Synthesis and Characterization of SomeBiologically Potent 2-(2-butyl-4-chloro-1H-imidazol-5-yl)-4H-chromen-4-onederivatives

Authors(5) :-S. S. Gaikwad, D. V. Sonawane, D. N. Gaikwad, M. D. Sangale, Y. V. Bare

In the present investigation, a series of novel chromone derivatives containing imidazole moiety has been synthesized. The condensation of 2-butyl-4-chloro-1H-imidazole-5-carbaldehyde with various substituted o-hydroxy acetophenones in the presence of 40% KOH in PEG- 400 gives the chalcones. Oxidative cyclisation of chalcones withcatalytic amount of iodine in the presence of DMSO gives chromones. Chalcones and Chromones were obtained in satisfactory yield.The structure of intermediate and titled compounds was confirmed by spectral tools.

Authors and Affiliations

S. S. Gaikwad
P.G. Department of Chemistry, Annasaheb Awate Arts, Commerce, Hutatma Babu Genu Science College, Manchar, Tal.-Ambegaon, Pune , Maharashtra, India
D. V. Sonawane
P.G. Department of Chemistry,R.B.N.B. College, Shrirampur, Ahmednagar (MS), India
D. N. Gaikwad
P.G. Department of Chemistry, Annasaheb Awate Arts, Commerce, Hutatma Babu Genu Science College, Manchar, Tal.-Ambegaon, Pune , Maharashtra, India
M. D. Sangale
P.G. Department of Chemistry, Annasaheb Awate Arts, Commerce, Hutatma Babu Genu Science College, Manchar, Tal.-Ambegaon, Pune , Maharashtra, India
Y. V. Bare
JubilantChemsys Ltd., Noida, Uttar Pradesh, India

Chalcones, Chromones, O-Hydroxyacetophenones, Imidazole, PEG-400

  1. Prakash O., Kumar A., Sadana A., Prakash R., Singh P. S., Claramunt M. R.,Sanz D., Alkortac I., Elgueroc J.,Study of the reaction of chalcone analogs of dehydroacetic acid and o-aminothiophenol: synthesis and structure of 1,5-benzothiazepines and 1,4-benzothiazines, Tetrahedron,61, 6642,(2005).
  2. Prasad R. Y., Rao A.L., Prasoona L., Murali K., Kumar P.R.,Synthesis and antidepressant activity of some 1,3,5-triphenyl-2-pyrazolines and 3-(2?-hydroxy naphthalen-1?-yl)-1,5-diphenyl-2-pyrazolines,Bioorg. Med. Chem.Lett.,, 15, 5030,(2005).
  3. Raghavan S., Anuradha K.,Solid-phase synthesis of 1,4-diketones by thiazolium salt promoted addition of aldehydes to Chalcones,Tetrahedron Lett.,43(29), 5181,(2002).
  4. Bohm B.A., Introduction to Flavonoids; Harwood Academic: Amsterdam, The Netherlands,(1998).
  5. Nowakowska Z.,A review of anti-infective and anti-inflammatory Chalcones,Eur. J. Med. Chem.,42(2), 125, (2007).
  6. Ballesteros J. F., Sanz M. J., Ubeda A., Miranda M. A., Iborra S., Paya M., Alcaraz M. J., Synthesis and Pharmacological Evaluation of 2'-Hydroxychalcones and Flavones as Inhibitors of Inflammatory Mediators Generation, J. Med. Chem.,, 38 (14),2794, (1995).
  7. Mukherjee S., Kumar V., PrasadA. K., RajH. G., BrackeM. E., Olsen C.E., Jain S. C., ParmarV. S.,Synthetic and biological activity evaluation studies on novel 1,3-diarylpropenones,Bioorg. Med. Chem.,
  8. 9(2), 337, (2001).
  9. Syahri J., Yuanita E., Nurohmah B. A., Armunanto R., Purwono B., Chalcone analogue as potent anti-malarial compounds against Plasmodium falciparum: Synthesis, biological evaluation, and docking simulation study,Asian Pac J Trop Biomed, 7(8),675, (2017).
  10. Kumar D., Kumar N. M., Akamatsu K., Kusaka E., Harada H., Ito T., Synthesis and biological evaluation of indolyl chalcones as antitumor agents, Bioorg Med Chem Lett., 20(13), 3916, (2010).
  11. Go M.L., Wu X., Liu X.L., Chalcones: an update on cytotoxic and chemoprotective properties, Curr Med Chem., 12(4), 481, (2005).
  12. Banfi E., Scialino G., Zampieri D., Mamolo M. G., Vio L., Ferrone M., Fermeglia M., Paneni M. S., Pricl S., Antifungal and antimycobacterial activity of new imidazole and triazole derivatives. A combined experimental and computational approach, J Antimicrob Chemother., 58(1),76,(2006).
  13. Rezaei Z., Khabnadideh S., Zomorodian K., Pakshir K., Kashi G., Sanagoei N., Gholami S., Design, synthesis and antifungal activity of some new imidazole and triazole derivatives, Arch Pharm (Weinheim), 344(10), 658, (2011).
  14. Slee D. H., Romano S. J., Yu J., Nguyen T. N., John J. K., Raheja N. K., Axe F. U., Jones T. K., Ripka W. C., Development of potent non-carbohydrate imidazole-based small molecule selectininhibitors with antiinflammatory activity,J. Med. Chem. 44, 2094, (2001).
  15. Khabnadideh S., Rezaei Z., Khalafi-Nezhad A., Bahrinajafi R.; Mohamadi R., Farrokhroz A. A.,Synthesis of N-alkylated derivatives of imidazole as antibacterial agents,Bioorg. Med. Chem. Lett.,13, 2863, (2003).
  16. Davood A., Khodarahmi Gh., Alipour E., Dehpour A. R., Amini M., Shafiee A., Synthesis andcalcium channel antagonist activity of nifedipine analogues containing 2- methyl-4(5)-chloro-5(4)-imidazolyl substituent. Boll. Chim. Farm., 140, 381, (2001).
  17. Davood A., AlipourE., ShafieeA.,Efficient Synthesis of Imidazole Derivatives: AnImportant Synthon for the Preparation of BiologicallyActive Compounds, Turk J Chem, 32, 389, (2008).
  18. HarborneJ.B., Williams C.A., Advances in flavonoid research since 1992,Phytochemistry,55(6), 481, (2000).
  19. Toh J.Y., Tan V.M., Lim P.C., Lim S.T., Chong M.F., Flavonoids from fruit and vegetables: a focus on cardiovascular risk factors,Curr Atheroscler Rep., 15(12), 368,(2013).
  20. Gaspar A., Matos M. J., Garrido J., Uriarte E., Borges F., Chromone: A Valid Scaffold in Medicinal Chemistry,Chem. Rev., 114 (9), pp 4960, (2014).
  21. Keri R.S., Budagumpi S., Pai R. K., Balakrishna R.G., Chromones as a privileged scaffold in drug discovery: A review,Eur. J. Med. Chem., 78, 340, (2014).
  22. Ekinci D., al-Rashida M., Abbas G., Senturk M., Supuran C. T., Chromone containing sulfonamides as potent carbonic anhydrase inhibitors, J. Enzyme Inhib. Med. Chem., 27(5), 744, (2012).
  23. Chohan Z.H., Rauf A., Naseer M.M., Somra M.A., Supuran C.T., Antibacterial, antifungal and cytotoxic properties of some sulfonamide-derived chromones,J Enzyme Inhib Med Chem.,21(2), 173,(2006).
  24. Li B.W., Zhang F.H., Serrao E., Chen H., Sanchez T.W., Yang L.M., Neamati N., Zheng Y.T., Wang H., Long Y.Q., Design and discovery of flavonoid-based HIV-1 integrase inhibitors targeting both the active site and the interaction with LEDGF/p75. Bioorg Med Chem., 22(12), 3146, (2014).
  25. NamD. H., Lee K. Y., MoonC. S., Lee Y. S., Synthesis and anticancer activity of chromone-based analogs of lavendustin A,Eur. J. Med. Chem., 45(9), 4288, (2010).
  26. Wei H., Yu D., Yan M., Ming-Zhen L., Yan L., , Guang-Fu Yanga,Synthesis and antitumor activity of novel dithiocarbamate substituted chromones, Eur. J. Med. Chem.,44(9),3687, (2009).
  27. JayapalM.R., Prasad K. S., Sreedhar N.Y., Synthesis and Characterization of 2,6-Dihydroxy Substituted Chalcones Using PEG-400 as a Recyclable Solvent,J. Pharm. Sci. & Res.,2(8), 450, (2010).
  28. Fries K., Finck G., ?ber Homologe des Cumaranons und ihre Abk?mmlinge, Ber. Dtsch. Chem. Ges., 41, 4271, (1908).
  29. Dawane B. S., Konda S. G., Shaikh B. M., Bhosale R. B., An improved procedure for synthesis ofsome new 1, 3-diaryl-2-propen-1-ones using PEG-400 as a recyclable solvent and their antimicrobialevaluation. Acta Pharm., 59, 473, (2009).

Publication Details

Published in : Volume 3 | Issue 9 | November-December 2017
Date of Publication : 2017-12-15
License:  This work is licensed under a Creative Commons Attribution 4.0 International License.
Page(s) : 69-74
Manuscript Number : IJSRST173914
Publisher : Technoscience Academy

Print ISSN : 2395-6011, Online ISSN : 2395-602X

Cite This Article :

S. S. Gaikwad, D. V. Sonawane, D. N. Gaikwad, M. D. Sangale, Y. V. Bare, " Synthesis and Characterization of SomeBiologically Potent 2-(2-butyl-4-chloro-1H-imidazol-5-yl)-4H-chromen-4-onederivatives", International Journal of Scientific Research in Science and Technology(IJSRST), Print ISSN : 2395-6011, Online ISSN : 2395-602X, Volume 3, Issue 9, pp.69-74, November-December-2017.
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