
CAS Name: 3-Hydroxy-4-phenyl-2(1H)-quinolinone
Additional Names: 3-hydroxy-4-phenylcarbostyril; 2,3-dihydroxy-4-phenylquinoline
Percent Composition: C 75.94%, H 4.67%, N 5.90%, O 13.49%
Literature References: Antibiotic substance from the mycelium of Penicillium viridicatum Westling, the chief mold on stored corn: Cunningham, Freeman, Biochem. J. 53, 328 (1953); from various strains of P. cyclopium Westling: Bracken et al., ibid. 57, 587 (1954); from P. puberulum Bainier: Austin, Meyers, J. Chem. Soc. 1964, 1197. Biosynthesis: Luckner, Tetrahedron Lett. 1962, 1035; Luckner, Mothes, Arch. Pharm. 296, 18 (1963); Framm et al., Eur. J. Biochem. 37, 78 (1973). Synthesis: Eistert, Selzer, Z. Naturforsch. 17b, 202 (1962). Mass spectra: Luckner et al., Tetrahedron 25, 2575 (1969). Antibacterial activity and inhibitory effect on plant growth: Taniguchi, Satomura, Agric. Biol. Chem. 34, 506 (1970).
CAS Name: [1aS-(1aa,8b,8aa,8ba)]-6-Amino-8-[[(aminocarbonyl)oxy]methyl]-1,1a,2,8,8a,8b-hexahydro-8a-methoxy-1,5-dimethylazirino[2',3':3,4]pyrrolo[1,2-a]indole-4,7-dione
Additional Names: N-meth...
Literature References: Antibiotic substance isolated from a Streptomyces ardus fermentation broth: Herr et al., Antimicrob. Agents Annu. 1960, 23. Isoln from S. verticillatus and structure: Webb et al., J. Am. Chem. Soc. 84, 3185, 3187 (1962). Production process: Bohonos et al., US 3219530 (1965 to Am. Cyanamid). Synthesis of (±)-form: F. Nakatsubo et al., J. Am. Chem. Soc. 99, 8115 (1977). For stereochemistry and other synthetic studies, see Mitomycins.
CAS Name: 2,3,5,6-Tetrachloro-4-methoxyphenol
Additional Names: p-methoxytetrachlorophenol
Percent Composition: C 32.10%, H 1.54%, Cl 54.14%, O 12.22%
Literature References: Antibiotic substance isolated from the basidiomycete Drosophila subatrata (Batsch ex Fr.) Quel., grown in a corn-steep medium: Kavanagh, Hervey, Proc. Natl. Acad. Sci. USA 38, 555 (1952). Prepn from tetrachloro-p-anisidine: Bures, Hutter, Cas. Cesk. Lek. 11, 29, 57 (1931); C.A. 25, 5153; Chem. Zentralbl. 1931, II, 225; from 1,4-dimethoxytetrachlorobenzene: Anchel, J. Am. Chem. Soc. 74, 2943 (1952).
CAS Name: 4-[(2R)-2-[(1S,3S,5S)-3,5-Dimethyl-2-oxocyclohexyl]-2-hydroxyethyl]-2,6-piperidinedione
Additional Names: 3-[2-(3,5-dimethyl-2-oxocyclohexyl)-2-hydroxyethyl]glutarimide; actidione; na...
Literature References: Antibiotic substance isolated from the beers of streptomycin-producing strains of Streptomyces griseus: B. E. Leach et al., J. Am. Chem. Soc. 69, 474 (1947); J. H. Ford, B. E. Leach, ibid. 70, 1223 (1948); A. J. Whiffen et al., US 2574519 (1951 to Upjohn). Production, assay and antibiotic activity: A. J. Whiffen, J. Bacteriol. 56, 283 (1948). Improved production method: Kominek, US 3915802; US 3915803 (both 1975 to Upjohn). Structure: E. C. Kornfeld et al., J. Am. Chem. Soc. 71, 150 (1949). Absolute configuration: E. J. Eisenbraun et al., ibid. 80, 1261 (1958); F. Johnson, N. A. Starkovsky, Tetrahedron Lett. 1962, 1173; F. Johnson et al., J. Am. Chem. Soc. 87, 4612 (1965). Synthesis of dl- and l-forms: F. Johnson et al., ibid. 88, 149 (1966).
Additional Names: GV
Percent Composition: C 55.33%, H 5.70%, N 8.80%, O 23.45%, S 6.71%
Literature References: Antibiotic substance obtained together with Etamycin (viridogrisein) from Streptomyces griseus: Bartz et al., Antibiot. Annu. 1954-1955, 777. Characterization: Ames et al., J. Chem. Soc. 1955, 4260; Ames, Bowman, ibid. 1955, 4264. Structure studies: Fallona et al., J. Am. Chem. Soc. 84, 4162 (1962); eidem, Can. J. Chem. 42, 371, 394 (1964). Revised structure: G. I. Birnbaum, S. R. Hall, J. Am. Chem. Soc. 98, 1926 (1976). Absolute configuration: B. W. Bycroft, T. J. King, J. Chem. Soc. Perkin Trans. 1 1976, 1996. Production of griseoviridin and viridogrisein: Bartz et al., US 3023204 (1962 to Parke, Davis). Synthetic study: A. I. Meyers, R. A. Amos, J. Am. Chem. Soc. 102, 870 (1980).
CAS Name: (4a,6b,8a,9b,13a,14b,16b,17Z)-6,16-Bis(acetyloxy)-3,7-dioxo-29-nordammara-1,17(20),24-trien-21-oic acid
Additional Names: (Z)-6b,16b-dihydroxy-3,7-dioxo-29-nor-8a,9b,13a,14b-dammara-1...
Literature References: Antibiotic substance of the fusidane class. Produced by Aspergillus fumigatus: Waksman et al., J. Bacteriol. 45, 233 (1943); by A. fumigatus mut. helvola: Chain et al., Br. J. Exp. Pathol. 24, 108 (1943). Structural studies: Okuda et al., Chem. Pharm. Bull. 12, 121 (1964); Oxley, Chem. Commun. 1966, 729; Okuda et al., Tetrahedron Lett. 1967, 2295. Revised structure and stereochemistry: Iwaki et al., Chem. Commun. 1970, 1119. Chemical and biological data: Reshetova, Antibiotiki 14, 554 (1969). Review of literature until 1960: Wilson, "Miscellaneous Aspergillus Toxins" in Microbial Toxins vol. VI, A. Ciegler et al., Eds. (Academic Press, New York, 1971) p 265.
CAS Name: (6R,7R)-3-[(Acetyloxy)methyl]-7-[[(5R)-5-amino-5-carboxy-1-oxopentyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
Additional Names: 7-(D-5-amino-5-carboxyvaleram...
Literature References: Antibiotic substance produced along with penicillin N by a Cephalosporium sp. cultivated from sea water near a sewage outlet on the coast of Sardinia: G. Brotzu, Lav. Ist. Igiene Cagliari (1948); Newton, Abraham, Nature 175, 548 (1955); eidem, Biochem. J. 62, 651 (1956); eidem, DE 1014711 (1957 to Natl. Res. Dev. Corp.); GB 810196 (1959); Kelly et al., US 3082155 (1963 to Natl. Res. Dev. Corp.); Demain, US 3116216; US 3116217 (both 1963 to Merck Co.). Biosynthesis: Demain, Newkirk, Appl. Microbiol. 10, 321 (1962). Has the same side chain as penicillin N, but the nucleus is different and is named 7-aminocephalosporanic acid: Jago, Heatley, Br. J. Pharmacol. 16, 170 (1961). Structure: Abraham, Newton, Biochem. J. 79, 377 (1961); Hodgkin, Maslen, ibid. 393. In cephalosporin CA the acetoxy group is replaced by a pyridinium group: Hale et al., ibid. 403. Transformation to cephalosporin CC for which greater activity is claimed: Abraham et al., US 3049541 (1962 to Natl. Res. Dev. Corp.). Total synthesis: Woodward et al., J. Am. Chem. Soc. 88, 852 (1966). Review of cephalosporin C and related compounds: Abraham, Q. Rev. Chem. Soc. 21, 231 (1967); Abraham, Loder, in Cephalosporins and Penicillins, E. H. Flynn, Ed. (Academic Press, New York, 1972) pp 1-26.
CAS Name: (3a,4a,6a,7b,8a,9b,13a,14b,16b,17Z)-6,16-Bis(acetyloxy)-3,7-dihydroxy-29-nordammara-17(20),24-dien-21-oic acid
Percent Composition: C 68.96%, H 8.77%, O 22.27%
Literature References: Antibiotic substance produced by a Cephalosporium sp. cultivated from the sea near Sardinia. Crude cephalosporin P contains at least 5 components: P1, P2, P3, P4, P5, the major active substance being cephalosporin P1. Isoln: Burton, Abraham, Biochem. J. 50, 168 (1951). Structure: Baird et al., Proc. Chem. Soc. London 1961, 257; Halsall et al., ibid. 1963, 16; Melera, Experientia 19, 565 (1963); Halsall et al., Chem. Commun. 1966, 685.
CAS Name: 2,3-Dimethoxy-5,6-dimethyl-2,5-cyclohexadiene-1,4-dione
Additional Names: 2,3-dimethoxy-5,6-dimethyl-p-benzoquinone
Percent Composition: C 61.22%, H 6.16%, O 32.62%
Literature References: Antibiotic substance produced by a Gliocladium sp similar to Gliocladium roseum (Link.) Bainier: Brian et al., Experientia 7, 266 (1951). Structure: Vischer, J. Chem. Soc. 1953, 815. Synthesis: Baker et al., ibid. 820; Seshadri, Venkatasubramanian, ibid. 1959, 1660. Biosynthesis: Pettersson, Acta Chem. Scand. 19, 1827 (1965).
Additional Names: Micrococcin
Literature References: Antibiotic substance produced by a species of Micrococcus: cf. Br. J. Exp. Pathol. 29, 473 (1948). Isoln of micrococcin P from B. pumilus: Heatley, Doery, Biochem. J. 50, 247 (1951). Probable identity of micrococcin and micrococcin P: Abraham et al., Nature 178, 44 (1956). Structure studies: Brookes et al., J. Chem. Soc. 1957, 689; Brookes et al., ibid. 1960, 916; Dean et al., ibid. 1961, 3394; James, Watson, ibid. C, 1966, 1361. The antibiotic is a mixture of two components, P1 (major) and P2. Proposed total structure of P1: J. Walker et al., Chem. Commun. 1977, 706. Revised structure of P1 and structure of P2: B. W. Bycroft, M. S. Gowland, ibid. 1978, 256. Mechanism of action: E. Cundliffe, J. Thompson, Eur. J. Biochem. 118, 47 (1981). Review: Pestka in Antibiotics vol. 3, J. W. Corcoran, F. E. Hahn, Eds. (Springer-Verlag, New York, 1975) pp 480-486.
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