Synthesis and biological evaluation of new benzofuran carboxamide derivatives

Journal of Saudi Chemical Society

Volumn 21, Issue 3, 2017, Pages 277-285

  Lavanya, Andiappan ^a,b   Sribalan, Rajendran ^b   Padmini, Vediappen ^b  

^a Orchid Chemicals and Pharmaceuticals Ltd   (India)

^b MADURAI KAMARAJ UNIVERSITY   (India)

Author keywords

Anti inflammatory; Antimicrobial; Antioxidant; Benzofuran; Carboxamide; Glycinamide; Alanamide

Indexed keywords

EID: 84937161029     PISSN: 13196103     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.jscs.2015.06.008     Document Type: Article

References (39)

1. [1] Lee, S.K., Cui, B., Mehta, R.R., Kinghorn, A.D., Pezzuto, J.M., Cytostatic mechanism and antitumor potential of novel 1H-cyclopenta[b]benzofuran lignans isolated from Aglaia elliptica. Chem. Biol. Interact. 115 (1998), 215–228.
2. [2] Janprasert, J., Satasook, C., Sukumalanand, P., Champagne, D.E., Isman, M.B., Wiriyachitra, P., Rocaglamide, a natural benzofuran insecticide from Aglaia odorata. Phytochemistry 32 (1992), 67–69.
3. [3] Sundaram, R., Ganesan, R., Murugesan, G., In vitro antiplasmodial activity of spiro benzofuran compound from mangrove plant of Southern India. Asian Pac. J. Trop. Med. 5 (2012), 358–361.
4. [4] Yu, B., Shi, X.J., Zheng, Y.F., Fang, Y., Zhang, E., Yu, D.Q., A novel [1,2,4] triazolo [1,5-a] pyrimidine-based phenyl-linked steroid dimer: synthesis and its cytotoxic activity. Eur. J. Med. Chem. 69 (2013), 323–330.
5. [5] Panno, M.L., Giordano, F., Mastroianni, F., Palma, M.G., Bartella, V., Carpino, A., Breast cancer cell survival signal is affected by bergapten combined with an ultraviolet irradiation. FEBS Lett. 584 (2010), 2321–2326.
6. [6] Hsieh, M.J., Chen, M.K., Yu, Y.Y., Sheu, G.T., Chiou, H.L., Psoralen reverses docetaxel-induced multidrug resistance in A549/D16 human lung cancer cells lines. Phytomed. Int. J. Phytother. Phytopharmacol. 21 (2014), 970–977.
7. [7] Hassan, G.S., Abou-Seri, S.M., Kamel, G., Ali, M.M., Celecoxib analogs bearing benzofuran moiety as cyclooxygenase-2 inhibitors: design, synthesis and evaluation as potential anti-inflammatory agents. Eur. J. Med. Chem. 76 (2014), 482–493.
8. [8] Sashidhara, K.V., Modukuri, R.K., Sonkar, R., Rao, K.B., Bhatia, G., Hybrid benzofuran–bisindole derivatives: new prototypes with promising anti-hyperlipidemic activities. Eur. J. Med. Chem. 68 (2013), 38–46.
9. [9] El-Sawy, E.R., Ebaid, M.S., Abo-Salem, H.M., Al-Sehemi, A.G., Mandour, A.H., Synthesis, anti-inflammatory, analgesic and anticonvulsant activities of some new 4,6-dimethoxy-5-(heterocycles)benzofuran starting from naturally occurring visnagin. Arab. J. Chem., 2012, 10.1016/j.arabjc.2012.12.041.
10. [10] Wu, J., Li, Y., Chen, K., Jiang, H., Xu, M.-H., Liu, D., Identification of benzofuran-3-yl(phenyl)methanones as novel SIRT1 inhibitors: binding mode, inhibitory mechanism and biological action. Eur. J. Med. Chem. 60 (2013), 441–450.
11. [11] Xiang, Y., Hirth, B., Asmussen, G., Biemann, H.-P., Bishop, K.A., Good, A., The discovery of novel benzofuran-2-carboxylic acids as potent Pim-1 inhibitors. Bioorg. Med. Chem. Lett. 21 (2011), 3050–3056.
12. [12] Jiang, X., Liu, W., Zhang, W., Jiang, F., Gao, Z., Zhuang, H., Synthesis and antimicrobial evaluation of new benzofuran derivatives. Eur. J. Med. Chem. 46 (2011), 3526–3530.
13. [13] Shankerrao, S., Bodke, Y.D., Santoshkumar, S., Synthesis and antimicrobial activity of some imidazothiazole derivatives of benzofuran. Arab. J. Chem., 2012, 10.1016/j.arabjc.2012.10.018.
14. [14] Kirilmis, C., Ahmedzade, M., Servi, S., Koca, M., Kizirgil, A., Kazaz, C., Synthesis and antimicrobial activity of some novel derivatives of benzofuran: Part 2. The synthesis and antimicrobial activity of some novel 1-(1-benzofuran-2-yl)-2-mesitylethanone derivatives. Eur. J. Med. Chem. 43 (2008), 300–308.
15. [15] Dawood, K.M., Abdel-Gawad, H., Rageb, E.A., Ellithey, M., Mohamed, H.A., Synthesis, anticonvulsant and anti-inflammatory evaluation of some new benzotriazole and benzofuran-based heterocycles. Bioorg. Med. Chem. 14 (2006), 3672–3680.
16. [16] Santana, L., Teijeira, M., Uriarte, E., Teran, C., Liñares, B., Villar, R., et al. AM1 theoretical study, synthesis and biological evaluation of some benzofuran analogues of anti-inflammatory arylalkanoic acids. Eur. J. Pharm. Sci. 7 (1999), 161–166.
17. [17] Malpani, Y., Achary, R., Kim, S.Y., Jeong, H.C., Kim, P., Han, S.B., et al. Efficient synthesis of 3H,3′H-spiro[benzofuran-2,1′-isobenzofuran]-3,3′-dione as novel skeletons specifically for influenza virus type B inhibition. Eur. J. Med. Chem. 62 (2013), 534–544.
18. [18] Rangaswamy, J., Kumar, H.V., Harini, S.T., Naik, N., Synthesis of benzofuran based 1,3,5-substituted pyrazole derivatives: as a new class of potent antioxidants and antimicrobials-A novel accost to amend biocompatibility. Bioorg. Med. Chem. Lett. 22 (2012), 4773–4777.
19. [19] Rangaswamy, J., Kumar, H.V., Harini, S.T., Naik, N., Functionalized 3-(benzofuran-2-yl)-5-(4-methoxyphenyl)-4,5-dihydro-1H-pyrazole scaffolds: a new class of antimicrobials and antioxidants. Arab. J. Chem., 2013, 10.1016/j.arabjc.2013.10.012.
20. [20] Galal, S.A., Abd El-All, A.S., Abdallah, M.M., El-Diwani, H.I., Synthesis of potent antitumor and antiviral benzofuran derivatives. Bioorg. Med. Chem. Lett. 19 (2009), 2420–2428.
21. [21] Hranjec, M., Sovic, I., Ratkaj, I., Pavlovic, G., Ilic, N., Valjalo, L., Antiproliferative potency of novel benzofuran-2-carboxamides on tumour cell lines: cell death mechanisms and determination of crystal structure. Eur. J. Med. Chem. 59 (2013), 111–119.
22. [22] Parekh, S., Bhavsar, D., Savant, M., Thakrar, S., Bavishi, A., Parmar, M., et al. Synthesis of some novel benzofuran-2-yl(4,5-dihyro-3,5-substituted diphenylpyrazol-1-yl) methanones and studies on the antiproliferative effects and reversal of multidrug resistance of human MDR1-gene transfected mouse lymphoma cells in vitro. Eur. J. Med. Chem. 46 (2011), 1942–1948.
23. [23] Ono, M., Kung, M.-P., Hou, C., Kung, H.F., Benzofuran derivatives as Aβ-aggregate-specific imaging agents for Alzheimer's disease. Nucl. Med. Biol. 29 (2002), 633–642.
24. [24] Marriott, K.S., Morrison, A.Z., Moore, M., Olubajo, O., Stewart, L.E., Synthesis of N-phenyl-N-(3-(piperidin-1-yl)propyl)benzofuran-2-carboxamides as new selective ligands for sigma receptors. Bioorg. Med. Chem. 20 (2012), 6856–6861.
25. [25] Xie, Y.-S., Kumar, D., Bodduri, V.D.V., Tarani, P.S., Zhao, B.-X., Miao, J.-Y., et al. Microwave-assisted parallel synthesis of benzofuran-2-carboxamide derivatives bearing anti-inflammatory, analgesic and antipyretic agents. Tetrahedron Lett. 55 (2014), 2796–2800.
26. [26] Pisarewicz, K., Mora, D., Pflueger, F.C., Fields, G.B., Marl, F., Polypeptide chains containing D-γ-hydroxyvaline. J. Am. Chem. Soc. 127 (2005), 6207–6215.
27. [27] Wolosker, H., Dumin, E., Balan, L., Foltyn, V.N., D-Amino acids in the brain: D-serine in neurotransmission and neurodegeneration. FEBS J. 275 (2008), 3514–3526.
28. [28] Zhou, T., Hider, R.C., Jenner, P., Campbell, B., Hobbs, C.J., Rose, S., et al. Design, synthesis and biological evaluation of L-dopa amide derivatives as potential prodrugs for the treatment of Parkinson's disease. Eur. J. Med. Chem. 45 (2010), 4035–4042.
29. [29] Zhou, T., Hider, R.C., Jenner, P., Campbell, B., Hobbs, C.J., Rose, S., Design, synthesis and biological evaluation of peptide derivatives of L-dopa as anti-parkinsonian agents. Bioorg. Med. Chem. Lett. 23 (2013), 5279–5282.
30. [30] Schechter, P.J., Barlow, J.L.R., Sjoerdsma, A., 16 – clinical aspects of inhibition of ornithine decarboxylase with emphasis on therapeutic trials of eflornithine (DFMO) in cancer and protozoan diseases. McCann, P.P., Pegg, A.E., Sjoerdsma, A., (eds.) Inhibition of Polyamine Metabolism, 1987, Acad. Press, 345–364.
31. [31] Kaur, H., Heapy, A.M., Kowalczyk, R., Amso, Z., Watson, M., Cornish, J., Synthesis and biological evaluation of the osteoblast proliferating cyclic peptides dianthins G and H. Tetrahedron, 2014, 10.1016/j.tet.2014.04.035.
32. [32] Ferreira da Costa, J., Caamaño, O., Fernández, F., Garcia-Mera, X., Sampaio-Dias, I.E., Brea, J.M., Synthesis and allosteric modulation of the dopamine receptor by peptide analogs of L-prolyl-L-leucyl-glycinamide (PLG) modified in the L-proline or L-proline and L-leucine scaffolds. Eur. J. Med. Chem. 69 (2013), 146–158.
33. [33] Cherney, R.J., Mo, R., Meyer, D.T., Voss, M.E., Yang, M.G., Santella, J.B. III, et al. γ-Lactams as glycinamide replacements in cyclohexane-based CC chemokine receptor 2 (CCR2) antagonists. Bioorg. Med. Chem. Lett. 20 (2010), 2425–2430.
34. [34] Sribalan, R., Padmini, V., Lavanya, A., Ponnuvel, K., Evaluation of antimicrobial activity of glycinate and carbonate derivatives of cholesterol: synthesis and characterization. Saudi Pharm J., 2015, 10.1016/j.jsps.2015.05.003.
35. [35] Lavanya, R., Uma Maheshwari, S., Harish, G., Bharath Raj, J., Kamali, S., Hemamalini, D., et al. Invitro anti-oxidant, anti-inflammatory and anti-arthritic activities in the leaves of Coldenia procumbens Linn. Res. J. Pharm. Bio. Chem. Sci. 4 (2010), 753–762.
36. [36] Kamatchi, T.S., Chitrapriya, N., Lee, H., Fronczek, C.F., Fronczek, F.R., Natarajan, K., Ruthenium(II)/(III) complexes of 4-hydroxy-pyridine-2,6-dicarboxylic acid with PPh3/AsPh3 as co-ligand: impact of oxidation state and co-ligands on anticancer activity in vitro. Dalton Trans. 41 (2012), 2066–2077.
37. [37] Tsuji, E., Ando, K., Kunitomo, J.-I., Yamashita, M., Ohta, S., Kohno, S., Ohishi, Y., Preparation of 3-acetoacetylaminobenzo[b]furan derivatives with cysteinyl leukotriene receptor 2 antagonistic activity. Org. Biomol. Chem. 1 (2003), 3139–3141.
38. [38] Tsuhako, A.L., Brown, D.S., Koltun, E.S., Aay, N., Arcalas, A., Chan, V., The design, synthesis, and biological evaluation of PIM kinase inhibitors. Bioorg. Med. Chem. Lett. 22 (2012), 3732–3738.
39. [39] CCDC No. of compound 5g. CCDC 1011897.