Title: Actinobolin
CAS Registry Number: 24397-89-5
CAS Name: (2S)-2-Amino-N-[(3R,4R,4aR,5R,6R)-3,4,4a,5,6,7-hexahydro-5,6,8-trihydroxy-3-methyl-1-oxo-1H-2-benzopyran-4-yl]propanamide
Additional Names: 4-(2-aminopropionamido)-3,4,4a,5,6,7-hexahydro-5,6,8-trihydroxy-3-methylisocoumarin
Molecular Formula: C13H20N2O6
Molecular Weight: 300.31
Percent Composition: C 51.99%, H 6.71%, N 9.33%, O 31.97%
Literature References: Antibiotic produced by Streptomyces griseoviridus var atrofaciens; (+)-form is naturally occurring. Isoln and characterization: T. H. Haskell, Q. R. Bartz, Antibiot. Annu. 1958-1959, 505; T. H. Haskell et al., US 3043830 (1962 to Parke, Davis). Structural studies: Struck et al., Tetrahedron Lett. 1967, 1589; Munk et al., J. Am. Chem. Soc. 89, 4158 (1967). Structure: eidem, ibid. 90, 1087 (1968). Absolute configuration and chemistry: Antosz et al., ibid. 92, 4933 (1970). Crystal structure: J. B. Wetherington, J. W. Moncrief, Acta Crystallogr. B31, 501 (1975). Total synthesis: M. Yoshioka et al., J. Am. Chem. Soc. 106, 1133 (1984); eidem, Heterocycles 21, 151 (1984); R. S. Garigipati et al., J. Am. Chem. Soc. 107, 7790 (1985). Antibacterial activity and toxicity: R. F. Pittillo et al., Antibiot. Annu. 1958-1959, 497. Series of articles on antineoplastic activity: ibid. 515-532. Inhibition of protein synthesis: D. Smithers et al., Mol. Pharmacol. 5, 433 (1969). Experimental use as cariostat: D. E. Hunt et al., J. Dent. Res. 50, 371 (1971). Reduction of periodontal syndrome in mice, rats: J. H. Shaw, J. K. Ivimey, Arch. Oral Biol. 18, 357 (1973).
Properties: Amorphous, fluffy, very hygroscopic powder. [a]D28 +59° (c = 0.5 in pH 7 phosphate buffer). pKa: 7.5, 8.8. Freely sol in water; mod sol in methanol, ethanol. Unstable in aqueous solns pH >7. uv max: 262 nm (0.1N HCl); 288 nm (0.1N NaOH). LD50 in mice, rats (mg/kg): 800 ±27, 1550 ±26 i.v. (Pittillo).
pKa: pKa: 7.5, 8.8
Optical Rotation: [a]D28 +59° (c = 0.5 in pH 7 phosphate buffer)
Absorption maximum: uv max: 262 nm (0.1N HCl); 288 nm (0.1N NaOH)
Toxicity data: LD50 in mice, rats (mg/kg): 800 ±27, 1550 ±26 i.v. (Pittillo)
Derivative Type: Acetate
Molecular Formula: C13H20N2O6.C2H4O2
Molecular Weight: 360.36
Percent Composition: C 49.99%, H 6.71%, N 7.77%, O 35.52%
Properties: Needles from ethanol; softens at 130°, resolidifies at 145°, mp 263-266°. [a]D26 +58°. pKa: 4.6, 7.5, 8.8. Very sol in water; sol in warm methanol, ethanol, acetone; sparingly sol in ethyl acetate. uv max: 264 nm (pH 7 phosphate buffer).
Melting point: mp 263-266°
pKa: pKa: 4.6, 7.5, 8.8
Optical Rotation: [a]D26 +58°
Absorption maximum: uv max: 264 nm (pH 7 phosphate buffer)
Derivative Type: Hydrochloride
Molecular Formula: C13H20N2O6.HCl
Molecular Weight: 336.77
Percent Composition: C 46.36%, H 6.29%, N 8.32%, O 28.51%, Cl 10.53%
Properties: Hygroscopic. [a]D22 +59° (c = 0.41) (natural); [a]D22 +55° (c = 0.47) (synthetic).
Optical Rotation: [a]D22 +59° (c = 0.41) (natural); [a]D22 +55° (c = 0.47) (synthetic)
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