Synthesis, antimicrobial, and anti-inflammatory activity, of novel s-substituted and n-substituted 5-(1-adamantyl)-1,2,4-triazole-3-thiols

Drug Design, Development and Therapy

Volumn 8, Issue , 2014, Pages 505-517

  Al Aabdullah, Ebtehal S ^a   Asiri, Hanadi H ^a   Lahsasni, Siham ^b   Habib, Elsayed E ^c   Ibrahim, Tarek M ^d   El Emam, Ali A ^a  

^a Department of Pharmaceutical chemistry College of Pharmacy ^*  (Saudi Arabia)

^b KING SAUD UNIVERSITY   (Saudi Arabia)

^c TAIBAH UNIVERSITY   (Saudi Arabia)

^d MANSOURA UNIVERSITY   (Egypt)

Author keywords

124 triazoles; Adamantane derivatives; Anti inflammatory activity; Antimicrobial activity; N mannich bases

Indexed keywords

2 [5 (1 ADAMANTYL) 4 PHENYL 1,2,4 TRIAZOL 3 YLSULFANYL]ACETIC ACID; 5 (1 ADAMANTYL) 3 ARYLMETHYLSULFANYL 4 PHENYL 1,2,4 TRIAZOLE DERIVATIVE; 5 (1 ADAMANTYL) 3 [(2 METHOXYETHYL)SULFANYL] 4 PHENYL 1,2,4 TRIAZOLE; 5 (1 ADAMANTYL) 4 METHYL 2 (2 AMINOETHYL) 1,2,4 TRIAZOLIN 3 THIONE DERIVATIVE; 5 (1 ADAMANTYL) 4 METHYL 3 (2 AMINOETHYLTHIO) 1,2,4 TRIAZOLE DERIVATIVE; AMPICILLIN; ANTIBIOTIC AGENT; ANTIFUNGAL AGENT; ANTIINFLAMMATORY AGENT; CARRAGEENAN; CLOTRIMAZOLE; ETHYL 2 [5 (1 ADAMANTYL) 4 PHENYL 1,2,4 TRIAZOL 3 YLSULFANYL]ACETATE; GENTAMICIN; INDOMETACIN; THIOL DERIVATIVE; TRIAZOLE DERIVATIVE; UNCLASSIFIED DRUG; ANTIINFECTIVE AGENT;

ANIMAL EXPERIMENT; ANIMAL MODEL; ANTIBACTERIAL ACTIVITY; ANTIFUNGAL ACTIVITY; ANTIINFLAMMATORY ACTIVITY; ARTICLE; BACILLUS SUBTILIS; CANDIDA ALBICANS; CONTROLLED STUDY; DISK DIFFUSION; DOSE RESPONSE; DRUG DETERMINATION; DRUG DOSE COMPARISON; DRUG POTENCY; DRUG SCREENING; DRUG STRUCTURE; DRUG SYNTHESIS; ESCHERICHIA COLI; FEMALE; IN VITRO STUDY; LETHAL DOSE; MALE; MICROCOCCUS LUTEUS; MINIMUM INHIBITORY CONCENTRATION; NONHUMAN; PAW EDEMA; PSEUDOMONAS AERUGINOSA; RAT; STAPHYLOCOCCUS AUREUS; SUBSTITUTION REACTION; TOXICITY TESTING; ANIMAL; SPRAGUE DAWLEY RAT; SYNTHESIS; TOXICITY;

ANIMALS; ANTI-INFECTIVE AGENTS; ANTI-INFLAMMATORY AGENTS; DOSE-RESPONSE RELATIONSHIP, DRUG; MALE; RATS; RATS, SPRAGUE-DAWLEY; SULFHYDRYL COMPOUNDS; TRIAZOLES;

EID: 84900456479     PISSN: 11778881     EISSN: None     Source Type: Journal    
DOI: 10.2147/DDDT.S62465     Document Type: Article

References (52)

1. Lamoureux G, Artavia G. Use of the adamantane structure in medicinal chemistry. Curr Med Chem. 2010;17:2967-2978.
2. Liu J, Obando D, Liao V, Lifa T, Codd R. The many faces of the adamantyl group in drug design. Eur J Med Chem. 2011;46:1949-1963.
3. Davies WL, Grunnert RR, Haff RF, et al. Antiviral activity of 1- adamantamine (amantadine). Science. 1964;144:862-863.
4. Wendel HA, Snyder MT, Pell S. Trial of amantadine in epidemic infu-enza. Clin Pharmacol Ther. 1966;7:38-43.
5. Togo Y, Hornick RB, Dawkins AT. Studies on induced infuenza in man. I. Double blind studies designed to assess prophylactic effcacy of amantadine hydrochloride against A2/Rockville/1/65 strain. JAMA. 1968;203:1089-1094.
6. Hayden FG, Gwaltney JM Jr, Van der Castle RL, Adams K F, Giordani B. Comparative toxicity of amantadine hydrochloride and rimantadine hydrochloride in healthy adults. Antimicrob Agents Chemother. 1981;19:226-233.
7. Ilyushina NA, Bovin N V, Webster RG, Govorkova EA. Combination chemotherapy, a potential strategy for reducing the emergence of drug-resistant infuenza A variants. Antiviral Res. 2006;70:121-131.
8. Tilley J W, Levitan P, Kramer MJ. Adamantyl thiourea derivatives as antiviral agents. J Med Chem. 1979;22:1009-1010.
9. Pérez-Pérez MJ, Balzarini J, Hosoya M, De Clercq E, Camarasa MJ. Synthesis of adamantane-spirosultones as potential antiviral agents. Bioorg Med Chem Lett. 1992;2:647-648.
10. Zoidis G, Fytas C, Papanastasiou I, et al. Heterocyclic rimanta-dine analogues with antiviral activity. Bioorg Med Chem. 2006;14: 3341-3348.
11. Van Derpoorten K, Balzarini J, De Clercq E, Poupaert JH. Anti-HIV activity of N-1-adamantyl-4-aminophthalimide. Biomed Pharmacother. 1997;51:464-468.
12. Balzarini J, Orzeszko B, Mauri JK, Orzeszko A. Synthesis and anti-HIV studies of 2 -adamantyl-substituted thiazolidin-4-ones. Eur J Med Chem. 2007;42:993-1003.
13. El-Emam AA, Al-Deeb OA, Al-Omar MA, Lehmann J. Synthesis, antimicrobial, and anti-HIV-1 activity of certain 5-(1-adamantyl)-2-substituted thio-1,3,4-oxadiazoles and 5 -(1-adamantyl)-3-substituted aminomethyl-1,3,4-oxadiazoline-2-thiones. Bioorg Med Chem. 2004;12:5107-5113.
14. Villhauer EB, Brinkman JA, Naderi GB, et al. 1-(3-Hydroxy-1- adamantyl)aminoacetyl-2-cyano-(S)-pyrrolidine: a potent, selective, and orally bioavailable dipeptidyl peptidase IV inhibitor with antihyperglycemic properties. J Med Chem. 2003;46:2774-2789.
15. Wang JJ, Wang SS, Lee CF, Chung MA, Chern YT. In vitro antitumor and antimicrobial activity of N-substituents of maliemide by adamantane and diamantane. Chemotherapy. 1997;43:182-189.
16. Antoniadou-Vyza E, Tsitsa P, Hytiroglou E, Tsantili-Kakoulidou A. New adamantan-2-ol and adamantan-1-methanol derivatives as potent antibacterials, synthesis, antibacterial activity and lipophilicity studies. Eur J Med Chem. 1996;31:105-110.
17. Omar K, Geronikaki A, Zoumpoulakis P, et al. Novel 4-thiazolidinone derivatives as potential antifungal and antibacterial drugs. Bioorg Med Chem. 2010;18:426-432.
18. Jia L, Tomaszewski JE, Hanrahan C, et al. Pharmacodynamics and pharmacokinetics of SQ109, a new diamine-based antitubercular drug. Br J Pharmacol. 2005;144:80-87.
19. Brown JR, North EJ, Hurdle JG, et al. The structure-activity relationship of urea derivatives as anti-tuberculosis agents. Bioorg Med Chem. 2011;19:5585-5595.
20. El-Emam AA, Al-Tamimi AMS, Al-Omar MA, Al-Rashood KA, Habib EE. Synthesis and antimicrobial activity of novel 5 -(1-adamantyl)-2-aminomethyl-4-substituted-1,2,4-triazoline-3-thiones. Eur J Med Chem. 2013;68:96-102.
21. Al-Deeb OA, Al-Omar MA, El-Brollosy NR, Habib EE, Ibrahim TM, El-Emam AA. Synthesis, antimicrobial, and anti-infammatory activities of novel 2-[3-(1-adamantyl)-4-substituted-5-thioxo-1,2,4-triazolin-1-yl]acetic acids, 2-[3-(1-adamantyl)-4-substituted-5-thioxo-1,2, 4-triazolin-1-yl]propionic acids and related derivatives. Arzneimittelforschung. 2006;56:40-47.
22. Kadi AA, El-Brollosy NR, Al-Deeb OA, Habib EE, Ibrahim TM, El-Emam AA. Synthesis, antimicrobial, and anti-infammatory activities of novel 2-(1-adamantyl)-5-substituted-1,3,4-oxadiazoles and 2-(1-adamantylamino)-5-substituted-1,3,4-thiadiazoles. Eur J Med Chem. 2007;42:235-242.
23. Al-Omar MA, Al-Abdullah ES, Shehata IA, Habib EE, Ibrahim TM, El-Emam AA. Synthesis, antimicrobial, and anti-infammatory activities of novel 5 -(1-adamantyl)-4-arylideneamino-3-mercapto-1,2,4-triazoles and related derivatives. Molecules. 2010;15:2526-2550.
24. El-Emam AA, Ibrahim TM. Synthesis, anti-infammatory and analgesic activity of certain 3-(1-adamantyl)-4-substituted-5-mercapto-1,2, 4-triazole derivatives. Arzneimittelforschung. 1991;41:1260-1264.
25. Kouatly O, Geronikaki A, Kamoutsis C, Hadjipavlou-Litina D, Eleftheriou P. Adamantane derivatives of thiazolyl-N-substituted amide, as possible non-steroidal anti-inflammatory agents. Eur J Med Chem. 2009;44:1198-1204.
26. Baxter A, Bent J, Bowers K, et al. Hit-to-lead studies: the discovery of potent adamantane amide P2X7 receptor antagonists. Bioorg Med Chem Lett. 2003;13:4047-4050.
27. Schwab RS, England AC Jr, Poskanzer DC, Young RR. Amantadine in the treatment of Parkinson's disease. JAMA. 1969;208:1168-1170.
28. Abou-Gharbia MA, Childers WE, Fletcher H, et al. Synthesis and SAR of adatanserin: novel adamantly aryl- and heteroarylpiperazines with dual serotonin 5-HT1A and 5-HT2 activity as potential anxiolytic and antidepressant agents. J Med Chem. 1999;42:5077-5094.
29. Bormann J. Memantine is a potent blocker of N-methyl-D-aspartate (NMDA) receptor channels. Eur J Pharmacol. 1989;166:59l-592.
30. Chai X, Zhang J, Yu S, et al. Design, synthesis, and biological evaluation of novel 1-(1H-1,2,4-triazole-1-yl)-2-(2,4-difuorophenyl)-3-substituted benzylamino-2-propanols. Bioorg Med Chem Lett. 2009;19:1811-1814.
31. Xu J, Cao Y, Zhang J, et al. Design, synthesis and antifungal activities of novel 1,2,4-triazole derivatives. Eur J Med Chem. 2011;46:3142-3148.
32. Karthikeyan MS, Prasad DJ, Boojary B, Bhat KS, Holla BS, Kumari NS. Synthesis and biological activity of Schiff and Mannich bases bearing 2,4-dichloro-5-fluorphenyl moiety. Bioorg Med Chem. 2006;14:7482-7489.
33. Almajan GL, Barbuceanu SF, Almajan E, Draghici C, Saramet G. Synthesis, characterization and antibacterial activity of some triazole Mannich bases carrying diphenylsulfone moieties. Eur J Med Chem. 2009;44:3083-3089.
34. Wade PC, Vogt BR, Kissick T P, Simpkins LM, Palmers DM. 1 - Acyltriazoles as anti-infammatory agents. J Med Chem. 1982;25:331-333.
35. Tozkoparan B, Küpeli E, Yeşilada E, Ertan M. Preparation of 5-aryl-3-alkylthio-l,2,4-triazoles and corresponding sulfones with anti-infammatory-analgesic activity. Bioorg Med Chem. 2007;15: 1808-1814.
36. Navidpour L, Shafaroodi H, Abdi K, et al. Design, synthesis, and biological evaluation of substituted 3 -alkylthio-4,5-diaryl-4H-1,2,4-triazoles as selective COX-2 inhibitors. Bioorg Med Chem. 2006;14:2507-2517.
37. Al-Abdullah ES, Shehata IA, Al-Deeb OA, El-Emam AA. Microwave-assisted dehydrosulphurization: an effcient, solvent-free synthesis of 5-(1-adamantyl)-2-arylamino-1,2,4-triazolo[3,4-b][1,3,4]thiadiazoles. Heterocycles. 2007;71:379-388.
38. El-Emam AA, Al-Tamimi AMS, Al-Rashood KA, et al. Structural and spectroscopic characterization of a novel potential chemotherapeutic agent 3-(1-Adamantyl)-1-{[4-(2-methoxyphenyl)piperazin-1-yl] methyl}-4-methyl-1H-1,2,4-triazole-5(4H)-thione by frst principle calculations. J Mol Struct. 2012;1022:49-60.
39. Al-Abdullah ES, Asiri HH, El-Emam AA, Ng SW. Ethyl 4-{[3-(adamantan-1-yl)-4-phenyl-5-sulfanylidene-4,5-dihydro-1H-1,2,4-triazol-1-yl]methyl}piperazine-1-carboxylate. Acta Crystallogr Sect E Struct Rep Online. 2012;E68:0531.
40. Al-Abdullah ES, Asiri HH, El-Emam AA, Ng SW. 3 -(Adamantan-1-yl)-4-phenyl-1-[(4-phenylpiperazin-1-yl)methyl]-4,5-dihydro-1H-triazole-5(4H)-thione. Crystallogr Sect E Struct Rep Online. 2012;E68:0345.
41. Al-Abdullah ES, Asiri HH, El-Emam AA, Ng SW. 3 -(Adamantan-1-yl)-4-phenyl-1-[(4-benzylpiperazin-1-yl)methyl]-4,5-dihydro-1H-triazole-5(4H)-thione. Crystallogr Sect E Struct Rep Online. 2012;E68:0344.
42. Sarvá MC, Romeo G, Guerrera F, et al. [1,2,4]Triazole derivatives as 5-HT1A serotonin receptor ligands. Bioorg Med Chem. 2001;10: 313-323.
43. Alam MM, Nazreen S, Haider S, et al. Synthesis of some new S- alkylated 1,2,4-triazoles, their Mannich bases and their biological activities. Arch Pharm (Weinheim). 2012;345:203-214.
44. Fun HK, Yeap CS, Prasad KDJ, Poojary B. N-(2-Chlorophenyl)-2-({5-[4-(methysulfanyl)benzyl]-4-phenyl-4H-1,2,4-triazol-3-yl}sulfanyl) acetamide. Crystallogr Sect E Struct Rep Online. 2011;E67:02063.
45. Fun HK, Asik SIJ, Chandrakantha B, Isloor AM, Shetty P. 4-(4-bromophenyl)-1-(2,6-difuorobenzyl)-5-(3,4,5-trimethoxyphenyl)-1H-1,2,4-triazole-5(4H)-thione. Crystallogr Sect E Struct Rep Online. 2011;E67:03422-03423.
46. El-Emam AA, Lahsasni S, Asiri HH, Quah CK, Fun HK. 2-{[5-(Ada-mantan-1-yl)-4-methyl-4H-1,2,4-triazol-3-yl]sulfanyl}-N,N-dimethyl-ethanamine. Crystallogr Sect E Struct Rep Online. 2012;E68: 01356.
47. El-Emam AA, Al-Abdullah ES, Asiri HH, Chantrapromma S, Fun HK. 5-(Adamantan-1-yl)-3-[(2-methoxyethyl)sulfanyl]-4-phenyl-4H-1,2,4-triazole. Crystallogr Sect E Struct Rep Online. 2012;E68:02326.
48. Woods GL, Washington JA. Antibacterial susceptibility tests: dilution and disk diffusion methods. In: Murray PR, Baron EJ, Pfaller MA, Tenover FC, Yolken RH, editors. Manual of Clinical Microbiology. Washington, DC, USA: American Society of Microbiology; 1995.
49. National Committee for Clinical Laboratory Standards. Approved standard document M-7A. Villanova, PA, USA: National Committee for Clinical Laboratory Standards; 1985.
50. Winter CA, Risely EA, Nuss GW. Carrageenin-induced paw oedema in hind paw of the rat as an assay for anti-infammatory drugs. Proc Soc Exp Biol Med. 1962;111:457-544.
51. Litchfeld JT, Wilcoxon T. A simplifed method of evaluating dose-effect experiments. J Pharmacol Exp Ther. 1949;96:99-104.
52. Hichens M. In: Scherrier RA, Whitehouse M W, editors. Anti-Infammatory Agents. Volume II. Academic Press, New York, NY, USA: 1974.