101554-10-3Relevant academic research and scientific papers
Synthesis and microbiological activity of some N-(o-hydroxyphenyl)benzamides and phenylacetamides as the possible metabolites of antimicrobial active benzoxazoles: Part II
Sener, Esin Aki,Bingoel, Kamuran K.,Oeren, Ilkay,Arpaci, Oezlem Temiz,Yalcin, Ismail,Altanlar, Nurten
, p. 469 - 476 (2007/10/03)
The synthesis of some N-(o-hydroxyphenyl)benzamides and benzacetamides (2a-2p) in order to determine their in vitro antimicrobial activity against two Gram-positive bacteria, three Gram-negative bacteria and the fungus Candida albicans is described. The new compounds were compared with several control drugs. The derivative 2g, 4-amino-N-(o-hydroxyphenyl)benzamide, was found active at an MIC value of 25 μg/ml against the Gram-negative microorganism Klebsiella pneumoniae. Most of the compounds exhibited antibacterial activity at an MIC value of 25 μg/ml against Pseudomonas aureginosa. For the antifungal activity against C. albicans, compounds 2e, 2h and 2m were found more active than the other derivatives (MIC 12.5 μg/ml). The antimicrobial activity of some of these benzamide and phenylacetamide derivatives (2a, 2b, 2f, 2g, 2h and 2k), possible metabolites of benzoxazoles, was also compared with that of the cyclic analogues 3-8. Compound 2f possesses two dilutions better antifungal activity than its cyclic analogue the benzoxazole derivative 5 against C. albicans, while having one dilution better antibacterial activity against Streptococcus faecalis and K. pneumoniae. (C) 2000 Elsevier Science S.A.
Tertiary Amine-Catalyzed Acyl Group Exchange Reaction of N,O-Diacyl-o-aminophenols. Its Mechanism and Factors Determining the Relative Stability of Acyl Exchanged Isomer Pairs
Sakurai, Tadamitsu,Kojima, Shuichi,Inoue, Hiroyasu
, p. 3141 - 3148 (2007/10/02)
Acyl substituent effects on the equilibrium and rate constants for the acyl group exchange reactions of various N,O-diacyl-o-aminophenols have been investigated in solvents with different polarities.It was found that the relative stability of acyl exchanged isomer pairs is determined solely by the inductive effect of acyl groups, provided that the steric hindrance of acyl substituents bonded to amide nitrogen affects the stability to the same extent.The importance of steric hindrance exerted by a bulky acyl group in determining the relative stability was demonstrated by analyzing the correlation between the standard free energy change (ΔG0) and pKa, which were used as the measure of the relative stability of isomer pairs and of the electron-with drawing ability of acyl groups, respectively.On the other hand, the logarithms of catalytic rate constants for the acyl migration reactions were correlated well to the pKa values.In addition to this finding, a large negative value of activation entropy (ΔS=-160 J K-1 mol-1) and the Broensted coefficient β of 0.65 for the reaction of N,O-(acetyl)-(1-naphthoyl) pair of N,O-diacyl-o-aminophenol provide a definitive evidence for the rate-determining proton transfer from this derivative to amine catalyst in the transition state.
