravikanth, “Synthesis, Characterization, Pharmacological Evaluation and Molecular Docking Studies of Novel Benzoxazine Derivatives for the Treatment of Inflammation,” International Journal of Pharmaceutical Sciences and Research 5, no. 9 (2014): 3987.
  • M. Akhter, A. Husain, N. Akhter, and M. Y. Khan, “Synthesis, antiinflammatory and Antimicrobial Activity of Some New 1-(3-Phenyl-3, 4-Dihydro-2H-1, 3-Benzoxazin-6-yl)-Ethanone Derivatives,” Indian Journal of Pharmaceutical Sciences 73, no. 1 (2011): 101.
  • R. Marcellino, T. Widiandani, and A. Syahrani, “Some Benzoxazine and Aminomethyl Derivatives of Eugenol: Cytotoxicity on Mcf-7 Cell Line,” International Journal of Pharmacy and Pharmaceutical Sciences 7, no. 5 (2015): 229–32.
  • E. Pomarnacka, A. Kornicka, A. Kuchnio, M. Heinrichs, R. Grünert, M. Gdaniec, and P. J. Bednarski, “Synthesis, Cytotoxicity Testing, and Structure–Activity Relationships of Novel 6‐Chloro‐7‐(4‐phenylimino‐4H‐3, 1‐benzoxazin‐2‐yl)‐3‐(Substituted)‐1, 4, 2‐benzodithiazine 1, 1‐Dioxides,” Archiv Der Pharmazie 344, no. 7 (2011): 431–41.
  • A. Varga, E. Aki-Sener, I. Yalcin, O. Temiz-Arpaci, B. Tekiner-Gulbas, G. Cherepnev, and J. Molnar, “Induction of Apoptosis and Necrosis by Resistance Modifiers Benzazoles and Benzoxazines on Tumour Cell Line Mouse Lymphoma L5718 Mdr + Cells,” In Vivo 19, no. 6 (2005): 1087–91.
  • F. Zilifdar, S. Alper-Hayta, S. Yilmaz, Ç. Kaplan-Özen, E. Foto, Z. Aydoğan, I. Yildiz, E. Aki, I. Yalçin, and N. Diril, “Genotoxic Potentials and Eukaryotic DNA Topoisomerase I Inhibitory Effects of Some Benzoxazine Derivatives,” Medicinal Chemistry Research 23, no. 1 (2014): 480–6.
  • Z. Hua, K.-H. Kam, H.-J. Kwon, L. Meng, C.-J. Ahn, T.-J. Won, T.-H. Kim, C. Reddy, S. Chandrasekhar, and D.-S. Shin, “Microwave-assisted Synthesis of 2H-Benzo [b][1, 4] oxazin-3 (4H)-Ones and 1H-Pyrido [2, 3-b][1, 4] oxazin-2 (3H)-Ones via Smiles Rearrangement,” Bulletin of the Korean Chemical Society 29, no. 7 (2008): 1379–85.
  • L.-J. Meng, H. Zuo, and G. Dupati, “Microwave-assisted Synthesis of Optically Active N-substituted 2-methyl-2H-benzo [b][1, 4] oxazin-3 (4H)-Ones and-thiazin-3 (4H)-Ones via Smiles Rearrangement,” Med Chem 3, (2013): 11–20.
  • Z.-T. Piao, L.-P. Guan, L.-M. Zhao, H.-R. Piao, and Z.-S. Quan, “Synthesis of Novel 7-benzylamino-2H-1,4-benzoxazin-3(4H)-ones as anticonvulsant agents,” European Journal of Medicinal Chemistry 43, no. 6 (2008): 1216–21.
  • M. O. Karataş, H. Uslu, S. Sarı, M. A. Alagöz, A. Karakurt, B. Alıcı, C. Bilen, E. Yavuz, N. Gencer, and O. Arslan, “Coumarin or Benzoxazinone Based Novel Carbonic Anhydrase Inhibitors: synthesis, molecular Docking and Anticonvulsant Studies,” Journal of Enzyme Inhibition and Medicinal Chemistry 31, no. 5 (2016): 760–72.
  • A. Capasso, A. Biondi, F. Palagiano, F. Bonina, L. Montenegro, P. de Caprariis, E. Pistorio, and L. Sorrentino, “Anticonvulsive Activity of a New GABA Mimetic Drug,” European Neuropsychopharmacology 7, no. 1 (1997): 57–63.
  • J. Kang, K.-H. Kam, M. Ghate, Z. Hua, T.-H. Kim, C. R. Reddy, S. Chandrasekhar, and D.-S. Shina, “An Efficient Synthesis of 2H-1, 4-benzoxazin-3 (4H)-Ones via Smiles Rearrangement,” ARKIVOC 14, (2008): 67–76.
  • L. Fang, H. Zuo, Z.-B. Li, X.-Y. He, L.-Y. Wang, X. Tian, B.-X. Zhao, J.-Y. Miao, and D.-S. Shin, “Synthesis of Benzo [b][1, 4] oxazin-3 (4H)-Ones via Smiles Rearrangement for Antimicrobial Activity,” Medicinal Chemistry Research 20, no. 6 (2011): 670–7.
  • Z.-Z. Huang, and L.-S. Zu, “Rapid n-alkylation of Benzoxazinones and Benzothiazinones under Microwave Irradiation,” Organic Preparations and Procedures International: The New Journal for Organic Synthesis 28, no. 1 (1996): 121–3.

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.