Title: Asperlicin
CAS Registry Number: 93413-04-8
CAS Name: (7S)-6,7-Dihydro-7-[[(2S,9S,9aS)-2,3,9,9a-tetrahydro-9-hydroxy-2-(2-methylpropyl)-3-oxo-1H-imidazo[1,2-a]indol-9-yl]methyl]quinazolino[3,2-a][1,4]benzodiazepine-5,13-dione
Molecular Formula: C31H29N5O4
Molecular Weight: 535.59
Percent Composition: C 69.52%, H 5.46%, N 13.08%, O 11.95%
Literature References: Naturally occurring, nonpeptide cholecystokinin (CCK) antagonist. Produced by several strains of Aspergillus alliaceus along with minor related compounds known as asperlicin B, C, D and E. Isoln from fermentation cultures of A. alliaceus Thom and Church, ATCC 20655 and ATCC 20656: R. L. Monaghan et al., EP 116150; eidem, US 4530790 (1984, 1985 both to Merck & Co.). Fermentation, isoln and bioactivity: M. A. Goetz et al., J. Antibiot. 38, 1633 (1985); of asperlicins B, C, D and E: eidem, ibid. 41, 875 (1988). Structure elucidation: J. M. Liesch et al., ibid. 38, 1638 (1985); of asperlicins B, C, D and E: eidem, ibid. 41, 878 (1988). Biosynthetic study: D. R. Houck et al., ibid. 882. Total synthesis of asperlicins C and E: M. G. Bock et al., J. Org. Chem. 52, 1644 (1987). Pharmacology of asperlicin: R. S. L. Chang et al., Science 230, 177 (1985). Effect on pancreatic enzyme secretion in vitro: K. A. Zucker et al., Surgery 102, 163 (1987). Effect in exptl pancreatitis in rats: J. R. Wisner, Jr., I. G. Renner, Pancreas 3, 174 (1988).
Properties: White crystals, mp 211-213°. [a]D26.5 -185.3° (c = 1.10 in methanol). uv max (methanol): 310.5 nm (e 4075). Sol in methylene chloride, acetone and lower alcohols. Insol in water.
Melting point: mp 211-213°
Optical Rotation: [a]D26.5 -185.3° (c = 1.10 in methanol)
Absorption maximum: uv max (methanol): 310.5 nm (e 4075)
Derivative Type: Asperlicin B
CAS Registry Number: 93413-08-2
Molecular Formula: C31H29N5O5
Molecular Weight: 551.59
Percent Composition: C 67.50%, H 5.30%, N 12.70%, O 14.50%
Properties: Colorless powder. uv max (methanol): 310 nm (e 4000).
Absorption maximum: uv max (methanol): 310 nm (e 4000)
Derivative Type: Asperlicin C
CAS Registry Number: 93413-06-0
Molecular Formula: C25H18N4O2
Molecular Weight: 406.44
Percent Composition: C 73.88%, H 4.46%, N 13.78%, O 7.87%
Properties: Off-white powder. uv max (methanol): 222, 268, 278, 310 nm (e 56300, 15100, 14000, 4650).
Absorption maximum: uv max (methanol): 222, 268, 278, 310 nm (e 56300, 15100, 14000, 4650)
Derivative Type: Asperlicin D
CAS Registry Number: 93413-07-1
Molecular Formula: C25H18N4O2
Molecular Weight: 406.44
Percent Composition: C 73.88%, H 4.46%, N 13.78%, O 7.87%
Properties: Colorless powder. uv max (methanol): 222, 290, 310 nm (e 61060, 14600, 5920).
Absorption maximum: uv max (methanol): 222, 290, 310 nm (e 61060, 14600, 5920)
Derivative Type: Asperlicin E
CAS Registry Number: 93413-05-9
Molecular Formula: C25H18N4O3
Molecular Weight: 422.44
Percent Composition: C 71.08%, H 4.29%, N 13.26%, O 11.36%
Properties: Off-white powder. uv max (methanol): 227, 268, 324 nm (e 38450, 8680, 3200).
Absorption maximum: uv max (methanol): 227, 268, 324 nm (e 38450, 8680, 3200)
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