8146. Resibufogenin

Nomenclature

CAS number: 465-39-4
(3β,5β,15β)-14,15-Epoxy-3-hydroxy-5-bufa-20,22-dienolide; Respigon (Taisho).
C24H32O4; mol wt 384.51.
C 74.97%, H 8.39%, O 16.64%.

Description and references

Cytotoxic constituent of toad venom. Isoln: Meyer, Helv. Chim. Acta 35, 2444 (1952); Linde, Meyer, Pharm. Acta Helv. 33, 327 (1958). Structure: Thiessen, Chem. Ind. (London) 1958, 440; Linde, Meyer, Experientia 14, 238 (1958); eidem, Helv. Chim. Acta 42, 807 (1959). Synthesis: Pettit et al., J. Org. Chem. 36, 3736 (1971); Haede et al., Ann. 1973, 5. Stereochemical study of cytotoxic properties: Y. Kamono et al., J. Chem. Res. Synop. 1977, 78. Pharmacology: Leigh, Caldwell, J. Pharm. Pharmacol. 21, 708 (1969).

Chemical structure

Properties

Crystals from acetone + water, mp 113-140°/155-168°. [α]D22 -7.1° (c = 1.259 in chloroform). Also obtained as an amorphous solid, [α]D16 -5.4° (c = 2.030 in chloroform).

Derivative

Hydrochloride.
C24H33ClO4; mol wt 420.97.
C 68.47%, H 7.90%, Cl 8.42%, O 15.20%.

Properties

Crystals from acetone, dec 230-232°. [α]D15 +15.1° (c = 0.5302 in chloroform). uv max (alc): 298 nm (log ε 3.74).

Therapeutic Category

Cardiotonic.

Keywords

Cardiotonic