90091-33-1Relevant academic research and scientific papers
N-(2-ethylamine) benzenesulfonamide cordycepin derivative as well as preparation method and application thereof
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Paragraph 0033; 0034, (2020/01/25)
The invention discloses an N-(2-ethylamine) benzenesulfonamide cordycepin derivative as well as a preparation method and an application thereof in inhibiting tumor cell proliferation, and the N-(2-ethylamine) benzenesulfonamide cordycepin derivative is pr
1,4-naphthoquinone derivative, preparation method and applications thereof
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Paragraph 0039; 0047, (2018/11/22)
The invention relates to a 1,4-naphthoquinone derivative, a preparation method and applications thereof. According to the present invention, the 1,4-naphthoquinone derivative is firstly synthesized, has good activity in the inhibition of human colon cance
Effect of substituent on regioselectivity and reaction mechanism in aminolysis of 2,4-dinitrophenyl X-substituted benzenesulfonates
Um, Ik-Hwan,Hong, Jin-Young,Seok, Jin-Ah
, p. 1438 - 1444 (2007/10/03)
(Chemical Equation Presented) We report on a kinetic study for the nucleophilic substitution reactions of 2,4-dinitrophenyl X-substituted benzensulfonates (X = 4-MeO, 1a, and X = 4-NO2, 1c) with a series of primary amines in 80 mol % H2O/20 mol % DMSO at 25.0 °C. The reactions proceed through S-O and C-O bond fission pathways competitively. The fraction of the S-O bond fission increases as the attaching amine becomes more basic and the substituent X changes from 4-MeO to 4-NO2, indicating that the regioselectivity is governed by the electronic nature of the substituent X as well as the basicity of amines. The S-O bond fission has been suggested to proceed through an addition intermediate with a change in the rate-determining step (RDS) at pK°a = 8.9 ± 0.1. The electronic nature of the substituent X influences kNS-O and k1 values, but not the k2/k-1 ratios and the pK°a value significantly. Stabilization of the ground state (GS) through resonance interaction between the electron-donating substituent and the electrophilic center has been suggested to be responsible for the decreased reactivity of 1a compared to 1c. The second-order rate constants for the C-O bond fission exhibit no correlation with the electronic nature of the substituent X. The distance effect and the nature of the reaction mechanism have been suggested to be responsible for the absence of the correlation.
