Login Register Cart 0
Generic placeholder image

Medicinal Chemistry

Editor-in-Chief

ISSN (Print): 1573-4064
ISSN (Online): 1875-6638

Back
Journal Home About Journal Editorial Board Journal Insight Current Issue Volumes/Issues
Subscribe
Research Article

Synthesis, Molecular Docking Studies and Biological Evaluation of Thiazolyl Hydrazone Derivatives of Chromone-3-carbaldehyde as Potent Anti-Oxidant and Anti-Inflammatory Agents

Author(s): Rakhi Gawali*, Raghunath Bhosale, Rohit Bavi, Shravan Jadhav and Nargisbano Peerzade

Volume 20, Issue 8, 2024

Published on: 26 April, 2024

Page: [818 - 830] Pages: 13

DOI: 10.2174/0115734064293848240408085039

Price: $65

Abstract

Introduction: A series of 15 thiazolyl hydrazone derivatives of chromone-3- carbaldehyde have been designed and synthesized by the cyclization of thiosemicarbazone derivatives of chromone-3-carbaldehydes with 4’-substituted-2-bromo acetophenones.

Method: All these derivatives were evaluated for antioxidant activity by their direct scavenging activity objects to reactive oxygen species such as DPPH, and nitric oxide, as well as in vitro antiinflammatory activity by a protein denaturation method. Most of these synthesized compounds have shown significant antioxidant activity, among which the compounds 5b, 5c, 5e, 5g, and 5j showed very good antioxidant activities in comparison with the standard ascorbic acid. The in vitro anti-inflammatory activity revealed that the compounds 5b, 5g, and 5h possessed significant activity compared to standard diclofenac sodium.

Result: Additionally, molecular docking studies of these molecules using ovalbumin as the protein showed remarkable interactions with its active site residues, and the results indicated that the binding mode of these compounds closely resembled that of the reference compound, diclofenac sodium.Thus, these compounds represent an attractive template for the evaluation of new antiinflammatory and antioxidant agents and might be useful for exploring new therapeutic tools.

Conclusion: Thus, these compounds represent an attractive template for the evaluation of new antiinflammatory and antioxidant agents and might be useful for exploring new therapeutic tools.

« Previous Next »
[1]
Tripathi, K.D. Essentials of medical pharmacology In: Jaypee Brothers Medical Publishers: Ltd, 6th ed;; New Delhi, 2008.
[http://dx.doi.org/10.5005/jp/books/10282]
[2]
Bennett, P.N.; Brown, M.J. Clinical pharmacology, 13th ed; Churchill Livingstone: New Delhi, 2005.
[3]
Chawla, A.S.; Handa, S.S.; Sharma, A.K.; Kaith, B.S. Plant anti-inflammatory agents. J. Sci. Ind. Res., 1987, 46, 214-223.
[4]
Shen, T.Y. Toward more selective antiarthritic therapy. J. Med. Chem., 1981, 24(1), 1-5.
[http://dx.doi.org/10.1021/jm00133a001] [PMID: 7205864]
[5]
Okeke, E.S.; Enechi, O.C.; Nwankwo, N.E.; Nwodo, O.F.C. Evaluation of the phytochemical constituents and anti-inflammatory potential of Fagara zanthoxyloides root-bark using in vivo and in vitro models, pharmacol. Online, 2019, 2, 212-224.
[6]
Reuter, S.; Gupta, S.C.; Chaturvedi, M.M.; Aggarwal, B.B. Oxidative stress, inflammation, and cancer: How are they linked? Free Radic. Biol. Med., 2010, 49(11), 1603-1616.
[http://dx.doi.org/10.1016/j.freeradbiomed.2010.09.006] [PMID: 20840865]
[7]
Davies, K.J.A. Oxidative stress: The paradox of aerobic life. Biochem. Soc. Symp., 1995, 61, 1-31.
[http://dx.doi.org/10.1042/bss0610001] [PMID: 8660387]
[8]
Domej, W.; Oetll, K.; Renner, W. Oxidative stress and free radicals in COPD: Implications and relevance for treatment. Int. J. Chron. Obstruct. Pulmon. Dis., 2014, 9, 1207-1224.
[http://dx.doi.org/10.2147/COPD.S51226] [PMID: 25378921]
[9]
Valko, M.; Leibfritz, D.; Moncol, J.; Cronin, M.T.D.; Mazur, M.; Telser, J. Free radicals and antioxidants in normal physiological functions and human disease. Int. J. Biochem. Cell Biol., 2007, 39(1), 44-84.
[http://dx.doi.org/10.1016/j.biocel.2006.07.001] [PMID: 16978905]
[10]
Sies, H. Oxidative stress: Oxidants and antioxidants. Exp. Physiol., 1997, 82(2), 291-295.
[http://dx.doi.org/10.1113/expphysiol.1997.sp004024] [PMID: 9129943]
[11]
Stadtman, E.R. Protein oxidation and aging. Science, 1992, 257(5074), 1220-1224.
[http://dx.doi.org/10.1126/science.1355616] [PMID: 1355616]
[12]
Schieber, M.; Chandel, N.S. ROS function in redox signaling and oxidative stress. Curr. Biol., 2014, 24(10), R453-R462.
[http://dx.doi.org/10.1016/j.cub.2014.03.034] [PMID: 24845678]
[13]
Rhee, S.G. Cell signaling. H2O2, a necessary evil for cell signaling. Science, 2006, 312(5782), 1882-1883.
[http://dx.doi.org/10.1126/science.1130481] [PMID: 16809515]
[14]
Farghaly, A.A.; Bekhit, A.A.; Young Park, J. Design and synthesis of some oxadiazolyl, thiadiazolyl, thiazolidinyl, and thiazolyl derivatives of 1H-pyrazole as anti-inflammatory antimicrobial agents. Arch. Pharm., 2000, 333(2-3), 53-57.
[http://dx.doi.org/10.1002/(SICI)1521-4184(200002)333:2/3<53:AID-ARDP53>3.0.CO;2-E] [PMID: 10783518]
[15]
Bekhit, A.; Fahmy, H.T.Y.; Rostom, S.A.; Baraka, A.M. Design and synthesis of some substituted 1H-pyrazolyl-thiazolo[4,5-d]pyrimidines as anti-inflammatory–antimicrobial Agents. Eur. J. Med. Chem., 2003, 38(1), 27-36.
[http://dx.doi.org/10.1016/S0223-5234(02)00009-0] [PMID: 12593914]
[16]
Bekhit, A.A.; Fahmy, H.T.Y. Design and synthesis of some substituted 1H-pyrazolyl-oxazolidines or 1H-pyrazolyl-thiazolidines as anti-inflammatory-antimicrobial agents. Arch. Pharm., 2003, 336(2), 111-118.
[http://dx.doi.org/10.1002/ardp.200390007] [PMID: 12761764]
[17]
Bekhit, A.A.; Abdel-Aziem, T. Design, synthesis and biological evaluation of some pyrazole derivatives as anti-inflammatory-antimicrobial agents. Bioorg. Med. Chem., 2004, 12(8), 1935-1945.
[http://dx.doi.org/10.1016/j.bmc.2004.01.037] [PMID: 15051061]
[18]
Bekhit, A.A.; Ashour, H.M.A.; Guemei, A.A. Novel pyrazole derivatives as potential promising anti-inflammatory antimicrobial agents. Arch. Pharm., 2005, 338(4), 167-174.
[http://dx.doi.org/10.1002/ardp.200400940] [PMID: 15864786]
[19]
Bekhit, A.A.; Abdel-Rahman, H.M.; Guemei, A.A. Synthesis and biological evaluation of some hydroxypyrazole derivatives as anti-inflammatory-antimicrobial agents. Arch. Pharm., 2006, 339(2), 81-87.
[http://dx.doi.org/10.1002/ardp.200500197] [PMID: 16470641]
[20]
Kashid, B.B.; Ghanwat, A.A.; Khedkar, V.M.; Dongare, B.B.; Shaikh, M.H.; Deshpande, P.P.; Wakchaure, Y.B. Design, synthesis, in vitro antimicrobial, antioxidant evaluation, and molecular docking study of novel benzimidazole and benzoxazole derivatives. J. Heterocycl. Chem., 2019, 56(3), 895-908.
[http://dx.doi.org/10.1002/jhet.3467]
[21]
Gawali, R.; Bhosale, R.; Nagesh, N.; Masand, V.H.; Jadhav, S.; Zaki, M.E.A.; Al-Hussain, S.A. Design, synthesis, docking studies and biological screening of 2-pyrimidinyl-2, 3-dihydro-1H-naphtho [1, 2-e][1, 3] oxazines as potent tubulin polymerization inhibitors. J. Biomol. Struct. Dyn., 2023.
[http://dx.doi.org/10.1080/07391102.2023.2266766]
[22]
Jadhav, S.; Peerzade, N.; Gawali, R.; Bhosale, R.; Kulkarni, A.; Varpe, B. Green synthesis and biological screening of some fluorinated pyrazole chalcones in search of potent anti-inflammatory and analgesic agents. Egypt. Pharm. J., 2020, 19(2), 172-181.
[http://dx.doi.org/10.4103/epj.epj_64_19]
[23]
Jadhav, S.Y.; Shirame, S.P.; Kulkarni, S.D.; Patil, S.B.; Pasale, S.K.; Bhosale, R.B. PEG mediated synthesis and pharmacological evaluation of some fluoro substituted pyrazoline derivatives as antiinflammatory and analgesic agents. Bioorg. Med. Chem. Lett., 2013, 23(9), 2575-2578.
[http://dx.doi.org/10.1016/j.bmcl.2013.02.105] [PMID: 23541672]
[24]
Peerzade, N.A.; Jadhav, S.Y.; Bhosale, R.B. Synthesis, molecular docking and biological evaluation of some novel N-carbamoyl pyrazolines as potent anti-inflammatory, antioxidant and antidiabetic agents. Rasayan J. Chem., 2020, 13(3), 1401-1411.
[http://dx.doi.org/10.31788/RJC.2020.1335637]
[25]
Patil, V.M.; Masand, N.; Verma, S.; Masand, V. Chromones: Privileged scaffold in anticancer drug discovery. Chem. Biol. Drug Des., 2021, 98(5), 943-953.
[http://dx.doi.org/10.1111/cbdd.13951] [PMID: 34519163]
[26]
Jovanovic, S.V.; Steenken, S.; Tosic, M.; Marjanovic, B.; Simic, M.G. Flavonoids as antioxidants. J. Am. Chem. Soc., 1994, 116(11), 4846-4851.
[http://dx.doi.org/10.1021/ja00090a032]
[27]
Grindlay, D.; Reynolds, T. The Aloe vera phenomenon: A review of the properties and modern uses of the leaf parenchyma gel. J. Ethnopharmacol., 1986, 16(2-3), 117-151.
[http://dx.doi.org/10.1016/0378-8741(86)90085-1] [PMID: 3528673]
[28]
Martens, S.; Mithöfer, A. Flavones and flavone synthases. Phytochemistry, 2005, 66(20), 2399-2407.
[http://dx.doi.org/10.1016/j.phytochem.2005.07.013] [PMID: 16137727]
[29]
Kuroda, M.; Uchida, S.; Watanabe, K.; Mimaki, Y. Chromones from the tubers of Eranthis cilicica and their antioxidant activity. Phytochemistry, 2009, 70(2), 288-293.
[http://dx.doi.org/10.1016/j.phytochem.2008.12.002] [PMID: 19162283]
[30]
Zhou, T.; Shi, Q.; Lee, K.H. Anti-AIDS agents 83. Efficient microwave-assisted one-pot preparation of angular 2,2-dimethyl-2H-chromone containing compounds. Tetrahedron Lett., 2010, 51(33), 4382-4386.
[http://dx.doi.org/10.1016/j.tetlet.2010.06.058] [PMID: 20936082]
[31]
Parmar, N.S.; Tariq, M.; Ageel, A.M. Effect of thromboxane A2 and leukotriene C4 inhibitors on the experimentally induced gastric lesions in the rat. Res. Commun. Chem. Pathol. Pharmacol., 1987, 58(1), 15-25.
[PMID: 3432732]
[32]
Gamal-Eldeen, A.M.; Djemgou, P.C.; Tchuendem, M.; Ngadjui, B.T.; Tane, P.; Toshifumi, H. Anti-cancer and immunostimulatory activity of chromones and other constituents from Cassia petersiana. Z. Naturforsch. C J. Biosci., 2007, 62(5-6), 331-338.
[http://dx.doi.org/10.1515/znc-2007-5-622] [PMID: 17708436]
[33]
Binbuga, N.; Ruhs, C.; Hasty, J.K.; Henry, W.P.; Schultz, T.P. Developing environmentally benign and effective organic wood preservatives by understanding the biocidal and non-biocidal properties of extractives in naturally durable heartwood. hfsg, 2008, 62(3), 264-269.
[http://dx.doi.org/10.1515/HF.2008.038]
[34]
Maho, S.; Yoshiyuki, K. Enhancing effects of a chromone glycoside, eucryphin, isolated from Astilbe rhizomes on burn wound repair and its mechanism. Phytomedicine, 2010, 17(10), 820-829.
[http://dx.doi.org/10.1016/j.phymed.2010.01.010]
[35]
Gábor, M. Anti-inflammatory and anti-allergic properties of flavonoids. Prog. Clin. Biol. Res., 1986, 213, 471-480.
[PMID: 2872680]
[36]
Djemgou, P.C.; Gatsing, D.; Tchuendem, M.; Ngadjui, B.T.; Tane, P.; Ahmed, A.A.; Gamal-Eldeen, A.M.; Adoga, G.I.; Hirata, T.; Mabry, T.J. Antitumor and immunostimulatory activity of two chromones and other constituents from Cassia Petersiana. Nat. Prod. Commun., 2006, 1(11), 1934578X0600101.
[http://dx.doi.org/10.1177/1934578X0600101109]
[37]
Borges, M.L.; Matos, O.C.; Pais, I.; De Melo, J.S.; Ricardo, C.P.; MacAnita, A.; Becker, R.S. Evaluation of a broad variety of coumarins, chromones, their furohomologues and thione analogues as phototoxins activated by UVA and visible light. Pestic. Sci., 1995, 44(2), 155-162.
[http://dx.doi.org/10.1002/ps.2780440208]
[38]
Marder, M.; Viola, H.; Bacigaluppo, J.A.; Colombo, M.I.; Wasowski, C.; Wolfman, C.; Medina, J.H.; Rúveda, E.A.; Paladini, A.C. Detection of benzodiazepine receptor ligands in small libraries of flavone derivatives synthesized by solution phase combinatorial chemistry. Biochem. Biophys. Res. Commun., 1998, 249(2), 481-485.
[http://dx.doi.org/10.1006/bbrc.1998.9146] [PMID: 9712722]
[39]
Keri, R.S.; Budagumpi, S.; Pai, R.K.; Balakrishna, R.G. Chromones as a privileged scaffold in drug discovery: A review. Eur. J. Med. Chem., 2014, 78, 340-374.
[http://dx.doi.org/10.1016/j.ejmech.2014.03.047] [PMID: 24691058]
[40]
Foltínová, P.; Lácová, M.; Loos, D. Activity of some 3-formylchromone derivatives on the induction of chloroplast-free mutants in Euglena gracilis. Farmaco, 2000, 55(1), 21-26.
[http://dx.doi.org/10.1016/S0014-827X(99)00114-7] [PMID: 10755227]
[41]
Abdel-Wahab, B.F.; Awad, G.E.A.; Badria, F.A. Synthesis, antimicrobial, antioxidant, anti-hemolytic and cytotoxic evaluation of new imidazole-based heterocycles. Eur. J. Med. Chem., 2011, 46(5), 1505-1511.
[http://dx.doi.org/10.1016/j.ejmech.2011.01.062] [PMID: 21353349]
[42]
Sah, P.P.T.; Peoples, S.A. Isonicotinyl hydrazones as antitubercular agents and derivatives for identification of aldehydes and ketones. J. Am. Pharm. Assoc., 1954, 43(9), 513-524.
[http://dx.doi.org/10.1002/jps.3030430902] [PMID: 13201471]
[43]
Gemma, S.; Kukreja, G.; Fattorusso, C.; Persico, M.; Romano, M.P.; Altarelli, M.; Savini, L.; Campiani, G.; Fattorusso, E.; Basilico, N.; Taramelli, D.; Yardley, V.; Butini, S. Synthesis of N1-arylidene-N2-quinolyl- and N2-acrydinylhydrazones as potent antimalarial agents active against CQ-resistant P. falciparum strains. Bioorg. Med. Chem. Lett., 2006, 16(20), 5384-5388.
[http://dx.doi.org/10.1016/j.bmcl.2006.07.060] [PMID: 16890433]
[44]
Todeschini, A.R.; de Miranda, A.L.P.; da Silva, K.C.M.; Parrini, S.C.; Barreiro, E.J. Synthesis and evaluation of analgesic, antiinflammatory and antiplatelet properties of new 2-pyridylarylhydrazone derivatives. Eur. J. Med. Chem., 1998, 33(3), 189-199.
[http://dx.doi.org/10.1016/S0223-5234(98)80008-1]
[45]
Al-Said, M.S.; Bashandy, M.S.; Al-qasoumi, S.I.; Ghorab, M.M. Anti-breast cancer activity of some novel 1,2-dihydropyridine, thiophene and thiazole derivatives. Eur. J. Med. Chem., 2011, 46(1), 137-141.
[http://dx.doi.org/10.1016/j.ejmech.2010.10.024] [PMID: 21093116]
[46]
Shirinzadeh, H.; Neuhaus, E.; Ince Erguc, E.; Tascioglu Aliyev, A.; Gurer-Orhan, H.; Suzen, S. New indole-7-aldehyde derivatives as melatonin analogues; synthesis and screening their antioxidant and anticancer potential. Bioorg. Chem., 2020, 104, 104219.
[http://dx.doi.org/10.1016/j.bioorg.2020.104219] [PMID: 32916391]
[47]
Wilson, K.J.; Illig, C.R.; Subasinghe, N.; Hoffman, J.B.; Jonathan Rudolph, M.; Soll, R.; Molloy, C.J.; Bone, R.; Green, D.; Randall, T.; Zhang, M.; Lewandowski, F.A.; Zhou, Z.; Sharp, C.; Maguire, D.; Grasberger, B.; DesJarlais, R.L.; Spurlino, J. Synthesis of thiophene-2-carboxamidines containing 2-amino-thiazoles and their biological evaluation as urokinase inhibitors. Bioorg. Med. Chem. Lett., 2001, 11(7), 915-918.
[http://dx.doi.org/10.1016/S0960-894X(01)00102-0] [PMID: 11294390]
[48]
Kaushik, D.; Khan, S.A.; Chawla, G.; Kumar, S.N. ′-[(5-chloro-3-methyl-1-phenyl-1H-pyrazol-4-yl)methylene] 2/4-substituted hydrazides: Synthesis and anticonvulsant activity. Eur. J. Med. Chem., 2010, 45(9), 3943-3949.
[http://dx.doi.org/10.1016/j.ejmech.2010.05.049] [PMID: 20573423]
[49]
Ergenç, N.; Günay, N.S.; Demirdamar, R. Synthesis and antidepressant evaluation of new 3-phenyl-5-sulfonamidoindole derivatives. Eur. J. Med. Chem., 1998, 33(2), 143-148.
[http://dx.doi.org/10.1016/S0223-5234(98)80039-1]
[50]
Silva, A.G.; Zapata-Sudo, G.; Kummerle, A.E.; Fraga, C.A.M.; Barreiro, E.J.; Sudo, R.T. Synthesis and vasodilatory activity of new N-acylhydrazone derivatives, designed as LASSBio-294 analogues. Bioorg. Med. Chem., 2005, 13(10), 3431-3437.
[http://dx.doi.org/10.1016/j.bmc.2005.03.003] [PMID: 15848755]
[51]
Heldebrant, D.J.; Jessop, P.G. Liquid poly(ethylene glycol) and supercritical carbon dioxide: a benign biphasic solvent system for use and recycling of homogeneous catalysts. J. Am. Chem. Soc., 2003, 125(19), 5600-5601.
[http://dx.doi.org/10.1021/ja029131l] [PMID: 12733876]
[52]
Bondock, S.; Khalifa, W.; Fadda, A.A. Synthesis and antimicrobial evaluation of some new thiazole, thiazolidinone and thiazoline derivatives starting from 1-chloro-3,4-dihydronaphthalene-2-carboxaldehyde. Eur. J. Med. Chem., 2007, 42(7), 948-954.
[http://dx.doi.org/10.1016/j.ejmech.2006.12.025] [PMID: 17316908]
[53]
Silva, G.A.; Costa, L.M.M.; Brito, F.C.F.; Miranda, A.L.P.; Barreiro, E.J.; Fraga, C.A.M. New class of potent antinociceptive and antiplatelet 10H-phenothiazine-1-acylhydrazone derivatives. Bioorg. Med. Chem., 2004, 12(12), 3149-3158.
[http://dx.doi.org/10.1016/j.bmc.2004.04.009] [PMID: 15158783]
[54]
Tomi, I.H.R.; Tomma, J.H.; Al-Daraji, A.H.R.; Al-Dujaili, A.H. Synthesis, characterization and comparative study the microbial activity of some heterocyclic compounds containing oxazole and benzothiazole moieties. J. Saudi Chem. Soc., 2015, 19(4), 392-398.
[http://dx.doi.org/10.1016/j.jscs.2012.04.010]
[55]
Tiperciuc, B.; Pârvu, A.; Tamaian, R.; Nastasă, C.; Ionuţ, I.; Oniga, O. New anti-inflammatory thiazolyl-carbonyl-thiosemicarbazides and thiazolyl-azoles with antioxidant properties as potential iNOS inhibitors. Arch. Pharm. Res., 2013, 36(6), 702-714.
[http://dx.doi.org/10.1007/s12272-013-0083-9] [PMID: 23504664]
[56]
Koca, İ.; Gumuş, M.; Özgür, A.; Dişli, A.; Tutar, Y. A novel approach to inhibit heat shock response as anticancer strategy by coumarine compounds containing thiazole skeleton. Anticancer. Agents Med. Chem., 2015, 15(7), 916-930.
[http://dx.doi.org/10.2174/1871520615666150407155623] [PMID: 25846761]
[57]
Telvekar, V.N.; Bairwa, V.K.; Satardekar, K.; Bellubi, A. Novel 2-(2-(4-aryloxybenzylidene) hydrazinyl)benzothiazole derivatives as anti-tubercular agents. Bioorg. Med. Chem. Lett., 2012, 22(1), 649-652.
[http://dx.doi.org/10.1016/j.bmcl.2011.10.064] [PMID: 22079026]
[58]
Lupascu, F.; Dragostin, O.; Foia, L.; Lupascu, D.; Profire, L. The synthesis and the biological evaluation of new thiazolidin-4-one derivatives containing a xanthine moiety. Molecules, 2013, 18(8), 9684-9703.
[http://dx.doi.org/10.3390/molecules18089684] [PMID: 23945643]
[59]
Gomha, S.; Badrey, M.; Abdalla, M.; Arafa, R. Novel anti-HIV-1 NNRTIs based on a pyrazolo[4,3-d]isoxazole backbone scaffold: design, synthesis and insights into the molecular basis of action. MedChemComm, 2014, 5(11), 1605-1692.
[http://dx.doi.org/10.1039/C4MD00282B]
[60]
Gawali, R.; Trivedi, J.; Bhansali, S.; Bhosale, R.; Sarkar, D.; Design, D.M. Synthesis, docking studies and biological screening of 2-thiazolyl substituted -2,3-dihydro-1H-naphth [1,2-e][1,3] oxazines as potent HIV-1 reverse transcriptase inhibitors. Eur. J. Med. Chem., 2018, 157, 310-319.
[http://dx.doi.org/10.1016/j.ejmech.2018.07.067]
[61]
Gawali, R.; Bhosale, R. Synthesis and characterization of novel phthalazinyl hydrazones of furan-2-carbaldehyde. Indian Streams Res. J., 2023, 8(9)
[62]
Alsantali, R.I.; Mughal, E.U.; Naeem, N.; Alsharif, M.A.; Sadiq, A.; Ali, A.; Jassas, R.S.; Javed, Q.; Javid, A.; Sumrra, S.H.; Alsimaree, A.A.; Zafar, M.N.; Asghar, B.H.; Altass, H.M.; Moussa, Z.; Ahmed, S.A. Flavone-based hydrazones as new tyrosinase inhibitors: Synthetic imines with emerging biological potential, SAR, molecular docking and drug-likeness studies. J. Mol. Struct., 2022, 1251, 131933.
[http://dx.doi.org/10.1016/j.molstruc.2021.131933]
[63]
Gulcin, İ.; Alwasel, S.H. DPPH radical scavenging assay. Processes, 2023, 11(8), 2248.
[http://dx.doi.org/10.3390/pr11082248]
[64]
Jones, G.; Willett, P.; Glen, R.C.; Leach, A.R.; Taylor, R. Development and validation of a genetic algorithm for flexible docking 1. J. Mol. Biol., 1997, 267(3), 727-748.
[http://dx.doi.org/10.1006/jmbi.1996.0897] [PMID: 9126849]
[65]
Verdonk, M.L.; Cole, J.C.; Hartshorn, M.J.; Murray, C.W.; Taylor, R.D. Improved protein–ligand docking using GOLD. Proteins, 2003, 52(4), 609-623.
[http://dx.doi.org/10.1002/prot.10465] [PMID: 12910460]
[66]
Stein, P.E.; Leslie, A.G.W.; Finch, J.T.; Carrell, R.W. Crystal structure of uncleaved ovalbumin at 1•95 Å resolution. J. Mol. Biol., 1991, 221(3), 941-959.
[http://dx.doi.org/10.1016/0022-2836(91)80185-W] [PMID: 1942038]
[67]
Tyagi, S.; Mishra, R.; Mazumder, A.; Jindaniya, V. Vilsmeier haack reaction: An exemplary tool for synthesis of different heterocycles. Lett. Org. Chem., 2024, 21(2), 131-148.
[http://dx.doi.org/10.2174/1570178620666230911152937]
[68]
Nalla, V.; Shaikh, A.; Bapat, S.; Vyas, R.; Karthikeyan, M.; Yogeeswari, P.; Sriram, D.; Muthukrishnan, M. Identification of potent chromone embedded [1,2,3]-triazoles as novel anti-tubercular agents. R. Soc. Open Sci., 2018, 5(4), 171750.
[http://dx.doi.org/10.1098/rsos.171750] [PMID: 29765644]
[69]
Wang, B.; Yang, Z.Y.; Lü, M.; Hai, J.; Wang, Q.; Chen, Z.N. Synthesis, characterization, cytotoxic activity and DNA binding Ni(II) complex with the 6-hydroxy chromone-3-carbaldehyde thiosemicarbazone. J. Organomet. Chem., 2009, 694(25), 4069-4075.
[http://dx.doi.org/10.1016/j.jorganchem.2009.08.024]
[70]
Gawali, R.; Phadatare, R. One pot synthesis of thiazolyl hydrazine derivatives and their characterization. Eur. Chem. Bull., 2021, 10, 157-162.
[http://dx.doi.org/10.53555/ecb/2021.10.1.04]
[71]
Kaplancıklı, Z.A.; Sever, B.; Altıntop, M.D.; Atlı, O.; Baysal, M.; Ozdemir, A. Synthesis and evaluation of new thiazolyl hydrazone derivatives as potential anticancer agents. Lett. Drug Des. Discov., 2017, 14(6), 672-677.
[http://dx.doi.org/10.2174/1570180814666161104161711]
[72]
Madhuranga, H.D.T.; Samarakoon, D.N.A.W. In vitro anti-inflammatory egg albumin denaturation assay: An enhanced approach. Nat. Ayurvedic Med., 2023, 7, 1-6.
[http://dx.doi.org/10.23880/jonam-16000410]
[73]
Berbert, A.A.; Kondo, C.R.M.; Almendra, C.L.; Matsuo, T.; Dichi, I. Supplementation of fish oil and olive oil in patients with rheumatoid arthritis. Nutrition, 2005, 21(2), 131-136.
[http://dx.doi.org/10.1016/j.nut.2004.03.023] [PMID: 15723739]
[74]
Geronikaki, A.; Gavalas, A. Antioxidants and inflammatory disease: Synthetic and natural antioxidants with anti-inflammatory activity. Comb. Chem. High Throughput Screen., 2006, 9(6), 425-442.
[http://dx.doi.org/10.2174/138620706777698481] [PMID: 16842224]
[75]
Bavi, R.; Kumar, R.; Choi, L.; Woo Lee, K. Exploration of novel inhibitors for Bruton’s tyrosine kinase by 3D QSAR modeling and molecular dynamics simulation. PLoS One, 2016, 11(1), e0147190.
[http://dx.doi.org/10.1371/journal.pone.0147190] [PMID: 26784025]
[76]
Kumar, R.; Parameswaran, S.; Bavi, R.; Baek, A.; Son, M.; Rampogu, S.; Park, C.; Lee, G.; Zeb, A.; Parate, S.; Rana, R.M.; Lee, K.W. Investigation of novel chemical scaffolds targeting prolyl oligopeptidase for neurological therapeutics. J. Mol. Graph. Model., 2019, 88, 92-103.
[http://dx.doi.org/10.1016/j.jmgm.2018.12.006] [PMID: 30665156]
[77]
Kumar, R.; Son, M.; Bavi, R.; Lee, Y.; Park, C.; Arulalapperumal, V.; Cao, G.P.; Kim, H.; Suh, J.; Kim, Y.; Kwon, Y.J.; Lee, K.W. Novel chemical scaffolds of the tumor marker AKR1B10 inhibitors discovered by 3D QSAR pharmacophore modeling. Acta Pharmacol. Sin., 2015, 36(8), 998-1012.
[http://dx.doi.org/10.1038/aps.2015.17] [PMID: 26051108]

Rights & Permissions Print Cite
© 2024 Bentham Science Publishers | Privacy Policy