SYNTHESIS OF COUMARIN HETEROCYCLIC DERIVATIVES WITH IN-VITRO ANTITUBERCULER ACTIVITY
In last few decades, though significant progress has been made in the treatment and control strategies of tubercular infections by introducing new diagnostic and monitoring tools and combination therapy, it still continues to be severe problem. The need of study was only because of there are many drugs in market to treat infection but most of the drugs are showing resistance because of the same it is difficult to treat the infection. In this study we chosen coumarin nucleus for study. Thus with the aim of developing novel molecule with improved potency for treating Mycobacterium tuberculosis H37Rv strain infections and with decreased probability of developing drug resistance. The synthesis of coumarin derivatives, starting from salicyaldehyde and ethyl acetoacetate, by conventional organic reaction and results of investigations of their anti-mycobacterial activity. MICs of the synthesized compounds are compared with existing drugs Cytotoxicity. Many compounds have shown promising activity while some were inactive. It was found that Compound A1, A2, B1, B2, C1, C2 have shown promising antitubercular activity against std. Streptomycin
Keywords: Coumarin derivative, well diffusion method, antitubercular activity.
2. Kostova I, Synthetic and natural coumarins as cytotoxic agents, Current Medicinal Chemistry, 2005; 5(1):29–46.
3. Takeuchi Y, Xie L, Cosentino LM, and Lee KH, Anti-AIDS agents-XXVIII.1 Synthesis and Anti-HIV activity of methoxy substituted 3′,4′-Di-O-(−)-camphanoyl-(+)-cis-khellactone (DCK) analogues, Bioorganic & Medicinal Chemistry Letters, 1997;7(20):2573–2578.
4. Shikishima Y, Takaishi Y, Honda G, Chemical constituents of Prangos tschimganica; structure elucidation and absolute configuration of coumarin and furanocoumarin derivatives with anti-HIV activity, Chemical and Pharmaceutical Bulletin, 2001; 49(7):877–880.
5. Manolov I, Maichle-Moessmer C, Danchev N, Synthesis, structure, toxicological andpharmacological investigations of4-hydroxycoumarin derivatives, European Journal of Medicinal Chemistry, 2006; 41(7):882–890.
6. Jung JC, Kim JC, Park OS, Simple and cost effective syntheses of 4-hydroxycoumarin, Synthetic Communications, 1999; 29(20):3587–3595.
7. Ostrov DA, Hernández Prada JA, Corsino PE, Finton KA, Discovery of novel DNA gyrase inhibitors by high-throughput virtual screening, Antimicrobial Agents and Chemotherapy, 2007; 51(10):3688–3698.
8. AlAmiery AA, Kadhum A, Mohamad A, Antifungal activities of new coumarins, Molecules, 2012; 17(5):5713–5723.
9. Koshy L, Dwarakanath BS, Raj HG, Chandra R, Lazar MT, Suicidal oxidative stress induced by certain antioxidants, Indian Journal of Experimental Biology, 2003; 41(11):1273–1278,.
10. Fylaktakidou KC, Hadjipavlou-Litina DJ, Litinas KE, Nicolaides DN, “Natural and synthetic coumarin derivatives with anti-inflammatory/antioxidant activities,” Current Pharmaceutical Design, 2004; 10(30):3813–3833.
11. Ghate M, Manohar D, Kulkarni V, Shobha R, Kattimani SY, Synthesis of vanillin ethers from 4-(bromomethyl) coumarins as anti-inflammatory agents, European Journal of Medicinal Chemistry, 2003; 38(3):297–302.
12. Kontogiorgis CA, Hadjipavlou-Litina DJ, Synthesis and antiinflammatory activity of coumarin derivatives, Journal of Medicinal Chemistry, 2005; 48(20):6400–6408,.
13. Baba M, Jin Y, Mizuno A, Studies on cancer chemoprevention by traditional folk medicines XXIV. Inhibitory effect of a coumarin derivative, 7-isopentenyloxycoumarin, against tumor-promotion, Biological and Pharmaceutical Bulletin, 2002; 25(2):244–246.
14. Thornes D, Daly L, Lynch G, Prevention of early recurrence of high risk malignant melanoma by coumarin, European Journal of Surgical Oncology, 1989; 15(5):431–435.
15. Al-Amiery AA, Al-Bayati R, Saour K, Radi M, Cytotoxicity, antioxidant, and antimicrobial activities of novel 2-quinolone derivatives derived from coumarin, Research on Chemical Intermediates, 2012; 38:559–569.
16. Kadhum A, Mohamad A, Al-Amiery AA, Takriff M, Antimicrobial and antioxidant activities of new metal complexes derived from 3-Aminocoumarin, Molecules, 2011;16:6969–6984.
17. Završnik D, Muratović S, Makuc D, Benzylidene-bis-(4-hydroxycoumarin) and benzopyrano-coumarin derivatives: synthesis, 1H/13C-NMR conformational and X-ray crystal structure studies and in vitro antiviral activity evaluations, Molecules, 2011; 16(7):6023–6040.
18. Ali Beyramabadi S, Morsali A, Intramolecular proton transfer of 2-[(2,4- dimethylphenyl)iminomethyl]-3,5-dimethoxyphenol schiff-base ligand: a density functional theory (DFT) study, International Journal of Physical Sciences, 2011; 6(7):1780–1788.
19. Monajjemi M, Sayadian M, Zare K, Ilkhani A, Mollaamin F, Computational study of hydrogen bonding on calixarene as nanostructure compound, International Journal of Physical Sciences, 2011; 6(16):4063–4066.
20. Kadhum A, Al-Amiery AA, Shikara M, Mohamad A, Synthesis, structure elucidation and DFT studies of new thiadiazoles, International Journal of the Physical Sciences, 2011; 6(29):6692–6697.
21. Al-Amiery AA, Musa A, Kadhum A, Mohamad A, The use of umbelliferone in the synthesis of new heterocyclic compounds, Molecules, 2011; 16:6833–6843.
22. Al-Amiery AA, Al-Majedy YK, Abdulreazak H, Abood H, Synthesis, characterization, theoretical crystal structure, and antibacterial activities of some transition metal complexes of the thiosemicarbazone (Z)-2-(pyrrolidin-2-ylidene) hydrazinecarbothioamide, 2011; vol. 201, Article ID 483101, 6.
23. Kadhum A, Wasmi B, Mohamad A, Al-Amiery A, Takriff M, Preparation, characterization, and theoretical studies of azelaic acid derived from oleic acid by use of a novel ozonolysis method, Research on Chemical Intermediates, 2011; 38:659–668.
24. Kadhum AH, Al-Amiery AA, Musa AY, Mohamad A, The antioxidant activity of new coumarin derivatives, International Journal of Molecular Sciences, 2011; 12:5747–5576.
25. Al-Amiery AA, Kadhum A, Mohamad A, Antifungal and antioxidant activities of pyrrolidone thiosemicarbazone complexes,” Bioinorganic Chemistry and Applications, 2012; vol. 2012, Article ID 795812, pages 6.
26. Al-Amiery AA, Al-Majedy YK, Ibrahim H, Al-Tamimi AA, Antioxidant, antimicrobial,and theoretical studies of the thiosemicarbazone derivative Schiff base 2-(2-imino-1-methylimidazolidin-4-ylidene)hydrazinecarbothioamide (IMHC), Organic and Medicinal Chemistry Letters, 2012; 2(4):115-120.
This work is licensed under a Creative Commons Attribution-NonCommercial 4.0 International License.
Authors who publish with this journal agree to the following terms:
- Authors retain copyright and grant the journal right of first publication with the work simultaneously licensed under a Creative Commons Attribution-NonCommercial 3.0 Unported License. that allows others to share the work with an acknowledgment of the work's authorship and initial publication in this journal.
- Authors are able to enter into separate, additional contractual arrangements for the non-exclusive distribution of the journal's published version of the work (e.g., post it to an institutional repository or publish it in a book), with an acknowledgment of its initial publication in this journal.
- Authors are permitted and encouraged to post their work online (e.g., in institutional repositories or on their website) prior to and during the submission process, as it can lead to productive exchanges, as well as earlier and greater citation of published work (SeeÂ The Effect of Open Access).