Abstract
New 1-[(tetrazol-5-yl)methyl]indole derivatives, their acyclic nucleoside analogs and the corresponding glycoside derivatives were synthesized. Furthermore, the [)(1,2,4-triazol-3-yl)methyl])-2H-tetrazole derivative as well as the corresponding thioglucoside were prepared. The synthesized compounds were tested for their antimicrobial activity against Aspergillus Niger, Penicillium sp, Candida albican, Bacillus subtilis, Streptococcus lacti, Escherichia coli, Pseudomonas sp., and streptomyces sp. Compounds 3, 5 and 19b exhibited potent antibacterial activity and compounds 4, 5 and 10 exhibited high activities against the tested fungi compared with fusidic acid.
Article PDF
Similar content being viewed by others
References
Al-Omar, M. A. and Amr, A. E. G. E., Synthesis of some new pyridine-2,6-carboxamide-derived Schiff bases as potential antimicrobial agents. Molecules, 15, 4711–4721 (2010).
Andreani, A., Rambaldi, M., Locatelli, A., and Pifferi, G., Synthesis and antiinflammatory activity of indolylacrylic and methylacrylic acids. Eur. J. Med. Chem., 29, 903–906 (1994).
Bal, T. R., Anand, B., Yogeeswari, P., and Sriram, D., Synthesis and evaluation of anti-HIV activity of isatin β-thiosemicarbazone derivatives. Bioorg. Med. Chem. Lett., 15, 4451–4455 (2005).
Blum, C. A., Xu, M., Orner, G. A., Fong, A. T., Bailey, G. S., Stoner, G. D., Horio, D. T., and Dashwood, R. H., β-Catenin mutation in rat colon tumors initiated by 1,2-dimethylhydrazine and 2-amino-3-methylimidazo[4,5-f]quinoline, and the effect of post-initiation treatment with chlorophyllin and indole-3-carbinol. Carcinogenesis, 22, 315–320 (2001).
Bond, A. D., Fleming, A., Kelleher, F., McGinley, J., and Prajapati, V., Reactions of 1,4-bis(tetrazole)benzenes: formation of long chain alkyl halides. Tetrahedron, 62, 9577–9581 (2006).
Chang, X., Tou, J. C., Hong, C., Kim, H. A., Riby, J. E., Firestone, G. L., and Bjeldanes, L. F., 3,3′-Diindolylmethane inhibits angiogenesis and the growth of transplantable human breast carcinoma in athymic mice. Carcinogenesis, 26, 771–778 (2005).
Chen, I., McDougal, A., Wang, F., and Safe, S., Aryl hydrocarbon receptor-mediated antiestrogenic and antitumorigenic activity of diindolylmethane. Carcinogenesis, 19, 1631–1639 (1998).
Cruickshank, R., Duguid, J. P., Marmion, B. P., and Swain, R. H., Medical Microbiology (12th ed). Longman group Ltd., Edinburgh, London, pp. 180–188, (1975).
Dahiya, R., Synthesis, characterization and antimicrobial studies on some newer imidazole analogs. Sci. Pharm., 76, 217–239 (2008).
Dekker, W. H., Selling, H. A., and Overeem, J. C., Structureactivity relationships to some antifungal indoles. J. Agric. Food Chem., 23, 785–791 (1975).
El-Sayed, W. A., Ramiz, M. M. M., and Abdel-Rahman, A. A. H., C-Furyl glycosides, I. Synthesis and antimicrobial evaluation of C-furyl glycosides and chalcones derived therefrom. Monatsh. Chem., 139, 1499–1505 (2008a).
El-Sayed, W. A., Fathi, N. M., Gad, W. A., and El-Ashry, E. S. H., Synthesis, and antiviral evaluation of some 5-Narylaminomethyl-2-glycosylsulphanyl-1,3,4-oxadiazoles and their analogues against hepatitis A and herpes simplex viruses. J. Carbohydr. Chem., 27, 357–372 (2008b).
El-Sayed, W. A., Ramiz, M. M. M., and Abdel-Rahman, A. A. H., Anti-hepatitis B virus activity of new N4-β-D-glycoside pyrazolo[)3,4-d])pyrimidine derivatives. Z. Naturforsch., 64, 323–328 (2009a).
El-Sayed, W. A., Nassar, I. F., and Abdel-Rahman, A. A. H., C-Furyl glycosides, II: synthesis and antimicrobial evaluation of C-furyl glycosides bearing pyrazolines, isoxazolines, and 5,6-dihydropyrimidine-2(1H)-thiones. Monatsh. Chem., 140, 365–370 (2009b).
El-Sayed, W. A., Rashad, A. E., Awad, S. M., and Ali, M. M., Synthesis and in vitro antitumor activity of some new substituted thiopyrimidine acyclic nucleosides and their thioglycoside analogs. Nucleosides Nucleotides Nucleic Acids, 28, 261–274 (2009c).
Hashimoto, Y., Shudo, K., and Okamoto, T., Deoxyribonu cleic acid modification by mutagenic 3-amino-1-methyl-5H-pyrido[)4,3-b])indole: the chemical events. Chem. Pharm. Bull., 32, 4300–4308 (1984).
Herr, R. J., 5-Substituted-1H-tetrazoles as carboxylic acid isosteres: medicinal chemistry and synthetic methods. Bioorg. Med. Chem., 10, 3379–3393 (2002).
Hong, C., Firestone, G. L., and Bjeldanes, L. F., Bcl-2 familymediated apoptotic effects of 3,3′-diindolylmethane (DIM) in human breast cancer cells. Biochem. Pharmacol., 63, 1085–1097 (2002).
Kamijo, S. and Yamamoto, Y., A bimetallic catalyst and dual role catalyst: synthesis of N-(alkoxycarbonyl)indoles from 2-(alkynyl)phenylisocyanates. J. Org. Chem., 68, 4764–4771 (2003).
Khalil, N. S. A. M., Efficient synthesis, structure, and antimicrobial activity of some novel N-and S-β-D-glucosides of 5-pyridin-3-yl-1,2,4-triazoles. Carbohydr. Res., 341, 2187–2199 (2006).
Khalil, N. S. A. M., N-and S-α-l-arabinopyranosyl[)1,2,4]) triazolo[)3,4-b])[)1,3,4])thiadiazoles. First synthesis and biological evaluation. Eur. J. Med. Chem., 42, 1193–1199 (2007).
Lundt, B. F. and Anderson, W., Analgesic 3-(aminoalkoxy) Indoles. Ger. Offen. 2,024,966 (1970).
Markham, P. N., Westhaus, E., Klyachko, K., Johnson, M. E., and Neyfakh, A. A., Multiple novel inhibitors of the NorA multidrug transporter of Staphylococcus aureus. Antimicrob. Agents Chemother., 43, 2404–2408 (1999).
Master, H. E., Khan, S. I., and Poojari, K. A., Design and synthesis of low molecular weight compounds with complement inhibition activity. Bioorg. Med. Chem., 13, 4891–4899 (2005).
Misra, U., Hitkari, A., Saxena, A. K., Gurtu, S., and Shanker, K., Biologically active indolylmethyl-1,3,4-oxadiazoles, 1,3,4-thiadiazoles, 4H-1,3,4-triazoles and 1,2,4-triazines. Eur. J. Med. Chem., 31, 629–634 (1996).
Nakashima, Y., Kawashima, Y., Amanuma, F., Sota, K., Tanaka, A., and Kameyama, T., Furo[)3,2-b])indole derivatives. I. Synthesis and analgesic and anti-inflammatory activities of 4, 6-disubstituted-furo[)3,2-b])indole-2-carboxamide derivatives. Chem. Pharm. Bull., 32, 4271–4280 (1984).
Pandeya, S. N., Sriram, D., Nath, G., and DeClercq, E., Synthesis, antibacterial, antifungal and anti HIV activities of Schiff and Mannich bases derived from isatin derivatives and N-[4-(4′-chlorophenyl)thiazol-2-yl]thiosemicarbazide. Eur. J. Pharm. Sci., 9, 25–31 (1999).
Pirrung, M. C., Pansare, S. V., Das Sarma, K., Keith, K. A., and Kern, E. R., Combinatorial optimization of isatin-β-thiosemicarbazones as anti-poxvirus agents. J. Med. Chem., 48, 3045–3050 (2005).
Poyner, T. F. and Dass, B. K., The role of Staphylococcus aureus in atopic eczema. J. Eur. Acad. Dermatol. Venereol., 7, S23–S30 (1996).
Rajasekaran, A. and Thampi, P. P., Synthesis and antinociceptive activity of some substituted-{5-[2-(1,2,3,4-tetrahydrocarbazol-9-yl)ethyl]tetrazol-1-yl}alkanones. Eur. J. Med. Chem., 40, 1359–1364 (2005).
Samosorn, S., Bremner, J. B., Ball, A., and Lewis, K., Synthesis of functionalized 2-aryl-5-nitro-1H-indoles and their activity as bacterial NorA efflux pump inhibitors. Bioorg. Med. Chem., 14, 857–865 (2006).
Saxton, J. E., Indoles. Wiely-Interscience, New York, Part 4 (1983).
Shimizu, M., Ishikawa, M., Komoda, Y., Nakajima, T., Yamaguchi, K., and Yoneda, N., Stereochemistry of methyl 2-benzyl-3-methoxycarbonyl-9-methyl-1, 2, 3, 4-tetrahydro-9H-pyrido[)3,4-b])indole-1-propionate. Chem. Pharm. Bull., 32, 463–474 (1984).
Sriram, D., Yogeeswari, P., and Gopal, G., Synthesis, anti-HIV and antitubercular activities of lamivudine prodrugs. Eur. J. Med. Chem., 40, 1373–1376 (2005).
Su, H. C., Ramkissoon, K., Doolittle, J., Clark, M., Khatun, J., Secrest, A., Wolfgang, M. C., and Giddings, M. C., The development of ciprofloxacin resistance in Pseudomonas aeruginosa involves multiple response stages and multiple proteins. Antimicrob. Agents Chemother., 54, 4626–4635 (2010).
Velezheva, V. S., Brennan, P. J., Marshakov, V. Y., Gusev, D. V., Lisichkina, I. N., Peregudov, A. S., Tchernousova, L. N., Smirnova, T. G., Andreevskaya, S. N., and Medvedev, A. E., Novel pyridazino[)4,3-b])indoles with dual inhibitory activity against Mycobacterium tuberculosis and monoamine oxidase. J. Med. Chem., 47, 3455–3461 (2004).
Webber, S. E., Tikhe, J., Worland, S. T., Fuhrman, S. A., Hendrickson, T. F., Matthews, D. A., Love, R. A., Patick, A. K., Meador, J. W., Ferre, R. A., Brown, E. L., DeLisle, D. M., Ford, C. E., and Binford, S. L., Design, synthesis, and evaluation of nonpeptidic inhibitors of human rhinovirus 3C protease. J. Med. Chem., 39, 5072–5082 (1996).
Zhang, H. Z., Kasibhatla, S., Kuemmerle, J., Kemnitzer, W., Ollis-Mason, K., Qiu, L., Crogan-Grundy, C., Tseng, B., Drewe, J., and Cai, S. X., Discovery and structure-activity relationship of 3-aryl-5-aryl-1,2,4-oxadiazoles as a new series of apoptosis inducers and potential anticancer agents. J. Med. Chem., 48, 5215–5223 (2005).
Author information
Authors and Affiliations
Corresponding author
Rights and permissions
About this article
Cite this article
El-Sayed, W.A., Abdel Megeid, R.E. & Abbas, HA.S. Synthesis and antimicrobial activity of new 1-[(tetrazol-5-yl)methyl] indole derivatives, their 1,2,4-triazole thioglycosides and acyclic analogs. Arch. Pharm. Res. 34, 1085–1096 (2011). https://doi.org/10.1007/s12272-011-0706-y
Received:
Revised:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s12272-011-0706-y