8295. Rugulovasines

C16H16N2O2; mol wt 268.31.
C 71.62%, H 6.01%, N 10.44%, O 11.93%.

Description and references

Mixture of the interconvertible diastereomers, rugulovasine A (cis-form) and rugulovasine B (trans-form). Isolated as the hydrochlorides from surface cultures of Penicillium concavo-rugulosum Abe and other penicillium strains: Abe et al., Agric. Biol. Chem. 33, 469 (1969); R. J. Cole et al., Can. J. Microbiol. 22, 741 (1976). Prepn and separation of isomers: Abe, DE 1919255 (1969 to Takeda), C.A. 72, 30311f (1970). Structure: Yamatodani et al., Agric. Biol. Chem. 34, 485 (1970). Abs config and mechanism of interconversion of the isomers: R. J. Cole et al., Tetrahedron Lett. 1976, 3849. Total synthesis: J. Rebek, Y. K. Shue, J. Am. Chem. Soc. 102, 5426 (1980). Hypotensive and cardiovascular activity studies of the hydrochloride isomers: Nagaoka et al., Arzneim.-Forsch. 22, 137, 143 (1972).

Chemical structure

Derivative

Rugulovasine A.

Nomenclature

CAS number: 26909-33-1
cis-(±)-3,4-Dihydro-4′-methyl-4-(methylamino)spiro[benz[cd]indole-5(1H),2′(5′H)-furan]-5′-one.

Properties

Colorless prisms from benzene, chloroform, or acetonitrile, mp 138° (dec). [α]22436 -3.0° (pyridine). uv max (ethanol): 224, 277, 288, 295 nm (log ε 4.37, 3.70, 3.78, 3.77). Sparingly sol in water, petr ether. Moderately sol in ether, chloroform, benzene, acetonitrile. Readily sol in ethyl acetate, acetone, methanol, ethanol, pyridine, and dil acids.

Derivative

Hydrochloride.

Nomenclature

CAS number: 28375-03-3
C16H16N2O2.HCl; mol wt 304.77.
C 63.05%, H 5.62%, N 9.19%, O 10.50%, Cl 11.63%.

Properties

Colorless prisms from water, mp 225° (dec).

Derivative

Rugulovasine B.

Nomenclature

CAS number: 26909-34-2

Properties

Difficult to crystallize from common solvents. Separated from benzene as colorless resinous oil. [α]22436 +1.4° (pyridine). uv max (ethanol): 227, 278, 288, 295 nm (log ε 4.16, 3.68, 3.73, 3.72). Same solubilities as rugulovasine A.

Derivative

Hydrochloride.

Nomenclature

CAS number: 28510-15-8
C16H16N2O2.HCl; mol wt 304.77.
C 63.05%, H 5.62%, N 9.19%, O 10.50%, Cl 11.63%.

Properties

White prisms from water, mp 187° (dec).