7-Chlorotetracycline Aureomycin

T. is an antibiotic substance produced by Strepto-myces spp., e.g., Streptomyces viridifaciens fermentation with Streptomyces rimoses leads to 5-hydroxy-t. (= oxytetracycline), with Streptomyces aureofaciens, 7-chlorotetracycline (= aureomycine) is obtained. Its hydrochloride, the phosphate complex and its lauryl sulfate complex are used as antibacterials against gram-positive as well as gram-negative bacteria t. acts as an anti-amebic and anti-rickettsial agent. 

Chlorotetracycline ( Aureomycin) Inhibits root and shoot growth... 

In structural studies on oxytetracycline (Terramycin) and chlorotetracycline (Aureomycin) a Pfizer group found that tosyl chloride in cold pyridine converts the antibiotics into nitrile derivatives through dehydration of the primary carbox-amido group. They then found that simpler amides are dehydrated to nitriles in good yield by adding 1 equivalent of tosyl chloride slowly to a mixture of the amide with 2.25 equivalents of pyridine at a rate such as to maintain a temperature of about 70°. The mechanism proposed involves O-tosylation. 

Aureomycin (7-chlorotetracycline) [57-62-5] M 478.5, m 172-174°(dec), [a] -275° (MeOH), pK 3.3, pK2 7.44, PK3 9.27. Dehydrated by azeotropic distn of its soln with toluene. On cooling anhydrous material crystallises out and is recrystd from CgH, then dried under vacuum at 100° over paraffin wax. (If it is crystd from MeOH, it contains MeOH which is not removed on drying.) [Stephens et al. J Am Chem Soc 76 3568 1954 Biochem Biophys Res Commun 14 137 1964]. 

Tetracycline and several related antibiotics (aureomycin = chlorotetracycline, terramycin — oxytetracycline dihydrate) are also obtained from various species of Streptomyces, but are of very different structure, being based on the fused polycyclic arene naphthacene. The presence of five hydroxy substituents (six for terramycin) and an NMe2 group, and possibilities for various conformations and tautomers, complicate the study of their... 

AUREOMYCIN A-377 AUREOMYKOIN BIO-MITSIN BIOMYCIN 7-CHLORO-4-(DIMETHYL-AMINO)-l,4,4a,5,5a,6,n,12a-OCTAHYDRO-2-NAPHTH-ACENECARBOXAMIDE 7-CHLOROTETRACYCLINE... 

Synonyma 7-Chloro-4-diinethylaniino-l, 4,4a,5,5a,6,11,12a-octahydro-3,6,10,12,12a-pentahydroxy-6-oethyl-l,ll-dioxo-2-naphthacene-carboxamide 7-chlorotetracycline Trade names Aureomycin... 

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