Synthesis of modified steroids as a novel class of non-ulcerogenic, anti-inflammatory and anti-nociceptive agents

dc.AffiliationOctober University for modern sciences and Arts (MSA)
dc.contributor.authorMohareb R.M.
dc.contributor.authorElmegeed G.A.
dc.contributor.authorAbdel-Salam O.M.E.
dc.contributor.authorDoss S.H.
dc.contributor.authorWilliam M.G.
dc.contributor.otherOrganic Chemistry Department
dc.contributor.otherFaculty of Pharmacy
dc.contributor.otherOctober University of Modern Sciences and Arts (MSA)
dc.contributor.otherElwahaat Road
dc.contributor.otherOctober City
dc.contributor.otherEgypt; Chemistry Department
dc.contributor.otherFaculty of Science
dc.contributor.otherCairo University
dc.contributor.otherCario
dc.contributor.otherEgypt; Hormones Department
dc.contributor.otherNational Research Centre
dc.contributor.other12622 Dokki
dc.contributor.otherCairo
dc.contributor.otherEgypt; Toxicology and Narcotics Department
dc.contributor.otherNational Research Centre
dc.contributor.other12622 Dokki
dc.contributor.otherCairo
dc.contributor.otherEgypt
dc.date.accessioned2020-01-25T19:58:30Z
dc.date.available2020-01-25T19:58:30Z
dc.date.issued2011
dc.descriptionScopus
dc.description.abstractThe identification of compounds able to treat both pain and inflammation with limited side effects is one of the prominent goals in biomedical research. This study aimed at the synthesis of new modified steroids with structures justifying non-ulcerogenic, anti-inflammatory and anti-nociceptive activities. The steroid derivatives were synthesized via straightforward and efficient methods and their structures were established based on the analytical and spectral data. The in vivo anti-inflammatory, anti-nociceptive and anti-ulcerogenic activities of some of these compounds were studied. The newly synthesized compounds 8b, 19b, 24 and 31a showed anti-inflammatory, anti-nociceptive and anti-ulcerogenic activity with various intensities. Oedema was significantly reduced by either dose 25 or 50 mg/kg of all tested compounds at 3 and 4 h post-carrageenan. Compound 19b was the most effective in alleviating thermal pain. The analgesic activity of either dose of the compounds 8b, 24, 31a as well as the high dose 19b was significantly higher than that for indomethacin (IND). Gastric mucosal lesions caused in the rats by the administration of 96% EtOH and IND were inhibited by all tested compounds administered at (50 mg/kg) dose in the study. � 2011 Elsevier Inc. All rights reserved.en_US
dc.description.urihttps://www.scimagojr.com/journalsearch.php?q=14805&tip=sid&clean=0
dc.identifier.doihttps://doi.org/10.1016/j.steroids.2011.05.011
dc.identifier.doiPubMed ID 21664368
dc.identifier.issn0039128X
dc.identifier.otherhttps://doi.org/10.1016/j.steroids.2011.05.011
dc.identifier.otherPubMed ID 21664368
dc.identifier.urihttps://t.ly/q2RA9
dc.language.isoEnglishen_US
dc.relation.ispartofseriesSteroids
dc.relation.ispartofseries76
dc.subjectAnti-inflammatoryen_US
dc.subjectAnti-nociceptiveen_US
dc.subjectAnti-ulcerogenicen_US
dc.subjectAzolesen_US
dc.subjectEpoxidsen_US
dc.subjectOxarineen_US
dc.subject17 (3' benzoyl 2' methyloxiran 2' yl)androst 4 ene 3 oneen_US
dc.subject17 (4',5' dihydro 3' hydroxy 5' methyl 4' phenylamino 1' phenylpyrazol 5' yl)androst 4 ene 3 oneen_US
dc.subject17 [4',5' dihydro 3',5' dimethyl 4' (4 chlorophenylamino) 1' phenylpyrazol 5' yl]androst 4 ene 3 oneen_US
dc.subject20 hydroxy 20 [1',3', 4' triphenyl 2' thioxo 1',3' imidazol 5' yl]pregn 4 ene 3 oneen_US
dc.subjectcarrageenanen_US
dc.subjectindometacinen_US
dc.subjectsteroiden_US
dc.subjecttramadolen_US
dc.subjectunclassified drugen_US
dc.subjectanimal experimenten_US
dc.subjectanimal modelen_US
dc.subjectantiinflammatory activityen_US
dc.subjectantinociceptionen_US
dc.subjectantiulcerogenic activityen_US
dc.subjectarticleen_US
dc.subjectcontrolled studyen_US
dc.subjectdrug activityen_US
dc.subjectdrug efficacyen_US
dc.subjectin vivo studyen_US
dc.subjectnonhumanen_US
dc.subjectpainen_US
dc.subjectpaw edemaen_US
dc.subjectraten_US
dc.subjectsteroidogenesisen_US
dc.subjectstomach lesionen_US
dc.subjectstomach ulceren_US
dc.subjectstructure activity relationen_US
dc.subjectthermal painen_US
dc.subjectAcetic Aciden_US
dc.subjectAnalgesicsen_US
dc.subjectAnimalsen_US
dc.subjectAnti-Inflammatory Agentsen_US
dc.subjectAzolesen_US
dc.subjectCarrageenanen_US
dc.subjectEdemaen_US
dc.subjectMiceen_US
dc.subjectPainen_US
dc.subjectRatsen_US
dc.subjectSteroidsen_US
dc.subjectRattusen_US
dc.titleSynthesis of modified steroids as a novel class of non-ulcerogenic, anti-inflammatory and anti-nociceptive agentsen_US
dc.typeArticleen_US
dcterms.isReferencedByKozuch, P.L., Hanauer, S.B., Treatment of inflammatory bowel disease: A review of medical therapy (2008) World Journal of Gastroenterology, 14 (3), pp. 354-377. , DOI 10.3748/wjg.14.354; Sondhi, S.M., Singhal, N., Johar, M., Narayan Reddy, B.S., Lown, J.W., Heterocyclic compounds as inflammation inhibitors (2002) Current Medicinal Chemistry, 9 (10), pp. 1045-1074; Gureje, O., Von Korff, M., Simon, G.E., Gater, R., Persistent pain and well-being: A World Health Organization study in primary care (1998) Journal of the American Medical Association, 280 (2), pp. 147-151. , DOI 10.1001/jama.280.2.147; Karthikeyan, K., Veenus Seelan, T., Lalitha, K.G., Perumal, P.T., Synthesis and antinociceptive activity of pyrazolyl isoxazolines and pyrazolyl isoxazoles (2009) Bioorg Med Chem Lett, 19, pp. 3370-3373; Wallace, J.L., Soldato, P.D., Cirino, G., Development of NSAIDs with reduced gastrointestinal and renal toxicity (1995) Exp Opin Invest Drugs, 4, pp. 613-619; Sadeghi, S., Bain, C.J., Pandeya, N., Webb, P.M., Green, A.C., Whiteman, D.C., Aspirin, nonsteroidal anti-inflammatory drugs, and the risks of cancers of the esophagus (2008) Cancer Epidemiol Biomarkers Prev, 17, pp. 1169-1178; Lipworth, B.J., Systemic adverse effects of inhaled corticosteroid therapy: A systematic review and meta-analysis (1999) Archives of Internal Medicine, 159 (9), pp. 941-955. , DOI 10.1001/archinte.159.9.941; Phillips, G.H., (1981) Mechanism of Topical Corticoid Activity, p. 1. , Livingstone Edinburgh, U.K; Criscuolo, D., Fraioli, F., Bonifacio, V., Effects of a new glucocorticoid, deflazacort, on pituitary-adrenal function in man: A comparison with prednisone (1980) International Journal of Clinical Pharmacology Therapy and Toxicology, 18 (1), pp. 37-41; Hoyte, R.M., Zhang, J.-X., Lerum, R., Oluyemi, A., Persaud, P., O'Connor, C., Labaree, D.C., Hochberg, R.B., Synthesis of halogen-substituted pyridyl and pyrimidyl derivatives of [3,2-c]pyrazolo corticosteroids: Strategies for the development of glucocorticoid receptor mediated imaging agents (2002) Journal of Medicinal Chemistry, 45 (24), pp. 5397-5405. , DOI 10.1021/jm0202775; Wust, F., Carlson, K.E., Katzenellenbogen, J.A., Synthesis of novel arylpyrazolo corticosteroids as potential ligands for imaging brain glucocorticoid receptors (2003) Steroids, 68 (2), pp. 177-191. , DOI 10.1016/S0039-128X(02)00171-X; Elmegeed, G.A., Wardakhan, W.W., Baiuomy, A.R., Synthesis of thiazolyl and thieno cholestane derivatives: A novel class of potent antiinflammatory steroids (2005) Pharmazie, 60 (5), pp. 328-333; Elmegeed, G.A., Baiuomy, A.R., Abdel-Salam, O.M.E., Evaluation of the anti-inflammatory and anti-nociceptive activities of novel synthesized melatonin analogues (2007) European Journal of Medicinal Chemistry, 42 (10), pp. 1285-1292. , DOI 10.1016/j.ejmech.2007.01.027, PII S0223523407000797; Wardakhan, W.W., Elmegeed, G.A., Abdel-Salam, O.M.E., New approaches for the synthesis of fused benzothiophene derivatives: New class of antidepressant, sedative or analgesic agents (2007) Acta Pharm, 58, pp. 1-14; Nomenclature of steroids (1989) Pure Appl Chem, 61, pp. 1783-1822. , IUPAC. Joint Commission on Biochemical Nomenclature (JCBN); The nomenclature of steroids, recommendations 1989 (1989) Eur J Biochem, 186, pp. 429-458. , IUPAC. Joint Commission on Biochemical Nomenclature (JCBN); Gacs-Baitz, E., Minuti, L., Taticchi, A., Synthesis and Complete 1H and 13C NMR Analysis of Some 4-Androsten-3-one Derivatives (1996) Journal of Chemical Research - Part S, (7), pp. 324-325; Frenkel, M., Marsh, K.N., (1994) TRC Data Series: Spectral Data for Steroids, p. 386. , College Station, Thermodynamics Research Center Texas, TX; Johnson, W.S., Schneider, W.P., Ethyl indole-2-carboxylate (1963) Org Synth, 4, pp. 132-136; Winter, C.A., Risley, E.A., Nuss, G.W., Carrageenan-induced edema in hind paw of the rat as an assay for antiinflammatory drugs (1962) Proc Soc Exp Biol Med, 111, pp. 544-552; Koster, R., Anderson, M., De Beer, E.J., Acetic acid for analgesic screening (1959) Fed Proc, 18, pp. 412-413; Mozsik, G., Moron, F., Javor, T., Cellular mechanisms of the development of gastric mucosal damage and of gastrocytoprotection induced by prostacyclin in rats. A pharmacological study (1982) Prostaglandins Leukotrienes and Medicine, 9 (1), pp. 71-84. , DOI 10.1016/0262-1746(82)90074-9; Rostom, S.A.F., El-Ashnawy, I.M., Abd El Razik, H.A., Badr, M.H., Ashour, H.M.A., Design and synthesis of some thiazolyl and thiadiazolyl derivatives of antipyrine as potential non-acidic anti-inflammatory, analgesic and antimicrobial agents (2009) Bioorg Med Chem, 17, pp. 882-895; Sauzem, P.D., Sant'Anna, G.S., MacHado, P., Duarte, M.M., Ferreira, J., Mello, C.F., Effect of 5-trifluoromethyl-4,5-dihydro-1H-pyrazoles on chronic inflammatory pain model in rats (2009) Eur J Pharmacol, 616, pp. 91-100; Tseng, C., Lin, C., Shih, P., Tsao, L., Wangd, J., Cheng, C., Fluro[3?,2?:3,4]naphtho[1,2-d]imidazole derivatives as potential inhibitors of inflammatory factors in sepsis (2009) Bioorg Med Chem, 17, pp. 6773-6779; Amer, H., Mereiter, K., Stanetty, C., Hofinger, A., Czollner, L., Beseda, I., Synthesis and crystal structures of ring A modified glycyrrhetinic acid derivatives derived from 2,3-oxirane and 2,3-thiirane intermediates (2010) Tetrahedron, 66 (26), pp. 4390-4402; Gella, I.M., Gladkova, A.I., Zolotukhina, V.A., Karpenko, N.A., Local antiandrogenic activity of steroid 3-spirooxiranes (1995) Pharm Chem J, 29 (11), pp. 753-756; Tanitame, A., Oyamada, Y., Ofuji, K., Fujimoto, M., Suzuki, K., Ueda, T., Terauchi, H., Yamagishi, J.-I., Synthesis and antibacterial activity of novel and potent DNA gyrase inhibitors with azole ring (2004) Bioorganic and Medicinal Chemistry, 12 (21), pp. 5515-5524. , DOI 10.1016/j.bmc.2004.08.010, PII S0968089604006133; Hackett, J.C., Kim, Y.-W., Su, B., Brueggemeier, R.W., Synthesis and characterization of azole isoflavone inhibitors of aromatase (2005) Bioorganic and Medicinal Chemistry, 13 (12), pp. 4063-4070. , DOI 10.1016/j.bmc.2005.03.050, PII S0968089605002750; Wong, F.F., Chen, C.-Y., Chen, T.-H., Huang, J.-J., Fang, H.-P., Yeh, M.-Y., Synthesis of 3?-hydroxy-21-(1?-imidazolyl)-3?-methoxyl- methyl-5?-pregnan-20-one via lithium imidazole with 17?- acetylbromopregnanone (2006) Steroids, 71 (1), pp. 77-82. , DOI 10.1016/j.steroids.2005.08.006, PII S0039128X05001972; Sandstrom, J.T., Measurement and calculation of [sup.13]C and [sup.15]N NMR chemical-shift tensors of a push-pull ethylene (1983) Top Stereochem, 14, pp. 83-181
dcterms.sourceScopus

Files

Original bundle

Now showing 1 - 1 of 1
Loading...
Thumbnail Image
Name:
avatar_scholar_256.png
Size:
6.31 KB
Format:
Portable Network Graphics
Description: