scholarly journals Hydride-induced Meisenheimer complex formation reflects activity of nitro aromatic anti-tuberculosis compounds

2021 ◽  
Author(s):  
Rui Liu ◽  
Lowell Markley ◽  
Patricia A. Miller ◽  
Scott Franzblau ◽  
Gauri Shetye ◽  
...  

The formation efficiency of hydride-induced Meisenheimer complexes of nitroaromatic compounds is consistent with their anti-TB activities exemplied by MDL860 and benzothiazol N-oxide (BTO) analogs.

1959 ◽  
Vol 37 (1) ◽  
pp. 231-244
Author(s):  
Guy Nadeau ◽  
Louis-Philippe Joly

The influence of pH, reagent composition, time, temperature, light, and various ions, on the reaction of fluorescence between adrenaline and ethylenediamine, has been investigated. The necessity of a preliminary oxidation to adrenochrome is confirmed. Optimum pH of reaction is situated at 10.4 ± 0.1, while extraction with isobutanol is best performed at pH 10.1 ± 0.1. A satisfactory reagent is one that contains 114.5 millimoles of ethylenediamine base per 100 ml of reacting mixture and sufficient hydrochloric acid to bring the pH to 10.3 ± 0.1. Temperature and length of reaction may be conveniently set at 50 °C and 20 to 30 minutes. Increasing the temperature significantly lowers the yield of fluorescent material; performing the reaction at room temperature increases the yield, but lengthens the procedure. Exposure to diffuse and ultraviolet light also affects the yield of fluorescence. All these factors (temperature, light, as well as excess of oxygen) appear to exert their influence in the first stages of the reaction, since the fluorescent material, once formed, is relatively stable. The beneficial effect of various ions, including Cu++, Al+++, and MoO4−−, is discussed in relation to complex formation. Efficiency of extraction with aliphatic alcohols has also been investigated; true yield from C14-adrenaline is estimated. In the light of recent findings on the structure of adrenochrome, new pathways for the reaction are suggested.


2012 ◽  
Vol 10 (2) ◽  
pp. 313-319 ◽  
Author(s):  
Anca Grigoras ◽  
Virgil Barboiu

AbstractCharge transfer interactions in mixtures of poly(9-vinylcarbazole) with three nitro compounds (4,4′dinitrodibenzyl, ethyl 3,5-dinitrobenzoate and 2,2′,4,4′-tetranitrodibenzyl) were examined. GPC shows an increase of apparent polymer weight average molecular weight (MW) in mixtures compared with pure PVK. Electron acceptors show upfield 1H-NMR shifts for all mixtures. The equilibrium association constants (k) calculated from the Benesi-Hildebrand equation are 0.511, 1.371, and 1.868 L mol−1 for PVK blends with DNDB, DNBE and TNDB, respectively. Shifts of (−NO2) stretch vibrations in mixtures support charge transfer complex formation between PVK chains and electron acceptors The ability to accept electrons decreases: TNDB>DNBE>DNDB.


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