Rapid synthesis and biological evaluation of 1,4-dihydropyridine derivatives containing a benzothiazolyl moiety

• Authors: Mithlesh , Pawan Pareek , Ravi Kant , Sanjeev Shukla , Krishan Ojha
• Languages of publication: EN

Abstracts

EN

A series of N-(6-methylbenzothiazolyl)-2,3,5,6-tetrasubstituted-4-(aryl)-1,4-dihydropyridines were synthesized by reaction of 2-amino-6-methylbenzothiazole, aromatic aldehyde and active methylene compound in methanol by conventional, as well as, microwave irradiation (solvent free and solid support) methods. The microwave irradiation technique gives better yield and shorter reaction time. Among solid supported microwave irradiation better yields are obtained in acidic alumina as compared to silica, neutral alumina, and basic alumina. All compounds were tested for antibacterial and antifungal activities and results have been compared with standard drugs. Entomological activities were also tested. The results showed that a change in the substitution pattern in 1,4-dihydropyridine derivatives may cause a marked effect on their antimicrobial activity. [...]

Keywords

EN

Benzothiazole; 1,4-Dihydropyridine; Antimicrobial activity; Microwave irradiation; Entomological activity

• Publisher: De Gruyter Open
• Journal: Open Chemistry
• Year: 2010
• Volume: 8
• Issue: 1
• Pages: 163-173

Dates

published

1 - 2 - 2010

online

16 - 2 - 2010

Contributors

author

Mithlesh

• Department of Pure and Applied Chemistry, M.D.S. University, Ajmer, 305009, India

author

Pawan Pareek

• Department of Pure and Applied Chemistry, M.D.S. University, Ajmer, 305009, India

author

Ravi Kant

• Hygia Institute of Pharmaceutical Education and Research, Lucknow, 226020, India

author

Sanjeev Shukla

• SAIF Division, Central Drug Research Institute, Lucknow, 226020, India

author

Krishan Ojha

• Department of Pure and Applied Chemistry, M.D.S. University, Ajmer, 305009, India

References

• [1] A. Hantzsch, Justus Liebigs Ann. Chem. 215, 1 (1882) http://dx.doi.org/10.1002/jlac.18822150102[Crossref]
• [2] U. Eisner, J. Kuthan, Chem. Rev. 72, 1 (1972) http://dx.doi.org/10.1021/cr60275a001[Crossref]
• [3] J. Kuthan, A. Kurfurst, Ind. Eng. Chem. Prod. Res. Dev. 191, (1982) [Crossref]
• [4] D. M. Stout, A. I. Meyers, Chem. Rev. 82, 223 (1982) http://dx.doi.org/10.1021/cr00048a004[Crossref]
• [5] G.V.M. Sharma, K.L. Reddy, P.S. Lakshmi, P.R. Krishna, Synthesis 1, 55 (2006) http://dx.doi.org/10.1055/s-2005-921744[Crossref]
• [6] I. Misane et al., European Neuro-Psychopharmacology 8, 329 (1998)
• [7] P.S. Eharkar et al., J. Med. Chem. 45, 4858 (2002) http://dx.doi.org/10.1021/jm020217z[Crossref]
• [8] B. Desai, D. Sureja, Y. Nalapara, A. Shah, A.K. Saxena, Bioorg. Med. Chem. 9, 1993 (2001) http://dx.doi.org/10.1016/S0968-0896(01)00141-9[Crossref]
• [9] H. Gaveriya, B. Desai, V. Vora, A. Shah, Indian J. Pharm. Sci. 64, 59 (2002)
• [10] T. Tsuruo, H. Iida, M. Nojiri, S. Tsukagoshi, Y. Sakurai, Pharmacology 29, 282 (1984) http://dx.doi.org/10.1159/000138024[Crossref]
• [11] W.J. Malaise, P.C. Mathias, Diabetologia 28, 153 (1985) http://dx.doi.org/10.1007/BF00281986[Crossref]
• [12] R. Peri, S. Padmanabhan, S. Singh, A. Rutledge, D.J. Triggle, J. Med. Chem. 43, 2906 (2000) http://dx.doi.org/10.1021/jm000028l[Crossref]
• [13] R.W. Chapman, G. Danko, M.I. Siegels, Pharmacology 29, 282 (1984) http://dx.doi.org/10.1159/000138024[Crossref]
• [14] A. Krauze, S. Germane, O. Eberlins, I. Sturms, V. Klusa, G. Duburs, Eur. J. Med. Chem. 34, 301 (1999) http://dx.doi.org/10.1016/S0223-5234(99)80081-6[Crossref]
• [15] K. Cooper, F.M. Johnathon, Dihydropyridine antiallergic and anti-inflammatory agents, Eur Patent 294074 (1988)
• [16] R.C. Johnson, D.J. Taylor, 4-(nitrone aryl) dihydropyridines, Us Patent 4758669 (1998)
• [17] B. Khadikar, S. Borkat, Synth. Commun. 28, 207, (1998) http://dx.doi.org/10.1080/00397919808005712[Crossref]
• [18] X. Zhou, L. Zhang, E. Tseng, E. Sctott-Ramsay, J.J. Schentag, R.A. Coburn, M.E. Morris, Drug Metab. Dispos. 33, 321 (2005) http://dx.doi.org/10.1124/dmd.104.002089[Crossref]
• [19] B.Z. Peterson, W.A. Catterall, Mol. Pharmacol. 70, 667 (2006) http://dx.doi.org/10.1124/mol.105.020644[Crossref]
• [20] A. Fassihi, H. Sadeghi, A. Zarghi, A. Shafiee, J. Res. Med. Science 1, 5 (2004)
• [21] G.P. Geewananda, K. Shigeo, P.G. Sarath, J.M. Oliver, E.K. Frank, J. Am. Chem. Soc. 110(14), 4856 (1988) http://dx.doi.org/10.1021/ja00222a071[Crossref]
• [22] G.P Geewananda, K. Shigeo, S.B. Neal, Tetrahedron Lett. 30, 4359 (1989) http://dx.doi.org/10.1016/S0040-4039(00)99360-2[Crossref]
• [23] G.P. Gunawardana, F.E. Koehn, A.Y. Lee, J. Clardy, H.Y. He, J.D. Faulkenr, J. Org. Chem. 57(5), 523 (1992) http://dx.doi.org/10.1021/jo00031a035[Crossref]
• [24] A.R. Carroll, P.J. Scheuer, J. Org. Chem. 55(14), 4426 (1990) http://dx.doi.org/10.1021/jo00301a040[Crossref]
• [25] F. Delmas, C.G. Di, M. Robin, Antimicrob. Agents Chemother. 46, 2588 (2002) http://dx.doi.org/10.1128/AAC.46.8.2588-2594.2002[Crossref]
• [26] G. Turan-Zitouni, S. Demyrayak, A. Ozdemir, Z.A. Kaplancikli, M.T. Yildiz, Eur. J. Med. Chem. 39, 267 (2004) http://dx.doi.org/10.1016/j.ejmech.2003.11.001[Crossref]
• [27] K. Srimanth, V.R. Rao, D.R. Krishna, Arzneimittelforschung 52, 388 (2002)
• [28] T.D. Bradshaw, M.F.G. Stevens, A.D. Westwell, Curr. Med. Chem. 8, 203 (2001)
• [29] P. Magdolen, P. Zahradnik, Arzeimittelforsch 50, 1023 (2000)
• [30] A.B. Nadkarni, R.V. Kamath, G.B. Khadse, Indian J. Heterocyclic Chem. 9, 309 (2000)
• [31] F. Delmas et al., Eur. J. Med. Chem, 39, 685 (2004) http://dx.doi.org/10.1016/j.ejmech.2004.04.006[Crossref]
• [32] P. Jimonet, A. Francois, M. Barreau, J.C. Blanchard, A. Boirean, Indian J. Med. Chem. 42, 2828 (1991) [Crossref]
• [33] E. Kashiyama et al., J. Med. Chem. 42(20), 4172 (1999) http://dx.doi.org/10.1021/jm990104o[Crossref]
• [34] D.F. Shi et al., J. Med. Chem. 39(17), 3375 (1996) http://dx.doi.org/10.1021/jm9600959[Crossref]
• [35] I.R. Baxendale, S.V. Ley, Nature Rev. 1, 573 (2002) http://dx.doi.org/10.1038/nrd871[Crossref]
• [36] M. Jeselnik, R.S. Varma, S. Polanc, M. Kooevar, Greenchem. 4, 35 (2002)
• [37] R. Kant, G. Amresh, K. Chandrashekar, K.K.S. Anil, Phosphorus, Sulfur, Silicon 183, 1410 (2008) http://dx.doi.org/10.1080/10426500701655932[Crossref]
• [38] R. Kant et al., Phosphorus, Sulfur, Silicon 183, 2029 (2008) http://dx.doi.org/10.1080/10426500701841763[Crossref]
• [39] V.S. Chauhan et al., International Journal of Biotechnology Research 2(1), 67 (2009)
• [40] K. Chandrashekar et al., PCT (Global) Patent. W.O. 2006/067800A-1
• [41] M. Mahmoudian, Iranian Journal of Pharmacology & Therapeutics 2 (Autumn 2003)
• [42] N.R. Natale, Chemical Innovation 30, 22 (2000)
• [43] J. Satoh, M. Ichihasi, K. Okumura, Chem. Pharm. Bull. 39, 4189 (1991)
• [44] H. Kanno, H. Yamaguchi, Y. Okamiya, K. Sunakawa. T. Takeshits, T. Naruchi, Chem. Pharm. Bull. 40, 2049 (1992) [Crossref]
• [45] A.M. Shelton, J.L. Robertson, J.D. Tang, J. Econ. Entomol. 86(9), 697 (1993) [Crossref]
• [46] H. Jinfeng, L. Pei, S. Xueyan, G. Xiwu, J. Insect. Sci. 8(3), 9 (2008)

Identifiers

DOI

10.2478/s11532-009-0114-z