* Corresponding Author
SYNTHESIS, CHARACTERIZATION AND ANTIMICROBIAL ACTIVITY OF FRIEDELIN [2, 3-d] SELENADIAZOLE
https://doi.org/10.22146/ijc.21554 Mehtab Parveen(1*), Sayed Hasan Mehdi(2), Raza Murad Ghalib(3), Mahboob Alam(4), Rokiah Hashim(5), Othman Sulaiman(6)
(1) Department of Chemistry, Aligarh Muslim University, Aligarh 202002, India
(2) Department of Chemistry, Aligarh Muslim University, Aligarh 202002, India
(3) Department of Chemistry, Aligarh Muslim University, Aligarh 202002, India
(4) Department of Chemistry, Aligarh Muslim University, Aligarh 202002, India
(5) School of Industrial Technology, Universiti Sains Malaysia, 11800 Pulau Penang Malaysia
(6) School of Industrial Technology, Universiti Sains Malaysia, 11800 Pulau Penang Malaysia
(*) Corresponding Author
Abstract
The new 1, 2, 3, selenadiazole derivative (3) was prepared from friedelin (1) via the corresponding semicarbazone (2) using Lalezari cyclization. The compounds were prepared, separated and characterized on the basis of microanalysis and spectral studies. The isolated friedelin and its selenadiazole were screened in vitro for their antimicrobial activities against various pathogenic bacterial were found to be highly active against all the selected pathogens. Compound 3 showed an inhibition zone of 14 mm and 12 mm respectively against highly resistant S. albus and C. albicans. A general mechanistic scheme for these reactions is also suggested based on current and previous results.
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[1] Corey, E.J. and Ursprung, J., 1965, J. Am. Chem. Soc., 78, 5041.
[2] Kane, V.V. and Stevenson, R., 1960, J. Org. Chem., 25, 1344.
[3] Gaikwad, M.S., Mane, A.S., Hamgorge, R.V., Chavan, V.P., and Shingore, M.S., 2003, Ind. J. Chem., 42B, 189.
[4] Reddy, D.B., Reddy, R.V., and Padmavati, 1999, Synth. Commun., 29, 667.
[5] Reddy, D.B., Padmavati, A., and Padmaja, A., 1999, Heterocycl. Commun., 5, 285.
[6] Hu, V., Baudort, S., and Porlo, J.A., 1999, J. Org. Chem., 64, 1049.
[7] Dchaen, W., Voets, M., and Bakuler,V.A., 2000, Adv. Nitrogen Heterocycl., 4, 37.
[8] Shafiee, A., 1976, J. Hetrocycl. Chem., 13, 301.
[9] Dzubak, P., Hajduch, M., Vydra, D., Hustova, A., Kvasnica, Bicdermann, Markova, Lenka, D., Urban, M., and Sarek., 2006, J. Nat. Prod. Res., 23, 394 and references cited therein.
[10] Ramsby, S.O., Ross, S.S., and Stjernstorm, 1973 Acta. Pharma. Secte., 10, 285.
[11] Wasson, B.K., Gibson, W.K., Stuart, R.S., Wittiams, H.W., and Yates, R.C.H., 1972, J. Med. Chem., 15, 651.
[12] Pain, D.L. and Stack, R., 1965, J. Chem. Soc., 5166.
[13] Parveen, M., Khan, N.U., Achari, B., and Dutta, P. K., 1990, Fitoterapia, LXI, 86.
[14] Mushfiq, M., Alam, M., and Akhtar, M.S., 2005, Molecules, 10, 803 and references cited therein.
[15] Geirasatilika, A.A.L., De-J, Y.M., Silva, A., Sotheeswaran, Balasabramonian, S., and Wazeer, M.M., 1984, Phytochemistry, 23, 323.
[16] Crawford, M. Hansan, S.W., and Kokar, M.E.S., 1975, Tetrahedron Lett., 3099.
[17] Budzikiswiez, H., Wilson, J.M., and Djerassi, C., 1963, J. Am. Chem. Soc., 85, 3688.
[18] Socrates, S., Infrared Characteristics Group Frequencies, John Wiley and Sons: New York, 1980, 118.
[19] Shafiee, A., Anaraki, M., and Bazzaz, A., 1986, J. Hetero. Chem., 23, 816.
[20] Karaman, I., Sahin, F., Gulluce, M., Ogutsu, H., Sengul, M., and Adiguezel, 1981, J. Ethnopharmacol., 85, 231-235.
[21] Candan, F., Unlu M., Tepe, B., Daferera, D., Polissiou, M., Sökmen, A., and Akpulat, H.A. 2003, J. Ethnopharmacol., 87, 215-220.
DOI: https://doi.org/10.22146/ijc.21554
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