9440. Tilorone

Nomenclature

CAS number: 27591-97-5
2,7-Bis[2-(diethylamino)ethoxy]-9H-fluoren-9-one; bis-DEAE-fluorenone.
C25H34N2O3; mol wt 410.55.
C 73.14%, H 8.35%, N 6.82%, O 11.69%.

Description and references

The first recognized synthetic, small mol wt compound that is an orally active interferon inducer: Krueger, Mayer, Science 169, 1213 sqq. (1970). Prepn: Fleming et al., DE 1964761 corresp to US 3592819 (1970, 1971 to Richardson Merrell); E. R. Andrews et al., J. Med. Chem. 17, 882 (1974); H. M. Burke, M. M. Joullie, ibid. 21, 1084 (1978). Mechanism of action: De Clercq, Merigan, J. Infect. Dis. 123, 190 (1971). Toxicity studies: Kaufman et al., Proc. Soc. Exp. Biol. Med. 137, 357 (1971). Review: P. Chandra et al., “Tilorone Hydrochloride” in Antibiotics vol. 5(pt. 2), F. E. Hahn, Ed. (Springer-Verlag, New York, 1979) pp 385-413.

Chemical structure

Derivative

Dihydrochloride.

Nomenclature

CAS number: 27591-69-1
C25H34N2O3.2HCl; mol wt 483.47.
C 62.11%, H 7.51%, N 5.79%, O 9.93%, Cl 14.67%.

Properties

Crystals from butanone-methanol, mp 235-237°. uv max (water): 269 nm (E1%1cm 1600). LD50 in mice, rats (single dose): 959, 852 mg/kg orally; 145, 244 mg/kg i.p. (Krueger, Mayer).