Design and synthesis of novel 1,3,2-benzoxazaphosphinine-2-one derivatives: an in vitro biological evaluation and in silico approaches

References

• Sampath, C.; Naga Raju, C.; Venkata Rao, C. Synthesis, Spectroscopic Characterization, Antimicrobial and Antioxidant Activities of Novel Phosphorylated Derivatives of Amlodipine. Phosphorus Sulfur Silicon Relat. Elem. 2015, 190, 11–19. DOI: 10.1080/10426507.2014.909429.
   Web of Science ®Google Scholar
• Lobo, V.; Patil, A.; Phatak, A.; Chandra, N. Free Radicals, Antioxidants and Functional Foods: Impact on Human Health. Pharmacogn. Rev. 2010, 4, 118–126. DOI: 10.4103/0973-7847.70902.
   PubMedGoogle Scholar
• Srivastava, S.; Singh, D.; Patel, S.; Singh, M. R. Role of Enzymatic Free Radical Scavengers in Management of Oxidative Stress in Autoimmune Disorders. Int. J. Biol. Macromol. 2017, 101, 502–517. DOI: 10.1016/j.ijbiomac.2017.03.100.
   PubMed Web of Science ®Google Scholar
• Kishore, N.; Kumar, P.; Shanker, K.; Verma, A. K. Human Disorders Associated with Inflammation and the Evolving Role of Natural Products to Overcome. Eur. J. Med. Chem. 2019, 179, 272–309. DOI: 10.1016/j.ejmech.2019.06.034.
   PubMed Web of Science ®Google Scholar
• Naik, G. H.; Priyadarsini, K. I.; Mohan, H. Evaluating the Antioxidant Activity of Different Plant Extracts and Herbal Formulations. Res. Chem. Intermed. 2005, 31, 145–151. DOI: 10.1163/1568567053146823.
   Web of Science ®Google Scholar
• Osborne, P. G.; Ko, Y. C.; Wu, M. T.; Lee, C. H. Intoxication and Substance Use Disorder to Areca Catechu Nut Containing Betel Quid: A Review of Epidemiological Evidence, Pharmacological Basis and Social Factors Influencing Quitting Strategies. Drug Alcohol Depen. 2017, 179, 188–197. DOI: 10.1016/j.drugalcdep.2017.06.039.
   Web of Science ®Google Scholar
• Abrahams, S.; Haylett, W. L.; Johnson, G.; Carr, J. A.; Bardien, S. Antioxidant Effects of Curcumin in Models of Neurodegeneration, Aging, Oxidative and Nitrosative Stress: A Review. Neuroscience 2019, 406, 1–21. DOI: 10.1016/j.neuroscience.2019.02.020.
   PubMed Web of Science ®Google Scholar
• Li, S.; Liu, M.; Zhang, C.; Tian, C.; Wang, X.; Song, X.; Jing, H.; Gao, Z.; Ren, Z.; Liu, W.; et al. Purification, in Vitro Antioxidant and in Vivo anti-Aging Activities of Soluble Polysaccharides by Enzyme-Assisted Extraction from Agaricus Bisporus. Int. J. Biol. Macromol. 2018, 109, 457–466. DOI: 10.1016/j.ijbiomac.2017.12.108.
   PubMed Web of Science ®Google Scholar
• Neha, K.; Haider, M. R.; Pathak, A.; Yar, M. S. Medicinal Prospects of Antioxidants: A Review. Eur. J. Med. Chem. 2019, 178, 687–704. DOI: 10.1016/j.ejmech.2019.06.010.
   PubMed Web of Science ®Google Scholar
• Elias, R.; Benhamou, R. I.; Jaber, Q. Z.; Dorot, O.; Zada, S. L.; Oved, K.; Pichinuk, E.; Fridman, M. Antifungal Activity, Mode of Action Variability, and Subcellular Distribution of Coumarin-Based Antifungal Azoles. Eur. J. Med. Chem. 2019, 179, 779–790. DOI: 10.1016/j.ejmech.2019.07.003.
   PubMed Web of Science ®Google Scholar
• Wen, F.; Jin, H.; Tao, K.; Hou, T. Design, Synthesis and Antifungal Activity of Novel Furancarboxamide Derivatives. Eur. J. Med. Chem. 2016, 120, 244–251. DOI: 10.1016/j.ejmech.2016.04.060.
   PubMed Web of Science ®Google Scholar
• Hossain, M. A.; Ghannoum, M. A. New Developments in Chemotherapy for Non-Invasive Fungal Infections. Expert Opin Investig Drugs 2001, 10, 1501–1511. DOI: 10.1517/13543784.10.8.1501.
   PubMed Web of Science ®Google Scholar
• Perlroth, J.; Choi, B.; Spellberg, B. Nosocomial Fungal Infections: Epidemiology, Diagnosis, and Treatment. Med. Mycol. 2007, 45, 321–346. DOI: 10.1080/13693780701218689.
   PubMed Web of Science ®Google Scholar
• Vorathavorn, V. I.; Sykes, J. E.; Feldman, D. G.; Vet, J. Cryptococcosis as an Emerging Systemic Mycosis in Dogs. J. Vet. Emerg. Crit. Care 2013, 23, 489–497. DOI: 10.1111/vec.12087.
   PubMed Web of Science ®Google Scholar
• Shiro, T.; Fukaya, T.; Tobe, M. The Chemistry and Biological Activity of Heterocycle-Fused Quinolinone Derivatives: A Review. Eur. J. Med. Chem. 2015, 97, 397–408. DOI: 10.1016/j.ejmech.2014.12.004.
   PubMed Web of Science ®Google Scholar
• Medina, F. G.; Marrero, J. G.; Macías-Alonso, M.; González, M. C.; Córdova-Guerrero, I.; García, A. G. T.; Osegueda-Robles, S. Coumarin Heterocyclic Derivatives: Chemical Synthesis and Biological Activity. Nat. Prod. Rep. 2015, 32, 1472–1507. DOI: 10.1039/c4np00162a.
   PubMed Web of Science ®Google Scholar
• Hernández-Díaz, J.; Flores-Parra, A.; Contreras, R. Phosphorus Heterocycles from 2‐(2‐Hydroxyphenyl)‐1H‐Benzimidazole. Heteroatom Chem. 2004, 15, 307–320. DOI: 10.1002/hc.20021.
   Web of Science ®Google Scholar
• Moyer, M. P.; Feldman, P. L.; Rapoport, H. Intramolecular Nitrogen-Hydrogen, Oxygen- Hydrogen and Sulfur-Hydrogen Insertion Reactions. Synthesis of Heterocycles from.alpha.- Diazo.beta.-Keto Esters. J. Org. Chem. 1985, 50, 5223–5230. DOI: 10.1021/jo00225a047.
   Web of Science ®Google Scholar
• Demkowicz, S.; Rachon, J.; Daśko, M.; Kozak, W. Selected Organophosphorus Compounds with Biological Activity. Applications in Medicine. RSC Adv. 2016, 6, 7101–7112. DOI: 10.1039/C5RA25446A.
   Web of Science ®Google Scholar
• Uchimiya, M.; Wartelle, L. H.; Boddu, V. M. Sorption of Triazine and Organophosphorus Pesticides on Soil and Biochar. J. Agric. Food Chem. 2012, 60, 2989–2997. DOI: 10.1021/jf205110g.
   PubMed Web of Science ®Google Scholar
• Montchamp, J. L. Phosphinate Chemistry in the 21st Century: A Viable Alternative to the Use of Phosphorus Trichloride in Organophosphorus Synthesis. Acc. Chem. Res. 2014, 47, 77–87. DOI: 10.1021/ar400071v.
   PubMed Web of Science ®Google Scholar
• Făgădar-Cosma, E.; Laichici, M.; Făgădar-Cosma, G.; Vlascici, D. Synthesis, Characterization and Correlative Biological Effects in Wheat of a Benzoxaza- and a Diaza-Phosphorus(V) heterocycles. J. Serb. Chem. Soc. 2006, 71, 1031–1038. DOI: 10.2298/JSC0610031F.
   Web of Science ®Google Scholar
• Abdel-Aziz, S. A.-G.; Ali, T. E.-S.; El-Mahdy, K. M.; Abdel-Karim, S. M. Synthesis and Antimicrobial Activities of Some Novel Bis-Pyrazole Derivatives Containing a Hydrophosphoryl Unit. Eur. J. Chem. 2011, 2, 25–35. DOI: 10.5155/eurjchem.2.1.25-35.208.
   Google Scholar
• Derbalah, A.; Chidya, R.; Jadoon, W.; Sakugawa, H. Temporal Trends in Organophosphorus Pesticides Use and Concentrations in River Water in Japan, and Risk Assessment. J. Environ. Sci. 2019, 79, 135–152. DOI: 10.1016/j.jes.2018.11.019.
   Web of Science ®Google Scholar
• Cycoń, M.; Wójcik, M.; Piotrowska-Seget, Z. Biodegradation of the Organophosphorus Insecticide Diazinon by Serratia sp. and Pseudomonas sp. and Their Use in Bioremediation of Contaminated Soil. Chemosphere 2009, 76, 494–501. DOI: 10.1016/j.chemosphere.2009.03.023.
   PubMed Web of Science ®Google Scholar
• Haribabu, Y.; Srinivasulu, K.; Reddy, C. S.; Reddy, C. D. Synthesis of Novel Fused Heterocyclic System: 5-(Substituted)-5-Oxo-5H-6,12-Dioxa-5λ5–Phosphabenzo (a) Anthracene-7-Ones. Arkivoc 2006, 2006, 95–103. DOI: 10.3998/ark.5550190.0007.f12.
   Google Scholar
• Zenneck, U.; Hofmann, M. Comprehensive Heterocyclic Chemistry III, 2008, 875.
   Google Scholar
• Zhou, Y.; Leonard, D. N.; Meyer, H. M. I. I.; Luo, H.; Qu, J. Does the Use of Diamond-Like Carbon Coating and Organophosphate Lubricant Additive Together Cause Excessive Tribochemical Material Removal? Adv. Mater. Interfaces 2015, 2, 1500213. DOI: 10.1002/admi.201500213.
   Web of Science ®Google Scholar
• Ali, T. E.; Reda, M.; Abdel-Rahman, S. M. Synthesis and Antioxidant Activities of Some Novel Fluorinated Spiro[Oxindole-Thiazolidine] Fused with Sulfur and Phosphorus Heterocycles. J. Sul. Chem. 2014, 35, 399–411. DOI: 10.1080/17415993.2014.896363.
   Web of Science ®Google Scholar
• Hassan, M. M.; Abdel-Kariem, S. M.; Ali, T. E. Synthesis and Antioxidant Properties of Some Novel 1,3,4,2-Oxadiazaphosphepino[6,7-c]Quinolinones and Pyrazolo[3,4:4′,3′]Quinolino[5,1-c][1,4,2]Oxazaphosphinine. Phosphorus Sulfur Silicon Relat. Elem. 2017, 192, 866–873. DOI: 10.1080/10426507.2017.1290625.
   Web of Science ®Google Scholar
• Ali, T. E.; Abdel-Rahman, R. M.; Hanafy, F. I.; El-Edfawy, S. M. Synthesis and Molluscicidal Activity of Phosphorus-Containing Heterocyclic Compounds Derived from 5,6-Bis (4-Bromophenyl)-3-Hydrazino-1,2,4-Triazine. Phosphorus Sulfur Silicon Relat. Elem. 2008, 183, 2565–2577. DOI: 10.1080/10426500801967864.
   Web of Science ®Google Scholar
• Nadiminti, K.; Strouse, C.; Sidiqi, M. H.; Dozeman, L.; Mott, S. L.; Schultz, A.; Claus, J.; Vikas, P.; Farooq, U.; Tomasson, M.; et al. Impact of Chemotherapy Based Induction Using Dexamethasone, Cisplatin, Doxorubicin, Cyclophosphamide and Etoposide (DPACE) versus Novel Agent Induction in Patients Undergoing Tandem Autologous Stem Cell Transplantation (ASCT) for Multiple Myeoma (MM). Biol. Blood Marrow Transplant. 2019, 25, S399–S400. DOI: 10.1016/j.bbmt.2018.12.813.
   Web of Science ®Google Scholar
• Noguchi, M.; Moriya, F.; Koga, N.; Matsueda, S.; Sasada, T.; Yamada, A.; Kakuma, T.; Itoh, K. A Randomized Phase II Clinical Trial of Personalized Peptide Vaccination with Metronomic Low-Dose Cyclophosphamide in Patients with Metastatic Castration-Resistant Prostate Cancer. Cancer Immunol. Immunother. 2016, 65, 151–160. 1781-6. DOI: 10.1007/s00262-015-.
   PubMed Web of Science ®Google Scholar
• Murthy, K.; Poojith, P.; Osório, N.; Valverde, F. A. P.; Sampath, C.; Suchetan, C.; Suneetha, P. A. V. An Analysis of Spectroscopic, Computational and Biological Activity Studies of L-Shaped Sulfamoylbenzoic Acid Derivatives: A Third Order Nonlinear Optical Material. J. Mol. Struct. 2020, 1210, 128070. DOI: 10.1016/j.molstruc.2020.128070.
   Web of Science ®Google Scholar
• Rasool, S. K.; Suresh, M.; Krishna Murthy, P.; Titinchi, S. J. J.; Basha, S. T.; Venkataramaiah, C.; Rajendra, W.; Venkateswarlu, N.; Vijaya, T.; Sampath, C.; et al. In Silico Molecular Docking and In Vitro Antioxidant Activity Studies of Novel α-aminophosphonates Bearing 6-amino-1,3-dimethyl Uracil. J. Recept. Signal Transduct. Res.. 2020, 40, 166–172. DOI: 10.1080/10799893.2020.1722166.
   PubMed Web of Science ®Google Scholar
• Kavitha, C.; Narendra, K.; Ratnakar, A.; Poojith, N.; Sampath, C.; Banik, S.; Suchetan, P. A.; Krishna Murthy, P.; Subba Naidu, N. V. An Analysis of Structural, Spectroscopic Signatures, Reactivity and Antibacterial Study of Synthetized 4-Chloro-3-Sulfamoylbenzoic Acid. J. Mol. Struct. 2020, 1202, 127176. DOI: 10.1016/j.molstruc.2019.127176.
   Web of Science ®Google Scholar
• Harika, P.; Abbo, H. S.; Krishna Murthy, P.; Titinchi, S. J. J.; Sampath, C. Polyethylene Glycol (PEG-400): an Efficient One-Pot Green Synthesis and Anti-Viral Activity of Novel α- Diaminophosphonates. Phosphorus Sulfur Silicon Relat. Elem. 2019, 194, 1035–1039. DOI: 10.1080/10426507.2019.1597365.
   Web of Science ®Google Scholar
• Maddila, S.; Gorle, S.; Sampath, C.; Lavanya, P. Synthesis and anti-Inflammatory Activity of Some New 1,3,4-Thiadiazoles Containing Pyrazole and Pyrrole Nucleus. J. Saudi Chem. Soc. 2016, 20, S306–S312. DOI: 10.1016/j.jscs.2012.11.007.
   Web of Science ®Google Scholar
• Sampath, C.; Harika, P.; Revaprasadu, N. Design, Green Synthesis, anti-Microbial, and anti- Oxidant Activities of Novel α-Aminophosphonates via Kabachnik-Fields Reaction. Phosphorus Sulfur Silicon Relat. Elem. 2016, 191, 1081–1085. DOI: 10.1080/10426507.2015.1035379.
   Web of Science ®Google Scholar
• Sampath, C.; Naga Raju, C.; Venkata Rao, C. An Efficient Synthesis, Spectral Characterization, anti-Microbial and anti-Oxidant Activities of Novel α-Hydroxyphosphonates and α-Hydroxyphosphinates. Phosphorus Sulfur Silicon Relat. Elem. 2016, 191, 95–99. DOI: 10426507.2015.1032412.
   Web of Science ®Google Scholar
• Reddy, M.; Venkataramaiah, S.; Krishna Murthy, C.; Sampath, P.; Naga Raju, C. C. In Silico Docking Studies and Synthesis of New Phosphoramidate Derivatives of 6- Fluoro-3-(Piperidin-4-yl)Benzo[d]Isoxazole as Potential Antimicrobial Agents. J. Recept. Signal Transduct. Res. 2020, 40, 486–492. DOI: 10.1080/10799893.2020.1752719.
   PubMed Web of Science ®Google Scholar
• Naga Raju, K.; Kotaiah, Y.; Sampath, C.; Hari Krishna, N.; Venkata Rao, C. A Facile Synthesis of Some Novel Fused [1,2,4]Triazolo[3,4-b][1,3,4]Thiadiazol Derivatives. J. Sulf. Chem. 2013, 34, 264–275. DOI: 10.1080/17415993.2012.734306.
   Web of Science ®Google Scholar
• Sampath, C.; Harika, P. An Efficient Green Synthesis of Novel α-Diaminophosphonates. Phosphorus Sulfur Silicon Relat. Elem. 2015, 190, 1893–1900. DOI: 10.1080/10426507.2015.1031756.
   Web of Science ®Google Scholar
• Cherukupalli, S.; Hampannavar, G. A.; Chinnam, S.; Chandrasekaran, B.; Sayyad, N.; Kayamba, F.; Reddy Aleti, R.; Karpoormath, R. An appraisal on synthetic and pharmaceutical perspectives of pyrazolo[4,3-d]pyrimidine scaffold. Bioorg. Med. Chem. 2018, 26, 309–339. DOI: 10.1016/j.bmc.2017.10.012.
   PubMed Web of Science ®Google Scholar
• Srinivasulu, K.; Suresh Kumar, K.; Hari Babu, B.; Stephen Babu, M. F.; Naga Raju, C.; Suresh Reddy, C. Synthesis and Bioactivity of Some New 2‐(Alkoxy Carbonyl Alkyl)‐6‐Bromo‐3,4‐Dihydro‐3‐(α‐Methyl Benzyl)‐2‐Oxo‐Benzo[e] [2H‐1,3,2‐Oxazaphosphinine] Derivatives. Chin. J. Chem. 2009, 27, 810–814. DOI: 10.1002/cjoc.200990135.
   Google Scholar
• Burits, M.; Bucar, F. Antioxidant Activity of Nigella Sativa Essential Oil. Phytother. Res. 2000, 14, 323–328. DOI: 10.1002/1099-1573(200008)14:5<323::AID-PTR621>3.0.CO;2-Q.
   PubMed Web of Science ®Google Scholar
• Habibi, A.; Eskandari, K.; Alizadeh, A. Synthesis and Dynamic NMR Study of New Stable Ylides Derived from the Reaction of Triphenylphosphine, Dialkyl Acetylenedicarboxylates, and 5- ACYL Meldrum’s Acid. Phosphorus Sulfur Silicon Relat. Elem. 2012, 187, 9, 1109–1117. DOI: 10.1080/10426507.2012.668988.
   Web of Science ®Google Scholar
• Awad, m. K.; Abdel-Aal, M. F.; Atlam, F. M.; Hekal, H. A. Molecular Docking, Molecular Modeling, Vibrational and Biological Studies of Some New Heterocyclic α-Aminophosphonates. Spectrochim. Acta A Mol. Biomol. Spectrosc. 2019, 206, 78–88. DOI: 10.1016/j.saa.2018.07.083.
   PubMed Web of Science ®Google Scholar
• Haribabu, Y.; Vasu Govardhana Reddy, P.; Suresh Reddy, C.; Devendranath Reddy, C.; Uma Maheswari Devi, P. Synthesis and Antimicrobial Activity of Novel 2‐Alkyl/Arylcarbamato‐6‐(1,1‐Dimethylethyl)‐3‐Cyclohexyl‐3,4‐Dihydro‐2H‐1,3,2‐Benzoxazaphosphorine‐2‐Oxides. J. Hetero. Chem. 2002, 39, 1039–1044. DOI: 10.1002/jhet.5570390529.
   Web of Science ®Google Scholar
• Morris, G. M.; Huey, R.; Lindstrom, W.; Sanner, M. F.; Belew, R. K.; Goodsell, D. S.; Olson, A. J. AutoDock4 and AutoDockTools4: Automated Docking with Selective Receptor Flexibility. J. Comput. Chem. 2009, 30, 2785–2791. DOI: 10.1002/jcc.21256.
   PubMed Web of Science ®Google Scholar
• Pettersen, E. F.; Goddard, T. D.; Huang, C. C.; Couch, G. S.; Greenblatt, D. M.; Meng, E. C.; Ferrin, T. E. UCSF Chimera-a Visualization System for Exploratory Research and Analysis. J. Comput. Chem. 2004, 25, 1605–1612. DOI: 10.1002/jcc.20084.
   PubMed Web of Science ®Google Scholar