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89-52-1Relevant articles and documents
Acylanthranils. 10. Influence of Hydrogen Bonding on Hydrolysis of Acetylanthranil in Organic Solvents
Errede, L. A.,McBrady, J. J.,Tiers, G. V. D.
, p. 3868 - 3875 (1980)
The hydrolysis of acetylanthranil (1) to give o-acetamidobenzoic acid (2) in organic solvents at room temperature was monitored by proton NMR and/or gravimetrically.The results show that the second-order rate constant in benzene is about equal to that in water at pH 6.8.The corresponding rate constant for hydrolysis by a stoichiometric amount of water in proton-acceptor solvents decreases in the order benzene > dimethyl-d6 sulfoxide > acetone-d6 > dimethylformamide-d7 > pyridine, and for hydrolysis in proton donor solvents, it decreases in the order benzene > chloroform-d > acetonitrile-d3.The observed second-order rate "constant" in organic solvents, however, is not a true constant, since it increases linearly with water concentration.It was observed also that the plots of log / as a function of time, t, show an inflection at some time, ti, that appears to correspond to a critical equilibrium concentration of available proton from the acid product 2.The magnitude of ti is decreased considerably by addition of 2 at time zero, and it is eliminated completely by addition of HCl.On the other hand, it is increased considerably by addition of solutes that are strong proton acceptors, such as 1,8-bis(dimethylamino)naphthalene or 1,4-diazabicyclooctane.These results are consistent with the hypothesis that hydrolysis of 1 in organic solvents involves interaction with molecular clusters of water such as (H2O)n in benzene, S*HOH*S or (HOH*S)n in proton-acceptor solvents, S, and H2O*HS in proton donor solvents, SH.
Synthesis and X-ray structure analysis of 2-acetylamino-benzoic acid
Rajnikant,Dinesh,Kamni,Deshmukh
, p. 471 - 475 (2004)
The title compound crystallizes in the orthorhombic space group Fdd2 with unit cell parameters a = 10.848(1) , b = 30.264(1) and c = 10.577(1) , V = 3472.47(2) 3, and Z = 4. The final reliability index is 0.030 for 700 observed reflections. Nitrogen of the amide group and carbon atom of the acid group deviate significantly below and above the plane of the phenyl ring. The crystal cohesion is accentuated by NbondHO and ObondHO hydrogen bonds.
Cleavage of Carboxylic Esters by Aluminum and Iodine
Sang, Dayong,Yue, Huaxin,Fu, Yang,Tian, Juan
, p. 4254 - 4261 (2021/03/09)
A one-pot procedure for deprotecting carboxylic esters under nonhydrolytic conditions is described. Typical alkyl carboxylates are readily deblocked to the carboxylic acids by the action of aluminum powder and iodine in anhydrous acetonitrile. Cleavage of lactones affords the corresponding ω-iodoalkylcarboxylic acids. Aryl acetylates undergo deacetylation with the participation of the neighboring group. This method enables the selective cleavage of alkyl carboxylic esters in the presence of aryl esters.
Design and synthesis of novel tranilast analogs: Docking, antiproliferative evaluation and in-silico screening of TGFβR1 inhibitors
Ismail, Magda M.F.,El-Zahabi, Heba S.A.,Ibrahim, Rabab S.,Mehany, Ahmed B.M.
, (2020/10/23)
The discovery of the antiproliferative potential of tranilast prompted additional studies directed at understanding the mechanisms of tranilast action. Its inhibitory effect on cell proliferation depends principally on the capacity of tranilast to interfere with transforming growth factor beta (TGFβR1) signaling. This work summarizes design, synthesis and biological evaluation of sixteen novel tranilast analogs on different tumors such as PC-3, HepG-2 and MCF-7 cell lines. The in vitro cytotoxicity was evaluated using MTT assay showed that, twelve compounds out of sixteen showed higher cytotoxic activities (IC50’s 1.1–6.29 μM), than that of the reference standard, 5-FU (IC50 7.53 μM). The promising cytotoxic hits (4b, 7a, b and 14c-e), proved to be selective to cancer cells when their cytotoxicity's are examined on human normal cell line (WI-38). Then they are investigated for their possible mode of action as TGFβR1 inhibitors; remarkable inhibition of TGFβR1 by these hits was observed at the range of IC50 0.087–3.276 μM. The cell cycle analysis of the most potent TGFβR1 inhibitor, 4b revealed cell cycle arrest at G2/M phase on prostate cancer cells. Additionally, it is clearly indicated apoptosis induction at Pre-G1 phase, this is substantiated by significant increase in the expression on the tumor suppressor gene, p53 and up regulation the level of apoptosis mediator, caspase-3. In addition, in silico study was performed for validating the physicochemical and ADME properties which revealed that, all compounds are orally bioavailable with no side effects complying with Lipinski rule. The proposed mode of action can be further explored on the light of molecular modeling simulation of the most potent compounds, 4b and 14e which were docked into the active sites of TGFβR1 to predict their affinities toward the receptor.