Abstract
Sugars bearing an isothiocyanate moiety at C-1 react with diazadienium
iodide to afford glycosyl triazines that represent, through an easy
cyclocondensation reaction step, a flexible entry to different nucleoside
analogues. We herein demonstrate that this [4+2] cycloaddition
reaction occurs with total regiocontrol and good yields. Subsequent
transformation of the thiocarbonyl into a carbonyl, and nucleophilic
substitution of the methylsulfanyl group by ammonia, yields the
5-azacytidine analogues. All compounds were fully characterised
by IR, HRMS, and ¹³ C and ¹ H
NMR (COSY, HMBC and HMQC).
Key words
nucleosides - triazines - cycloaddition - 5-azacytidine - heterochemistry
References
1 Pramod G.
Prasanthkumar KP.
Mohan H.
Manoj
VM.
Manoj P.
Suresh CH.
Aravindakumar CT.
J. Phys. Chem. A
2006,
110:
11517
2 Townsend A.
Leclerc JM.
Dutschman G.
Cooney D.
Cheng YC.
Cancer
Res.
1985,
45:
3522
3 Revankar GR.
Gupta PK.
Adams AD.
Dalley NK.
McKernan PA.
Cook PD.
Canonico PG.
Robins
RK.
J.
Med. Chem.
1984,
27:
1389
4a Hrdlicka PJ.
Jepsen JS.
Nielsen C.
Wengel J.
Bioorg. Med. Chem.
2005,
13:
1249
4b Hrdlicka PJ.
Jepsen JS.
Wengel J.
Nucleosides, Nucleotides Nucleic Acids
2005,
24:
397
5 Gaubert G.
Mathé C.
Imbach JL.
Eriksson S.
Vincenzetti S.
Salvatori D.
Vita A.
Maury G.
Eur. J. Med. Chem.
2000,
35:
1011
6 Gama Y.
Shibuya I.
Shimizu M.
Goto M.
J.
Carbohydr. Chem.
2001,
20:
459
7 Galm O.
Herman JG.
Baylin SB.
Blood
Rev.
2006,
20:
1
8 Chang HC.
Cho CY.
Hung WC.
Cancer
Res.
2006,
66:
8413
9 Levine HL.
Brody RS.
Westheimer FH.
Biochemistry
1980,
19:
4993
10 Poduch E.
Bello AM.
Tang S.
Fujihashi M.
Pai EF.
Kotra LP.
J. Med. Chem.
2006,
49:
4937
11 Al-Etaibi A.
Makhseed S.
Al-Awadi NA.
Ibrahim
YA.
Tetrahedron
Lett.
2005,
46:
31
12 Chun MW.
Kim MJ.
Kim HO.
Kim HD.
Kim
JH.
Moon HR.
Jeong LS.
Nucleosides, Nucleotides Nucleic
Acids
2003,
22:
915
13 El-Barbary AA.
Sakran MA.
El-Madani AM.
J. Heterocycl. Chem.
2005,
42:
935
14 Mansour AK.
Eid MM.
Khalil NSA.
Nucleosides, Nucleotides Nucleic Acids
2003,
22:
21
15 Yamauchi M.
Kinoshita M.
J. Chem. Soc., Perkin Trans.
1
1973,
8:
391
16 Müller CE.
Tetrahedron Lett.
1991,
32:
6539
17 Matsuda A.
Kurasawa Y.
Watanabe K.
Synthesis
1981,
748
18a Jayakumar S.
Ishar MPS.
Mahajan MP.
Tetrahedron
2002,
58:
379
18b Abbiati G.
Cirrincione de Carvalho A.
Rossi E.
Tetrahedron
2003,
59:
7397
18c Mohan C.
Kumar V.
Mahajan MP.
Tetrahedron
Lett.
2004,
45:
6075
18d Jayakumar S.
Singh P.
Mahajan MP.
Tetrahedron
2004,
60:
4315
19a Landreau C.
Deniaud D.
Meslin JC.
J. Org. Chem.
2003,
68:
4912
19b Landreau C.
Deniaud D.
Reliquet A.
Meslin JC.
Eur. J. Org. Chem.
2003,
3:
421
19c Robin A.
Meslin JC.
Deniaud D.
Synthesis
2004,
1633
19d Robin A.
Julienne K.
Meslin JC.
Deniaud D.
Tetrahedron Lett.
2004,
45:
9557
19e Landreau C.
Janvier P.
Julienne K.
Meslin JC.
Deniaud D.
Tetrahedron
2006,
62:
9226
20 Landreau C.
Deniaud D.
Reliquet A.
Meslin JC.
Phosphorus, Sulfur
Silicon Relat. Elem.
2002,
177:
2651
21 Pearson MSM.
Robin A.
Bourgougnon N.
Meslin JC.
Deniaud D.
J. Org. Chem.
2003,
68:
8583
22a Robin A.
Julienne K.
Raimbault S.
Meslin JC.
Deniaud D.
Synlett
2005,
18:
2805
22b Robin A.
Julienne K.
Meslin JC.
Deniaud D.
Eur. J. Org. Chem.
2006,
41:
634
23a Lindhorst TK.
Kieburg C.
Synthesis
1995,
1228
23b Kuehne M.
Gyoergydeak Z.
Lindhorst TK.
Synthesis
2006,
949
23c Witczak ZJ.
Adv. Carbohydr. Chem. Biochem.
1986,
44:
91
24 Koch A.
Lamberth C.
Wetterich F.
Giese B.
J. Org. Chem.
1993,
58:
1083
25 Camarasa MJ.
Fernandez-Resa P.
Garcia-Lopez MT.
de las Heras FG.
Mendez-Castrillon PP.
San Felix A.
Synthesis
1984,
509
26a Garcia-Fernandez JM.
Ortiz-Mellet C.
Adv. Carbohydr. Chem. Biochem.
2000,
55:
35
26b Jiménez-Blanco JL.
Sylla B.
Ortiz-Mellet C.
Garcia-Fernandez JM.
J.
Org. Chem.
2007,
72:
4547
27a Bundle DR.
Lemieux RU.
Method. Carbohydr. Chem.
1976,
7:
79
27b Marino C.
Varela O.
de Lederkremer RM.
Carbohydr.
Res.
1989,
190:
65
27c de Lederkremer RM.
Nahmad VB.
Varela O.
J. Org. Chem.
1994,
59:
690
27d Menuel S.
Porwanski S.
Marsura A.
New
J. Chem.
2006,
30:
603
28a Banijamali AR.
Foye WO.
J. Heterocycl. Chem.
1986,
23:
1613
28b Foye WO.
Banijamali AR.
Patarapanich C.
J. Pharm. Sci.
1986,
75:
1180
29 Masuda R.
Hojo M.
Ichi T.
Sasano S.
Kobayashi T.
Kuroda C.
Tetrahedron Lett.
1991,
32:
1195
30a Hori M.
Kataoka T.
Shimizu H.
Imai E.
Yokomoto M.
Ando Y.
Synthesis
1987,
278
30b Nikiforov TT.
Connolly BA.
Tetrahedron
Lett.
1991,
32:
2505
31a Elgemeie GH.
Sood SA.
J. Chem. Res., Synop.
2001,
439
31b Chen N.
Murata S.
Yoshikawa K.
Chem.
Eur. J.
2005,
11:
4835
31c Dalai S.
Belov VN.
Nizamov S.
Rauch K.
Finsinger D.
de Meijere A.
Eur. J. Org. Chem.
2006,
41:
2753
32 Kamitori Y.
Hojo M.
Masuda R.
Fujitani T.
Ohara S.
Yokoyama T.
J. Org. Chem.
1988,
53:
129
33a Larsen C.
Steliou K.
Harpp DN.
J. Org. Chem.
1978,
43:
337
33b Larsen C.
Harpp DN.
J. Org. Chem.
1981,
46:
2465
34a Reliquet A.
Besbes R.
Reliquet F.
Meslin JC.
Synthesis
1991,
543
34b Gil MJ.
Reliquet A.
Meslin
JC.
Phosphorus, Sulfur Silicon
Relat. Elem.
1997,
128:
105
34c Charrier JD.
Reliquet A.
Meslin JC.
Tetrahedron: Asymmetry
1998,
9:
1531
35 MOPAC2007, J. J. P. Stewart, Stewart
Computational Chemistry, Version 7.334W.
36 Stewart JJP.
J. Mol. Mod.
2007,
13:
1173
