7721-66-6Relevant articles and documents
Enols of carboxylic acid amides with β-electron-withdrawing substituents
Mukhopadhyaya, Jayanta Kumar,Sklenak, Stepan,Rappoport, Zvi
, p. 1325 - 1336 (2000)
The effect of stabilizing enols of carboxamides by several two β- electron-withdrawing substituents was studied with the R1R2CHCONHPh systems. When R1R2CH2 = Meldrum's acid (MA), the solid-state structure is that of the enol R1R2C=C(OH)NHPh (7). In CDCl3 solution the structure is 7, but there may be some exchange on the NMR time scale with a tautomer. B3LYP/6-31G** calculations show a significant preference for the enol R1R2C=C(OH)NH2 (12a) (R1R2C = MA moiety) and a small preference for (MeO2C)2C=C(OH)NHPh (11b) over the amide structures. However, solid 11 has the amide structure (MeO2C)2CHCONHPh (11a). NMR spectra in CDCl3 show >90% of 11a, but a minor species, probably 11b, is also present. In DMSO this species is not observed. The analogous dimedone-substituted anilide 10 exists both in the solid state and in solution as an enol of a ring carbonyl. Calculations show that HC(CO2Me)3 has a lower energy than its tautomeric enol. The effects of the push-pull structures of the enols on structural and spectrometric parameters, of the β-substituents, of the planarity of the system, of the acid derivative group (ester or anilide), and of the solvent as enol-stabilizing factors are discussed. Destabilization of the acid form contributes to the increased relative stability of the enols.
Synthesis, Structure–Activity Relationship Studies, and ADMET Properties of 3-Aminocyclohex-2-en-1-ones as Chemokine Receptor 2 (CXCR2) Antagonists
Dai, Weiyang,Chen, Wenmin,Debnath, Bikash,Wu, Yong,Neamati, Nouri
, p. 916 - 930 (2018/05/15)
Herein we describe the synthesis and structure–activity relationships of 3-aminocyclohex-2-en-1-one derivatives as novel chemokine receptor 2 (CXCR2) antagonists. Thirteen out of 44 derivatives were found to inhibit CXCR2 downstream signaling in a Tango a
