Synthesis and Characterization of S(-)1-Phenyl-1,2,3,4-Tetrahydro Isoquinoline Acetamide Analogues

N. Krishna Rao; M. Surendra Babu; M.V. Basaveswara  Rao; R. Keshavi; N. Sundara Rao; N.H. Eswara Prasad; Y.L.N. Murthy

doi:10.14233/ajchem.2017.20398

Issue

Vol. 29 No. 5 (2017): Vol 29 Issue 5

Issue Published : March 10, 2017

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

Synthesis and Characterization of S(-)1-Phenyl-1,2,3,4-Tetrahydro Isoquinoline Acetamide Analogues

https://doi.org/10.14233/ajchem.2017.20398

N. Krishna Rao

Department of Chemistry, Krishna University, Machilipatnam-521 328, India

M. Surendra Babu

Department of Chemistry, GITAM University, Hyderabad-502 329, India

M.V. Basaveswara Rao

Department of Chemistry, Krishna University, Machilipatnam-521 328, India

R. Keshavi

Department of Organic Chemistry, School of Chemistry, Andhra University, Visakhapatnam-530 003, India

N. Sundara Rao

Department of Organic Chemistry, School of Chemistry, Andhra University, Visakhapatnam-530 003, India

N.H. Eswara Prasad

Department of Organic Chemistry, School of Chemistry, Andhra University, Visakhapatnam-530 003, India

Y.L.N. Murthy

Department of Organic Chemistry, School of Chemistry, Andhra University, Visakhapatnam-530 003, India

Corresponding Author(s) : M. Surendra Babu

surendra@gitam.edu

Asian Journal of Chemistry, Vol. 29 No. 5 (2017): Vol 29 Issue 5
Article Published : March 10, 2017

Abstract

S(-)1-Phenyl-1,2,3,4-tetrahydro isoquinoline acetamide analogues are prepared by sequence of reactions which involve a metal hydride reduction of 3,4-dihydroisoquinoline followed by separation of S-form with mandelic acid (chiral reagent) by resolution. The product S(-)1-phenyl-1,2,3,4-tetrahydro isoquinoline is treated with halosubstituted acetyl chlorides to obtain tetrahydro isoquinoline acetyl chloride which is further employed to synthesize acetamide derivatives of tetrahydro isoquinoline using various substituted aryl amines. The products were characterized by advanced spectroscopic techniques.

Keywords

1-Phenyl-3,4-dihydro isoquinoline Resolution Aryl amines Acetamide analogues of tetrahydro isoquinoline

Rao, N. K., Babu, M. S., Rao, M. B. ., Keshavi, R., Rao, N. S., Prasad, N. E., & Murthy, Y. (2017). Synthesis and Characterization of S(-)1-Phenyl-1,2,3,4-Tetrahydro Isoquinoline Acetamide Analogues. Asian Journal of Chemistry, 29(5), 1035–1038. https://doi.org/10.14233/ajchem.2017.20398

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References

J. Lundstrom and A. Brossi, The Alkaloids, Academic Press: New York, USA, vol. 21, p. 255 (1983).
M.A. Collins and A. Bross, The Alkaloids, Academic Press: New York, USA, vol. 21, p. 329 (1983).
M. Chrzanowska, B. Schönenberger, A. Brossi and J.L. Flippen-Anderson, Helv. Chim. Acta, 70, 1721 (1987); https://doi.org/10.1002/hlca.19870700707.
Z. Czarnocki, D. Suh, D.B. MacLean, P.G. Hultin and W.A. Szarek, Can. J. Chem., 70, 1555 (1992); https://doi.org/10.1139/v92-191.
E.H. Corey and D.A. Gin, Tetrahedron Lett., 37, 7163 (1996); https://doi.org/10.1016/0040-4039(96)01622-X.
B. Zhou, J. Guo and S.J. Danishefsky, Org. Lett., 4, 43 (2002); https://doi.org/10.1021/ol016844k.
J.D. Scott and R.M. Williams, Chem. Rev., 102, 1669 (2002); https://doi.org/10.1021/cr010212u.
R. Menchaca, V. Martínez, A. Rodríguez, N. Rodríguez, M. Flores, P. Gallego, I. Manzanares and C. Cuevas, J. Org. Chem., 68, 8859 (2003); https://doi.org/10.1021/jo034547i.
G. Blasko and A. Brossi, The Alkaloids, Academic Press: New York, USA, vol. 48, p. 249 (1990).
J. Sousek, G. Guedon, T. Adam, H. Bochorakova, E. Taborska, I. Valka and V. Simanek, Phytochem. Anal., 10, 6 (1999); https://doi.org/10.1002/(SICI)1099-1565(199901/02)10:1<6::AIDPCA431>3.0.CO;2-0.
Z. Kaluza, D. Mostowicz, G. Dolega and R. Wójcik, Tetrahedron, 64, 2321 (2008); https://doi.org/10.1016/j.tet.2008.01.011.
K. Funabashi, H. Ratni, M. Kanai and M. Shibasaki, J. Am. Chem. Soc., 123, 10784 (2001); https://doi.org/10.1021/ja016935c.
J. Houston and I. Rodger, Clin. Exp. Pharmacol., 1, 401 (1974); https://doi.org/10.1111/j.1440-1681.1974.tb00562.x.
M. Ohkubo, A. Kuno, K. Katsuta, Y. Ueda, K. Shirakawa, H. Nakanishi, I. Nakanishi, T. Kinoshita and H. Takasugi, Chem. Pharm. Bull. (Tokyo), 44, 95 (1996); https://doi.org/10.1248/cpb.44.95.
W.J. Thompson, P.S. Anderson, S.F. Britcher, T.A. Lyle, J.E. Thies, C.A. Magill, S.L. Varga, J.W. Schwering, P.A. Lyle and M.E. Christry, J. Med. Chem., 33, 789 (1990); https://doi.org/10.1021/jm00164a052.
J. Olney, M. Price, K.S. Salles, J. Labruyere and G. Frierdich, Eur. J. Pharmacol., 141, 357 (1987); https://doi.org/10.1016/0014-2999(87)90552-8.
J.W. McDonald, F.S. Silverstein and M.V. Johnston, Eur. J. Pharmacol., 140, 359 (1987); https://doi.org/10.1016/0014-2999(87)90295-0.
H. Kubota, T. Watanabe, A. Kakefuda, N. Masuda, K. Wada, N. Ishii, S. Sakamoto and S. Tsukamoto, Bioorg. Med. Chem., 12, 871 (2004); https://doi.org/10.1016/j.bmc.2003.12.032

References

J. Lundstrom and A. Brossi, The Alkaloids, Academic Press: New York, USA, vol. 21, p. 255 (1983).

M.A. Collins and A. Bross, The Alkaloids, Academic Press: New York, USA, vol. 21, p. 329 (1983).

M. Chrzanowska, B. Schönenberger, A. Brossi and J.L. Flippen-Anderson, Helv. Chim. Acta, 70, 1721 (1987); https://doi.org/10.1002/hlca.19870700707.

Z. Czarnocki, D. Suh, D.B. MacLean, P.G. Hultin and W.A. Szarek, Can. J. Chem., 70, 1555 (1992); https://doi.org/10.1139/v92-191.

E.H. Corey and D.A. Gin, Tetrahedron Lett., 37, 7163 (1996); https://doi.org/10.1016/0040-4039(96)01622-X.

B. Zhou, J. Guo and S.J. Danishefsky, Org. Lett., 4, 43 (2002); https://doi.org/10.1021/ol016844k.

J.D. Scott and R.M. Williams, Chem. Rev., 102, 1669 (2002); https://doi.org/10.1021/cr010212u.

R. Menchaca, V. Martínez, A. Rodríguez, N. Rodríguez, M. Flores, P. Gallego, I. Manzanares and C. Cuevas, J. Org. Chem., 68, 8859 (2003); https://doi.org/10.1021/jo034547i.

G. Blasko and A. Brossi, The Alkaloids, Academic Press: New York, USA, vol. 48, p. 249 (1990).

J. Sousek, G. Guedon, T. Adam, H. Bochorakova, E. Taborska, I. Valka and V. Simanek, Phytochem. Anal., 10, 6 (1999); https://doi.org/10.1002/(SICI)1099-1565(199901/02)10:1<6::AIDPCA431>3.0.CO;2-0.

Z. Kaluza, D. Mostowicz, G. Dolega and R. Wójcik, Tetrahedron, 64, 2321 (2008); https://doi.org/10.1016/j.tet.2008.01.011.

K. Funabashi, H. Ratni, M. Kanai and M. Shibasaki, J. Am. Chem. Soc., 123, 10784 (2001); https://doi.org/10.1021/ja016935c.

J. Houston and I. Rodger, Clin. Exp. Pharmacol., 1, 401 (1974); https://doi.org/10.1111/j.1440-1681.1974.tb00562.x.

M. Ohkubo, A. Kuno, K. Katsuta, Y. Ueda, K. Shirakawa, H. Nakanishi, I. Nakanishi, T. Kinoshita and H. Takasugi, Chem. Pharm. Bull. (Tokyo), 44, 95 (1996); https://doi.org/10.1248/cpb.44.95.

W.J. Thompson, P.S. Anderson, S.F. Britcher, T.A. Lyle, J.E. Thies, C.A. Magill, S.L. Varga, J.W. Schwering, P.A. Lyle and M.E. Christry, J. Med. Chem., 33, 789 (1990); https://doi.org/10.1021/jm00164a052.

J. Olney, M. Price, K.S. Salles, J. Labruyere and G. Frierdich, Eur. J. Pharmacol., 141, 357 (1987); https://doi.org/10.1016/0014-2999(87)90552-8.

J.W. McDonald, F.S. Silverstein and M.V. Johnston, Eur. J. Pharmacol., 140, 359 (1987); https://doi.org/10.1016/0014-2999(87)90295-0.

H. Kubota, T. Watanabe, A. Kakefuda, N. Masuda, K. Wada, N. Ishii, S. Sakamoto and S. Tsukamoto, Bioorg. Med. Chem., 12, 871 (2004); https://doi.org/10.1016/j.bmc.2003.12.032

Issue

Vol. 29 No. 5 (2017): Vol 29 Issue 5

Synthesis and Characterization of S(-)1-Phenyl-1,2,3,4-Tetrahydro Isoquinoline Acetamide Analogues

Corresponding Author(s) : M. Surendra Babu

Abstract

Keywords

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