Kinetic and thermodynamic control in β-phenylethylamines reaction with isatin

Vélez, Yormari; Díaz-Oviedo, Christian; Quevedo, Rodolfo

doi:10.1016/j.molstruc.2016.12.039

Cited by 7 publications

(4 citation statements)

References 8 publications

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“…The 2LV (LOO) model was used for prediction of a potency of three compounds that were not soluble under experimental conditions (7,12,13). The predicted potency of compound 7 was 3.070 (in pMIC units, which corresponds to 215 μg/mL).…”

Section: Quantitative Structure-activity Relationship (Qsar)mentioning

confidence: 99%

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Detailed solvent, structural, quantum chemical study and antimicrobial activity of isatin Schiff base

Brkić

Božić

Marinković

et al. 2018

Spectrochimica Acta Part A: Molecular and Biomolecular Spectros

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The ratios of E/Z isomers of sixteen synthesized 1,3-dihydro-3-(substituted phenylimino)-2H-indol-2-one were studied using experimental and theoretical methodology. Linear solvation energy relationships (LSER) rationalized solvent influence of the solvent-solute interactions on the UV-Vis absorption maxima shifts (ν) of both geometrical isomers using the Kamlet-Taft equation. Linear free energy relationships (LFER) in the form of single substituent parameter equation (SSP) was used to analyze substituent effect on pK, NMR chemical shifts and ν values. Electron charge density was obtained by the use of Quantum Theory of Atoms in Molecules, i.e. Bader's analysis. The substituent and solvent effect on intramolecular charge transfer (ICT) were interpreted with the aid of time-dependent density functional (TD-DFT) method. Additionally, the results of TD-DFT calculations quantified the efficiency of ICT from the calculated charge-transfer distance (D) and amount of transferred charge (Q). The antimicrobial activity was evaluated using broth microdilution method. 3D QSAR modeling was used to demonstrate the influence of substituents effect as well as molecule geometry on antimicrobial activity.

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Section: Quantitative Structure-activity Relationship (Qsar)mentioning

confidence: 99%

“…The ratio of the integrals in 1 H NMR spectra pointed to the conclusion that the isomers were obtained in a 5:1 ratio (E:Z). Such pattern resulted in conclusion that E isomer is the kinetic product and Z isomer is the thermodynamic product [12].…”

Section: Introductionmentioning

confidence: 99%

Detailed solvent, structural, quantum chemical study and antimicrobial activity of isatin Schiff base

Brkić

Božić

Marinković

et al. 2018

Spectrochimica Acta Part A: Molecular and Biomolecular Spectros

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“…In view of the antiproliferative activity of both THIQs and OXs (including spirooxindoles), we proposed that this particular class of spirofused molecular hybrids of THIQ and OX would display anti-proliferative activity. A review of the literature at the beginning of the study revealed that the 3 0 ,4 0 -dihydro-2 0 Hspiro[indoline-3,1 0 -isoquinolin]-2-one scaffold had been mentioned merely as a by-product of the reaction between isatin and some amines [44] and in a subsequent study of the kinetic and thermodynamic control of the Pictet-Spengler reaction of phenethylamines and isatin [45]. The present study thus focuses on the synthesis of 3 0 ,4 0 -dihydro-2 0 H-spiro[indoline-3,1 0 -isoquinolin]-2ones as molecular hybrids of THIQ and OX, and the evaluation of their anti-proliferative activity (figure 2).…”

Section: Introductionmentioning

confidence: 99%

3′,4′-Dihydro-2′H-spiro[indoline-3,1′-isoquinolin]-2-ones as potential anti-cancer agents: synthesis and preliminary screening

Lobe

Efange

2020

R. Soc. open sci.

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Both tetrahydroisoquinolines (THIQs) and oxindoles (OXs) display a broad range of biological activities including anti-cancer activity, and are therefore recognized as two privileged scaffolds in drug discovery. In the present study, 24 3′,4′-dihydro-2′H-spiro[indoline-3,1′-isoquinolin]-2-ones, designed as molecular hybrids of THIQ and OX, were synthesized and screened in vitro against 59 cell lines in the NCI-60 screen. Twenty compounds displayed weak to moderate inhibition of cell proliferation; among them, three compounds displayed at least 50% inhibition of cell proliferation. The compounds appeared to target primarily renal cell cancer lines; however, leukaemia, melanoma, non-small cell lung cancer, prostate, ovarian and even breast cancer cell lines were also affected. Therefore, this class of spirooxindoles may provide useful leads in the search for new anti-cancer agents.

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“…14 For example, β-phenylethylamines in the reaction with isatin form the mixtures of the two stereoisomers E and Z, which can be thermodynamically or kinetically controlled, but their ratios may vary, depending on compounds structure and conditions. [20][21][22][23][24] It was of interest to find out which of all the mentioned A SURVEY ON ISATIN DERIVATIVES 981 characteristics of the isatin derivatives have the impact on their biological activity.…”

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confidence: 99%

A survey on the characterization and biological activity of isatin derivatives

Drmanic

Petrović

Brkic

et al. 2020

JSCS

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The derivatives of isatin have already been known to display a variety of biological activities. Therefore, the studies on their activity and its relation to structure have recently become a popular subject for investigation. The examined compounds were synthesized by the reaction of isatin and substituted primary amines and characterized by spectroscopic methods. The investigation of the antimicrobial and antioxidative activity of the synthesized compounds was performed by broth microdilution method. As for the characterization of the investigated isatin based Schiff bases, the linear solvation energy relationships (LSER) were used to analyze the solvent influence on the UV absorption maxima shifts (?max), using the well known Kamlet?Taft model and taking geometrical isomers into consideration when possible. Linear free energy relationships (LFER) were used to analyze substituent effect on pKa, as well as NMR chemical shifts and ?max values. The antimicrobial activity and characterization were related using both experimental and theoretical methods. [Project of the Serbian Ministry of Education, Science and Technological Development, Grant no. 172013]

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Kinetic and thermodynamic control in β-phenylethylamines reaction with isatin

Cited by 7 publications

References 8 publications

Detailed solvent, structural, quantum chemical study and antimicrobial activity of isatin Schiff base

Detailed solvent, structural, quantum chemical study and antimicrobial activity of isatin Schiff base

3′,4′-Dihydro-2′H-spiro[indoline-3,1′-isoquinolin]-2-ones as potential anti-cancer agents: synthesis and preliminary screening

A survey on the characterization and biological activity of isatin derivatives

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