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Synthesis and Biological Evaluation of Furo[3,2-c]pyrazole-5-carbimidates
Corresponding Author(s) : Sravanthi Siliveri
Asian Journal of Chemistry,
Vol. 31 No. 10 (2019): Vol 31 Issue 10
Abstract
In the present work, novel pyrazole fused dihydrofurans synthesized via a chronological addition of N-chloro succinimide and base piperidine to pyrano[3,2-c]pyrazole carbonitrile derivatives in methanol medium. Oxidative difunctionalization was done with the reagent N-chloro succinimide by the addition of both chlorine and alkoxy groups crosswise the chromene double bond. The addition of base results in the construction of dihydrofuran derivatives by ring contraction. The structures of newly synthesized compounds were characterized on the basis of physical and spectral data. Synthesized compounds were evaluated for antibacterial and anti-inflammatory activities. All the compounds exhibited significant antibacterial activity against all the four strains of bacteria and their MICs ranged between 1.56 and 12.55 μg/mL. In anti-inflammatory screening, among all the tested compounds, compounds 7, 8, 9, 11, 12, 13, 14, 16, 17 and 18 exhibited significant protection against the edema formation at a concentration of 100 mg/kg.
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- K. Karrouchi, S. Radi, Y. Ramli, J. Taoufik, Y.N. Mabkhot, F.A. AlAizari and M. Ansar, Molecules, 23, 134 (2018); https://doi.org/10.3390/molecules23010134.
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- K.K. Sivakumar, A. Rajasekharan, R. Rao and B. Narasimhan, Indian J. Pharm. Sci., 75, 463 (2013); https://doi.org/10.4103/0250-474X.119832.
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- K.K. Søby, J.D. Mikkelsen, E. Meier and C. Thomsen, Neuropharmacology, 43, 95 (2002); https://doi.org/10.1016/S0028-3908(02)00071-0.
- T. de Paulis, The Investigational Drugs J., 3, 193 (2007).
- B.P. Bandgar, S.S. Gawande, R.G. Bodade, J.V. Totre and C.N. Khobragade, Bioorg. Med. Chem., 18, 1364 (2010); https://doi.org/10.1016/j.bmc.2009.11.066.
- K.D. Tripathy, Essentials of Medical Pharmacology, Jay-Pee Brothers Medical Publishers (P) Limited: New Delhi, edn 6, p. 97-98, 134, 735, 862, 630 (2009).
- E. Braunwald, P. Zipes and P. Libby, Heart Disease-A Textbook of Cardiovascular Medicine, W.B. Saunders Company, edn 6, pp. 717-736 (2001).
- D. Girlich, L. Poirel, A. Carattoli, I. Kempf, M.F. Lartigue, A. Bertini and P. Nordmann, Appl. Environ. Microbiol., 73, 4681 (2007); https://doi.org/10.1128/AEM.02491-06.
- R. Banerjee, H.K. Kumar and M. Banerjee, Int. J. Rev. Life Sci., 2, 7 (2012).
- S. Rossi, Australian Medicines Handbook, Australian Medicines Handbook Pvt. Ltd., Adelaide, Australia, edn 5 (2004).
- V.P. Vaidya, M.N. Kumaraswamy, C. Chandrashekhar, H. Shivakumar, D.A. Prathima Mathias and K.M. Mahadevan, Indian J. Pharm. Sci., 70, 715 (2008); https://doi.org/10.4103/0250-474X.49090.
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- P. Gunasekaran, Laboratory Manual in Microbiology, New Age International Publisher: New Delhi, p. 39 (1995).
- NCCLS, Performance Standards for Antimicrobial Susceptibility Testing: Twelfth Information Supplement M, In National Committee for Clinical Laboratory Standards, Wayne, PA, pp. 100-512 (2002).
- Indian Pharmacopoeia II, Ministry of Health and Family Welfare, Govt of India, New Delhi, A-105 (1996).
- N.S. Parmer and Shiva Prakash, Screening Methods in Pharmacology, (2011).
References
K. Karrouchi, S. Radi, Y. Ramli, J. Taoufik, Y.N. Mabkhot, F.A. AlAizari and M. Ansar, Molecules, 23, 134 (2018); https://doi.org/10.3390/molecules23010134.
J. Dwivedi, S. Sharma, S. Jain and A. Singh, Mini Rev. Med. Chem., 18, 918 (2018); https://doi.org/10.2174/1389557517666170927160919.
G. Demir, M.B. Gürdere, M. Ceylan and Y. Budak, Org. Commun., 10, 90 (2017); https://doi.org/10.25135/acg.oc.12.16.12.453.
P. Ahirrao, Mini Rev. Med. Chem., 8, 1441 (2008); https://doi.org/10.2174/138955708786786516.
K.K. Sivakumar, A. Rajasekharan, R. Rao and B. Narasimhan, Indian J. Pharm. Sci., 75, 463 (2013); https://doi.org/10.4103/0250-474X.119832.
C. Sanchez and M. Papp, Behav. Pharmacol., 11, 117 (2000); https://doi.org/10.1097/00008877-200004000-00003.
K.K. Søby, J.D. Mikkelsen, E. Meier and C. Thomsen, Neuropharmacology, 43, 95 (2002); https://doi.org/10.1016/S0028-3908(02)00071-0.
T. de Paulis, The Investigational Drugs J., 3, 193 (2007).
B.P. Bandgar, S.S. Gawande, R.G. Bodade, J.V. Totre and C.N. Khobragade, Bioorg. Med. Chem., 18, 1364 (2010); https://doi.org/10.1016/j.bmc.2009.11.066.
K.D. Tripathy, Essentials of Medical Pharmacology, Jay-Pee Brothers Medical Publishers (P) Limited: New Delhi, edn 6, p. 97-98, 134, 735, 862, 630 (2009).
E. Braunwald, P. Zipes and P. Libby, Heart Disease-A Textbook of Cardiovascular Medicine, W.B. Saunders Company, edn 6, pp. 717-736 (2001).
D. Girlich, L. Poirel, A. Carattoli, I. Kempf, M.F. Lartigue, A. Bertini and P. Nordmann, Appl. Environ. Microbiol., 73, 4681 (2007); https://doi.org/10.1128/AEM.02491-06.
R. Banerjee, H.K. Kumar and M. Banerjee, Int. J. Rev. Life Sci., 2, 7 (2012).
S. Rossi, Australian Medicines Handbook, Australian Medicines Handbook Pvt. Ltd., Adelaide, Australia, edn 5 (2004).
V.P. Vaidya, M.N. Kumaraswamy, C. Chandrashekhar, H. Shivakumar, D.A. Prathima Mathias and K.M. Mahadevan, Indian J. Pharm. Sci., 70, 715 (2008); https://doi.org/10.4103/0250-474X.49090.
S.R. Mandha, S. Siliveri, M. Alla, V.R. Bommena, M.R. Bommineni and S. Balasubramanian, Bioorg. Med. Chem. Lett., 22, 5272 (2012); https://doi.org/10.1016/j.bmcl.2012.06.055.
P. Gunasekaran, Laboratory Manual in Microbiology, New Age International Publisher: New Delhi, p. 39 (1995).
NCCLS, Performance Standards for Antimicrobial Susceptibility Testing: Twelfth Information Supplement M, In National Committee for Clinical Laboratory Standards, Wayne, PA, pp. 100-512 (2002).
Indian Pharmacopoeia II, Ministry of Health and Family Welfare, Govt of India, New Delhi, A-105 (1996).
N.S. Parmer and Shiva Prakash, Screening Methods in Pharmacology, (2011).