6671. Nogalamycin

Nomenclature

CAS number: 1404-15-5
[2R-(2α,3β,4α,5β,6α,11β,13α,14α)]-11-[(6-Deoxy-3-C-methyl-2,3,4-tri-O-methyl-α-l-mannopyranosyl)oxy]-4-(dimethylamino)-3,4,5,6,9,11,12,13,14,16-decahydro-3,5,8,10,13-pentahydroxy-6,13-dimethyl-9,16-dioxo-2,6-epoxy-2H-naphthaceno[1,2-b]oxocin-14-carboxylic acid methyl ester; U-15167; NSC-70845.
C39H49NO16; mol wt 787.80.
C 59.46%, H 6.27%, N 1.78%, O 32.49%.

Description and references

Antitumor antibiotic isolated from Streptomyces nogalater var. nogalater: B. K. Bhuyan, A. Dietz, Antimicrob. Agents Chemother. 1965, 836; B. K. Bhuyan et al., US 3183157 (1965 to Upjohn). Characterization: P. F. Wiley et al., Tetrahedron Lett. 1968, 663. Structure: eidem, J. Am. Chem. Soc. 99, 542 (1977). Stereochemistry: eidem, J. Org. Chem. 44, 4030 (1979). Biosynthesis: eidem, ibid. 43, 3457 (1978). Synthesis of l-nogalose, sugar component: L. Valente et al., Tetrahedron Lett. 1979, 1153; J. Yoshimura et al., Chem. Lett. 1979, 687. Partial stereospecific synthesis: R. P. Joyce et al., Tetrahedron Lett. 27, 4885 (1986). Molecular structure, absolute stereochemistry and interactions with DNA: S. K. Arora, J. Am. Chem. Soc. 105, 1328 (1983). Toxicity data: Z. Hadidian, PB Report 173334 (1966). Review of pharmacology: B. K. Bhuyan, C. G. Smith, Handb. Exp. Pharmacol. 38, (pt. 2) 623-632 (1975).

Chemical structure

Properties

Orange-red solid from methanol, mp 195-196° (dec). [α]D25 +425° (c = 0.11 in CHCl3). pKa′ 7.45 (60% ethanol). uv max (ethanol): 236, 258, 292 nm (ε 52360, 24755, 9890). Sol in methylene chloride, acetone, chloroform, ethyl acetate. Insol in water, methanol, ethanol. LD50 in mice (mg/kg): 11.75 i.v., 4.79 i.p. (Hadidian).