Abstract
The synthesis of 2-anilino-1,3-benzothiazoles was achieved by reacting N,N′-diarylthioureas with iodine–alumina under solvent-free conditions. The synthesized compounds were screened for antibacterial and antifungal activities, and their minimum inhibition concentrations against some microbial strains were determined.
REFERENCES
Soni, B., Ranawat, M.S., Sharma, R., Bhandari, A., and Sharma, S., Eur. J. Med. Chem., 2010, vol. 45, p. 2938. https://doi.org/10.1016/j.ejmech.2010.03.019
Yildiz-Oren, I., Yalcin, I., Aki-Sener, E., and Ucarturk, N., Eur. J. Med. Chem., 2004, vol. 39, p. 291. https://doi.org/10.1016/j.ejmech.2003.11.014
Westley, J.W., Liu, C.-M., Blount, J.F., Sello, L.H., Troupe, N., and Miller, P.A., J. Antibiot., 1983, vol. 36, p. 1275. https://doi.org/10.7164/antibiotics.36.1275
Ferrari, S., Morandi, F., Motiejunas, D., Nerini, E., Henrich, S., Luciani, R., Venturelli, A., Lazzari, S., Calo, S., Gupta, S., Hannaert, V., Michels, P.A.M., Wade, R.C., and Costi, M.P., J. Med. Chem., 2011, vol. 54, p. 211. https://doi.org/10.1021/jm1010572
Powers, J.P., Li, S., Jaen, J.C., Liu, J., Walker, N.P.C., Wang, Z., and Wesche, H., Bioorg. Med. Chem. Lett., 2006, vol. 16, p. 2842. https://doi.org/10.1016/j.bmcl.2006.03.020
Katsura, Y., Nishino, S., Inoue, Y., Tomoi, M., and Takasugi, H., Chem. Pharm. Bull., 1992, vol. 40, p. 2062. https://doi.org/10.1248/cpb.40.371
McKee, M.L. and Kerwin, S.M., Bioorg. Med. Chem., 2008, vol. 16, p. 1775. https://doi.org/10.1016/j.bmc.2007.11.019
Ramalingan, C., Balasubramanian, S., Kabilan, S., and Vasudevan, M., Eur. J. Med. Chem., 2004, vol. 39, p. 527. https://doi.org/10.1016/j.ejmech.2004.02.005
Jordan, A.D., Luo, C., and Reitz, A.B., J. Org. Chem., 2003, vol. 68, p. 8693. https://doi.org/10.1021/jo0349431
Yella, R. and Patel, B.K., J. Comb. Chem., 2010, vol. 12, p. 754. https://doi.org/10.1021/cc100124q
van Heusden, J., van Ginckel, R., Bruwiere, H., Moelans, P., Janssen, B., Floren, W., van der Leede, B.J., van Dun, J., Sanz, G., Venet, M., Dillen, L., van Hove, C., Willemsens, G., Janicot, M., and Wouters, W., Br. J. Cancer, 2002, vol. 86, p. 605. https://doi.org/10.1038/sj/bjc/6600056
Catalano, A., Carocci, A., Defrenza, I., Muraglia, M., Carrieri, A., van Bambeke, F., Rosato, A., Corbo, F., and Franchini, C., Eur. J. Med. Chem., 2013, vol. 64, p. 357. https://doi.org/10.1016/j.ejmech.2013.03.064
McDonnell, M.E., Vera, M.D., Blass, B.E., Pelletier, J.C., King, R.C., Fernandez-Metzler, C., Smith, G.R., Wrobel, J., Chen, S., Wall, B.A., and Reitz, A., Bioorg. Med. Chem., 2012, vol. 20, p. 5642. https://doi.org/10.1016/j.bmc.2012.07.004
Massari, S., Daelemans, D., Barreca, M.L., Knezevich, A., Sabatini, S., Cecchetti, V., Marcello, A., Pannecouque, C., and Tabarrini, O., J. Med. Chem., 2010, vol. 53, p. 641. https://doi.org/10.1021/jm901211d
Abdel-Aziz, M., Matsuda, K., Otsuka, M., Uyeda, M., Okawara, T., and Suzuki, K., Bioorg. Med. Chem. Lett., 2004, vol. 14, p. 1669. https://doi.org/10.1016/j.bmcl.2004.01.060
Patel, N.B., Khan, I.H., and Rajani, S.D., Eur. J. Med. Chem., 2010, vol. 45, p. 4293. https://doi.org/10.1016/j.ejmech.2010.06.031
Ben-Alloum, A., Bakkas, S., and Soufiaoui, M., Tetrahedron Lett., 1997, vol. 38, p. 6395. https://doi.org/10.1016/S0040-4039(97)01490-1
Seijas, J.A., Vazquez-Tato, M.P., CarballidoReboredo, M.R., Crecente-Campo, J., and RomarLopez, L., Synlett, 2007, vol. 2007, no. 2, p. 313. https://doi.org/10.1055/s-2007-967994
Jaseer, E.A., Prasad, D.J.C., Dandapat, A., and Sekar, G., Tetrahedron Lett., 2010, vol. 51, p. 5009. https://doi.org/10.1016/j.tetlet.2010.07.079
Ranu, B.C., Jana, R., and Dey, S.S., Chem. Lett., 2004, vol. 33, p. 274. https://doi.org/10.1246/cl.2004.274
Li, Y., Wang, Y.-L., and Wang, J.-Y., Chem. Lett., 2006, vol. 35, p. 460. https://doi.org/10.1246/cl.2006.460
Moghaddam, F.M., Ismaili, H., and Bardajee, G.R., Heteroat. Chem., 2006, vol. 17, p. 136. https://doi.org/10.1002/hc.20191
Ryabukhin, S.V., Plaskon, A.S., Volochnyuk, D.M., and Tolmachev, A.A., Synthesis, 2006, vol. 21, p. 3715. https://doi.org/10.1055/s-2006-950289
Chakraborti, A.K., Rudrawar, S., Jadhav, K.B., Kaur, G., and Chankeshwara, S.V., Green Chem., 2007, vol. 9, p. 1335. https://doi.org/10.1039/b710414f
Praveen, C., Kumar, K.H., Muralidharan, D., and Perumal, P.T., Tetrahedron, 2008, vol. 64, p. 2369. https://doi.org/10.1016/j.tet.2008.01.004
Bahrami, K., Khodaei, M.M., and Naali, F., J. Org. Chem., 2008, vol. 73, p. 6835. https://doi.org/10.1021/jo8010232
Kumar, P., Meenakshi, Kumar, S., Kumar, A., Hussain, K., and Kumar, S., J. Heterocycl. Chem., 2012, vol. 49, p. 1243. https://doi.org/10.1002/jhet.962
Yella, R. and Patel, B.K., J. Comb. Chem., 2010, vol. 12, p. 754. https://doi.org/10.1021/cc100124q
Guo, Y.-J., Tang, R.-Y., Zhong, P., and Li, J.-H., Tetrahedron Lett., 2010, vol. 51, p. 649. https://doi.org/10.1016/j.tetlet.2009.11.086
Ding, Q., He, X., and Wu, J., J. Comb. Chem., 2009, vol. 11, p. 587. https://doi.org/10.1021/cc900027c
Shen, G., Lv, X., and Bao, W., Eur. J. Org. Chem., 2009, vol. 34, p. 5897. https://doi.org/10.1002/ejoc.200900953
Nahakpam, L., Chingakham, B.S., and Laitonjam, W.S., J. Heterocycl. Chem., 2015, vol. 52, p. 267. https://doi.org/10.1002/jhet.1928
Zeng, L.-Y. and Cai, C., J. Comb. Chem., 2010, vol. 12, p. 35. https://doi.org/10.1021/cc9000983
Nath, J., Ghosh, H., Yella, R., and Patel, B.K., Eur. J. Org. Chem., 2009, vol. 12, p. 1849. https://doi.org/10.1002/ejoc.200801270
Boyle, P.D. and Godfrey, S.M., Coord. Chem. Rev., 2001, vol. 223, p. 265. https://doi.org/10.1016/S0010-8545(01)00386-1
Shibahara, F., Kitagawa, A., Yamaguchi, E., and Murai, T., Org. Lett., 2006, vol. 8, p. 5621. https://doi.org/10.1021/ol0623623
Campaigne, E. and Cline, R.E., J. Org. Chem., 1956, vol. 21, p. 39. https://doi.org/10.1021/jo01107a007
Townsend, N.O. and Jackson, Y.A., Org. Biomol. Chem., 2003, vol. 1, p. 3557. https://doi.org/10.1039/B307124C
Tanaka, K., Solvent-Free Organic Synthesis, Weinheim: Wiley-VCH, 2003. https://doi.org/10.1021/op034052v
Pagni, R.M., Kabalka, G.W., Boothe, R., Gaetano, K., Stewart, L.J., Conaway, R., Dial, C., Gray, D., Larson, S., and Luidhardt, T., J. Org. Chem., 1988, vol. 53, p. 4477. https://doi.org/10.1021/jo00254a011
Saxena, I., Borah, D.C., and Sarma, J.C., Tetrahedron Lett., 2005, vol. 46, p. 1159. https://doi.org/10.1016/j.tetlet.2004.12.081
Rajbangshi, M., Rohman, Md.R., Kharkongor, I., Mecadon, H., and Myrboh, B., Org. Chem. Int., 2011, vol. 2011, article ID 514620. https://doi.org/10.1155/2011/514620
Rohman, Md.R., Rajbangshi, M., Laloo, B.M., Sahu, P.R., and Myrboh, B., Tetrahedron Lett., 2010, vol. 51, p. 2862. https://doi.org/10.1016/j.tetlet.2010.03.084
Downer-Riley, N.K. and Jackson, Y.A., Tetrahedron, 2007, vol. 63, p. 10276. https://doi.org/10.1016/j.tet.2007.07.076
Nahakpam, L., Chipem, F.A.S., Chingakham, B.S., and Laitonjam, W.S., New J. Chem., 2015, vol. 39, p. 2240. https://doi.org/10.1039/C4NJ02021A
Cheng, Y., Peng, Q., Fan, W., and Li, P., J. Org. Chem., 2014, vol. 79, p. 5812. https://doi.org/10.1021/jo5002752
Motiwala, H.F., Kumar, R., and Chakraborti, A.K., Aust. J. Chem., 2007, vol. 60, p. 369. https://doi.org/10.1071/CH06391
Cerniani, A. and Passerini, R., J. Chem. Soc., 1954, p. 2261. https://doi.org/10.1039/JR9540002261
Khatun, N., Jamir, L., Ganesh, M., and Patel, B.K., RSC Adv., 2012, vol. 2, p. 11557. https://doi.org/10.1039/C2RA21826G
Perez, C., Pauli, M., and Bazerque, P., Acta Biol. Med. Exp., 1990, vol. 15, p. 113.
Tereschuk, M.L., Riera, M.V.Q., Castro, G.R., and Abdala, L.R., J. Ethnopharmacol., 1997, vol. 56, p. 227. https://doi.org/10.1016/S0378-8741(97)00038-X
Zgoda, J.R. and Porter, J.R., Pharm. Biol., 2001, vol. 39, p. 221. https://doi.org/10.1076/phbi.39.3.221.5934
Kuete, V., Ngameni, B., Simo, C.C.F., Tankeu, R.K., Ngadjui, B.T., Meyer, J.J.M., Lall, N., and Kuiate, J.R., J. Ethnopharmacol., 2008, vol. 120, p. 17. https://doi.org/10.1016/j.jep.2008.07.026
Funding
L.N. is grateful to UGC, New Delhi, for the financial support under the scheme of UGC-BSR Research Fellowship in Science 2011–2012 [vide order no. F.4-1/2006(BSR)/7-230/2009(BSR)].
Author information
Authors and Affiliations
Corresponding author
Ethics declarations
The authors declare no conflict of interest.
Supplementary information
Rights and permissions
About this article
Cite this article
Nahakpam, L., Thiyam, M.D. & Laitonjam, W.S. Simple and Facile Synthesis of 2-(Arylamino)-1,3-benzothiazoles Using Iodine–Alumina (I2-Al2O3) as Heterogenous Catalyst and Their Antimicrobial Activity. Russ J Org Chem 59, 133–141 (2023). https://doi.org/10.1134/S1070428023010141
Received:
Revised:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1134/S1070428023010141