Chloramphenicol (Chloromycetin).<sup>1</sup> V. Synthesis

Controulis, John.; Rebstock, Mildred C.; Crooks, Harry M.

doi:10.1021/ja01175a066

Cited by 161 publications

(44 citation statements)

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“…It has also been obtained synthetically by several routes (Controulis, Rebstock & Crooks, 1949;Long & Troutman, 1949). The crystal structure of chloramphenicol has been shown to be isomorphous with bromamphenicol, for which two-dimensional Xray work has been reported (Dunitz, 1952).…”

Section: Introductionmentioning

confidence: 99%

The structure of chloramphenicol

Acharya¹,

Gowda²,

Post³

1979

Acta Crystallogr Sect B

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Section: Introductionmentioning

confidence: 99%

The structure of chloramphenicol

Acharya¹,

Gowda²,

Post³

1979

Acta Crystallogr Sect B

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“…Chloramphenicol is an antibiotic which initially was isolated from culture filtrates of the fungus Streptomyces venezuelae (1-3) by Bartz (4) and subsequently was synthesized chemically (5)(6)(7).…”

mentioning

confidence: 99%

Chloramphenicol (Chloromycetin), an Antibiotic. Pharmacological and Pathological Studies in Animals 123

Gruhzit¹,

Fisken²,

Reutner³

et al. 1949

J. Clin. Invest.

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Chloramphenicol is an antibiotic which initially was isolated from culture filtrates of the fungus Streptomyces venezuelae (1-3) by Bartz (4) and subsequently was synthesized chemically (5-7).Chloramphenicol ( Material for this study consisted of crystalline chloramphenicol obtained from culture filtrates, and the synthetic product.Chloramphenicol was administered intravenously in aqueous propylene glycol or acetamide solutions to small animals at a rate of 0.1 cc. per ten seconds; dogs received 1.0 to 3.0 cc./min. Acute toxicity results are based on a seven-to 14-day observation period and chronic tolerance studies were carried out for two to four weeks in small animals and for periods of three and five weeks and over four months in dogs. The Dragstedt et al. (8) method served to interpolate results.

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“…Of the four optical isomers possible only the natural form had appreciable antibacterial activity. The erythro forms were inactive and the ( + )-threo was only 0.5 per cent as active as the natural ( -)-threo isomer (120).…”

Section: Cahsochoh·cb(nh2)·ch20hmentioning

confidence: 88%

“…(Chloramphenicol does not react with peri- The synthesis of chloramphenicol was achieved by several methods. The base XXIV was prepared by condensing benzaldehyde with nitro ethanol and reducing the nitro group catalytically (120). It was also pre pared ,(as the N-acetyl derivative) by condensing formaldehyde with aacetamido-acetophenone and reducing the ketone group catalytically (Raney nickel) (121).…”

Section: Compounds Containing Organically-bound Chlorinementioning

confidence: 99%