8544. Sinefungin

Nomenclature

CAS number: 58944-73-3
6,9-Diamino-1-(6-amino-9H-purin-9-yl)-1,5,6,7,8,9-hexadeoxy-d-glycero-α-l-talo-decofuranuronic acid; Compd 57926; Antibiotic 32232RP; A-9145.
C15H23N7O5; mol wt 381.39.
C 47.24%, H 6.08%, N 25.71%, O 20.98%.

Description and references

Adenine-containing antibiotic produced by Streptomyces griseoleus NRRL 3739. Isoln: R. L. Hamill, M. M. Hoehn, US 3758681 (1973 to Lilly); eidem, J. Antibiot. 26, 463 (1973). Antifungal activity: R. S. Gordee, T. F. Butler, ibid. 466. Antiprotozoal activity: D. K. Dube et al., Am. J. Trop. Med. Hyg. 32, 31 (1983); A. Ferrante et al., Trans. R. Soc. Trop. Med. Hyg. 78, 837 (1984); P. Paolantonacci et al., Antimicrob. Agents Chemother. 28, 528 (1985); E. Zweygarth et al., Trop. Med. Parasitol. 37, 255 (1986); in vivo antileishmanial activity: J. L. Avila et al., Am. J. Trop. Med. Hyg. 43, 139 (1990). Synthesis: M. Geze et al., J. Am. Chem. Soc. 105, 7638 (1983); stereoselective synthesis: M. P. Maguire et al., J. Org. Chem. 55, 948 (1990). Inhibition of methyltransferase: R. T. Borchardt et al., Biochem. Biophys. Res. Commun. 89, 919 (1979).

Chemical structure

Properties

White powder. Sol in water, very slightly sol in methanol and ethanol. Insol in organic solvents. Stable at room temp in aq soln from pH 1 to 11. pKa (66% DMF): 2.9, 3.9, 8.9, 10.2. uv max in neutral solns: 206 nm, 258 nm (E1cm1% 520, 325); in basic solns: 256 nm (E1cm1% 325). [α]D25 -2.61° (c = 5 in water). Also reported as [α]D23 +12 ±2° (c = 0.227 in water). LD50 s.c. in mice: 185 mg/kg (Hamill, Hoehn, J. Antibiot.)