51774-35-7Relevant academic research and scientific papers
Copper-Catalyzed Radical N-Demethylation of Amides Using N-Fluorobenzenesulfonimide as an Oxidant
Yi, Xuewen,Yi, Xuewen,Lei, Siyu,Liu, Wangsheng,Che, Fengrui,Yu, Chunzheng,Liu, Xuesong,Wang, Zonghua,Zhou, Xin,Zhang, Yuexia
supporting information, p. 4583 - 4587 (2020/05/05)
An unprecedented N-demethylation of N-methyl amides has been developed by use of N-fluorobenzenesulfonimide as an oxidant with the aid of a copper catalyst. The conversion of amides to carbinolamines involves successive single-electron transfer, hydrogen-atom transfer, and hydrolysis, and is accompanied by formation of N-(phenylsulfonyl)benzenesulfonamide. Carbinolamines spontaneously decompose to N-demethylated amides and formaldehyde, because of their inherent instability.
Design, synthesis, and biological activity of a novel series of human sirtuin-2-selective inhibitors
Suzuki, Takayoshi,Khan, Mohammed Naseer Ahmed,Sawada, Hideyuki,Imai, Erika,Itoh, Yukihiro,Yamatsuta, Katsura,Tokuda, Natsuko,Takeuchi, Jun,Seko, Takuya,Nakagawa, Hidehiko,Miyata, Naoki
, p. 5760 - 5773 (2012/07/28)
Selective inhibitors of human sirtuin 2 (SIRT2), a deacetylase, are candidate therapeutic agents for neurodegenerative diseases such as Parkinson's disease and Huntington's disease as well as potential tools for elucidating the biological functions of SIRT2. On the basis of homology models of SIRT1 and SIRT2, we designed and prepared a series of 2-anilinobenzamide analogues. Enzyme assays using recombinant SIRT1 and SIRT2 revealed that 3'-phenethyloxy-2- anilinobenzamide analogues such as 33a and 33i are potent and selective SIRT2 inhibitors, showing more than 3.5-fold greater SIRT2-inhibitory activity and more than 35-fold greater SIRT2-selectivity compared with AGK2 (3), a previously reported SIRT2-selective inhibitor. Compound 33a also induced a dose-dependent selective increase of α-tubulin acetylation in human colon cancer HCT116 cells, indicating selective inhibition of SIRT2 in the cells. These 3'-phenethyloxy-2-anilinobenzamide derivatives represent an entry into a new class of SIRT2-selective inhibitors.
17β-HSD2 inhibitors for the treatment of osteoporosis: Identification of a promising scaffold
Wetzel, Marie,Marchais-Oberwinkler, Sandrine,Hartmann, Rolf W.
supporting information; experimental part, p. 807 - 815 (2011/03/17)
17β-Hydroxysteroid dehydrogenase type 2 (17β-HSD2) catalyses the conversion of active 17β-hydroxysteroids into the less active 17-ketosteroids thereby controlling the availability of biologically active estrogens (E2) and androgens (T) in the tissues. The skeletal disease osteoporosis occurs mainly in post-menopausal women and in elderly men when the levels of estrogens and androgens, respectively, decrease. Since 17β-HSD2 is present in osteoblasts, inhibition of this enzyme may provide a new and promising approach to prevent the onset of osteoporosis, keeping a certain level in estrogens and androgens in bone cells of ageing people. Hydroxynaphthyl, hydroxyphenyl and hydroxymethylphenyl-substituted moieties were synthesised as mimetics of the steroidal substrate. Compound 8 has been identified as promising scaffold for 17β-HSD2 inhibitors displaying high activity and good selectivity toward 17β-HSD1, ERα and ERβ.
CROSSED EFFECT OF THE POLAR CHARACTERISTICS OF THE MEDIUM AND THE STRUCTURE OF THE SUBSTRATE IN THE REACTIONS OF AROYL CHLORIDES WITH N-METHYLANILINES
Shpan'ko, I. V.,Litvinenko, L. M.,Goncharov, A. N.,Korzhilova, O. I.
, p. 847 - 853 (2007/10/02)
A kinetic investigation was undertaken into the reactions of aroyl chlorides with 3-bromo- and 3-nitro-N-methylanilines in chlorobenzene, nitrobenzene, cyclohexane, and binary mixtures of chlorobenzene with nitrobenzene and cyclohexane at 25 deg C.The second-order rate constants of the reaction involving N-methyl-3-bromoaniline were treated by means of the Kirkwood, Hammet, and crossed structure-medium correlation equations.It was found that the correlations according to the Kirkwood and Hammet equation can be linear or broken, depending on the structure of the reagents and the characteristics of the medium.The presence of bends on the correlation curves is due to the appearance on the reaction coordinate in low-polarity media of a cyclic transition state, the formation of which is promoted by increase in the electron-withdrawing characteristics of the substituents in the benzene ring of both the amine and the aroyl chloride.The attainment of an isoparametric point with respect to the structure of the substrate in the region corresponding to the realization of the cyclic transition state was demonstrated by crossed correlation.
