10286-92-7Relevant academic research and scientific papers
KINETICS AND MECHANISM OF THE AMINOLYSIS OF BENZOIC ANHYDRIDES
Lee, Byung Choon,Yoon, Ji Hyun,Lee, Cheal Gyu,Lee, Ikchoon
, p. 273 - 279 (1994)
Nucleophilic substitution reactions of benzoic anhydrides, in which one of the rings is substituted, with anilines were investigated in methanol.The product-formation step coincides with the rate-limiting step so that the two rate constants, kXY and kXZ, for the competitive reaction pathways can be dissected.The two cross-interaction constants, ρXY and ρXZ, especially an unusually large magnitude of the latter, indicate that the reaction proceeds by a frontside SN2 attack on either one of the carbonyl carbon with a strong interaction between the nucleophile (X) and the leaving group (Z).The mechanism is also supposed by the trends in the activation parameters.
Supported-Pd catalyzed tandem approach for N-arylbenzamides synthesis
Bhattacherjee, Dhananjay,Das, Pralay,Giri, Kousik,Shaifali,Sharma, Ajay Kumar,Sharma, Navneet,Sheetal
, (2021/11/24)
Aryl iodides as dual arylating agent for C-terminal from oxalic acid [(CO2H)2] and N-terminal from sodium azide (NaN3) for N-aryl benzamides (Ar-CO-NH-Ar) synthesis is a rare invention which has been attempted successfully under this study. A single step tandem approach for the synthesis of N-aryl benzamides has been developed through bifunctional transformation of aryl iodides with in-situ CO from (CO2H)2 and NaN3 following two different pathways of carbonylation and azidation. The polystyrene supported palladium (Pd@PS) catalyst was found to be well compatible to perform the domino-reaction in a double layer vial (DLV) system under base, ligand and additive-free conditions. Moreover, the same approach was further extended with aryl azides for unsymmetric N-aryl benzamides (Ar-CO-NH-Ar') synthesis. Furthermore, the DFT studies were also performed to support the proposed mechanism.
N-Phenylbenzamide derivatives as alternative oxidase inhibitors: Synthesis, molecular properties, 1H-STD NMR, and QSAR
Barsottini, Mario R. O.,Carazzolle, Marcelo F.,Costa, Paulo C. S.,Evangelista, Joel S.,Miranda, Paulo C. M. L.,Nascimento, Andrey F. Z.,Pereira, Gon?alo A. G.,Pires, Bárbara A.,Rocco, Silvana A.,Sfor?a, Maurício L.,Silva, Jaqueline S.,Vieira, Maria L. L.,Zeri, Ana C. M.
, (2020/02/27)
In the present work, 117 N-phenylbenzamides (NPDs) were prepared and evaluated against recombinant AOX from the fungal pathogen Moniliophthora perniciosa. 1H, 13C NMR, FTIR, and mass spectra provided structural information on NPDs. The library compounds were tested as Alternative Oxidase inhibitors in two different assays using the model yeast Pichia pastoris: cell growth and oxygen consumption assays. The most active compound, 3FH, was further characterized by DRX and 1H-NMR-STD. Single crystal X-ray diffraction showed intra- and intermolecular interactions of 3FH in solid-state and elucidated its 3D structural configuration. 1H-NMR-STD allowed us to derive protein-ligand interactions in a membrane-mimetic system and evidenced an outstanding interaction of 3FH with this enzyme. Results of both biological assays were used as input to Quantitative Structure-Activity Relationship models, which highlighted the more important molecular fragments contributions for protein-ligand interaction.
New insights into the bacterial RNA polymerase inhibitor CBR703 as a starting point for optimization as an anti-infective agent
Zhu, Weixing,Haupenthal, J?rgm,Groh, Matthias,Fountain, Michelle,Hartmann, Rolf W.
supporting information, p. 4242 - 4245 (2014/07/08)
CBR703 was reported to inhibit bacterial RNA polymerase (RNAP) and biofilm formation, considering it to be a good candidate for further optimization. While synthesized derivatives of CBR703 did not result in more-active RNAP inhibitors, we observed promising antibacterial activities. These again correlated with a significant cytotoxicity toward mammalian cells. Furthermore, we suspect the promising effects on biofilm formation to be artifacts. Consequently, this class of compounds can be considered unattractive as antibacterial agents. Copyright
Synthesis and Biological Evaluation of 2,3,5-Substituted [1,2,4]Thiadiazoles as Allosteric Modulators of Adenosine Receptors
Van Den Nieuwendijk, Adrianus M. C. H.,Pietra, Daniele,Heitman, Laura,G?bly?s, Anikó,IJzerman, Adriaan P.
, p. 663 - 672 (2007/10/03)
A number of 2,3,5-substituted [1,2,4]thiadiazole analogues of SCH-202676 (N-(2,3-diphenyl-[1,2,4]thiadiazole-5(2H)-ylidene)methanamine, 7a) were synthesized and tested as potential allosteric modulators of adenosine receptors. All compounds were capable of displacing the binding of the radiolabeled agonist [3H]CCPA to human A1 adenosine receptors, whereas modest and varying effects were observed on the binding of [3H]DPCPX, a radiolabeled antagonist for this receptor subtype. Four compounds, 7a (SCH-202676), 7k (LUF5792), 71 (LUF5794), and 8e (LUF5789), were selected for more detailed characterization. They all proved allosteric inhibitors of agonist binding, with 7k being most potent, whereas their effects on antagonist binding were more ambiguous. Subsequently, experiments were done on human adenosine A2A and A3 receptors. Compounds 7a and 7l displayed peculiar displacement characteristics of both radiolabeled agonist and antagonist binding to A2A receptors, whereas 7a showed some activity on A3 receptors.
IMIDAZO [1,2-A] PYRIDINES AND THEIR PHARMACEUTICAL USE
-
, (2008/06/13)
The invention relates to novel bradykinin antagonists of the formula: STR1 wherein R 1 is halogen,R 2 and R 3 are each hydrogen, lower alkyl, halo(lower)alkyl or acyl,R 4 is aryl having suitable substituent(s), or a heterocyclic group optionally having suitable substituent(s),Q is O or N--R 11, in which R 11 is hydrogen or acyl, andA is lower alkylene,and pharmaceutically acceptable salts thereof.
Facile and Effective Synthesis of Unusually Substituted Aromatic N-Phenylamides
Kobs, Uwe,Neumann, Wilhelm P.
, p. 2191 - 2194 (2007/10/02)
A mild and effective new method for the preparation of a variety of arylamides 3a-i as well as heterocyclic 5a, b and 6 and olefinic amides 7, 9 is described.The reaction of trialkylstannyl-substituted aromatic, heterocyclic or vinylic hydrocarbons with aryl isocyanates in the presence of aluminium trichloride provides the corresponding N-aryl-substituted amides in good to excellent yields.The stannyl group serves as a powerful leaving group superior to hydrogen by several powers of ten which allows, via ipso substitution, to obtain isomer patterns not accessible by normal electrophilic substitution reactions, e. g. substitution in meta position with respect to a methoxy group.
JOINT EFFECT OF STRUCTURE OF REAGENTS AND TEMPERATURE ON REACTIVITY OF AROYL BROMIDE-PRIMARY ARYLAMINE SYSTEMS IN BENZENE. CROSSED CORRELATION
Shpan'ko, I. V.,Goncharov, A. N.,Likhomanenko, E. E.
, p. 522 - 530 (2007/10/02)
The kinetics of the reactions of aroyl bromides with primary arylamines in benzene were studied at 10, 25, 40, and 55 deg C.The effects of factors (temperature, the structure of the aroyl bromides and primary arylamines) varied separately and in pairs and also the joint effect of the three factors on the process rate were assessed quantitatively.The joint effect of the structure of the primary arylamines and the temperature on the reactivity of the system is nonadditive, and the effect of the structure of the aroyl bromides and temperature is additive.The influence of the varied parameters on the nature of the translation states in the reactions is discussed.
Joint effect of the structure and medium on the rate of reactions of aroyl chlorides with primary arylamines in mixtures of tert-butyl alcohol with chlorobenzene. Isoparametric points with respect to the variable parameters
Likhomanenko, E. E.,Shpan'ko, I. V.
, p. 139 - 144 (2007/10/02)
The effects of the composition of the medium (3.5, 5, and 7 M solutions of tert-butyl alcohol in chlorobenzene), of pairs of variable factors (the composition of the medium with the structure of the aroyl chlorides and the composition of the medium with the structure of the primary arylamines), and of all three factors together on the rate of the reactions of aroyl chlorides with primary arylamines were determined quantitatively.It was found that the mutual effects of the structure and the medium on the reactivity of the system were nonadditive.It was shown experimentally that there are isoparametric points with respect to the medium, the structure of the substrate, and the structure of the nucleophile, and the transition was made through some of these points.
EFFECT OF THE STRUCTURE ON THE RATE OF THE REACTIONS OF AROYL CHLORIDES WITH PRIMARY ARYLAMINES IN MIXTURES OF tert-BUTYL ALCOHOL AND CHLOROBENZENES. THE TRANSITION THROUGH ISOPARAMETRIC POINTS WITH RESPECT TO THE STRUCTURE PARAMETERS
Shpan'ko, I. V.,Likhomanenko, E. E.
, p. 1702 - 1710 (2007/10/02)
The rate of the reactions of aroyl chlorides with primary arylamines in 3.5, 5, and 7M solutions of tert-butyl alcohol in chlorobenzene at 25 deg C was measured.The effect of the structure of the reagents on the process rate was determined quantitatively by means of the Hammett-Taft and crossed correlation equations.The isoparametric points with respect to the structure of the substrate and the nucleophile were reached experimentally, and the transition through some of these points was also realised.It was found that the specific solvation of the primary arylamines by the tert-butyl alcohol was nonuniform in that an incre ase in the concentration of the alcohol in the investigated range reduced, did not change, and increased the rates of the reactions with 3-chloroaniline, 3-nitroaniline, and 3-nitro-5-methoxycarbonylaniline respectively.The effect of specific solvation on the behavior of the correlation parameters is discussed.
