Subscribe to our Newsletter and get informed about new publication regulary and special discounts for subscribers!

ILCPA > ILCPA Volume 71 > Synthesis and Bio-Evaluation of Novel...
< Back to Volume

Synthesis and Bio-Evaluation of Novel N-(4-(8-Methoxy-2-Oxo-2H-Chromen-3-Yl) Thiazol-2-Yl) Amide Derivatives

Full Text PDF


In present work, novel derivatives of substituted N-(4-(8-methoxy-2-oxo-2H-chromen-3-yl) thiazol-2-yl) amide have been synthesized. The solvent free reaction of 2-Hydroxy-3-methoxybenzaldehyde with Ethyl acetoacetate in presence of Piperidine catalyst produces 3-acetyl-8-methoxy-2H-chromen-2-one (C). Compound C was α- brominated using CuBr2 and subsequently cyclized using Thiourea to produce 3-(2-aminothiazol-4-yl)-8-methoxy-2H-chromen-2-one as main scaffold (E). This scaffold E was finally reacted with different Acid chloride to isolate title compound derivatives. The chemical structures of synthesized compounds were confirmed by 1H-NMR, FT-IR and Mass spectral/LCMS analysis. The synthesized compounds were screened for potential Antimicrobial, Antifungal and Antimalarial activity.


International Letters of Chemistry, Physics and Astronomy (Volume 71)
N. Shah et al., "Synthesis and Bio-Evaluation of Novel N-(4-(8-Methoxy-2-Oxo-2H-Chromen-3-Yl) Thiazol-2-Yl) Amide Derivatives", International Letters of Chemistry, Physics and Astronomy, Vol. 71, pp. 19-28, 2016
Online since:
November 2016

[1] D. Davyt, G. Serra, Thiazole and oxazole alkaloids: Isolation and synthesis, Mar. Drugs. 8 (2010) 2755–2780.

[2] A. Geronikakil, G. Theophilidis, Synthesis of 2-(aminoacetylamino) thiazole derivatives and comparison of their local anaesthetic activity by the method of action potential, European journal of medicinal chemistry. 2 (1992) 709–716.

[3] M. Li, Y. Sim, S.W. Ham, Discovery of 2-aminothiazole derivatives as antitumor agents, Bull. Korean Chem. Soc. 31 (2010) 1463–1464.

[4] N. Singh et al., Synthesis and antimicrobial activity of some novel 2-amino thiazole derivatives, J. Chem. Pharm. Res. 2(3) (2010) 691–698.

[5] K. Prakasha, Design, synthesis and antimicrobial screening of amino acids conjugated 2-amino-4-arylthiazole derivatives, Int. J. Pharm. Pharm. Sci. 3 (2011) 120-125.

[6] C.A. Kontogiorgis, D.J. Hadjipavlou-Litina, Synthesis and antiinflammatory activy of coumarin derivatives, J. Med. Chem. 48 (2005) 6400–6408.

[7] M. Pieroni et al., Design, synthesis and investigation on the structure-activity relationships of N-substituted 2-aminothiazole derivatives as antitubercular agents, Eur. J. Med. Chem. 72 (2014) 26–34.

[8] S.N. Mokale et al., Bioorganic & Medicinal Chemistry Letters Synthesis, hypolipidemic and hypoglycemic activity of some novel propanoic acid derivatives, Bioorg. Med. Chem. Lett. 21 (2011) 682–685.

[9] C. -Y. Tsai et al., Synthesis and Evaluation of Aminothiazole-Paeonol Derivatives as Potential Anticancer Agents, Molecules. 21 (2016) 2–9.

[10] Z.M. Nofal, M.I. El-Zahar, S.S. Abd El-Karim, Novel coumarin derivatives with expected biological activity, Molecules. 5 (2000) 99–113.

[11] A.M. El-Agrody et al., Heteroaromatization with 4-Hydroxycoumarin Part II: Synthesis of Some New Pyrano [2, 3-d] pyrimidines, [1, 2, 4] triazolo [1, 5-c] pyrimidines and Pyrimido [1, 6-b]-[1, 2, 4] triazine Derivatives, Molecules. 6(6) (2001).

[12] A.A. Al-Amiery, A.A.H. Kadhum, A.B. Mohamad, Antifungal activities of new coumarins, Molecules. 17 (2012) 5713–5723.

[13] P. Sharma, S. Pritmani, Note Synthesis, characterization and antimicrobial studies of some novel 3-arylazo-7 -hydroxy-4- methylcoumarins, Indian J. Chem. B. 38 (1999) 1139–1142.

[14] S.O. Lee et al., Antidiabetic Coumarin and Cyclitol Compounds from Peucedanum japonicum, Archives of pharmacal research. 27(2) (2004) 1207–1210.

[15] A.A.H. Kadhum et al., The antioxidant activity of new coumarin derivatives, Int. J. Mol. Sci. 12 ( 2011) 5747–5761.

[16] I. Kostova, G. Momekov, New cerium(III) complexes of coumarins- Synthesis, characterization and cytotoxicity evaluation, Eur. J. Med. Chem. 43 (2008) 178–188.

[17] M.A. Musa, J.S. Cooperwood, M.O.F. Khan, A review of coumarin derivatives in pharmacotherapy of breast cancer, Curr. Med. Chem. 15 (2008) 2664–2679.

[18] J. Jung, Y. Jung, O. Park, A convenient one-pot synthesis of 4-hydroxythiocoumarin and4-hydroxyquinolin-2(1H)-one, Synth. Commun. 31 (2001) 1195–1200.

[19] R.K. Arora et al., Novel coumarin–benzimidazole derivatives as antioxidants and safer anti-inflammatory agents, Acta Pharm. Sin. B. 4 (2014) 368–375.

[20] T. Sugino, K. Tanaka, Solvent-Free Coumarin Synthesis, Chem. Lett. 2 (2001) 110–111.

[21] V. La Pietra et al., Identification of novel molecular scaffolds for the design of MMP-13 inhibitors: A first round of lead optimization, Eur. J. Med. Chem. 47 (2012) 143–152.

[22] J. Heinicke, E. Nietzschmann, A. Tzschach, Synthese von o-Halogenphenoxy-, o-Halogenphenylthio- und o-Halogen-methylanilinoderivaten der IVb- und Vb-Elemente, Journal für Praktische Chemie. 325(3) (1983) 511–516.

[23] B.Z. Kurt et al., Synthesis, antioxidant and anticholinesterase activities of novel coumarylthiazole derivatives, Bioorganic chemistry. 59 (2015) 80-90.

[24] B. Naik, K.R. Desai, Novel approach for the rapid and efficient synthesis of heterocyclic Schiff bases and azetidinones under microwave irradiation, Indian J. Chem. 45 (2006) 267–271.

Show More Hide
Cited By:
This article has no citations.