2882-35-1Relevant articles and documents
Synthesis of highly potent anti-inflammatory compounds (ROS inhibitors) from isonicotinic acid
Yaqoob, Sana,Nasim, Nourina,Khanam, Rahila,Wang, Yan,Jabeen, Almas,Qureshi, Urooj,Ul-Haq, Zaheer,El-Seedi, Hesham R.,Jiang, Zi-Hua,Khan, Farooq-Ahmad
, (2021/05/31)
In search of anti-inflammatory compounds, novel scaffolds containing isonicotinoyl motif were synthesized via an efficient strategy. The compounds were screened for their in vitro antiinflammatory activity. Remarkably high activities were observed for isonicotinates 5-6 and 8a-8b. The compound 5 exhibits an exceptional IC50 value (1.42 ± 0.1 μg/mL) with 95.9% inhibition at 25 μg/mL, which is eight folds better than the standard drug ibuprofen (11.2 ± 1.9 μg/mL). To gain an insight into the mode of action of anti-inflammatory compounds, molecular docking studies were also performed. Decisively, further development and fine tuning of these isonicotinates based scaffolds for the treatment of various aberrations is still a wide-open field of research.
Kinetic study on aminolysis of 4-nitrophenyl isonicotinate in acetonitrile: Effect of amine basicity on reactivity and reaction mechanism
Shin, Minah,Kim, Min-Young,Um, Ik-Hwan
, p. 2130 - 2134 (2014/11/08)
A kinetic study is reported on nucleophilic substitution reactions of 4-nitrophenyl isonicotinate (7) with a series of cyclic secondary amines in MeCN. The plots of kobsd vs. [amine] curve upward for the reactions with weakly basic amines (e.g.
Metal ion catalysis and inhibition in nucleophilic substitution reactions of 4-nitrophenyl nicotinate and isonicotinate with alkali metal ethoxides in anhydrous ethanol
Choi, Seo-Young,Hong, Yeon-Ju,Um, Ik-Hwan
experimental part, p. 1951 - 1956 (2012/02/05)
A kinetic study is reported on nucleophilic substitution reactions of 4-nitrophenyl nicotinate 5 and isonicotinate 6 with alkali metal ethoxide EtOM (M = K, Na, and Li) in anhydrous ethanol at 25.0 ± 0.1 °C. Plots of pseudofirst- order rate constant kobsd vs. EtOM concentration exhibit upward curvature for the reactions of 5 and 6 with EtOK and EtONa but are almost linear for those with EtOLi. Dissection of kobsd into k EtO- and kEtOM (i.e., the second-order rate constant for the reaction with dissociated EtO- and ion-paired EtOM, respectively) has shown that kEtOK ≥ kEtONa > k EtO- but kEtOLi EtO -. It has been concluded that K+ and Na+ ions catalyze the reactions by increasing the electrophilicity of the carbonyl carbon atom through formation of a 4- embered cyclic transition state TS3 or TS4. However, M+ ion catalysis has been found to be much less significant for the reactions of 5 and 6 than for the corresponding reactions of 4-nitrophenyl picolinate 4, which was reported to proceed through a 5-membered cyclic transition state TS2. Although 5 and 6 are significantly more reactive than 4-nitrophenyl benzoate 3, the reactions of 5 and 6 result in smaller kEtOK/kEtO- ratios than those of 3. The electron-withdrawing ability of the nitrogen atom in the acyl moiety of 5 and 6 has been suggested to be responsible for the increase in reactivity and the decrease in the kEtOK/kEtO- ratio.