STUDIES ON INCLUSION COMPLEXES OF 1-NICOTINOYL-4-ARYL-3-METHYL 3A, 4-DIHYDROPYRAZOLO [3, 4C] PYRAZOLES WITH Β-CYCLODEXTRIN
Abstract
Some 1-Nicotinoyl-4-aryl-3-methyl 3a, 4-dihydropyrazole [3, 4c] pyrazoles were synthesised and their inclusion complexes were prepared with β-cyclodextrin. The compounds and their inclusion complexes were characterised by the study of their physical and spectral properties. The determination of stability constant of inclusion complexes and other thermodynamic parameters such as change in free energy, change in enthalpy and change in entropy, suggested the inclusion complex formation to be thermodynamically allowed. Further, the compounds and their inclusion complexes were screened for antibacterial activities against Escherichia coli (MTCC 40), Bacillus subtilis (MTCC 441), Staphylococcus aureus (MTCC 87) and Proteus vulgaris (MTCC 426). It was found that that the formation of inclusion complex causes an increase in antibacterial activity.
Keywords:
Nicotinic hydrazide, Fused pyrazoles, Inclusion complex, Thermodynamic stability, Antibacterial activityDOI
https://doi.org/10.25004/IJPSDR.2013.050303References
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25. Rajewski RA, Stella VJ. Pharmaceutical applications of cyclodextrins in vivo drug delivery. J Pharma Sci. 1996; 85: 1142-1169.
26. Loukas YL, Vraka V, Gregordias G. Novel non-acidic formulations of haloperidol complexed with β-cyclodextrin derivatives. J Pharma Biomed Analysis. 1997; 16: 263-268.
27. Stalin T, Vasantharani P, Shanti B, Sekhar A, Rajendiran N. Inclusion Complexes of trihydroxybenzene with α- and β-cyclodextrin. Indian J Chem Sec A. 2006; 45: 1113- 1120.
28. Astakhova AV, Demina NB. Astakhova AV, Demina NB. Modern drug technologies: Synthesis, characterization and use of inclusion complexes between drugs and cyclodextrins (A Review). J Pharma Chem. 2004; 38(2): 105-108.
29. Cruickshank R, Marmion J P, Swain R H A, Medicinal Microbiology, London. 1975.
30. Tagashira M, Ohtake Y. A new antioxidative 1, 3-benzodioxide from Melissa official. Planta Med J. 1998; 64: 555-558.
2. E L-Emary TI. Synthesis and biological activity of some new pyrazole[3,4-b]pyrazines. J Chin Chem Society 2006; 53:391-401.
3. Mansoor AK, Eid MM, Khalil NSAM. Synthesis and reactions of some new heterocyclic carbohydrazides and related compounds as potential anticancer agents. Molecules 2003; 8:744-755.
4. Korgaokar SS, Patil PH, Shah MJ, Parekh HH. Synthesis and characterization of a novel 2- pyrazoline. Indian J Pharm Sci. 1996; 58:222-225.
5. Palaska E, Aytemir M, Uzbay IT, Erol D. Synthesis and antidepressant activities of some 3,5-diphenyl-2-pyrazolines. Eur J Med Chem. 2001; 36:539-543.
6. Rajendra PY, Lakshmana RA, Prasoona L, Murali K, Rav KP. Synthesis and characterization of 1-formyl-3-phenyl-5-uryl-2-pyrazolines. Bioorg Med Chem Lett. 2005; 15:5030-5034.
7. Ozdemir Z, kandilici HB, Gumusel B, Calis U, Bilgin AA. Synthesis and studies on antidepressant and anticonvulsant activities of some 3-(2-furyl)-pyrazoline derivatives. Eur J Med Chem. 2007; 42:373-379.
8. Ruhogluo O, Ozdemir Z, Calis U, Gumusel B, Bilgin AA. Synthesis and pharmacological studies on the Antidepressant and anticonvulsant activities of some 1, 3, 5-Trisubstituted pyrazolines. Arzneim Forsch. 2005; 55:431-433.
9. Udupi RH, Kushnoor AS , Bhat AR. Synthesis and Biological evaluation of certain pyrazolidine derivatives of 2-[6-Methoxy naphthyl]-propionic acid. Indian J Het Chem. 1998; 8:63-66.
10. Joshi A, Sain DK, Thadhaney B, Ojha S, Hussain N, Talesara GL. Synthetic and biological studies on some fused pyrazoles and their ethoxyphthalimide derivatives. Indian J Chem. 2010; 49:965-970.
11. Panda S, Tripathy JK. Studies on inclusion complexes of substituted indole derivatives with activating and deactivating group. J Chem Pharm Res. 2010; 2: 722-732.
12. Panda S, Tripathy JK. Thermodynamic, spectral and antimicrobial properties of inclusion complex of 2-[Benzylidenamino]-1, 3, 4- thiadiazino[6,5b] indole and 2-[Furfurlidenamino]-1,3,4- thiadiazino[6,5b] indole –a comparative study. Res J Pharma Tech. 2011; 4: 1693-1698.
13. Panda S, Tripathy JK. Thermodynamic and spectral studies of inclusion complexes of substituted indole derivatives with β- cyclodextrin. Asian J Chem. 2011; 23: 1631-1635.
14. Higuchi T, Connors K. Phase solubility technique. Adv Anal Chem Instument. 1965; 4: 117-212.
15. Panda S, Nayak SS. Inclusion complex of acridone & its semicarbazone derivatives with β-cyclodextrin: A thermodynamic, spectral & antimicrobial study. Asian J Res Chem. 2009; 2(4): 539-543.
16. Panda S, Sahu R, Nayak SK. Studies on Inclusion complexes of 4-methyl 3-phenyl 2- thiocarbamoyl-3,3adihydro pyrazolo[3,4-c] pyrazole. J Chem Pharm Res. 2012; 4(5): 2540-2544.
17. Mohammed KG, Moji CA. Elucidation of solution state complexation in wet granulated oven Dried Ibuprofen and β- cyclodextrin: FTIR and 1H NMR Studies. Pharma Dev Tech. 2001; 6: 315-324.
18. Nayak SS, Panda S, Panda P, Padhy MS. Studies on acridone derivatives with and without inclusion complex formation with β-CD. Bul Chem Comm. 2010; 42(2): 147-152.
19. Panda S, Tripathy JK, Panda JR. A Comparative Study of Antioxidant Properties of 2-[Substituted arylideamino]-1, 3, 4-thiadiazino [6, 5B] Indoles and Their Inclusion Complexes with β-Cyclodextrin. Int. J Pharma Sc Drug Res. 2012; 4(3): 191-194.
20. Bollela, VR, Sato DN, Fonseca BAL. McFarland nephelometer as a simple method to estimate the sensitivity of the polymerase chain reaction using Mycobacterium tuberculosis as a research tool. Braz J Med Biol Res. 1999; 32: 1073-1076.
21. Benesi HA, Hilderband JH. A Spectrophotometric Investigation of the Interaction of Iodine with Aromatic Hydrocarbons. J Am Chem Soc. 1999; 71: 2703-2707.
22. Mukna AP, Nagarsenkar MS. American Association of Pharmaceutical Science. Pharma Sc Tech. 2001; 5(1): 19.
23. Szetli J. Molecular entrapment and release properties of drugs by cyclodextrins. Controlled Drug Bio-availability. Vol. 3, Willey Interscience publications, New York, 1985.
24. Tommasini S, Raneri D, Ficarra R, Calabro ML, Stancanelli R. Improvement in solubility and dissolution rate of flavonoids by complexation with β-cyclodextrin. J Pharma Biomed Analysis. 2004; 35: 379-387.
25. Rajewski RA, Stella VJ. Pharmaceutical applications of cyclodextrins in vivo drug delivery. J Pharma Sci. 1996; 85: 1142-1169.
26. Loukas YL, Vraka V, Gregordias G. Novel non-acidic formulations of haloperidol complexed with β-cyclodextrin derivatives. J Pharma Biomed Analysis. 1997; 16: 263-268.
27. Stalin T, Vasantharani P, Shanti B, Sekhar A, Rajendiran N. Inclusion Complexes of trihydroxybenzene with α- and β-cyclodextrin. Indian J Chem Sec A. 2006; 45: 1113- 1120.
28. Astakhova AV, Demina NB. Astakhova AV, Demina NB. Modern drug technologies: Synthesis, characterization and use of inclusion complexes between drugs and cyclodextrins (A Review). J Pharma Chem. 2004; 38(2): 105-108.
29. Cruickshank R, Marmion J P, Swain R H A, Medicinal Microbiology, London. 1975.
30. Tagashira M, Ohtake Y. A new antioxidative 1, 3-benzodioxide from Melissa official. Planta Med J. 1998; 64: 555-558.
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01-07-2013
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“STUDIES ON INCLUSION COMPLEXES OF 1-NICOTINOYL-4-ARYL-3-METHYL 3A, 4-DIHYDROPYRAZOLO [3, 4C] PYRAZOLES WITH Β-CYCLODEXTRIN”. International Journal of Pharmaceutical Sciences and Drug Research, vol. 5, no. 3, July 2013, pp. 96-100, https://doi.org/10.25004/IJPSDR.2013.050303.
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“STUDIES ON INCLUSION COMPLEXES OF 1-NICOTINOYL-4-ARYL-3-METHYL 3A, 4-DIHYDROPYRAZOLO [3, 4C] PYRAZOLES WITH Β-CYCLODEXTRIN”. International Journal of Pharmaceutical Sciences and Drug Research, vol. 5, no. 3, July 2013, pp. 96-100, https://doi.org/10.25004/IJPSDR.2013.050303.
