Synthesis of (2S,4S)-2-Substituted-3- (3-Sulfanylpropanoyl)-6- Oxohexahydropyrimidine-4-Carboxylic Acids as Potential Antihypertensive Drugs

Andrei Ershov^*, Dmitry Nasledov, Igor Lagoda, Valery Shamanin

Institute of Macromolecular Compouns of Russian Academy of Sciences, Saint Petesburg, Russia.

DOI: 10.4236/msce.2015.36002                

Abstract

Proceeding from natural amino acid L-asparagine and commercially available aldehydes a stereoselective synthesis was developed of (2S,4S)-2-alkyl(aryl)-3-(3-sulfanylpropanoyl)-6-oxohexahy- dropyrimidine-4-carboxylic acids, potential antihypertensive drugs, inhibitors of the angiotensin converting enzyme.

Keywords

Synthesis of (2S, 4S)-2-Substituted-3- (3-Sulfanylpropanoyl)-6- Oxohexahydropyrimidine-4-Carboxylic Acids as Potential Antihypertensive Drugs

Conflicts of Interest

The authors declare no conflicts of interest.

References

[1]	Wyvratt, M.J. and Patchett, A.A. (1985) Medicinal Research Reviews, 5, 483-531. http://dx.doi.org/10.1002/med.2610050405
[2]	Brown, N.J. and Vaughan, D.E. (1998) Circulation, 97, 1411-1420. http://dx.doi.org/10.1161/01.CIR.97.14.1411
[3]	Ondetti, M.A., Rubin, B. and Cushman, D.W. (1977) Science, 196, 441-444. http://dx.doi.org/10.1126/science.191908
[4]	Ondetti, M.A. and Cushman, D.W. (1978) US Patent No. 4105776.
[5]	Ryono, D.E. and Ondetti, M.A. (1982) US Patent No. 4321392.
[6]	Ondetti, M.A. (1981) US Patent No. 4282235.
[7]	Yakhontov, L.N., Mashkovskij, M.D., Kugaevskaya, E.V., Orekhovich, V.N., Pavlikhina, L.V., Eliseeva, Y.E., Mastafanova, L.I., Evstratova, M.I. and Shvarts, G.Y. (1993) SU Patent No. 1838298.
[8]	Nozawa, K., Yoshizawa, T. and Kuroda, N. (1985) US Patent No. 4537967.
[9]	Stanton, J.L. and Gruenfeld, N. (1986) UA Patent No. 4599357.
[10]	Robl, J.A. (1999) US Patent No. 5856476.
[11]	Nakamura, S., Tsuda, Y. and Doi, T. (1983) JP Patent No. 58110573.
[12]	Juaristi, E., Lopez-Ruiz, H., Madrigal, D., Ramirez-Quiros, Y. and Escalante, J. (1998) Journal of Organic Chemistry, 63, 4706-4710. http://dx.doi.org/10.1021/jo980367a
[13]	Juaristi, E., Quintana, D., Balderas, M. and Gareia-Perez, E. (1996) Tetrahedron: Asymmetry, 7, 2233-2246. http://dx.doi.org/10.1016/0957-4166(96)00278-9
[14]	Lakner, F.J. and Negrete, G.R. (2002) Synlett, 643-645. http://dx.doi.org/10.1055/s-2002-22712
[15]	Mfuh, A.M., Mahindaratne, M.P.D., Quintero, M.V., Lakner, F.J., Bao, A., Goins, B.A., Phillips, W.T. and Negrete, G.R. (2011) Langmuir, 27, 4447-4455. http://dx.doi.org/10.1021/la105085k
[16]	Kundu, S.K., Mahindaratne, M.P.D., Quinones, B., Negrete, G.R. and Tiekink, E.R.T. (2010) Acta Crystallographica, E66, o3.
[17]	Ershov, A.Yu., Nasledov, D.G., Nasonova, K.V., Sezyavina, K.V., Susarova, T.V., Lagoda, I.V. and Shamanin, V.V. (2013) Chemistry of Heterocyclic Compounds, 49, 598-603. http://dx.doi.org/10.1007/s10593-013-1287-0
[18]	Negrete, G.R., Mahindaratne, M.P.D., Mfuh, A.M. and Quintero, M.V. (2011) US Patent No. 20110268653.
[19]	Ershov, A.Yu., Nasledov, D.G., Parilova, E.V., Lagoda, I.V. and Shamanin, V.V. (2013) Russian Journal of Organic Chemistry, 50, 1164-1174. http://dx.doi.org/10.1134/S1070428014080168
[20]	Daeniker, H.U. and Druey, J. (1957) Helvetica Chimica Acta, 40, 2148-2156. http://dx.doi.org/10.1002/hlca.19570400714
[21]	Ershov, A.Yu., Susarova, T.V., Chernitsa, B.V. and Shamanin, V.V. (2011) RF Patent No. 245528.
[22]	Kadouri-Puchot, C. and Comesse, S. (2005) Amino Acids, 29, 101-130. http://dx.doi.org/10.1007/s00726-005-0193-x