31706-15-7Relevant articles and documents
Synthesis of aryl-substituted or aryl-fused N-hydroxyethyl and N-hydroxymethypyrazole derivatives as potential ligands for the estrogen receptor
Allahyari-Devin, Maryam,Abedi, Behnam,Navidpour, Latifeh,Shafiee, Abbas
, p. 43 - 53 (2013/02/25)
A new series of N-hydroxyethylpyrazole (12a-f) and N-hydroxymethylpyrazole derivatives (15a-f) were designed for their estrogenic activities, having a 11.0 ± 0.5 A distance between their two hydroxyl groups, aliphatic-OH and phenolic-OH similar to 17β-estradiol (E2) as an endogenous hormone. To synthesize the title compounds, the key intermediate 1,3-dicarbonyl derivatives (2 and 8), were treated with hydrazine hydrate to produce the pyrazole ring 5 and 9. Further hydroxyalkylation of the latter produced the title pyrazoles. The position of hydroxyethyl or hydroxymethyl substituents in the products was determined through 2D NOE NMR spectroscopy.
Identification and optimisation of 5-amino-7-aryldihydro-1,4-diazepines as 5-HT2A ligands
Swain, Christopher J.,Teran, Ana,Maroto, Marta,Cabello, Angeles
, p. 6058 - 6062 (2007/10/03)
A several series of low molecular weight 5-HT2A leads were identified from an analysis of HTS data, the exploration of SAR and optimization of one series using parallel synthesis are described, affording compound 22 (5-HT2A IC50 1.1 nM).
Spectroscopy and absolute reactivity of ketenes in acetonitrile studied by laser flash photolysis with time-resolved infrared detection
Wagner, Brian D.,Arnold, Bradley R.,Brown, Gerald S.,Lusztyk, Janusz
, p. 1827 - 1834 (2007/10/03)
Laser flash photolysis with time-resolved infrared detection of transients (LFP-TRIR) has been used to study the IR spectroscopy and reactivity of a number of substituted ketenes, prepared by the 308-nm photolysis of α-diazocarbonyl precursors in acetonitrile solution at room temperature. The correlation of the experimental ketene asymmetric stretching frequency to the Swain-Lupton field (F) and resonance (R) effect substituent parameters was unsatisfactory, whereas the correlation to the inductive substituent parameter (σ1) of Charton gave excellent results. This suggests that the asymmetric stretching frequency of substituted ketenes depends mainly on the inductive (i.e., field) effect of the substituents. The mechanism and kinetics of the reactions of these ketenes with various amines in acetonitrile were also studied. An intermediate species identified as either zwitterionic ylide or amide enol formed in the nucleophilic addition of the secondary amine to the C(α) of the ketene is observed by TRIR. The decay of this species is assisted by the amine and is concomitant with the formation of an amide, the final product of the reaction. Our kinetic data on ketene amine reactions show a general trend, indicating a much higher reactivity (ca. 3 orders of magnitude difference in the corresponding rate constants) of secondary amines compared with that of tertiary amines. Secondary diethylamine shows reactivity similar to those observed for primary amines, while secondary piperidine seems to be, in general, somewhat more reactive. The observed trend is rationalized in terms of the steric effects exerted by both amine and ketene substituents. Our data on para-substituted phenyl ketenes provide support for the negative charge development on the ketene moiety in the transition state, with electron-withdrawing substituents accelerating and electron-releasing substituents slowing down the addition reaction.