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6-Amino-1-(2’-deoxy-b-D-ribofuranosyl)-4,5-dihydro-8H-imidazo[4,5-e][1,3]diazepine-4,8-dione

1
Laboratory for Drug Design and Synthesis, Department of Chemistry & Biochemistry, University of Maryland, Baltimore County, 1000 Hilltop Circle, Baltimore, MD 21250, USA
2
Nabi, 12280 Wilkins Avenue, Rockville, MD 20852, USA
*
Author to whom correspondence should be addressed.
Molecules 2001, 6(12), M264; https://doi.org/10.3390/M264
Received: 8 June 2001 / Accepted: 15 December 2001 / Published: 20 December 2001
(This article belongs to the Section Molbank Section of Molecules, 1997-2001)
Molecules 06 m264 i001
The starting methyl 1-(2’-deoxy-β-d-ribofuranosyl)imidazole-4,5-dicarboxylate (1) was prepared by deoxygenation of the corresponding riboside, employing the literature procedure [1]. To a solution of 1 (150 mg, 0.5 mmol) and guanidine hydrochloride (240 mg, 2.5 mmol) in 30 mL of absolute methanol was added 1 mL of 25% (w/v) sodium methoxide solution in methanol. The reaction mixture was stirred for 24 h at room temperature, then 1 g of silica gel was added. The resulting mixture was evaporated to dryness and the product was isolated by silica gel flash chromatography. The column was successively eluted with chloroform/methanol (10:1) and methanol. The proper fraction was collected and evaporated to afford title product 2 as a colorless solid. Yield 110 mg (74.5%).
M.p. >250 oC.
1H NMR (DMSO-d6): δ 10.65 (brs, 1H, NH, exchangeable with D2O), 8.47 (s,1H, imidazole), 7.62 (brs, 1H, NH, exchangeable with D2O), 6.65 (t, 1H, J=5.7 Hz, 1H), 6.54 (brs, 1H, NH, exchangeable with D2O), 5.27 (d, 1H, J=4.5 Hz, OH, exchangeable with D2O), 5.09 (t, 1H, J=4.8 Hz, OH, exchangeable with D2O), 4.24 (m, 1H, 4H), 3.84 (m, 1H, 3H), 3.60 (m, 2H, 5H), 2.18 (dt, 1H, J=13.5 and 5.7 Hz, 2H), 2.02 (d, 1H, J=13.5 Hz, 2H).
HRMS (FAB): C11H14N5O5 (MH+): Calcd., 296.0995; Found, 296.0994.
Anal. Calcd. For C11H13N5O5.0.25 H2O: C, 44.09; H, 4.51; N, 23.37. Found: C, 44.08; H, 4.54; N, 23.36.

Supplementary materials

Supplementary File 1Supplementary File 2

References

  1. Chen, H. -M.; Hosmane, R. S. Molecules 2000, 5, 1187–1193.
  • Sample Availability: Available from the authors and from MDPI.
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