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.
Kinetic study on aminolysis of 4-nitrophenyl nicotinate and isonicotinate: Factors influencing reactivity and reaction mechanism
Kim, Min-Young,Shin, Minah,Um
supporting information, p. 2443 - 2447 (2014/12/10)
A kinetic study is reported on nucleophilic substitution reactions of 4-nitrophenyl nicotinate (7) and 4- nitrophenyl isonicotinate (8) with a series of cyclic secondary amines in H2O containing 20 mol % DMSO at 25.0 °C. The Bronted-type plots
Bimolecular catalysis and turnover from a macromolecular host system
Ellis, Adam,Gooch, David,Twyman, Lance J
, p. 5364 - 5371 (2013/07/26)
The synthesis of a globular macromolecule and its application as a bimolecular catalyst are reported. The macromolecular structure supports (at least) two zinc-metalated porphyrin units, each capable of binding a single reactant. The proximity of the two
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.
A simple method for synthesis of active esters of isonicotinic and picolinic acids
Christensen, Jorn B.
, p. 47 - 51 (2007/10/03)
A method for preparation of the p-nitrophenyl-, N-hydroxysuccinimidyl- and pentafluorophenyl esters of isonicotinic and picolinic acids from the corresponding acids is reported.
Divalent Metal Ion Catalysis in the Hydrolysis of Esters of Picolinic Acid. Metal Ion Promoted Hydroxide Ion and Water Catalyzed Reactions
Fife, Thomas H.,Przystas, Theodore J.
, p. 1041 - 1048 (2007/10/02)
Rate constants have been determined for hydrolysis of a series of phenolic and aliphatic esters of picolinic acid in H2O.Hydroxide ion, hydronium ion, and water catalyzed reactions were observed in hydrolysis of the phenolic esters.Catalysis by low concentrations of Ni2+ and Cu2+ occurs even though binding of the metal ions is weak (saturation effects were not observed).Both metal ion promoted water and OH- catalyzed reactions were observed with the esters having leaving groups with pKa values of 12.4 or less.Rate enhancements produced by 0.01 M Ni2+ and 0.001 M Cu2+ range from 10- to near 200-fold in the pH-independent water reactions and from 102- to over 105-fold in the OH- catalyzed reactions.Significant metal ion catalysis was not observed in the hydrolysis of 4-nitrophenyl isonicotinate or 8-(5-nitroquinolyl) isonicotinate; therefore, metal ion catalysis in the hydrolysis of the esters with the pyridine nitrogen ortho to the ester function must be associated with a chelation effect.The rate constants k0 and kOH for hydrolysis of the picolinate esters in the metal ion promoted water and OH- catalyzed reactions are little affected by the leaving group (β1g ca. 0) for leaving groups with pKa values ranging from 4.1 with 2,4-dinitrophenol to 12.4 with trifluoroethanol, and ratios of kOH/k0 are nearly constant.This indicates that there is little or no C-O bond breaking in the critical transition state, i.e., in both reactions the nucleophilic attack step is rate determining.When the leaving group is ethanol, then kOH is markedly less than in the case of the trifluoroethyl ester, and a metal ion promoted water reaction is not detected even at pH values as low as 4.Thus, a change in rate-determining step has occurred with the change in the leaving group.Likewise only metal ion promoted OH- catalysis is observed with ethyl 6-carboxypicolinate.Rate enhancements produced by saturating concentrations of Ni2+ and Cu2+ are in that the case 2.7*104- and 1.3*105-fold, respectively.Intramolecular general base catalysis does not occur in the metal ion promoted water reaction of 8-quinolyl picolinate or 8-(5-nitroquinolyl) picolinate.With the nitro substituted esters of picolinic acid a metal ion promoted formate and acetate ions are attacking the metal ion complexes as nucleophiles.
