Green Synthesis and Antiviral Activity of Novel Triarylmethane Derivatives via Friedel-Crafts Alkylation by Polyethylene Glycol (PEG-400)

N. Revaprasadu; C. Sampath; P. Harika

doi:10.14233/ajchem.2016.19122

Issue

Vol. 28 No. 3 (2016): Vol 28 Issue 3

Issue Published : December 5, 2015

This work is licensed under a Creative Commons Attribution 4.0 International License.

Green Synthesis and Antiviral Activity of Novel Triarylmethane Derivatives via Friedel-Crafts Alkylation by Polyethylene Glycol (PEG-400)

https://doi.org/10.14233/ajchem.2016.19122

N. Revaprasadu

Department of Chemistry, University of Zululand, Private Bag X1001, KwaDlangezwa, KwaZulu-Natal 3886, South Africa

C. Sampath

Department of Chemistry, University of Zululand, Private Bag X1001, KwaDlangezwa, KwaZulu-Natal 3886, South Africa

P. Harika

Department of Chemistry, Andhra Loyola Institute of Engineering and Technology, Vijayawada-520 008, India

Corresponding Author(s) : N. Revaprasadu

sevaprasaduN@unizulu.ac.za

Asian Journal of Chemistry, Vol. 28 No. 3 (2016): Vol 28 Issue 3
Article Published : December 5, 2015

Abstract

A series of novel triarylmethane derivatives (3a-j) were synthesized by a one-pot, two-component method via Friedel-Crafts alkylation of various electron-rich arenes (1a-j) with a wide variety of aldehydes (2a-j) in presence of the polyethylene glycol (PEG-400) as a green solvent at 50-60 °C in good to excellent yields (76-96 %). Their structures were confirmed by FT-IR, ¹H NMR, ¹³C NMR, mass spectrometry and elemental analysis. All the triarylmethanes were tested and evaluated for their antiviral and antifungal activities. Compounds 3b, 3f, 3g and 3i exhibited highest antiviral activities against tobacco mosaic virus (TMV).

Keywords

Triarylmethanes Friedel-Crafts alkylation Green synthesis Antiviral activity

Revaprasadu, N., Sampath, C., & Harika, P. (2015). Green Synthesis and Antiviral Activity of Novel Triarylmethane Derivatives via Friedel-Crafts Alkylation by Polyethylene Glycol (PEG-400). Asian Journal of Chemistry, 28(3), 473–478. https://doi.org/10.14233/ajchem.2016.19122

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References

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References

Y.F. Wu, R. Cao, N.S. Wei and G.H. Zhou, World Agr., 35, 229 (1995).

M. Bandini, A. Melloni and A. Umani-Ronchi, Angew. Chem. Int. Ed., 43, 550 (2004); doi:10.1002/anie.200301679.

(a) V. Nair, S. Thomas, S.C. Mathew and K.G. Abhilash, Tetrahedron, 62, 6731 (2006); doi:10.1016/j.tet.2006.04.081; (b) M.S. Shchepinov and V.A. Korshun, Chem. Soc. Rev., 32, 170 (2003); doi:10.1039/b008900l; (c) M.B. Dinger and M.J. Scott, J. Chem. Soc. Perkin Trans. II, 1741 (2000); doi:10.1039/b001032o.

(a) N. Mibu, K. Yokomizo, M. Uyeda and K. Sumoto, Chem. Pharm. Bull. (Tokyo), 53, 1171 (2005); doi:10.1248/cpb.53.1171; (b) N. Mibu, K. Yokomizo, M. Uyeda and K. Sumoto, Chem. Pharm. Bull. (Tokyo), 51, 1325 (2003); doi:10.1248/cpb.51.1325.

M.R. Lewis and P.P. Goland, Cancer Res., 12, 130 (1952).

(a) M.K. Parai, G. Panda, V. Chaturvedi, Y.K. Manju and S. Sinha, Bioorg. Med. Chem. Lett., 18, 289 (2008); doi:10.1016/j.bmcl.2007.10.083; (b) G. Panda, J.K. Shagufta, V. Mishra, V. Chaturvedi, A.K. Srivastava, R. Srivastava and B.S. Srivastava, Bioorg. Med. Chem., 12, 5269 (2004); doi:10.1016/j.bmc.2004.07.058.

S. Podder, J. Choudhury, U.K. Roy and S.J. Roy, Org. Chem., 72, 3100 (2007); doi:10.1021/jo062633n.

R. Muthyala, A.R. Katritzky and X. Lan, Dyes Pigments, 25, 303 (1994); doi:10.1016/0143-7208(94)87017-9.

(a) S. Lin and X. Lu, J. Org. Chem., 72, 9757 (2007); doi:10.1021/jo071232k; (b) S. Shirakawa and S. Kobayashi, Org. Lett., 9, 311 (2007); doi:10.1021/ol062813j.

(a) Z. Tu, B. Rama Raju, T.-R. Liou, V. Kavala, C.-W. Kuo, Y. Jang, Y.-H. Shih, C.-C. Wang and C.-F. Yao, Tetrahedron, 65, 2436 (2009); doi:10.1016/j.tet.2009.01.075; (b) C.M. Chu, W.J. Huang, J.T. Liu and C.F. Yao, Tetrahedron Lett., 48, 6881 (2007); doi:10.1016/j.tetlet.2007.07.178.

V. Nair, K.G. Abhilash and N. Vidya, Org. Lett., 7, 5857 (2005); doi:10.1021/ol052423h.

J. Choudhury, S. Podder and S. Roy, J. Am. Chem. Soc., 127, 6162 (2005); doi:10.1021/ja0506004.

J. Esquivias, R. Gómez Arrayás and J.C. Carretero, Angew. Chem. Int. Ed., 45, 629 (2006); doi:10.1002/anie.200503305.

K.U.M. Rao, S.H. Jayaprakash, S.K. Nayak and C.S. Reddy, Catal. Sci. Technol., 1, 1665 (2011); doi:10.1039/c1cy00295c.

G.V. Jr Gooding and T. T. Hebert, Phytopathology, 57, 1285 (1967).

B.A. Song, H.P. Zhang, H. Wang, S. Yang, L.H. Jin, D.Y. Hu, L.L. Pang and W.J. Xue, Agric. Food Chem., 53, 7886 (2005); doi:10.1021/jf051050w.

(a) G. Kamalakar, K. Komura and Y. Sugi, Ind. Eng. Chem. Res., 45, 6118 (2006); doi:10.1021/ie060440k; (b) H. Weingartner and E.U. Franck, Angew. Chem. Int. Ed., 44, 2672 (2005); doi:10.1002/anie.200462468.

Issue

Vol. 28 No. 3 (2016): Vol 28 Issue 3

Green Synthesis and Antiviral Activity of Novel Triarylmethane Derivatives via Friedel-Crafts Alkylation by Polyethylene Glycol (PEG-400)

Corresponding Author(s) : N. Revaprasadu

Abstract

Keywords

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