Abstract
A new series of 2-N-(phthalyl- or tosylamino acid)pyrimidines have been synthesised from the coupling of pyrimidine derivatives with phthalyl- or tosylamino acids. Hydrazinolysis of 2-N-phthalyl derivatives afforded unprotected amino acid derivatives. New derivatives of peptidylpyrimidines have been synthesised from the reaction of pyrimidine derivatives with α-amino acids methyl ester hydrochloride viz different routes. Also, new glycosides have been prepared from the reaction of pyrimidine derivatives with α-D-glucopyranosyl bromide. Most of the synthesised compounds showed a significant antimicrobial activity.
References
1.
Gangjee A.
,
Jain H.D.
,
Phan J.
,
Guo X.
,
Queener S.F.
, and
Kisliuk R.L.
, Bioorg. Med. Chem. , 2010 , 18 , 953 .
2.
Tangeda S.J.
, and
Garlapati A.
, Eur. J. Med. Chem. , 2010 , 45 , 1453 .
3.
Pellegrino G.
,
Leonetti F.
,
Carotti A.
,
Nicolotti O.
,
Pisani L.
,
Stefanachi A.
, and
Catto M.
, Tetrahedron Lett. , 2010 , 51 , 1702 .
4.
Borisenko V.E.
,
Krekov S.A.
,
Fomenko M.Y.
,
Koll A.
, and
Lipkovski P.
, J. Mol. Struct. , 2008 , 882 , 9 .
5.
Rai U.S.
,
Isloor A.M.
,
Shetty P.
,
Vijesh A.M.
,
Prabhu N.
,
Isloor S.
,
Thiageeswaran M.
, and
Fun H.K.
, Eur. J. Med. Chem. , 2010 , 45 , 2695 .
6.
Farmer L.J.
,
Bemis G.
,
Britt S.D.
,
Cochran J.
,
Connors M.
,
Harrington E.M.
,
Hoock T.
,
Markland W.
,
Nanthakumar S.
,
Taslimi P.
,
Ter Haar E.
,
Wang J.
,
Zhaveri D.
, and
Salituro F.G.
, Bioorg. Med. Chem. Lett. , 2008 , 18 , 6231 .
7.
Pomeisl K.
,
Holy A.
, and
Votruba I.
, Nucleic Acids Symp. Ser. , 2008 , 657 .
8.
Palmer R.A.
,
Potter B.S.
,
Leach M.J.
, and
Chowdhry B.Z.
, J. Chem. Crystallogr. , 2008 , 38 , 407 .
9.
Gedi V.
,
Jayaraman K.
,
Kalme S.
,
Park H.Y.
,
Park H.C.
,
La I.J.
,
Hahn H.G.
, and
Yoon M.Y.
, Biochim. Biophys. Acta , 2010 , 1804 , 1369 .
10.
Gangjee A.
,
Kurup S.
,
Ihnat M.A.
,
Thorpe J.E.
, and
Shenoy S.S.
, Bioorg. Med. Chem. , 2010 , 18 , 3575 .
11.
Phoon C.W.
,
Somanadhan B.
,
Heng S.C.H.
,
Ngo A.
,
Ng S.B.
,
Butler M.S.
,
Buss A.D.
, and
Sim M.M.
, Tetrahedron , 2004 , 60 , 11619 .
12.
Amagata T.
,
Minoura K.
, and
Numata A.
, J. Nat. Prod. , 2006 , 69 , 1384 .
13.
Hosoya T.
,
Kato Y.
,
Yamamoto Y.
,
Hayashi M.
,
Komiyama K.
, and
Ishibashi M.
, Heterocycles , 2006 , 69 , 463 .
14.
Curini M.
,
Epifano F.
, and
Genovese S.
, Bioorg. Med. Chem. Lett. , 2005 , 15 , 5049 .
15.
Auernheimer J.
,
Dahmen C.
,
Hersel U.
,
Bausch A.
, and
Kessler H.
, J. Am. Chem. Soc. , 2005 , 127 , 16107 .
16.
Durand A.
,
Giardina T.
,
Villard C.
,
Roussel A.
,
Puigserver A.
, and
Perrier J.
, Biochimie , 2003 , 85 , 953 .
17.
Jensen C.M.
,
Lindsay K.B.
,
Andreasen P.
, and
Skrydstrup T.
, J. Org. Chem. , 2005 , 70 , 7512 .
18.
Brunel J.M.
,
Salmi C.
, and
Letourneux Y.
, Tetrahedron Lett. , 2005 , 46 , 217 .
19.
Pellissier H.
, Tetrahedron , 2005 , 61 , 2947 .
20.
Hu X.
,
Yu S.Y.
,
Cao S.
, and
Ruan W.Z.
, Chem. Res. Appl. , 2007 , 19 , 465 .
21.
El Ashry E.S.H.
,
Aly A.A.
,
Amer M.R.M.
,
Shah R.
, and
Ng S.W.
, Carbohydr. Res. , 2011 , 346 , 169 .
22.
El-Sayed W.A.
,
Fathi N.M.
,
Gad W.A.
, and
El Ashry E.S.H.
, J. Carbohydr. Chem. , 2008 , 27 , 357 .
23.
Aly A.A.
, Curr. Org. Chem. , 2009 , 13 , 1758 .
24.
Aly A.A.
, J. Heterocycl. Chem. , 2009 , 46 , 895 .
25.
Behalo M.S.
, and
Aly A. A.
, J. Chem. Res. , 2009 , 12 , 753 .
26.
Pennington R.M.
, and
Fischer R.R.
, J. Biol. Chem. , 1981 , 256 , 8963 .
27.
Katritzky A.
,
Suzuki K.
, and
Singh S.K.
, Arkivoc , 2004 , (i), 12 .
28.
Aly A.A.
, J. Heterocycl. Chem. , 2008 , 45 , 993 .
29.
Fischer P.M.
, Med. Res. Rev. , 2007 , 27 , 755 .
30.
Kamolkijkarn P.
,
Prasertdee T.
,
Netirojjanakul C.
,
Sarnpitak P.
,
Ruchirawat S.
, and
Deechongkit S.
, Peptides , 2010 , 31 , 533 .
31.
Arima J.
,
Morimoto M.
,
Usuki H.
,
Mori N.
, and
Hatanaka T.
, J. Biotechnol. , 2010 , 147 , 52 .
32.
Bondanszky M.
, Principle of peptides synthesis , 2nd edn, 1993 , pp. 1 –55 , 273.
33.
Leiferet C.
,
Chidbouree S.
,
Hampson S.
,
Workman S.
,
Sigee D.
,
Epton H.A.
, and
Harbour A.
, J. Appl. Bacteriol. , 1995 , 78 , 97 .
