Esters, amides and substituted derivatives of cinnamic acid: synthesis, antimicrobial activity and QSAR investigations

Narasimhan, Balasubramanian; Belsare, D. P.; Pharande, Devayani; Mourya, Vishnukant; Dhake, Avinash S.

doi:10.1016/j.ejmech.2004.06.013

Cited by 207 publications

(135 citation statements)

References 15 publications

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“…The cinnamic acid and its derivatives are well known for their biological and pharmacological properties: antimicrobial, antioxidant, antiinflamatory, antitumoral (Da Cunha et al, 2004;Narasimhan et al, 2004). Some cinnamic acid derivatives represent secondary metabolites in plants and they have been the subject of a great number of chemical, biological, agricultural and medical studies, the most important category being the hydroxy-cinnamic acids (Urquiaga and Leighton, 2000).…”

Section: Introductionmentioning

confidence: 99%

“…During previous research, a series of cinnamic acid derivatives was synthesized and their antimicrobial activity was evaluated ( Jităreanu, 2011;Narasimhan et al, 2004). The majority of the synthesized compounds proved to be moderately active against gram positive bacteria and some were remarkably active against Candida albicans ( Jitareanu, 2011).…”

Section: Introductionmentioning

confidence: 99%

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Toxicity of Some Cinnamic Acid Derivatives to Common Bean (Phaseolus vulgaris)

Jităreanu

Tătărîngă

Zbancioc

et al. 2011

Not Bot Hort Agrobot Cluj

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Cinnamic acid derivatives are an important class of biologically active compounds, playing an important role in the plants' development, but may also present a wide range of actions: antimicrobial, antioxidant, antiinflamatory, antitumoral. The present study investigated the toxicity of ten cinnamic acid derivatives on Phaseolus vulgaris, this being the first step in evaluating their pharmacotoxicological potential (usually, plant toxicity tests are used for ecotoxicity assessment, but they can also provide some useful general information about the toxic potential of a pharmaceutical substance to living organisms). The bean seeds were exposed to three different concentrations of each substance (28.6 μg/cm 2 , 57.3 μg/cm 2 , 114.6 μg/cm 2 ). All the tests were conducted in Petri dishes, using an artificial substrate (Whatman filter paper) impregnated with the investigated compounds. The analyzed elements were seedling length, root length, percentage of seeds that developed into seedlings, fresh seedling weight and the total polyphenols content. The tested compounds showed phytotoxic effects, inhibiting the growth of the plants and the biosynthesis of polyphenols as compared to the control. The substances with high logP values showed greater phytotoxic potential, but to establish an exact correlation between hydrophobicity and toxicity of the molecules a QSAR analysis must be further done.

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Toxicity of Some Cinnamic Acid Derivatives to Common Bean (Phaseolus vulgaris)

Jităreanu

Tătărîngă

Zbancioc

et al. 2011

Not Bot Hort Agrobot Cluj

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“…This was further supported by the plot of MLR predicted pIC 50 (AT 1 ) values against the observed pIC 50 (AT 1 ) values (Figure 1) and the lowest values of the statistical parameters PE, LSE, LOF and SEP estimated in Table 6 are also in favor of the biparametric model containing log P and LUMO. ) signifies the degree of branching, connectivity of atoms, and the unsaturation in the molecule 19 , which accounts for the variation in the activity of imdazopyridines. To investigate the existence of systemic error in developing the MLR model, the residuals of MLR predicted values of pIC50(AT 1 ) were plotted against the experimental values in Figure 2.…”

Section: Qsar Model For Atmentioning

confidence: 99%

QSAR studies of 4,5-dihydro-4-oxo-3H-imidazo[4,5-c]pyridines as potent angiotensin II receptor antagonists by MLR and NLR analysis

Narasimhan¹,

Dhake²,

Mourya³

2007

Arkivoc

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A quantitative structure activity relationship (QSAR) was employed to find out the correlation between the structural properties and angiotensin II receptor antagonistic activity of 4,5-dihydro-4-oxo-3H-imidazo [4,5-c]pyridines collected from the literature. The multiple linear regression (MLR) and non-linear regression (NLR) analyses have been carried out to derive best QSAR models. The developed models were cross-validated by the 'leave one out' technique as well as by the calculation of statistical parameters. The present investigation indicated the importance of the quantum chemical descriptor, energy of lowest unoccupied molecular orbital, LUMO and the lipophilic parameter, log P, in contribution to the studied biological activity. The results of NLR showed that neglecting log P, based on its low correlation by MLR, as followed by most of the QSAR studies, can lead to fortuitous results and one must perform non-linear regression before coming to a decision on the contribution of the lipophilic parameter, log P.

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“…Furthermore, cinnamic acids derivatives have demonstrated antibacterial and antifungic activities as well as inhibitory activity against low density lipoprotein (LDL) and acetyl-CoA oxidation. [7][8][9] It has been demostrated that caffeic acid (a cinnamic acid analogue) possesses antioxidant properties and may prevent and/or revert acute or chronic hepatic damage caused by CCl 4 administration 10 . Anti oxidant compounds can diminish the oxidative rancidity in foods, as well as prevent several related diseases, such as cancer, diabetes, Alzheimer's and Parkinson's diseases 11 .…”

Section: Introductionmentioning

confidence: 99%

Structural study and antioxidant activity determination of (2E)-N-[2-(morpholin-4-yl)ethyl]-cinnamanilide

Vélez-González¹,

Ortegón-Reyna²,

Ramos-Organillo³

et al. 2007

Arkivoc

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Herein we report the structural study and antioxidant activity of (2E)-N-[2-(morpholin-4-yl) ethyl)-cinnamanilide (1) and its salt (1-HCl). Compound 1 crystallizes as orthorhombic P bca system while its salt is monoclinic P2 1 /n. The supramolecular structures are held in shape by classical (D-H⋅⋅⋅A) and non classical (C-H⋅⋅⋅A) interactions. The antioxidant capability of both compounds shows a structural relationship, compound 1 has moderate capability, meanwhile compound 1-HCl increases its properties owing to the presence of N-H + in the structure.

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Esters, amides and substituted derivatives of cinnamic acid: synthesis, antimicrobial activity and QSAR investigations

Cited by 207 publications

References 15 publications

Toxicity of Some Cinnamic Acid Derivatives to Common Bean (Phaseolus vulgaris)

Toxicity of Some Cinnamic Acid Derivatives to Common Bean (Phaseolus vulgaris)

QSAR studies of 4,5-dihydro-4-oxo-3H-imidazo[4,5-c]pyridines as potent angiotensin II receptor antagonists by MLR and NLR analysis

Structural study and antioxidant activity determination of (2E)-N-[2-(morpholin-4-yl)ethyl]-cinnamanilide

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