Synthesis, molecular docking, and biological evaluation of some novel hydrazones and pyrazole derivatives as anti-inflammatory agents

Chemical Biology and Drug Design

Volumn 84, Issue 4, 2014, Pages 473-488

  Mohammed, Khaled O ^a   Nissan, Yassin M ^a  

^a CAIRO UNIVERSITY   (Egypt)

Author keywords

4 benzenesulfonamide; anti inflammatory; hydrazone; pyrazole

Indexed keywords

ANTIINFLAMMATORY AGENT; CARRAGEENAN; CYCLOOXYGENASE 1; CYCLOOXYGENASE 2; HYDRAZONE DERIVATIVE; PROSTAGLANDIN E2; PROSTAGLANDIN SYNTHASE INHIBITOR; PYRAZOLE; PYRAZOLE DERIVATIVE;

ANIMAL; ANTAGONISTS AND INHIBITORS; BINDING SITE; BLOOD; CHEMICALLY INDUCED; CHEMISTRY; DRUG EFFECTS; EDEMA; ENZYME ACTIVE SITE; MALE; METABOLISM; MOLECULAR DOCKING; RAT; STOMACH; SYNTHESIS; WISTAR RAT;

ANIMALS; ANTI-INFLAMMATORY AGENTS; BINDING SITES; CARRAGEENAN; CATALYTIC DOMAIN; CYCLOOXYGENASE 1; CYCLOOXYGENASE 2; CYCLOOXYGENASE INHIBITORS; DINOPROSTONE; EDEMA; HYDRAZONES; MALE; MOLECULAR DOCKING SIMULATION; PYRAZOLES; RATS; RATS, WISTAR; STOMACH;

EID: 84922660737     PISSN: 17470277     EISSN: 17470285     Source Type: Journal    
DOI: 10.1111/cbdd.12336     Document Type: Article

References (35)

1. Mosely M.J., (1953) The perspective in ACTH and cortisone therapy. J Natl Med Assoc; 45: 192-195.
2. Bjarnason I., Hayllar J., MacPherson A.J., Russell A.S., (1993) Side effects of nonsteroidal anti-inflammatory drugs on the small and large intestine in humans. Gastroenterology; 104: 1832-1874.
3. Forey A., Yonida M., (2002) Treating acute gouty arthritis with selective COX-2 inhibitors. BMJ; 325: 980-981.
4. Hiou G., Farengs M., (2005) Popularity uncovers COX-2 inhibitor side effects. Ann Rheum Dis; 64: 94.
5. Kearney P.M., Baigent C., Godwin J., Halls H., Emberson J.R., Patrono C., (2006) Do selective cyclo-oxygenase-2 inhibitors and traditional non-steroidal anti-inflammatory drugs increase the risk of atherothrombosis? Meta-analysis of randomised trials. BMJ; 332: 1302-1305.
6. Burdan F., Korobowicz A., (2003) Coxibs: highly selective cyclooxygenase-2 inhibitors. Part II. Side effects. Pol Merkur Lekarski; 14: 352-355.
7. Rao1 P.N.P., Knaus E.E., (2008) Evolution of nonsteroidal anti-inflammatory drugs (NSAIDs): cyclooxygenase (COX) inhibition and beyond. J Pharm Pharm Sci; 11: 81s-110s.
8. Travis A.S., (2007) The Chemistry of Anilines Part 1. In Zvi Rappoprt: Wiley-VCH; 764.
9. Friderichs E., Christoph T., Buschmann H., (2005) Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH.
10. Morse H.N., (1878) Ueber eine neue Darstellungsmethode der Acetylamidophenole. Ber Dtsch Chem Ges; 11: 232-233.
11. Jawed H., Shah S.U., Jamall S., Simjee S.U., (2010) N-(2-hydroxy phenyl) acetamide inhibits inflammation-related cytokines and ROS in adjuvant-induced arthritic (AIA) rats. Int Immunopharmacol; 10: 900-905.
12. Berest G.G., Yu Voskoboynik O., Kovalenko S.I., Antypenko O.M., Nosulenko I.S., Katsev A.M., Shandrovskaya O.S., (2011) Synthesis and biological activity of novel N-cycloalkyl-(cycloalkylaryl)-2-[(3-R-2-oxo-2H-[1,2,4]triazino[2,3-c]quinazoline-6-yl)thio]acetamides. Eur J Med Chem; 46: 6066-6074.
13. Khanum S.A., Shashikanth S., Deepak A.V., (2004) Synthesis and anti-inflammatory activity of benzophenone analogues. Bioorg Chem; 32: 211-222.
14. Supuran C.T., Casini A., Scozzafava A., (2003) Protease inhibitors of the sulfonamide type: anticancer, antiinflammatory, and antiviral agents. Med Res Rev; 23: 535-558.
15. Shah S.S., Rivera G., Ashfaq M., (2013) Recent advances in medicinal chemistry of sulfonamides. Rational design as anti-tumoral, anti-bacterial and anti-inflammatory agents. Mini Rev Med Chem; 13: 70-86.
16. Penning T.D., Talley J.J., Bertenshaw S.R., Carter J.S., Collins P.W., Docter S., Graneto M.J., et al,. (1997) Synthesis and biological evaluation of the 1.5 diarylpyrazole class of cyclooxygenase-2 inhibitors: identification of 4-[5-(4-Methylphenyl)-3-(trifluoromethyl)-1H-pyrazole-1-yl]benzenesulfonamide (SC-58634, Celecoxib). J Med Chem; 40: 1347-1365.
17. Sondhi S.M., Dinodiaa M., Kumar A., (2006) Synthesis, anti-inflammatory and analgesic activity evaluation of some amidine and hydrazone derivatives. Bioorg Med Chem; 14: 4657-4663.
18. El-Sayed M.A., Abdel-Aziz N.I., Abdel-Aziz A.A., El-Azab A.S., Asiri Y.A., Eltahir K.E., (2011) Design, synthesis, and biological evaluation of substituted hydrazone and pyrazole derivatives as selective COX-2 inhibitors: molecular docking study. Bioorg Med Chem; 19: 3416-3424.
19. De Oliveira K.N., Souza M.M., Sathler P.C., Magalhães U.O., Rodrigues C.R., Castro H.C., Palm P.R., Sarda M., Perotto P.E., Cezar S., De Brito M.A., Ferreira A.S., Cabral L.M., Machado C., Nunes R.J., (2012) Sulphonamide and sulphonyl-hydrazone cyclic imide derivatives: antinociceptive activity, molecular modeling and In Silico ADMET screening. Arch Pharm Res; 35: 1713-1722.
20. Bashir R., Ovais S., Yaseen S., Hamid H., Alam M.S., Samim M., Singh S., Javed K., (2011) Synthesis of some new 1,3,5-trisubstituted pyrazolines bearing benzenesulfonamide as anticancer and anti-inflammatory agents. Bioorg Med Chem Lett; 21: 4301-4305.
21. Bano S., Javed K., Ahmad S., Rathish I.G., Singh S.M., Alam S., (2001) Synthesis and biological evaluation of some new 2-pyrazolines bearing benzenesulfonamide moiety as potential anti-inflammatory and anti-cancer agents. Eur J Med Chem; 46: 5763-5768.
22. Bekhit A.A., Ashour H.M., Abdel Ghany Y.S., Bekhit A.A., Baraka A., (2008) Synthesis and biological evaluation of some thiazolyl and thiadiazolyl derivatives of 1H-pyrazole as anti-inflammatory antimicrobial agents. Eur J Med Chem; 43: 456-463.
23. Kumar P., Chandak N., Kaushik P., Sharma C., Kaushik D., Aneja K.R., Sharma P.K., (2014) Benzenesulfonamide bearing pyrazolylpyrazolines: synthesis and evaluation as anti-inflammatory-antimicrobial agents. Med Chem Res; 23: 882-895.
24. Winter C.A., Risley E.A., Nuss G.W., (1962) Carrageenin-induced edema in hind paw of the rat as an assay for antiiflammatory drugs. Proc Soc Exp Biol Med; 111: 544-547.
25. Vinegar R., Schreiber W., Hugo R., (1969) Biphasic development of carrageenin edema in rats. J Pharmacol Exp Ther; 166: 96-103.
26. Farman N., Pradelles P., Bonvalet J.P., (1986) Determination of prostaglandin E2 synthesis along rabbit nephron by enzyme immunoassay. Am J Physiol; 251: 238-244.
27. COX (ovine) inhibitor screening assay kit (Catalog No. 560101), Cayman Chemical Co., USA. https://www.caymanchem.com/app/template/Product.vm/catalog/560101 (accessed on April 29th 2014.)
28. Rainsford K.D., (1977) The comparative gastric ulcerogenic activities of non-steroid anti-inflammatory drugs. Agents Actions; 7: 573-577.
29. Addy P.S., Saha B., Singh N.D.P., Das A.K., Lejeune C., Bush J.T., Schofield C.J., Basak A., (2013) 1,3,5-Trisubstituted benzenes as fluorescent photoaffinity probes for human carbonic anhydrase II capture. Chem Commun; 49: 1930-1932.
30. Voskiene A., Mickevicius V., Mikulskiene G., (2007) Synthesis and structural characterization of products condensation 4-carboxy-1-(4-styrylcarbonylphenyl)-2-pyrrolidinones with hydrazines. Arkivoc; 15: 303-314.
31. Rowlinson S., Kiefer J., Prusakiewicz J., Pawlitz J., Kozak K., Kalgutkar A., Stallings W., Kurumbail R., Marnett L., (2003) A novel mechanism of cyclooxygenase-2 inhibition involving interactions with Ser-530 and Tyr-385. J Biol Chem; 278: 45763-45769.
32. Shimokawa T., Kulmacz R., DeWitt D., Smith W., (1990) Tyrosine 385 of prostaglandin endoperoxide synthase is required for cyclooxygenase catalysis. J Biol Chem; 265: 20073-20076.
33. DeWitt D., El-Harith E., Kraemer S., Andrews M., Yao E., Armstrong R., Smith W., (1990) The aspirin and heme-binding sites of ovine and murine prostaglandin endoperoxide synthases. J Biol Chem; 265: 5192-5198.
34. Rieke C., Mulichak A., Garavito R., Smith W., (1999) The role of arginine 120 of human prostaglandin endoperoxide H synthase-2 in the interaction with fatty acid substrates and inhibitors. J Biol Chem; 274: 17109-17114.
35. Gautam R., Karkhile K.V., Bhutani K.K., Jachak S.M., (2010) Anti-inflammatory, cyclooxygenase (COX)-2, COX-1 inhibitory, and free radical scavenging effects of Rumex nepalensis. Planta Med; 76: 1564-1569.