Synthesis, antimicrobial and hypoglycemic activities of novel N-(1-adamantyl)carbothioamide derivatives

Molecules

Volumn 20, Issue 5, 2015, Pages 8125-8143

  Al Abdullah, Ebtehal S ^a   Al Tuwaijri, Hanaa M ^a   Hassan, Hanan M ^b   Al Alshaikh, Monirah A ^c   Habib, Elsayed E ^d,e   El Emam, Ali A ^a  

^a KING SAUD UNIVERSITY   (Saudi Arabia)

^b PRINCESS NOURAH BINT ABDULRAHMAN UNIVERSITY   (Saudi Arabia)

^c KING SAUD UNIVERSITY   (Saudi Arabia)

^d University of Mansoura   (Egypt)

^e TAIBAH UNIVERSITY   (Saudi Arabia)

Author keywords

Adamantane derivatives; Antimicrobial activity; Carbothioamides; Hypoglycemic activitydoi

Indexed keywords

1,2,4-TRIAZOLE; ADAMANTANE; ADAMANTYL ISOTHIOCYANATE; ANTIDIABETIC AGENT; ANTIINFECTIVE AGENT; CARBOHYDRAZIDE; HYDRAZINE; HYDRAZINE DERIVATIVE; ISOTHIOCYANIC ACID DERIVATIVE; TRIAZOLE DERIVATIVE;

ANALOGS AND DERIVATIVES; ANIMAL; CANDIDA ALBICANS; CHEMISTRY; DIABETES MELLITUS, EXPERIMENTAL; DRUG EFFECTS; GRAM NEGATIVE BACTERIUM; GRAM POSITIVE BACTERIUM; MALE; MICROBIAL SENSITIVITY TEST; PROCEDURES; RAT; SPRAGUE DAWLEY RAT;

ADAMANTANE; ANIMALS; ANTI-BACTERIAL AGENTS; CANDIDA ALBICANS; DIABETES MELLITUS, EXPERIMENTAL; GRAM-NEGATIVE BACTERIA; GRAM-POSITIVE BACTERIA; HYDRAZINES; HYPOGLYCEMIC AGENTS; ISOTHIOCYANATES; MALE; MICROBIAL SENSITIVITY TESTS; RATS; RATS, SPRAGUE-DAWLEY; TRIAZOLES;

EID: 84929190806     PISSN: None     EISSN: 14203049     Source Type: Journal    
DOI: 10.3390/molecules20058125     Document Type: Article

References (47)

1. 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.
2. Lamoureux, G.; Artavia, G. Use of the adamantane structure in medicinal chemistry. Curr. Med. Chem. 2010, 17, 2967-2978.
3. Davies, W.L.; Grunnert, R.R.; Haff, R.F.; McGahen, J.W.; Neumeyer, E.M.; Paulshock, M.; Watts, J.C.; Wood, T.R.; Hermann, E.C.; Hoffmann, C.E. Antiviral activity of 1-adamantamine (amantadine). Science 1964, 144, 862-863.
4. Togo, Y.; Hornick, R.B.; Dawkins, A.T. Studies on induced influenza in man. I. Double blind studies designed to assess prophylactic efficacy of amantadine hydrochloride against A2/Rockville/1/65 strain. J. Am. Med. Assoc. 1968, 203, 1089-1094.
5. Wendel, H.A.; Snyder, M.T.; Pell, S. Trial of amantadine in epidemic influenza. Clin. Pharmacol. Ther. 1966, 7, 38-43.
6. Schwab, R.S.; England, A.C., Jr.; Poskanzer, D.C.; Young, R.R. Amantadine in the treatment of Parkinson's disease. J. Am. Med. Assoc. 1969, 208, 1168-1170.
7. Owen, J.C.E.; Whitton, P.S. Effect of amantadine and budipune on antidepressant drug-evoked changes in extracellular dopamine in the frontal cortex of freely moving rats. Brain Res. 2006, 1117, 206-212.
8. Rabinovich, S.; Baldini, J.T.; Bannister, R. Treatment of influenza. The therapeutic efficacy of rimantadine HCl in a naturally occurring influenza A2 outbreak. Am. J. Med. Sci. 1969, 257, 328-335.
9. Rosenthal, K.S.; Sokol, M.S.; Ingram, R.L.; Subramanian, R.; Fort, R.C. Tromantadine: Inhibitor of Early and Late Events in Herpes Simplex Virus Replication. Antimicrob. Agents Chemother. 1982, 22, 1031-1036.
10. Burstein, M.E.; Serbin, A.V.; Khakhulina, T.V.; Alymova, I.V.; Stotskaya, L.L.; Bogdan, O.P.; Manukchina, E.E.; Jdanov, V.V.; Sharova, N.K. Inhibition of HIV-1 replication by newly developed adamantane-containing polyanionic agents. Antivir. Res. 1999, 41, 135-144.
11. Van Derpoorten, K.; Balzarini, J.; de Clercq, E.; Poupaert, J.H. Anti-HIV activity of N-1-adamantyl-4-aminophthalimide. Biomed. Pharmacother. 1997, 51, 464-468.
12. El-Emam, A.A.; Al-Deeb, O.A.; Al-Omar, M.A.; 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.
13. Balzarini, J.; Orzeszko, B.; Mauri, J.K.; Orzeszko, A. Synthesis and anti-HIV studies of 2-adamantyl-substituted thiazolidin-4-ones. Eur. J. Med. Chem. 2007, 42, 993-1003.
14. Sun, S.Y.; Yue, P.; Chen, X.; Hong, W.K.; Lotan, R. The synthetic retinoid CD437 selectively induces apoptosis in human lung cancer cells while sparing normal human lung epithelial cells. Cancer Res. 2002, 62, 2430-2436.
15. 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.
16. Omar, K.; Geronikaki, A.; Zoumpoulakis, P.; Camoutsis, C.; Soković, M.; Ćirić, A.; Glamoćlija, J. Novel 4-thiazolidinone derivatives as potential antifungal and antibacterial drugs. Bioorg. Med. Chem. 2010, 18, 426-432.
17. Scherman, M.S.; North, E.J.; Jones, V.; Hess, T.N.; Grzegorzewicz, A.E.; Kasagami, T.; Kim, I.H.; Merzlikin, O.; Lenaerts, A.J.; Lee, R.E.; et al. Screening a library of 1600 adamantyl ureas for anti-Mycobacterium tuberculosis activity in vitro and for better physical chemical properties for bioavailability. Bioorg. Med. Chem. 2012, 20, 3255-3262.
18. El-Emam, A.A.; Al-Tamimi, A.-M.S.; Al-Omar, M.A.; Al-Rashood, K.A.; Habib, E.E. 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.
19. Al-Deeb, O.A.; Al-Omar, M.A.; El-Brollosy, N.R.; Habib, E.E.; Ibrahim, T.M.; El-Emam, A.A. Synthesis, antimicrobial, and anti-inflammatory 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. Arzneim.-Forsch./Drug Res. 2006, 56, 40-47.
20. Kadi, A.A.; El-Brollosy, N.R.; Al-Deeb, O.A.; Habib, E.E.; Ibrahim, T.M.; El-Emam, A.A. Synthesis, antimicrobial, and anti-inflammatory 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.
21. Kadi, A.A.; Al-Abdullah, E.S.; Shehata, I.A.; Habib, E.E.; Ibrahim, T.M.; El-Emam, A.A. Synthesis, antimicrobial and anti-inflammatory activities of novel 5-(1-adamantyl)-1,3,4-thiadiazole derivatives. Eur. J. Med. Chem. 2010, 45, 5006-5011.
22. Al-Abdullah, E.S.; Asiri, H.H.; Lahsasni, S.; Habib, E.E.; Ibrahim, T.M.; El-Emam, A.A. Synthesis, antimicrobial, and anti-inflammatory activity, of novel S-substituted and N-substituted 5-(1-adamantyl)-1,2,4-triazole-3-thiols. Drug Des. Dev. Ther. 2014, 8, 505-518.
23. Al-Abdullah, E.S.; Al-Tuwaijri, H.M.; Hassan, H.M.; Haiba, M.E.; Habib, E.E.; El-Emam, A.A. Antimicrobial and hypoglycemic activities of novel N-Mannich bases derived from 5-(1-adamantyl)-4-substituted-1,2,4-triazoline-3-thiones. Int. J. Mol. Sci. 2015, 15, 22995-23010.
24. Jia, L.; Tomaszewski, J.E.; Hanrahan, C.; Coward, L.; Noker, P.; Gorman, G.; Nikonenko, B.; Protopopova, M. Pharmacodynamics and pharmacokinetics of SQ109, a new diamine-based antitubercular drug. Br. J. Pharmacol. 2005, 144, 80-87.
25. Protopopova, M.; Hanrahan, C.; Nikonenko, B.; Samala, R.; Chen, P.; Gearhart, J.; Einck, L.; Nacy, C.A. Identification of a new antitubercular drug candidate, SQ109, from a combinatorial library of 1,2-ethylenediamines. J. Antimicrob. Chemother. 2005, 56, 968-974.
26. Villhauer, E.B.; Brinkman, J.A.; Naderi, G.B.; Burkey, B.F.; Dunning, B.E.; Prasad, K.; Mangold, B.L.; Russell, M.E.; Hughes, T.E. 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.
27. Augeri, D.J.; Robl, J.A.; Betebenner, D.A.; Magnin, D.R.; Khanna, A.; Robertson, J.G.; Wang, A.; Simpkins, L.M.; Taunk, P.; Huang, Q.; et al. Discovery and preclinical profile of saxagliptin (BMS-477118): A highly potent, long-acting, orally active dipeptidyl peptidase IV inhibitor for the treatment of type 2 diabetes. J. Med. Chem. 2005, 48, 5025-5037.
28. Olson, S.; Aster, S.D.; Brown, K.; Carbin, L.; Graham, D.W.; Hermanowski-Vosatka, A.; LeGrand, C.B.; Mundt, S.S.; Robbins, M.A.; Schaeffer, J.M.; et al. Adamantyl triazoles as selective inhibitors of 11β-hydroxysteroid dehydrogenase type 1. Bioorg. Med. Chem. Lett. 2005, 15, 4359-4362.
29. Cheng, H.; Hoffman, J.; Le, P.; Nair, S.K.; Cripps, S.; Matthews, J.; Smith, C.; Yang, M.; Kupchinsky, S.; Dress, K.; et al. The development and SAR of pyrrolidine carboxamide 11β-HSD1 inhibitors. Bioorg. Med. Chem. Lett. 2010, 20, 2897-2902.
30. Cott, J.S.; Choormun, J. 11β-Hydroxysteroid dehydrogenase Type 1 (11β-HSD-1) inhibitors in development. In New Therapeutic Strategies for Type-2 Diabetes, Small Molecule Approaches; Jones, R.N., Ed.; RSC: Cambridge, UK, 2012; Chapter 5, pp. 109-133.
31. El-Emam, A.A.; Ibrahim, T.M. Synthesis, anti-inflammatory and analgesic activity of certain 3-(1-adamantyl)-4-substituted-5-mercapto-1,2,4-triazole derivatives. Arzneim.-Forsch./Drug Res. 1991, 41, 1260-1264.
32. 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.
33. Baxter, A.; Bent, J.; Bowers, K.; Braddock, M.; Brough, S.; Fagura, M.; Lawson, M.; McInally, T.; Mortimore, M.; Robertson, M.; et al. Hit-to-lead studies: The discovery of potent adamantane amide P2X7 receptor antagonists. Bioorg. Med. Chem. Lett. 2003, 13, 4047-4050.
34. Joubert, J.; van Dyk, S.; Green, I.R.; Malan, S.F. Synthesis and evaluation of fluorescent heterocyclic aminoadamantanes as multifunctional neuroprotective agents. Bioorg. Med. Chem. 2011, 19, 3935-3944.
35. Sorensen, B.; Winn, M.; Rohde, J.; Shuai, Q.; Wang, J.; Fung, S.; Monzon, K.; Chiou, W.; Stolarik, D.; Imade, H.; et al. Adamantane sulfone and sulfonamide 11-β-HSD1 inhibitors. Bioorg. Med. Chem. Lett. 2007, 17, 527-532.
36. Rohde, J.J.; Pliushchev, M.A.; Sorensen, B.K.; Wodka, D.; Shuai, Q.; Wang, J.; Wang, S.; Monzon, K.; Patel, J.R.; Shuai, Q.; et al. Discovery and metabolic stabilization of potent and selective 2-amino-N-(adamant-2-yl)acetamide 11β-hydroxysteroid dehydrogenase type 1 inhibitors. J. Med. Chem. 2007, 50, 149-164.
37. Malik, S.; Bahare, R.S.; Khan, S.A. Design, synthesis and anticonvulsant evaluation of N-(benzo[b]thiazol-2-ylcarbamoyl)-2-methyl-4-oxoquinazoline-3(4H)-carbothioamide derivatives: A hybrid pharmacophore approach. Eur. J. Med. Chem. 2013, 67, 1-13.
38. Zhu, S.-L.; Wu, Y.; Liu, C.-J.; Wei, C.-Y.; Tao, J.-C.; Liu, H.-M. Synthesis and in vitro cytotoxic activity evaluation of novel heterocycle bridged carbothioamide type derivatives as antitumor agents. Bioorg. Med. Chem. Lett. 2013, 23, 1343-1346.
39. Munch, H.; Hansen, J.S.; Pittelkow, M.; Christensen, J.B.; Boas, U.A. A new efficient synthesis of isothiocyanates from amines using di-tert-butyl dicarbonate. Tetrahedron Lett. 2008, 49, 3117-3119.
40. Spilovska, K.; Korabecny, J.; Kral, J.; Horova, A.; Musilek, K.; Soukup, O.; Drtinova, L.; Gazova, Z.; Siposova, K.; Kuca, K. 7-Methoxytacrine-adamantylamine heterodimers as cholinesterase inhibitors in Alzheimer's disease treatment-synthesis, biological evaluation and molecular modeling studies. Molecules 2013, 18, 2397-2418.
41. El-Emam, A.A.; Al-Abdullah, E.S.; Al-Tuwaijri, H.M.; Chidan Kumar, C.S.; Fun, H.-K. N-(Adamantan-1-yl)-1,2,3,4-tetrahydroisoquinoline-2-carbothioamide. Acta Crystallogr. 2013, E69, o1815.
42. Woods, G.L.; Washington, J.A. Antibacterial susceptibility tests: Dilution and disk diffusion methods. In Manual of Clinical Microbiology; Murray, P.R., Baron, E.J., Pfaller, M.A., Tenover, F.C., Yolken, R.H., Eds.; American Society of Microbiology: Washington, DC, USA, 1995.
43. Performance Standards for Antimicrobial Disk Susceptibility Tests; Approved Standard Document M2-A3; National Committee for Clinical Laboratory Standards (NCCLS): Villanova, PA, USA, 1985.
44. Rossini, A.A.; Like, A.A.; Chick, W.L.; Appel, M.C.; Cahill, G.F., Jr. Studies of streptozotocin-induced insulitis and diabetes. Proc. Natl. Acad. Sci. USA 1977, 74, 2485-2489.
45. Olajide, O.A.; Awe, S.O.; Makinde, J.M.; Morebise, O. Evaluation of the antidiabetic property of Morinda lucida leaves in streptozotocin diabetes rats. J. Pharm. Pharmacol. 1999, 51, 1321-1324.
46. Litchfield, J.T.; Wilcoxon, T. A simplified method of evaluating dose-effect experiments. J. Pharmacol. Exp. Ther. 1949, 96, 99-104.
47. Serradas, P.; Bailbe, D.; Portha, B. Long-term gIiclazide treatment improves the in vitro glucose-induced insulin release in rats with type 2 (non-insulin-dependent) diabetes induced by neonatal streptozotocin. Diabetologia 1989, 32, 577-584.