28240-15-5Relevant academic research and scientific papers
β-LACTAMASE TARGETED PHOTOSENSITIZER FOR PESTICIDE AND PEST DETECTION
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, (2014/01/09)
Photoactivatable pesticide compounds and methods for the use thereof in the elimination and detection of pests are provided.
PHOTOACTIVATABLE ANTIMICROBIAL AGENTS AND THERAPEUTIC AND DIAGNOSTIC METHODS OF USING SAME
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, (2011/05/16)
The present invention provides photosensitizer compounds for use in detecting beta-lactamase activity. Methods and kits that utilize the photosensitizer compounds of the invention for the detection of, quantitation of, and classification or typing of microbial beta-lactamases.
Enzymatic deprotection of the cephalosporin 3′-acetoxy group using Candida antarctica lipase B
Patterson, Leslie D.,Miller, Marvin J.
supporting information; scheme or table, p. 1289 - 1292 (2010/04/29)
(Chemical Equation Presented) Cephalosporins remain one of themost important classes of antibiotics. A useful site for derivatization involves generation of and chemistry at the 3′-hydroxymethyl position. While 3′-acetoxymethyl-substituted cephalosporins are readily available, deacetylation to access the free 30-hydroxymethyl group is problematic when the carboxylic acid is protected as an ester. Herein we report that this important transformation has been efficiently accomplished using Candida antarctica lipase B. Although this transformation is difficult to carry out using chemical methods, the enzymatic deacetylation has been successful on gram scale, when the cephalosporin is protected as either the benzhydryl or tert-butyl esters and on the corresponding sulfoxide and sulfone of the tert-butyl ester.
An improved process for the preparation of diphenylmethyl7β- Phenylacetamido-3-hydroxymethyl-3-cephem-4-carboxylate
Keping, Yu,Nan, Sun,Shanzong, Fang,Weimin, Mo,Baoxiang, Hu,Zhenlu, Shen,Xinquan, Hu
body text, p. 815 - 819 (2010/04/22)
An efficient and improved process for the preparation of diphenylmethyl 7-phenylacetamido-3-hydroxymethyl-3-cephem-4-carboxylate was developed. With the commercially available 7-aminocephalosporanic acid (7-ACA) as starting material, up to 73.5% overall isolated yield of the titled compound was synthesized in two steps via direct phenylacetylation with phenylacetyl chloride, followed by basic hydrolysis and esterification with diphenyldiazomethane. The newly developed process obviated the use of protecting groups, reduced the environmental footprint, and could be easily controlled and conveniently scaled up for this pivotal intermediate in cephalosporin chemistry.
PHOTOACTIVATABLE ANTIMICROBIAL AGENTS
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Page/Page column 42, (2008/06/13)
Photoactivatable antimicrobial compounds and methods for the use thereof in the treatment of infections are provided.
Syntheses and studies of quinolone-cephalosporins as potential anti-tuberculosis agents
Zhao, Gaiying,Miller, Marvin J.,Franzblau, Scott,Wan, Baojie,Moellmann, Ute
, p. 5534 - 5537 (2007/10/03)
The syntheses and anti-tuberculosis activity of quinolone-cephalosporin conjugates (1 and 2) are described. Both showed broad-spectrum antibacterial activity and significant anti-TB activity. The carbamate-linked quinolone-cephem 2 showed better antimycobacterial activity, including anti-TB activity, than the direct amine-linked quinolone-cephem 1, while quinolone-cephem 1 was slightly more effective against some Gram-negative bacterial strains.
An alternative procedure for preparation of cefdinir
Gonzalez, Maritza,Rodriguez, Zalua,Tolon, Blanca,Rodriguez, Juan C.,Velez, Herman,Valdes, Barbara,Lopez, Miguel A.,Fini, Adamo
, p. 409 - 418 (2007/10/03)
Cefdinir, a broad spectrum third-generation cephalosporin for oral administration, was prepared by the following synthetic pathway: synthesis of diphenylmethyl 7β-amino-3-vinyl-3-cephem-4-carboxylate hydrochloride from 7-aminocephalosporanic acid (7-ACA), preparation of sodium 2-(2-tritylaminothiazol-4-yl)-(Z)-2-(tritylhydroxyimino) acetate from ethyl acetoacetate, coupling of both intermediaries to obtain diphenylmethyl 7β-[2-(2-tritylaminothiazol-4-yl)-(Z)-2-tritylhydroxyimino-3- vinyl-3-cephem-4-carboxylate and final cleavage of trityl and diphenylmethyl protective groups. This procedure allows to obtain better yields of cefdinir and to avoid the use of diketene during the synthesis of this antibiotic by the previously reported method.
A new convenient synthesis of 3-carboxycephems starting from 7-aminocephalosporanic acid (7-ACA)
Keltjens, Rolf,Vadivel, Subramanian K.,De Vroom, Erik,Klunder, Antonius J. H.,Zwanenburg, Binne
, p. 2529 - 2534 (2007/10/03)
New convenient syntheses of 3-carboxycephems starting from 7-ACA are reported. All three possible cephem derivatives with respect to the position of the double bond in the six-membered ring and oxidation state of the sulfur atom have been synthesized in high overall yield.
The synthesis and evaluation of 3-substituted-7-(alkylidene)cephalosporin sulfones as β-lactamase inhibitors
Buynak, John D.,Doppalapudi, Venkata Ramana,Adam, Greg
, p. 853 - 857 (2007/10/03)
A series of 3-substituted-7-(alkylidene)cephaloporin sulfones were prepared and evaluated as inhibitors of representative class A and class C serine β-lactamase. Appropriate substituents resulted in a 1000-fold improvement in the inhibition of the class A enzymes and a simultaneous 20-fold improvement in the inhibition of class C. These new compounds have achieved the goal of creating broad scale inhibitors in the cephalosporin series. (C) 2000 Elsevier Science Ltd. All rights reserved.
