Synthesis of Polysubstituted Analogues of the 4-Methyl-2-phenylquinoline

A.A. Al-Qahtani; T.M. Al-Turki; M. Khan; A.A. Mousa; H.Z. Alkhathlan

doi:10.14233/ajchem.2013.14253

Issue

Vol. 25 No. 11 (2013): Vol 25 Issue 11

Issue Published : May 18, 2013

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

Synthesis of Polysubstituted Analogues of the 4-Methyl-2-phenylquinoline

https://doi.org/10.14233/ajchem.2013.14253

A.A. Al-Qahtani

Department of Chemistry, College of Science, King Saud University, P.O. Box 2455, Riyadh-11451, Saudi Arabia

T.M. Al-Turki

Department of Chemistry, College of Science, King Saud University, P.O. Box 2455, Riyadh-11451, Saudi Arabia

M. Khan

Department of Chemistry, College of Science, King Saud University, P.O. Box 2455, Riyadh-11451, Saudi Arabia

A.A. Mousa

Department of Chemistry, College of Science, King Saud University, P.O. Box 2455, Riyadh-11451, Saudi Arabia

H.Z. Alkhathlan

Department of Chemistry, College of Science, King Saud University, P.O. Box 2455, Riyadh-11451, Saudi Arabia

Corresponding Author(s) : H.Z. Alkhathlan

khathlan@ksu.edu.sa

Asian Journal of Chemistry, Vol. 25 No. 11 (2013): Vol 25 Issue 11
Article Published : June 5, 2013

Abstract

A simple and convenient synthetic method for the direct synthesis of a series of polysubstituted analogues of the putative antifungal agent 4-methyl-2-phenylquinoline, a mimic of the natural bioactive 4-methoxy-2-phenylquinoline is reported.

Keywords

Quinolines 2-Aminoacetophenone 2-Hydroxyacetophenones 2-(4-Methyl2-quinolinyl)aniline

Al-Qahtani, A., Al-Turki, T., Khan, M., Mousa, A., & Alkhathlan, H. (2013). Synthesis of Polysubstituted Analogues of the 4-Methyl-2-phenylquinoline. Asian Journal of Chemistry, 25(11), 6055–6058. https://doi.org/10.14233/ajchem.2013.14253

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References

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(a) H.Z. Alkhathlan, Tetrahedron, 59, 8163 (2003); (b) H.Z. Alkhathlan, M.A. Al-Saad, H.M. Al-Hazmi, K.A. Al-Farhan and A.A. Mousa, J. Chem. Res. (M), 1023, 473 (2002); (c) H.Z. Alkhathlan, M.A. Al-Saad, H.M. Al-Hazmi, K.A. Al-Farhan and A.A. Mousa, J. Chem. Res. (M), 1201, 587 (2002), (d) H.Z. Alkhathlan, Synth. Commun., 34, 71 (2004); (e) A.S. Al-Bogami, A.M. Al-Majid, M.A. Al-Saad, A.A. Mousa, S.A. Al-Mazroa and H.Z. Alkhathlan, Molecules, 14, 2147 (2009).
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References

(a) R.D. Larsen and J.F. Marcoux, In eds.: G.W. Gribble and T.L. Gilchrist, In Progress in Heterocyclic Chemistry, Pergamon, Oxford, UK, Vol. 12, p. 237 (2000); (b) L.A. Mitscher, Chem. Rev., 105, 559 (2005); (c) S. Yokoshima, T. Ueda, S. Kobayashi,A. Sato, T. Kuboyama, H. Tokuyama and T. Fukuyama, J. Am. Chem. Soc,. 124, 2137 (2002); (d) Y.-L. Chen, K.-C. Fang, J.-Y. Sheu, S.-L. Hsu and C.-C. Tzeng, J. Med. Chem., 44, 2374 (2001); (e) A.W. Erian, Chem. Rev., 93, 1991 (1993).

M. Kidwai, K. Bhushan, P. Sapra, R. Saxena and R. Gupta, Bioorg. Med. Chem., 8, 69 (2000).

R. Musiol, J. Jampilek, V. Buchta, L. Silva, H. Niedbala, B. Podeszwa, A. Palka, K. Majerz-Maniecka, B. Oleksyn and J. Polanski, Bioorg. Med. Chem., 14, 3592 (2006).

Y. Zhao, Y. Chen, F. Chang and C. Tzeng, Eur. J. Med. Chem., 40, 792 (2005).

Y. Chen, C. Huang, Z. Huang, C. Tseng, F. Chang, S. Yang, S. Lin and C. Tzeng, Bioorg. Med. Chem., 14, 3098 (2006).

J. Charris, J. Dominguez, N. Gamboa, J. Rodrigues and J. Angel, Eur. J. Med. Chem., 40, 875 (2005).

W. Cunico, C. Cechinel, H. Bonacorso, M. Martins, N. Zannata, N. de Souza, I. Freitas, R. Soares and A. Krettli, Bioorg. Med. Chem. Lett., 16, 649 (2006).

K.S. Sreevinasa, Farmaco, 53, 399 (1998).

J. Dade, O. Provot, H. Moskowitz, J. Mayrargue and E. Prina, Chem. Pharm. Bull., 49, 480 (2001).

M. Jain, S. Khan, B. Tekwani, M. Jacob, S. Singh, B. Singh and R. Jain, Bioorg. Med. Chem., 13, 4458 (2005).

D. Doube, M. Blouin, C. Brideau, C. Chan, S. Desmarais, D. Ethier, J.P. Falgueyret, R.W. Friesen, M. Girard, Y. Girard, J. Guay, P. Tagari and R.N. Young, Bioorg. Med. Chem. Lett., 8, 1255 (1998).

T.R. Govindachari, K.R. Ravindranath and N. Viswanathan, J. Chem. Soc. Perkin Trans. I, 1215 (1974).

D. Bailey, E. Mount, J. Siggins, J. Carlson, A. Yarinsky and R. Slighter, J. Med. Chem., 22, 599 (1979).

M.P. Maguire, K.R. Sheets, K. McVety, A.P. Spada and A. Zilberstein, J. Med. Chem., 37, 2129 (1994).

(a) A.K. Aggarwal and S.A. Jenekhe, Macromolecules, 24, 6806 (1991); (b) X. Zhang, A.S. Shetty and S.A. Jenekhe, Macromolecules, 32, 7422 (1999); (c) S.A. Jenekhe, L. Lu and M.M. Alam, Macromolecules, 34, 7315 (2001).

I. Saito, S. Sando and K. Nakatani, Biol. Org. Med. Chem., 9, 2381 (2001).

(a) C.S. Cho, B.H. Oh, J.S. Kim, T.J. Kim and S.C. Shim, Chem. Commun., 1885 (2000); (b) B. Jiang and Y.C. Si, J. Org. Chem., 67, 9449 (2002); (c) J.I. Ubeda, M. Villacampa and C. Avendano, Synthesis, 1176 (1998); (d) R.J. Linderman and S.K. Kirollos, Tetrahedron Lett., 31, 2689 (1990); (e) M.E. Theclitou and L.A. Robinson, Tetrahedron Lett., 43, 3907 (2002).

(a) J. Wu, H.G. Xia and K. Gao, Org. Biomol. Chem., 4, 126 (2006); (b) M. Ali, Z.P. Salehi, A. Ghaderi and M. Shiri, Catal. Commun., 8, 1214 (2007); (c) J.S. Yadav, P. Rao, D. Sreenu, R.S. Rao, V.N. Kumar, K. Nagaiah and A.R. Prasad, Tetrahedron Lett., 46, 7249 (2005); (d) C.S. Jia and G.W. Wang, Lett. Org. Chem., 3, 289 (2006).

(a) L. Strekowski and A. Czamy, J. Fluorine Chem., 104, 281 (2000); (b) Y.Z. Hu, G. Zang and R.P. Thummel, Org. Lett., 5, 2251 (2003); (c) A. Arcadi, M. Chiarini, S. Di Giuseppe and F. Marinelli, Synlett, 203 (2003); (d) B.R. McNaughton and B.L. Miller, Org. Lett., 5, 4257 (2003); (e) J.S. Yadav, B.V.S. Reddy and K. Premlatha, Synlett, 963

(2004); (f) J.S. Yadav, B.V.S. Reddy, P. Sreedhar, R.S. Rao and K. Nagaiah, Synthesis, 2381 (2004); (g) K. Mogilaih and C.S. Reddy, Synth. Commun., 3131 (2003); (h) A. Walser, T. Flyll and R.I. Fryer, J. Heterocycl. Chem., 12, 737 (1975); (i) S.K. De and R.A. Gibbs, Tetrahedron Lett., 46, 1647 (2005); (j) P. Arumugam, G. Karthikeyan, R. Atchudan, D. Muralidharan and P.T. Perumal, Chem. Lett., 34, 314 (2005); (k) J. Wu, L. Zhang and T.N. Diao, Synlett, 2653 (2005).

(a) A. Fournet, B. Vagneur, P. Richomme and J. Bruneton, Can. J. Chem., 67, 2116 (1989); (b) G.P. Sidyakin, V.I. Pastukhova and Y.S. Yu, Uzbeksk. Khim. Zh., 6, 56 (1962) [Chem. Abstr., 58, 4608g (1963)]; (c) P.C. Vieira and I. Kubo, Phytochemistry, 29, 813 (1990); (d) S. Goodwin, A.F. Smith, A.A. Valsquez and E.C. Horning, J. Am. Chem. Soc., 81, 6209 (1959); (e) S. Goodwin, A.F. Smith and E.C. Horning, J. Am. Chem. Soc., 79, 2239 (1957); (f) A. Fournet, R. Hocquemiller, F. Roblot, A. Cave, P. Richomme and J. Bruneton, J. Nat. Prod., 56, 1547 (1993); (g) F. Zanatta, R. Becker, R.B. Gandolfi, M. Lemos, J.C. Ticonn,A. Gimenez, B.K. Clasen, V.C. Filho and S.F. Andrade, Chem.-Biol. Interact., 180, 312 (2009); (h) A. Fournet, A.A. Barrios, V. Munoz, R. Hocquemiller, A. Cave and D. Bruneton, Agents Chemother., 37, 859 (1993); (i) M. Guarachi, M. Paz, R. Chuqui, M. Sauvain, N. Flores, M.T. Alvarez and A. Gimenez, Rev. Boliv. Quim, 25, 10 (2008); (j) S. Metallidis, J. Nikolaidis, G. Lazaraki, E. Koumentaki, V. Gogou, D. Topsis, P. Nikolaidis, N. Charokopos and G. Theodoridis, Int. J. Antimicrob. Agents, 29, 738 (2007).

(a) T.C. Ko, M.J. Hour, J.C. Lien, C.M. Teng, K.H. Lee, S.C. Kuoa and L.J. Huanga, Bioorg. Med. Chem. Lett., 11, 279 (2001); (b) J.M. Urbina, J.C.G. Cortea, A. Palma, S.N.L. Pez, S.A. Zacchino, R.D. Enriz, J.C. Ribas and V.V. Kouznetzov, Bioorg. Med. Chem., 8, 691 (2000); (c) C.M.M. Gomez, V.V. Kouznetsov, M.A. Sortino, S.L. Alvarez and S.A. Zacchino, Bioorg. Med. Chem., 16, 7908 (2008); (d) M.L.Y. Vargas, M. V. Castelli, V.V. Kouznetsov, J.M.G. Urbina, S.N. Lopez, M. Sortino, R.D. Enriz, J.C. Ribas and S.A. Zacchino, Bioorg. Med. Chem., 11, 1531 (2003); (e) Z.Y. An, Y.Y. Yan, D. Peng, T.M. Ou, J.H. Tan, S.L. Huang, L.K. An, L.Q. Gu and Z.S. Huang, Eur. J. Med. Chem. 45, 3895 (2010).

E.C. Elderfield and J.B. White, J. Am. Chem. Soc., 68, 1276 (1946).

(a) O.V. Singh and R.S. Kapil, Synlett., 751 (1992); (b) R.S. Verma and D. Kumar, Tetrahedron Lett., 39, 9113 (1998); (c) M.J. Mphahlele, F.K. Mogamisi, M. Tsanwani, M.S. Hlatshwayo and M.R.J. Mampa, Chem. Res. Synop., 706 (1999); (d) A. Arcadi, F. Marinelli and E. Rossi, Tetrahedron, 55, 13233 (1999).

(a) H.Z. Alkhathlan, Tetrahedron, 59, 8163 (2003); (b) H.Z. Alkhathlan, M.A. Al-Saad, H.M. Al-Hazmi, K.A. Al-Farhan and A.A. Mousa, J. Chem. Res. (M), 1023, 473 (2002); (c) H.Z. Alkhathlan, M.A. Al-Saad, H.M. Al-Hazmi, K.A. Al-Farhan and A.A. Mousa, J. Chem. Res. (M), 1201, 587 (2002), (d) H.Z. Alkhathlan, Synth. Commun., 34, 71 (2004); (e) A.S. Al-Bogami, A.M. Al-Majid, M.A. Al-Saad, A.A. Mousa, S.A. Al-Mazroa and H.Z. Alkhathlan, Molecules, 14, 2147 (2009).

N. Sakai, K. Annaka,A. Fujita,A. Sato and T. Konakahara, J. Org. Chem., 73, 4160 (2008).

P. Molina, C. Conesa, A. Alias, A. Arques, M.D. Velasco, A.L. LlamasSaiz, C. Foces-Foces, Tetrahedron, 49, 7599 (1993).

Issue

Vol. 25 No. 11 (2013): Vol 25 Issue 11

Synthesis of Polysubstituted Analogues of the 4-Methyl-2-phenylquinoline

Corresponding Author(s) : H.Z. Alkhathlan

Abstract

Keywords

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