A short stereoselective synthesis of (−)-chloramphenicol and (+)-thiamphenicol

Synthesis, Characterization, and Antimicrobial Studies of Novel Benzodipyran Analog of Chloramphenicol

“…The present study has shown that for both antibacterial and antifungal activities of series of coumarin derivatives (2)(3)(4)(5)(6)(7), involving four strains of bacteria and fungi, in four concentrations (100, 50, 25, and 10 mg/mL, respectively), it is observed that the benzodipyran analog of chloramphenicol 7 was most active against Gram-positive bacteria, S.a, and the fungal strains R.b and P even at 10 mg/mL and showed moderate activity for other bacterial and fungal organisms when compared with their precursors (2)(3)(4)(5)(6). In this paper, we have established the detail structureantimicrobial activity relationship of 2-7 with standard chloramphenicol (drug sample).…”

“…In view of the various biological properties associated with coumarins in general and chloramphenicol in particular, it was thought to be of interest to incorporate the active 2-dichloroacetamidopropandiol side chain of chloramphenicol in to the C-9 position of benzodipyran, and the benzodipyran analog of chloramphenicol is synthesized (Scheme 1). A detail structure-antimicrobial activity relationship study was developed to deduce possible antimetabolite-metabolite relationships between the derivatives of coumarin (2)(3)(4)(5)(6), benzodipyran analog of chloramphenicol (7), and chloramphenicol (drug) in this paper.…”

“…It is only the first antibiotic to be produced in optically active form by chemical synthesis rather than by fermentation. Many new methods of synthesis of this active antibiotic have been reported recently , and there has been no lack of attempts to relate the structure of chloramphenicol to the structures of biologically important substances to deduce possible antimetabolite–metabolite relationships. Many efforts have been devoted to the synthesis of compounds in which the structural components of chloramphenicol have been varied systematically.…”

Electron Paramagnetic Resonance Investigation of Radiation Effect on Certain Types of Drug Powders

“…PA, which is poorly water soluble, white and in the form of crystalline powder, is used in the treatment of tuberculosis [15]. CP is a broad spectrum antibiotic used for the treatment of typhoid, dysentery and ocular bacterial infections [16]. Due to the fact that irradiation at low doses has the advantage of minimizing the damage to the products, [17] up to 15 kGy of irradiated SD, PA, and CP samples were used in this study.…”

Chloramphenicol

“…The first synthesis of chloramphenicol was reported in 1949 and involved eight steps, including an enantiomeric resolution in the second-last step (a particularly wasteful process as 50% of the racemate is discarded after having been carried through the previous six steps) (Controulis et al, 1949). The subsequent steps are all stereospecific, with the lone pair of the imidate nitrogen attacking the epoxide from the side opposite to the oxygen of the ring (in order to minimise the repulsion between this lone pair and those on the oxygen), resulting in an inversion of the stereochemistry at this centre, from (S) to (R) (Bhaskar et al, 2004). Among the attractive features of this particular route is that it is short (only three steps and an overall yield of 23% from 4-nitrobenzaldehyde) and gives the desired, (À)-chloramphenicol, enantiomer in high purity, as the epoxide intermediate is formed in 95% enantiomeric excess (i.e.…”