Penicillin derivative

However, the sulfathiazoles have now been superseded by penicillin derivatives. 

Therapeutics. Compounds containing the furan or tetrahydrofuran ring are biologically active and are present in a number of pharmaceutical products. Eurfurjdamine [617-89-0] is an intermediate in the diuretic, furosemide. Tetrahydrofurfurylamine [4795-29-3] may also have pharmaceutical applications. 5-(E)imethyiaininomethyi)furfuryi alcohol [15433-79-17 is an intermediate in the preparation of ranitidine, which is used for treating ulcers. 2-Acet5dfuran [1192-62-7] prepared from acetic anhydride and furan is an intermediate in the synthesis of cefuroxime, a penicillin derivative. 2-Euroic acid is prepared by the oxidation of furfural. Both furoic acid [88-14-2] and furoyl chloride [527-69-5] are used as pharmaceutical intermediates. 

J) Degradation of readily available penicillin derivatives cf Section 5.09.3.3.4). 

The acylation of 6-APA (Scheme 59) has been a very versatile way in which to generate new penicillin derivatives which differ from fermentation-produced penicillins in the 6-side chain. As will be discussed in Section 5.11.5.1, this approach has led to significant improvements in the therapeutic properties of penicillins, and, in fact, of the penicillins in medical use today, only benzylpenicillin and phenoxymethylpenicillin are produced directly by fermentation. 

Another synthetic sequence leading to penicillin derivatives is illustrated in Scheme 61 (77MI51102). Note that the cycloaddition of azidoacetyl chloride to the thiazoline affords an azidopenam with the 6-epi configuration. Equilibration leads to a mixture of (81) and (82) in a ratio of 4 1, but repeated recycling allowed the isolation of (82) in 40% yield. A related synthesis was shown in Scheme 26. 

In contrast to the preceding synthetic routes, the sequence shown in Scheme 62 forms the /3-lactam ring before closing the thiazolidine ring (80JCS(P1)2228 and refs, therein). The product (83) had been previously reported and converted to the corresponding penicillin derivative (see Scheme 61) (77MI51102). 

The A,A -diisopropylhydrazide, prepared to protect penicillin derivatives, is cleaved oxidatively by the following methods. ... 

Solvolysis in MeOH/H20 at 21°. This method was developed for a series of penicillin derivatives where conventional cleavage methods resulted in partial /3-lactam cleavage. ... 

Some hydroxamic acids of the isoxazole series also display a marked antituberculosis activity. The penicillin derivatives, acylated with isoxazole carboxylic acids possess an antibacterial activity similar to that of penicillin, against resistant species.Among other isoxazole derivatives possessing activity one should especially mention the sulfonamides of this series, and 4-hydroxyiminoisoxazol-5-... 

The nature of the penicillin derivatives accessible by this "feeding" route was severely limited by the fact that the acylat-ing enzyme of the Penicillium molds would accept only those carboxylic acids which bore at least some resemblance to its natural substrates. A breakthrough in this field was achieved by the finding that rigid exclusion of all possible side-chain substrate from the culture medium afforded 6-APA as the main fermentation... 

The detection limits for penicillin derivatives and cephalosporins are 0.5 to 1 pg substance per chromatogram zone. 

Spray solution III, which is suitable for the detection of antibiotics, also contains potassium iodide To detect penicillin derivatives the chromatograms must first be placed - while still damp with mobile phase — for ca. 15 min in an ammonia chamber before treatment with spray solution III [5]. 

Penicillin derivatives and cephalosporins e.g. penicillic acid, oxacillin, clonacillin,... 

Alkaloids produce pale yellow, pink, green, brown, blue or violet zones [23]. Urethanes blue-green to dark violet zones [36]. Thiols and penicillin derivatives appear immediately as white zones and sulfoxides only after a few minutes as yellow to yellowish-blue zones on a reddish background [37, 39], which becomes deep purple on spraying with water [37]. 

Development of new synthetic routes to optically active (3-lactam derivatives is still an attractive problem in organic chemistry. As a synthetic approach to penicillin derivatives, photocyclization of oe-oxoamides 76 to (3-lactams has long been studied 41, 42). This reaction (Scheme 6), however, results in a complex mixture of racemic cis-and trans-isomers of (3-lactams 72 and of oxazolidin-4-ones 73, since the reaction proceeds via a zwitterionic intermediate 7143>. Of these isomers, only the optically... 

Penicillin Derivatives. Gordon L. Coppoc, School of Veterinary Medicine, Purdue University, http //www.vet.purdue.edu/depts/bms/courses/chmrx/penems.htm... 

Lactams are a broad class of antibiotics that include penicillin derivatives, cephalosporins, monobactams, carbapenems, and clavams (/8-lactamase inhibitors). The metabolic engineering of penicillin and cephalosporins production has been summarized by several good reviews [71,72], so the focus here is clavulanic acid, which has attracted interest in recent years. 

Case reports have shown a reduction in EE levels when CHCs are taken with tetracyclines and penicillin derivatives. The Council on Scientific... 

Penicillin derivatives + OH- CTABr 0.05 M NaOH. Effect of structure Gesmantel and Page, 1982... 

Use ofCI2(PCy3)2RuCHPh to Generate Multivalent Penicillin Derivatives... 

Fig. 13. The generation of multivalent penicillin derivatives by ROMP. It is proposed that such materials may function as drug delivery agents...

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