Synthesis and in-vitro antimicrobial screening of 3-cinnamoyl coumarin and 3-[3-(1H-indol-2-yl)-3-aryl-propanoyl]-2H-chromen-2-ones
محورهای موضوعی : Iranian Journal of Catalysis
Somnath Gholap
1
(
Department of Chemistry, Padmashri Vikhe Patil College, Pravaranagar (Loni Kd), Tal- Rahata, Dist -Ahmednagar, Pin-413713,(MS), India.
)
Umesh Deshmukh
2
(
Department of Chemistry, Padmashri Vikhe Patil College, Pravaranagar (Loni Kd), Tal- Rahata, Dist -Ahmednagar, Pin-413713,(MS), India.
)
Macchindra Tambe
3
(
Department of Chemistry, Padmashri Vikhe Patil College, Pravaranagar (Loni Kd), Tal- Rahata, Dist -Ahmednagar, Pin-413713,(MS), India.
)
کلید واژه: 1, Antibacterial activity, Cellulose sulphonic acid(CSA), 3-acetyl coumarinn, Chalcones, Indole, 4-Michael addition,
چکیده مقاله :
An efficient synthesis of some novel coumarin derivatives via 1, 4- Michael addition of indole to coumarin chalcones catalyzed by cellulose sulphonic acid (CSA) under solvent free conditions is described. The corresponding Michael addition products were obtained in good to excellent yield. The synthesized compounds were screened for their antibacterial activity against E. coli, S. aureus and anti-fungal activity against C. albicans. All the synthesized compounds show moderate to good antimicrobial activity.
[1] M. Laposata, C. Van; E. Lev, Nation Master Encyclopedia, 356 (2007) 178- 82.
[2] (a) A.M. El-Agrody, M.S. Abd El-Latif; N.A. El-Hady; A.H. Fakery; A.H. Bedair, Molecules, 6 (2001) 519- 527; (b) S. Prathiba, P. Shreeya, Indian J. Chem., 38B, (1999) 1139-1142.
[3] (a) T. Patonay, G. Y. Litkei, R.Bognar, J. Erdei, C. Misztic, Pharmazie, 39 (1984) 86-91; (b) R.M. Shaker, Pharmazie, 51 (1996) 148-151.
[4] A.F. El-Farargy, Egypt J. Pharm. Sci., 32 (1991) 625-632.
[5] I. Manolov, N.D. Danchev, Eur. J. Med. Chem., 30 (1995) 531- 536.
[6] (a) A.A. Emmanuel-Glota, K.C. Fylaktakidou, D.J. Hadjipavlou-Litina, K.E. Litinas, D.N. Nicolaides, J. Heterocycl. Chem., 38 (2001) 717-722; (b) L.Raev, E. Voinov, I. Ivanov; D. Popov, Pharmazie, 45 (1990) 696-698.
[7] Z.M. Nofal, M.El-Zahar, S. Abd El-Karim Molecules, 5 (2000) 99- 113.
[8] L. Xie, Y. Tukeuchi, L.M. Consetino, K. Lee, J. Med. Chem., 42 (1999) 2662-2672.
[9] R. OKennedy, R.D. Thornes, Coumarins: Biology, Applications and Mode of Action; John Wiley & Sons Ltd.: Chichester, UK, (1997).
[10] M.V. Nora de Souza, J. Sulfur Chem., 26 (2005) 429-449.
[11] A. Geronikaki, E. Babaev, J. Dearden, W. Dehaen, D. Filimonov, I. Galaeva, V. Krajneva, A.Lagunin, F. Macaev, G. Molodavkin, V. Poroikov, S. Pogrebnoi, V. Saloutin, A. Stepanchikova, E. Stingaci, N. Tkach, L. Vlad, T. Voronina, Bioorg. Med. Chem., 12 (2004) 6559-6568.
[12] R.E. Sammelson, P. Caboni, K.A. Durkin, J.E. Casida, Bioorg. Med. Chem., 12 (2004) 3345-3355.
[13] (a) A. Bekhit, T. Abdel-Aziem, Bioorg. Med. Chem., 12 (2004) 1935-1945; (b) M.P. Leze, M. Le Borgne, P. Marchand, D. Loquet, M. Kogler, C. Le Bant, A. Palusczak, R.W. Hartmann, J. Enz. Inhib. Med. Chem., 19 (2004) 549-557; (c) M. Le Borgne, P. Marchand, B. Delevoye-Seiller, J.M. Robert, C. Le Bant, R.W. Hartmann, M. Palzer, Bioorg. Med. Chem. Lett., 9 (1999) 333-336.
[14] K. Irena, Curr. Med., (2005) 45-52.
[15] N.S. Radulovic, B.R. Dekic, V.S. Dekic, R.D. Vukicevic, R.M. Palic, Molecules, 15 (2010) 2246-2256.
[16] Y.R. Prasad, P.R. Kumar, C.A. Deepti, R.M. Venkata, E. J. Chem,, 3 (2006) 236-241.
[17] F. Radoslav, S. Henrieta, G. Anton, D. Jana, Molecules, 14 (2009) 4838-4848.
[18] S. Govori, S. Spahiu, V. Kalaj, O. Leci, A. Haziri, H. Ibrahimi, Am. J. Biochem. Biotech., 6 (2010) 275- 278.
[19] B.P. Langi, V.V. Mulwad, A.C. Chaskar, Act. Polon. Pharm. Drug Res., 68 (2011) 441- 446.
[20] S. Stefan, B. Petra, T. Samo, J. Cesar, L.R. Tea, S. Gobec, J. Med. Chem., 54 (2011) 248–261.
[21] R.M. Brown, I.M. Saxena, Cellulose: Molecular and Structural Biology: Selected Articles On The Synthesis, Stracture and Application Of Cellulose; Springer: Netherlands (2007).
[22] K. Molvinger, F. Quignard, D. Brunel, M.J.M. Boissiere, Chem. Matter., 16 (2004) 3367-3372.
[23] A. Shaabani, A. Maleki, Appl. Catal. A, 331 (2007) 149-151.
[24] H.A. Oskooie, L. Tahershamsi, M.M. Heravi; B. Baghernejad, E. J. Chem., 7 (2010) 717.
[25] A. Shaabani, A. Maleki, J.M. Rad, E. Soleimani; Chem. Pharm. Bull., 55 (2007) 957-958.
[26] B.V.S. Reddy, A. Venkateswarlu, G.G.K.S. Narayana Kumar, A. Vinu, Tetrahedron Lett., 51 (2010) 6511–6515.
[27] R.S. Joshi, P.G. Mandhane, D.R. Nagargoje, M.S. Shingare, C. H. Gill, Bull. Catal. Soc. India, 8 (2008) 7-10.
[28] H. Alinezhad, A. Haghigh, F. Salehian, Chin. Chem. Lett., 21 (2010) 183-186.
[29] K.F. Shelke, S.B. Sapkal, G.K. Kakade, B.B. Shingate, M.S. Shingare, Green Chem. Lett. Rev., 3(2010) 27-32.
[30] H.A. Oskooie, M.M. Heravi, L. Tahershamsi, S. Sadjadi, M. Tajbakhsh, Synth Commun., 3 (2010) 1772-1777.
[31] K.F. Shelke, S.B. Sapkal, K.S. Niralwad, B.B. Shingate, M.S. Shingare, Cent. Eur J. Chem., 8 (2010) 12-18.
[32] A. Shaabani, M. Seyyedhamzeh, A. Maleki, F. Rezazadeh, Appl. Catal. A, 358 (2009) 146-149.
[33] (a) S. Gholap, V. Dhakane, S. Gholap, Jordan J. Chem., 7 (2012) 279-285; (b) S.S. Gholap, V.D. Dhakane, U.P. Deshmukh, H.V. Chavan, B.P. Bandgar, Comptes Rendus Chimie, (2013) In Press, http:// dx.doi.org/10.1016/ j.crci.2013.06.002; (c) S.S. Gholap, N. Gunjal, Arabian J. Chem. (2013) In Press, http:// dx.doi.org/10.1016/j.arabjc.2013.10.021; (d) S.S. Gholap, P.B. Wakchaure, G.R. Pandhare, C.H. Gill, Indian J. Heterocycl. Chem., (2009) 279-282; (e) S.S. Gholap, V.D. Dhakane, S.N. Shelke, M.S. Tambe, Bull. Catal. Soc. India, 11 (2012) 50-55; (f) S.S. Gholap, G.B. Tambe, C.H. Gill, J. Indian Chem. Soc., 86 (2009) 179-82; (g) S.N. Shelke, Y.J. Pawar, S.B. Pawar, S.S. Gholap, C.H. Gill, J. Indian Chem. Soc., 43 (2012) DOI: 10.1002/chin.201203091; (h) S.S. Gholap, C.H. Gill, Bull. Cat. Soc. India, 9 (2010) 13-17; (i) S.S. Gholap, Heterocycl. Lett., 2 (2012) 461-466.
