SYNTHESIS, CHARACTERISATION AND DNA PHOTOCLEAVAGE ACTIVITY OF NEW 2-(THIOXO/OXO) QUINOLINE-4,6-DIMETHYL PYRIMIDINYL HYDRAZONES
Keywords:
Qunioline-3-carbaldehyde, 2-Hydrazinopyrimidine, Hydrazone, DNA photocleavage activityAbstract
Objective: The main objective of present work is to synthesize, characterize and evaluate DNA photocleavage activity of hydrazones containing quinoline and pyrimidine rings.
Methods: The syntheses of new 2-(Thioxo/Oxo)quinoline-4,6-dimethyl pyrimidinyl hydrazones has been achieved by the reaction of 2-(Thioxo/Oxo)quinoline-3-carbaldehydes and 2-hydrazino-4, 6-dimethylpyrimidine. The structure of synthesized compounds is established on basis of data obtained from the spectroscopic techniques such as 1H NMR, 13C NMR, FT-IR and mass. The synthesized compounds were evaluated for their DNA photocleavage activity at 40 μg/μl concentration by agarose gel electrophoresis method.
Results: The synthesized compounds 5e showed complete cleavage of DNA while 5a, 5b and 6e showed significant cleavage potential.
Conclusion: A series of novel hydrazones bearing quinoline and pyrimidine moiety has been synthesized and well characterized on the basis of spectroscopic data and further evaluated for their DNA photocleavage activity. It has been observed that compounds having bromo and thio group displayed good activity.
Downloads
References
Katritzky AR, Rees CW. Comprehensive Heterocyclic Chemistry vol. 2. Oxford NY: Pergamon Press; 1997.
Brown DJ. Pyrimidines and their Benzo Derivatives, In: Katritzky AR, Rees CW, editors. Comprehensive Heterocyclic Chemistry vol. 3, Oxford: Pergamon Press; 1997. p. 55-155.
Abdel-Wahab BF, Khidre RE, Farahat AA, El-Ahl AAS. 2-Chloroquinoline-3-carbaldehydes: synthesis, reactions and applications. J Arkivoc 2012;(i):211-76.
Selvam TP, James CR, Dniandev PV, Valzita SK. A mini review of pyrimidine and fused pyrimidine marketed drugs. J Res Pharm 2012;2:1-9.
Dinakaran VS, Bomma B, Srinivasan KK. Fused pyrimidines: The heterocycle of diverse biological and pharmacological significance. J Der Pharma Chemica 2012;4:255-65.
Jain KS, Chitre TS, Miniyar PB, Kathiravan MK, Bendre VS, Veer VS, Shahane SR, Shishoo CJ. Biological and medicinal significance of pyrimidines. J Curr Sci 2006;90:793-803.
Keri RS, Hosamani KM, Shingalapur RV, Hugar MH. Analgesic, anti-pyretic and DNA cleavage studies of novel pyrimidine derivatives of coumarin moiety. Eur J Med Chem 2010;45:2597-605.
Rollas S, Kucukguzel SG. Biological activities of hydrazone derivatives. J Molecules 2007;12:1910-39.
Singh RB. Hydrazones as analytical reagents: A review. J Talanta 1982;29:77-84.
Katyal M, Dutt Y. Analytical applications of hydrazones. J Talanta 1975;22:151-66.
Fouda AA, Al-Sarawy AA, Radwan MS. Some aromatic hydrazone derivatives as inhibitors for the corrosion of C-steel in phosphoric acid solution. J Ann Chim 2006;96:85-96.
Negm NA, Morsy SMI, Said MM. Corrosion inhibition of some novel hydrazone derivatives. J Surfactants Deterg 2005;8:95-8.
Sherif ESM, Ahmed AH. Synthesizing new hydrazone derivatives and studying their effects on the inhibition of copper corrosion in sodium chloride solutions. J Synth React Inorg, Met-Org Nano-Met Chem 2010;40:365-72.
Zelenin KN, Khorseeva LA, Alekseev VV. Physiologically active complexes of hydrazones (review). Pharm Chem J 1992;26:395-405.
Hajipour AR, Baltork IM, Bigdeli M. A convenient and mild procedure for the synthesis of hydrazones and semicarbazones from aldehydes or ketones under solvent-free conditions. J Chem Res Synop 1999:570-1.
Siddiqui SM, Salahuddin A, Azam A. Synthesis, characterization and antiamoebic activity of some hydrazone and azole derivatives bearing pyridyl moiety as a promising heterocyclic scaffold. Eur J Med Chem 2012;49:411-6.
El-Sayed MAA, Abdel-Aziz NI, Abdel-Aziz AAM, El-Azab AS, Asiri YA, El-Tahir KEH. Design, synthesis, and biological evaluation of substituted hydrazone and pyrazole derivatives as selective COX-2 inhibitors: Molecular docking study. J Bioorg Med Chem 2011;19:3416-24.
Ozkay Y, Tunal Y, Karaca H, Iskdag I. Antimicrobial activity and a SAR study of some novel benzimidazole derivatives bearing hydrazone moiety. Eur J Med Chem 2010;45:3293-8.
Kumar V, Gupta GK, Kaur K, Singh R. Fluorophenylhydrazones as potential COX-2 inhibitors: A novel, efficient, one pot solid phase synthesis, docking study and pharmacological evaluation. J Med Chem Res 2013;22:5890-900.
Sharma A, Khare R, Kumar V, Gupta GK, Beniwal V. 1-(Subsituted)-4, 4, 6-trimethyl-3, 4-dihydropyrimidine-2(1H)-thione: Green synthesis, antibacterial activity and DNA photocleavage activity. Int J Pharm Pharm Sci 2014;6:171-5.
Srivastava A, Singh RM. Vilsmeier-Hack reagent: A facile synthesis of 2-chloro-3-formylquinolines from N-arylacetamides and transformation into different functionalities. Ind J Chem 2005;44B: 1868-75.
Kumar V, Aggarwal R, Tyagi P, Singh SP. Synthesis and antibacterial activity of some new 1-heteraryl-5-amino-4-phenyl-3-trifluoromethylpyrazoles. Eur J Med Chem 2005;40:922-7.
Aggarwal R, Kumar V, Tyagi P, Singh SP. Synthesis and antibacterial study of some new 1-heteroaryl-5-amino-3H/methyl-4-phenylpyrazole. Bioorg Med Chem 2006;14:1785-91.
Toshima K, Takano R, Maeda Y, Suzuki M, Asai A, Matsumura S. 2-Phenylquinoline-Carbohydrate hybrids: molecular design, chemical synthesis, and evaluation of a new family of light-activatable DNA-cleaving agents. J Angew Chem Int Ed 1999;38:3733-35.
Bindu PJ, Mahadevan KM, Satyanarayan ND, Naik TRR. Synthesis and DNA cleavage studies of novel quinoline oxime esters. J Bioorg Med Chem Lett 2012;22:898-900.