H. Keypour et al. / Tetrahedron Letters 50 (2009) 169–171
171
3. Bell, C.; Cory, M.; Fairley, T.; Hall, J.; Tidwell, R. Antimicrob. Agents Chemother.
1991, 35, 1099.
Synthesis of the dication
4. Del Poeta, M.; Schell, W.; Dykstra, C.; Jones, S.; Tidwell, R.; Czarny, A.; Bajic, M.;
Bajic, M.; Kumar, A.; Boykin, D.; Perfect, J. Antimicrob. Agents Chemother. 1998,
42, 2495.
5. Patrick, D.; Boykin, D.; Wilson, W.; Tanious, F.; Spychala, J.; Bender, B.; Hall, J.;
Dykstra, C.; Ohemeng, K.; Tidwell, R. Eur. J. Med. Chem. 1997, 32, 781.
6. Blagburn, B. L.; Drain, K. L.; Land, T. M.; Kinard, R. G.; Moore, P. H.; Lindsay, D.
S.; Boykin, D. W.; Tidwell, R. R. Antimicrob. Agents Chemother. 1998, 42, 2877.
7. Blagburn, B.; Drain, K.; Land, T.; Moore, P.; Kinard, R.; Lindsay, D.; Kumar, A.;
Shi, J.; Boykin, D.; Tidwell, R. J. Parasitol. 1998, 84, 851.
8. Patrick, D.; Hall, J.; Bender, B.; McCurdy, D.; Wilson, W.; Tanious, F.; Saha, S.;
Tidwell, R. Eur. J. Med. Chem. 1999, 34, 575.
9. Bell, C.; Hall, J.; Kyle, D.; Grogl, M.; Ohemeng, K.; Allen, M.; Tidwell, R.
Antimicrob. Agents Chemother. 1990, 34, 1381.
10. Basselin, M.; Lawrence, F.; Robert-Gero, M. Biochem. J. 1996, 315, 631.
11. Callahan, H. L.; Portal, A. C.; Deveraux, R.; Grogl, M. Antimicrob. Agents
Chemother. 1997, 41, 818.
12. Sereno, D.; Lemesre, J. L. Antimicrob. Agents Chemother. 1997, 41, 972.
13. Werbovetz, K.; Brendle, J.; Sackett, D. Biochem. Parasitol. 1999, 98, 53.
14. Basch, H.; Hoz, S.; Goldberg, M. Isr. J. Chem. 1993, 33, 403.
15. Hensen, K.; Mayr-Stein, R.; Stumpf, T.; Pickel, P.; Bolte, M.; Fleischer, H. J. Chem.
Soc., Dalton Trans. 2000, 473.
To a solution of N,N0-bis(2-aminophenyl)-1,2-ethanediamine
(0.24 g, 1 mmol) and 2-pyridinecarboxaldehyde (0.43 g, 4 mmol)
in methanol (50 mL), manganese chloride (0.13 g, 1 mmol) was
added and the reaction was stirred for 6 h at room temperature.
Next, sodium perchlorate (0.245 g, 2 mmol) was added. When
the solution volume was reduced to 10 mL by evaporation a pre-
cipitate formed. This was filtered off, washed with ether, and dried
in vacuo. Vapour diffusion of diethyl ether into a solution of the
dication in MeOH afforded pale yellow crystals. Yield: (31%), IR
(KBr, cmꢀ1) 3050 (ClO4ꢀ). Anal.
m(CH), 1591 m(py), 1097 and 738 m
Calcd for C38H32Cl2N8O8: C, 57.08; H, 4.03; N, 14.01. Found: C,
57.16; H, 4.08; N, 13.96. Melting point: 111 °C.
Acknowledgments
16. Hensen, K.; Stumpf, T.; Bolte, M.; Nather, C.; Fleischer, H. J. Am. Chem. Soc. 1998,
120, 10402.
We are grateful to the Faculty of Chemistry of Bu-Ali Sina Uni-
versities and the Ministry of Science Research and Technology for
the financial support. The authors thank Professor Michael D. Ward
(Department of Chemistry, University of Sheffield, Sheffield, UK S3
7HF) for his invaluable support in X-ray data collection.
ꢀ
17. Compound 3: C38H32Cl2N8O8, FW = 799.62, triclinic, space group P1,
a = 9.437(2), b = 11.967(3), c = 15.871(4) Å, = 86.137(4), b = 81.274(4),
= 79.979(4)°, V = 1742.9(7) Å3, Z = 2, calcd = 1.524 mg/mꢀ3
F(000) = 828,
a
c
q
,
k = 0.71073, T = 150 K, crystal size = 0.23 ꢁ 0.23 ꢁ 0.19 mm, of the 19,953
reflections collected (1.30 6 h 6 27.630) 7830 [Rint = 0.0516] were
independent, R1 = 0.0597 (I > 2r (I)) and wR2 = 0.1409. Crystallographic data
for the structure reported in this Letter have been deposited with the
Cambridge Crystallographic Data Centre, CCDC 691720. Copies of this
information may be obtained free of charge front the Director, CCDC, 12
Union Road, Cambridge, CB2 1EZ, UK(Telephone: (44) 01223 762910: (44)
References and notes
1. Berman, J. D. Clin. Infect. Dis. 1997, 24, 684.
2. Seaman, J.; Mercer, A.; Sondorp, E. Int. J. Epidemiol. 1996, 25, 862.