
CAS Name: 2-Hydroxy-3-methyl-1,4-naphthalenedione
Additional Names: 2-hydroxy-3-methyl-1,4-naphthoquinone
Percent Composition: C 70.21%, H 4.29%, O 25.51%
Literature References: Antibiotic substance produced by Mycobacterium tuberculosis: Terni, Boll. Soc. Ital. Biol. Sper. 25, 60 (1949), C.A. 45, 2054f (1951). Possesses some vitamin K activity. Isoln and synthesis: Anderson, Newman, J. Biol. Chem. 101, 773 (1933); 103, 197, 405 (1933); L. F. Fieser, ibid. 133, 391 (1940); Tarbell et al., J. Am. Chem. Soc. 72, 379 (1950); Burton, Praill, J. Chem. Soc. 1952, 755; Eistert, Müller, Ber. 92, 2071 (1959); H. Kallmayer, Arch. Pharm. 307, 806 (1974); K. Maruyama, S. Arakawa, J. Org. Chem. 42, 3793 (1977).
CAS Name: 3,5,7,8-Tridecatetraene-10,12-diynoic acid
Percent Composition: C 78.77%, H 5.08%, O 16.14%
Literature References: Antibiotic substance produced by Nocardia acidophilus: Johnson, Burdon, J. Bacteriol. 54, 281 (1947); Johnson, Soc. Am. Bacteriologists, 49th General Meeting (May, 1949), Abstracts of Papers, p 68; Celmer, Solomons, 121st A.C.S. Meeting (Milwaukee, 1952), Abstracts of Papers, p 17-J; J. Am. Chem. Soc. 74, 1870, 2245 (1952); 75, 1372 (1953). Synthesis: Bohlmann, Sucrow, Angew. Chem. 76, 611 (1964).
CAS Name: 8,9-Dihydroxy-2-methyl-4-oxo-4H,5H-pyrano[3,2-c][1]benzopyran-10-carboxylic acid
Additional Names: frequentic acid
Percent Composition: C 57.94%, H 3.47%, O 38.59%
Literature References: Antibiotic substance produced by Penicillium frequentans Westling and P. vesiculosum Bainier and by Citromyces spp: Hetherington, Raistrick, Philos. Trans. R. Soc. London Ser. B 220, 209 (1931); Grove, Brian, Nature 167, 995 (1951). Structure: Robertson et al., J. Chem. Soc. 1951, 2013. Biosynthesis: Birch et al., ibid. 1958, 4576; Money, Nature 199, 592 (1963). Total synthesis: M. Yamauchi et al., J. Chem. Soc. Perkin Trans. 1 1987, 395.
CAS Name: (1'S,6'R)-7-Chloro-2',4,6-trimethoxy-6'-methylspiro[benzofuran-2(3H),1'-[2]cyclohexene]-3,4'-dione
Additional Names: 7-chloro-4,6-dimethoxycoumaran-3-one-2-spiro-1'-(2'-methoxy-6'-met...
Literature References: Antibiotic substance produced by Penicillium griseofulvum Dierckx and by P. janczewskii Zal. [same as P. nigricans (Banier)Thom]. Isoln: Oxford et al., Biochem. J. 33, 240 (1939); Brian et al., Trans. Br. Mycol. Soc. 29, 173 (1946); Hockenhull, Dorey et al., US 3069328, US 3069329 (both 1962 to Glaxo). Structure: Grove et al., Chem. Ind. (London) 1951, 219; J. Chem. Soc. 1952, 3977. Stereochemistry: MacMillan, ibid. 1959, 1823; Brown, Sim, ibid. 1963, 1050. Total synthesis: Brossi et al., Helv. Chim. Acta 43, 1444, 2071 (1960); Taub et al., Tetrahedron 19, 1 (1963); Stork, Tomasz, J. Am. Chem. Soc. 86, 471 (1964); S. Danishefsky, F. J. Walker, ibid. 101, 7018 (1979). Conformation: Levine, Hicks, Tetrahedron Lett. 1971, 311. Crystal structure: G. Malmros et al., Cryst. Struct. Commun. 6, 463 (1977). Review and evaluation of studies of carcinogenic action in laboratory animals: IARC Monographs 10, 153-161 (1976). Review: Grove, Q. Rev. Chem. Soc. 17, 1 (1963); Huber in Antibiotics vol. 3, J. W. Corcoran, F. E. Hahn, Eds. (Springer-Verlag, New York, 1975) pp 606-613. Comprehensive description: E. R. Townley, Anal. Profiles Drug Subs. 8, 219-249 (1979).
CAS Name: 5,6,7-Trihydroxy-1H-cyclohepta[c]furan-1,3,4-trione
Additional Names: 4,5,6-trihydroxy-7-oxo-1,3,5-cycloheptatriene-1,2-dicarboxylic anhydride
Percent Composition: C 48.23%, H 1.80...
Literature References: Antibiotic substance produced by Penicillium puberulum, P. aurantiovirens, P. johannioli, P. cyclopium viridicatum. Isoln: Birkinshaw, Raistrick, Biochem. J. 26, 441 (1932); Barger, Dorrer, ibid. 28, 11 (1934). Structure: McGowan, Chem. Ind. (London) 1947, 205; Aulin-Erdtman, Acta Chem. Scand. 4, 1325 (1950). Johnson et al., J. Chem. Soc. 1951, 1139. Synthesis: Nozoe et al., Bull. Chem. Soc. Jpn. 33, 1071 (1960). Biosynthesis: Ferritti, Richards, Proc. Natl. Acad. Sci. USA 46, 1438 (1960); A. I. Scott, E. Lee, Chem. Commun. 1972, 655. Review: Nozoe, Fortschr. Chem. Org. Naturst. 13, 232-301 (1956).
CAS Name: 3,4,6-Trihydroxy-5-oxo-1,3,6-cycloheptatriene-1-carboxylic acid
Percent Composition: C 48.50%, H 3.05%, O 48.45%
Literature References: Antibiotic substance produced by Penicillium puberulum, P. aurantiovirens, P. johannioli, P. cyclopium viridicatum. Isoln: Birkinshaw, Raistrick, Biochem. J. 26, 441 (1932); Barger, Dorrer, ibid. 28, 11 (1934). Structure: McGowan, Chem. Ind. (London) 1947, 205; Corbett et al., ibid. 1949, 626; J. Chem. Soc. 1950, 6. Synthesis: Johns et al., ibid. 1954, 198. Biosynthesis: Ferretti, Richards, Proc. Natl. Acad. Sci. USA 46, 1438 (1960). Review: Nozoe, Fortschr. Chem. Org. Naturst. 13, 232-301 (1956).
Percent Composition: C 57.58%, H 8.50%, N 11.19%, O 22.73%
Literature References: Antibiotic substance produced by Pseudomonas viscosa. Isoln: Kochi et al., Bact. Proc. 1951, 29; Groupé et al., Proc. Soc. Exp. Biol. Med. 78, 354 (1951); Ohno et al., J. Agric. Chem. Soc. Jpn. 27, 665 (1953); C.A. 49, 3012 (1955); Toki, Ohno, C.A. 53, 243b (1959). Synthesis studies: Fukuda, Bani, C.A. 56, 10265i (1962). Structure: Toki, Ohno, loc. cit. Revised structure: Hiramoto et al., Tetrahedron Lett. 1970, 1087; eidem, Chem. Pharm. Bull. 19, 1308, 1315 (1971). Shows antitubercular activity.
CAS Name: (5S)-5-[(1R)-1-(1H-Indol-3-yl)ethyl]-2-(methylamino)-4(5H)-oxazolone
Additional Names: (1R,5S)-5-(1-indol-3-ylethyl)-2-(methylamino)-2-oxazolin-4-one; 2-methylamino-5a-(b-indolyl)ethy...
Literature References: Antibiotic substance produced by Streptomyces albus: Rao, Antibiot. Chemother. 10, 312 (1960); Marsh et al., ibid. 316; GB 862685 (1961 to Pfizer). Structure: M. Schach von Wittenau, H. Els, J. Am. Chem. Soc. 83, 4678 (1961). Total synthesis: eidem, ibid. 85, 3425 (1963); Preobrazhenskaya et al., Tetrahedron 24, 6131 (1968); T. Takeda, T. Mukaiyama, Chem. Lett. 1980, 163. Abs config: T. H. Chan, R. K. Hill, J. Org. Chem. 35, 3519 (1970). Biosynthetic studies: Hornemann et al., Chem. Commun. 1969, 245; eidem, J. Am. Chem. Soc. 93, 3028 (1971).
Trademarks: Amimycin; Landomycin; Romicil
Percent Composition: C 61.11%, H 8.94%, N 2.04%, O 27.91%
Literature References: Antibiotic substance produced by Streptomyces antibioticus no. ATCC 11891: Sobin et al.; Ratajak, Nubel, US 2757123; US 2842481 (1956, 1958 to Pfizer). Structure: Hochstein et al., J. Am. Chem. Soc. 82, 3225 (1960). Absolute configuration: Celmer, ibid. 87, 1797 (1965); Celmer, Hobbs, Carbohydr. Res. 1, 137 (1965); S. Omura et al., Tetrahedron Lett. 1975, 2939. Synthetic study: K. Tatsuta et al., ibid. 29, 3975 (1988). Activity: Hahn, Antibiotics 1, 378, 755 (1967). For a review of macrolide antibiotics see Keller-Schierlein, Fortschr. Chem. Org. Naturst. 30, 313-460 (1973). Toxicity: H. Sous et al., Arzneim.-Forsch. 8, 386 (1958).
CAS Name: 2-[(2-Hydroxybenzoyl)oxy]ethyl 6,8-dideoxy-7-O-methyl-6-[[[(2S)-1-methyl-2-pyrrolidinyl]carbonyl]amino]-1-thio-D-erythro-a-D-galacto-octopyranoside
Additional Names: a-2-hydroxyethyl ...
Literature References: Antibiotic substance produced by Streptomyces caelestis from a soil obtained from Emigration Canyon near Salt Lake City: DeBoer et al., Antibiot. Annu. 1954-1955, 831; Hoeksema et al., ibid. 837. Structure: Hoeksema, J. Am. Chem. Soc. 86, 4224 (1964); 90, 755 (1968).
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