Anti-inflammatory Potentials of Various Oxine Compound Series as Cyclooxygenase-2 (COX-2) and Lipoxygenase (LOX) Inhibitors: Induced-Fit Molecular Docking and Pharmacokinetic Prediction Studies

Tomy Muringayil Joseph, Debarshi Kar Mahapatra

Abstract


The present investigation is an exploration of multiple oxine series in inhibiting crucial anti-inflammatory targets such as cyclooxygenase-2 (COX-2) (PDB ID: 3LN1) and lipoxygenase (LOX) (PDB ID: 1N8Q) by employing the Glide module of Maestro 9.1 software for induced fit docking (IFD). The study also focuses in exploration towards the essential pharmacokinetic parameters (QPlogPo/w, QPlogS, predicted aqueous solubility, QPPCaco, QPPMDCK, and percentage of human oral absorption). The study highlighted the prime importance of oxine-based hererocycles in the upcoming anti-inflammatory drug discovery research programs and their further development as emerging candidates in the near future.
Keywords: Oxine, docking, anti-inflammatory, COX-2, LOX

Cite this Article

Joseph TM, Mahapatra DK. Anti-inflammatory Potentials of Various Oxine Compound Series as Cyclooxygenase-2 (COX-2) and Lipoxygenase (LOX) Inhibitors: Induced-Fit Molecular Docking and Pharmacokinetic Prediction Studies. Research & Reviews: Journal of Computational Biology. 2018; 7(3):
16-23p.


Keywords


Oxine, Docking, Anti-inflammatory, COX-2, LOX, Pharmacokinetics

Full Text:

PDF

References


Chhajed SS, Upasani C, Wadher SJ, Mahapatra DK. Medicinal Chemistry. 1st Ed. Career Publications Private Limited, Nashik, 2017.

Mahapatra DK, Bharti SK. Drug Design. 1st Ed. Tara Publications Private Limited, New Delhi, 2016.

Mahapatra D.K., Bharti S.K. Handbook of Research on Medicinal Chemistry. 1st Ed. Apple Academic Press, New Jersey, 2017.

Mahapatra DK, Bharti SK, Asati V. Chalcone derivatives: Anti-inflammatory potential and molecular targets perspectives. Curr Top Med Chem. 2017; 17(28): 3146-3169p.

Smith CW, Bailey JM, Billingham ME, Chandrasekhar S, Dell CP, Harvey AK, Hicks CA, Kingston AE, Wishart GN. The anti-rheumatic potential of a series of 2, 4-di-substituted-4H-naphtho [1, 2-b] pyran-3-carbonitriles. Bioorg Med Chem Lett. 1995; 5(23): 2783-2788p.

Nandakumar A, Thirumurugan P, Perumal PT, Vembu P, Ponnuswamy MN, Ramesh P. One-pot multicomponent synthesis and anti-microbial evaluation of 2′-(indol-3-yl)-2-oxospiro (indoline-3, 4′-pyran) derivatives. Bioorg Med Chem Lett. 2010; 20(14): 4252-4258p.

Kasaplar P, Yılmazer Ö, Çağır A. 6-Bicycloaryl substituted (S)-and (R)-5, 6-dihydro-2H-pyran-2-ones: Asymmetric synthesis, and anti-proliferative properties. Bioorg Med Chem Lett. 2009; 17(1): 311-318p.

Archer RA, inventor; Eli Lilly and Co Ltd (GB), assignee. Hexahydro-dibenzo {8 b, d {9 pyran-9-ones as an anti-anxiety drug. United States Patent US3928598, 1975.

Coudert P, Couquelet JM, Bastide J, Marion Y, Fialip J. Synthesis and anti-allergic properties of N-arylnitrones with furo-pyran structure. Ann Pharm Franc. 1998; 46(2): 91p.

Mohareb RM, Zaki MY, Abbas NS. Synthesis, anti-inflammatory and anti-ulcer evaluations of thiazole, thiophene, pyridine and pyran derivatives derived from androstenedione. Steroids. 2015; 98: 80-91p.

El-Sayed NN, Abdelaziz MA, Wardakhan WW, Mohareb RM. The Knoevenagel reaction of cyanoacetylhydrazine with pregnenolone: Synthesis of thiophene, thieno [2, 3-d] pyrimidine, 1, 2, 4-triazole, pyran and pyridine derivatives with anti-inflammatory and anti-ulcer activities. Steroids. 2016; 107: 98-111p.

Archer RA, inventor; Eli Lilly and Co Ltd (GB), assignee. Hexahydro-dibenzo [b, d,] pyran-9-ones as psychotropic, particularly anti-depressant drugs. United States Patent US3953603, 1976.

Mohareb RM, Schatz J. Anti-tumor and anti-leishmanial evaluations of 1, 3, 4-oxadiazine, pyran derivatives derived from cross-coupling reactions of β-bromo-6H-1, 3, 4-oxadiazine derivatives. Bioorg Med Chem. 2011; 19(8): 2707-2713p.

Evans JM, Buckingham RE, Willcocks K, inventors; Beecham Group PLC, assignee. Anti-hypertensive benzo [b] pyran-3-ols. United States Patent US 4,555,509, 1985.

Morahan PS, McCord RS. Resistance to herpes simplex type 2 virus induced by an immunopotentiator (pyran) in immunosuppressed mice. J Immunol. 1975; 115(1): 311-313p.

Kharkwal G, Fatima I, Kitchlu S, Singh B, Hajela K, Dwivedi A. Anti-implantation effect of 2-[piperidinoethoxyphenyl]-3-[4-hydroxyphenyl]-2H-benzo (b) pyran, a potent antiestrogenic agent in rats. Fert Ster. 2011; 95(4): 1322-1327p.

Gopalsamy A, Aplasca A, Ciszewski G, Park K, Ellingboe JW, Orlowski M, Feld B, Howe AY. Design and synthesis of 3, 4-dihydro-1H-[1]-benzothieno [2, 3-c] pyran and 3, 4-dihydro-1H-pyrano [3, 4-b] benzofuran derivatives as non-nucleoside inhibitors of HCV NS5B RNA dependent RNA polymerase. Bioorg Med Chem Lett. 2006; 16(2): 457-460p.

Ferreira SB, de Carvalho da Silva F, Bezerra FA, Lourenco M, Kaiser CR, Pinto AC, Ferreira VF. Synthesis of α‐and β‐Pyran Naphthoquinones as a New Class of Antitubercular Agents. Archiv Pharm. 2010; 343(2): 81-90.

Su CR, Yeh SF, Liu CM, Damu AG, Kuo TH, Chiang PC, Bastow KF, Lee KH, Wu TS. Anti-HBV and cytotoxic activities of pyranocoumarin derivatives. Bioorg Med Chem. 2009; 17(16): 6137-6143p.

Hamilton HW, Tait BD, Gajda C, Hagen SE, Ferguson D, Lunney EA, Pavlovsky A, Tummino PJ. 6-Phenyl-6-alkylamido-5, 6-dihydro-2H-pyran-2-ones: novel HIV protease inhibitors. Bioorg Med Chem Lett. 1996; 6(6): 719-724p.

Rho HS, Baek HS, You JW, Kim SJ, Lee JY, Kim DH, Chang IS. New 5-hydroxy-2-(hydroxymethyl)-4H-pyran-4-one derivative has both tyrosinase inhibitory and antioxidant properties. Bull Korean Chem Soc. 2007; 28(3): 471-473p.

Archer RA, Lemberger L, inventors; Eli Lilly and Co Ltd (GB), assignee. Hexahydro-dibenzo [b, d] pyran-9-ones as antiemetic drugs. United States Patent US4087545, 1978.

Wei YB, Yang XD. Synthesis, characterization and anti-diabetic therapeutic potential of a new benzyl acid-derivatized kojic acid vanadyl complex. Biometals. 2012; 25(6): 1261-1268p.

Mahapatra DK, Das D, Shivhare RS. Substituted thiazole linked murrayanine-Schiff’s base derivatives as potential anti-breast cancer candidates: Future EGFR Kinase inhibitors. Int J Pharm Sci Drug Res. 2017; 9(3): 139-144p.

Chhajed SS, Chaskar S, Kshirsagar SK, Haldar AGM, Mahapatra DK. Rational design and synthesis of some PPAR-γ agonists: substituted benzylideneamino-benzylidene-thiazolidine-2,4-diones. Comp Biol Chem. 2017; 67: 260-265p.

Mahapatra DK, Das D, Shivhare RS, Borkar SS. Murrayanine-hydantoin and -thiohydantoin analogs as promising anti-convulsant agents: Synthesis, Characterization and Molecular Docking Studies. MOJ Bioorg Org Chem. 2018; 2(2): 47-51p.

Joseph TM, Mahapatra DK. A Nascent Step towards the Discovery of New Generation Non-Steroidal Anti-inflammatory Agents (NSAIDs): Induced-Fit Molecular Docking and Pharmacokinetic Prediction Studies of Some Chromene Derivatives as Potential Cyclooxygenase-2 (COX-2) and Lipoxygenase (LOX) Inhibitors. Res Rev J Boinformat. 2018; 5(2): 1-7p.




DOI: https://doi.org/10.37591/rrjocb.v7i3.508

Refbacks

  • There are currently no refbacks.