Title: Rugulovasines
Molecular Formula: C16H16N2O2
Molecular Weight: 268.31
Percent Composition: C 71.62%, H 6.01%, N 10.44%, O 11.93%
Literature 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).
Derivative Type: Rugulovasine A
CAS Registry Number: 26909-33-1
Additional Names: 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). [a]22436 -3.0° (pyridine). uv max (ethanol): 224, 277, 288, 295 nm (log e 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.
Melting point: mp 138° (dec)
Optical Rotation: [a]22436 -3.0° (pyridine)
Absorption maximum: uv max (ethanol): 224, 277, 288, 295 nm (log e 4.37, 3.70, 3.78, 3.77)
Derivative Type: Hydrochloride
CAS Registry Number: 28375-03-3
Molecular Formula: C16H16N2O2.HCl
Molecular Weight: 304.77
Percent Composition: C 63.05%, H 5.62%, N 9.19%, O 10.50%, Cl 11.63%
Properties: Colorless prisms from water, mp 225° (dec).
Melting point: mp 225° (dec)
Derivative Type: Rugulovasine B
CAS Registry Number: 26909-34-2
Properties: Difficult to crystallize from common solvents. Separated from benzene as colorless resinous oil. [a]22436 +1.4° (pyridine). uv max (ethanol): 227, 278, 288, 295 nm (log e 4.16, 3.68, 3.73, 3.72). Same solubilities as rugulovasine A.
Optical Rotation: [a]22436 +1.4° (pyridine)
Absorption maximum: uv max (ethanol): 227, 278, 288, 295 nm (log e 4.16, 3.68, 3.73, 3.72)
Derivative Type: Hydrochloride
CAS Registry Number: 28510-15-8
Molecular Formula: C16H16N2O2.HCl
Molecular Weight: 304.77
Percent Composition: C 63.05%, H 5.62%, N 9.19%, O 10.50%, Cl 11.63%
Properties: White prisms from water, mp 187° (dec).
Melting point: mp 187° (dec)
|