Synthesis of Novel Cinnamoyl Amides Using a Solvent-Free Microwave-Assisted Method

REFERENCES

• Aoyagi , Y. ; Masuko , N. ; Ohkubo , S. ; Kitade , M. ; Nagai , K. ; Okazaki , S. ; Wierzba , K. ; Terada , T. ; Sugimoto , Y. ; Yamada , Y. A novel cinnamic acid derivative that inhibits Cdc25 dual-specificity phosphatase activity . Cancer Sci. 2005 , 96 ( 9 ), 614 – 619 .
   Web of Science ®Google Scholar
• Kumar , A. ; Katiyar , S. B. ; Agarwal , A. ; Chauhan , P. M. S. Current trends in antimalarial chemotherapy . Drugs Fut. 2003 , 28 ( 3 ), 243 – 251 .
   Web of Science ®Google Scholar
• Hee Kong , Y. ; Ock Jo , Y. ; Cho , C. ; Son , D. ; Park , S. ; Rho , J. ; Yoon Choi , S. Inhibitory effects of cinnamic acid on melanin biosynthesis in skin . Biol. Pharm. Bull. 2008 , 31 ( 5 ), 946 – 948 .
   Web of Science ®Google Scholar
• Lee , S. ; Han , J. M. ; Kim , H. ; Kim , E. ; Jeong , T. S. ; Lee , W. S. ; Cho , K. H. Synthesis of cinnamic acid derivatives and their inhibitory effects on LDL-oxidation, acyl-CoA:cholesterol acyltransferase-1 and -2 activity, and decrease of HDL-particle size . Bioorg. Med. Chem. Lett. 2004 , 14 ( 18 ), 4677 – 4681 .
   PubMed Web of Science ®Google Scholar
• Yesilada , A. ; Zurlo , E. 3,4-Dimethoxycinnamic acid terciary amides: Síntesis and evaluation of anti-inflammatory and anlagesic activities . Farmaco 1996 , 8 ( 9 ), 595 – 599 .
   Google Scholar
• Pardo , G. L. ; Inada , N. M. ; Pellón , R. F. ; Docampo , M. L. ; Fascio , M. L. ; D' Accorso , N. B. ; Vercesi , A. E. In vitro effect of a new cinnamic acid derivative against the epimastigote form of Tripanosoma cruzi . Arzneimittelforschung 2009 , 59 ( 4 ), 207 – 211 .
   Web of Science ®Google Scholar
• Wiesner , J. ; Mitsch , A. ; Jomaa , H. ; Schlitzer , M. Structure–activity relationships of novel anti-malarial agents, part 7: N-(3-Benzoyl-4-tolylacetylaminophenyl)-3-(5-aryl-2-furyl)acrylic acid amides with polar moieties . Bioorg. Med. Chem. Lett. 2003 , 13 , 2159 – 2161 .
   Web of Science ®Google Scholar
• Spasova , M. ; Philipov , S. ; Nikolaeva-Glomb , L. ; Galabov , A. ; Milkova , T. Cinnamoyl- and hydroxycinnamoyl amides of glaucine and their biological activity . Bioorg. Med. Chem. 2008 , 16 , 7457 – 7461 .
   PubMed Web of Science ®Google Scholar
• Webb , C. N. Benzanilide . Org. Synth. 1941 , 1 , 82 – 88 .
   Google Scholar
• Kivinen , J. The Chemistry of Acyl Halides ; Interscience : New York , 1972 ; p. 170 – 230 .
   Google Scholar
• Nomura , E. ; Hosoda , A. ; Mori , H. ; Taniguchi , H. Rapid base-catalyzed decarboxylation and amide-forming reaction of substituted cinnamic acids via microwave heating . Green Chem. 2005 , 7 , 863 – 866 .
   Web of Science ®Google Scholar
• Pellón , R. F. ; Docampo , M. ; Fascio , M. Mild method for Ullmann reaction of 2-chlorobenzoic acids and aminothiazoles or aminobenzothiazoles under ultrasonic irradiation. Synth. Commun. 2007, 37 (11), 1853–1864; (b) Docampo , M. ; Pellón , R. F. ; Estevez-Braun , A. G. ; Ravelo , A. Ultrasound-promoted reaction of 2-chlorobenzoic acids and aliphatic amines. Eur. J. Org. Chem. 2007, 24, 4111–4115; (c) Pellón , R. F. ; Martín , A. ; Mesa , M. ; Docampo , M. L. ; Gómez , V. Microwave-assisted synthesis of 2-phenoxybenzoic acids. J. Chem. Res. Synop. 2006, 8, 527–529; (d) Martín , A. ; Mesa , M. ; Docampo , M. L. ; Gómez , V. ; Pellón , R. F. Fast synthesis of substituted N-phenylanthranilic acids using Ullmann condensation under microwave irradiation in dry media. Synth. Commun. 2006, 36 (3), 271–277.
   Web of Science ®Google Scholar
• Chunavala , K. C. ; Joshi , G. ; Suresh , E. ; Adimurthy , S. Thermal and microwave-assisted rapid synthesis of substituted imidazo[1,2-a]pyridines under solvent- and catalyst-free conditions . Synthesis 2011 , 4 , 635 – 641 .
   Google Scholar
• Pellón , R. F. ; Martin , A. ; Docampo , M. ; Mesa , M. Microwave-promoted Ullmann condensation of 2-aminopyridines with 2-chlorobenzoic acids . Synth. Commun. 2006 , 36 ( 6 ), 1715 – 1719 .
   Google Scholar