Synthesis, antimycobacterial activity evaluation, and QSAR studies of chalcone derivatives

Sivakumar, Ponnurengam Malliappan; Subbiah, Seenivasan; Kumar, Vanaja; Doble, Mukesh

doi:10.1016/j.bmcl.2006.12.112

Cited by 105 publications

(65 citation statements)

References 27 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…In fact a number of studies have reported positive correlation between log P values and antimycobacterial properties. 4,29 Hence the log P figures of the compounds in series 1-8 were calculated and are presented in Table 1. While no definite conclusions were drawn between the antimycobacterial potencies and hydrophobicity, two observations may be noted.…”

Section: Discussionmentioning

confidence: 99%

N-Aroyl-3,5-bis(benzylidene)-4-piperidones: A novel class of antimycobacterial agents

Das

Bandy

et al. 2008

Bioorganic & Medicinal Chemistry

View full text Add to dashboard Cite

A number of 3,5-bis(benzylidene)-4-piperidones 1 and some N-4-(2-aminoethoxy)phenylcarbonyl analogs 3-6 display excellent in vitro antimycobacterial properties. In particular, 1c and 6d are potent antimycobacterials which are well tolerated in mice and are identified as important lead molecules. The nature of both the benzylidene aryl rings and the terminal basic groups which affect the antimycobacterial potencies and the absence of neurotoxic side effects were identified. Several representative compounds stimulated respiration in mitochondria isolated from rat liver and this effect was not caused by the swelling of these organelles. Various guidelines for the creation of further related novel antimycobacterial agents are provided.

show abstract

Section: Discussionmentioning

confidence: 99%

N-Aroyl-3,5-bis(benzylidene)-4-piperidones: A novel class of antimycobacterial agents

Das

Bandy

et al. 2008

Bioorganic & Medicinal Chemistry

View full text Add to dashboard Cite

show abstract

“…where N is the number of compounds in the training set; r 2 the indicators of the model data fit; and r 2 CV is an indication of the predictive capability of the model [38]. The inter-correlation of the descriptors appeared in the above best model was taken into account and the descriptors were found to be reasonably orthogonal (Table 6).…”

Section: D-qsar Modelmentioning

confidence: 99%

Quantitative Structure–Activity Relationship Analysis of Some Thiourea Derivatives with Activities Against HIV‐1 (IIIB)

Chen

Xie

et al. 2009

QSAR Comb. Sci.

View full text Add to dashboard Cite

Two-dimensional (2D) and Three-dimensional (3D) Quantitative Structure -Activity Relationship (QSAR) studies have been carried out on a series of 42 recently synthesized thiourea derivatives to find out the structural requirements of their protection of MT-4 cells against Human Immunodeficiency Virus (HIV)-1 (IIIB). The statistically significant 2D-QSAR model (r 2 ¼ 0.897) was developed by Genetic Function Approximation (GFA) when the number of descriptors in equation was set to four, indicating descriptors of S_aaCH, Shadow_XYfrac, Lowest Unoccupied Molecular Orbital (LUMO), and Hydrogen-Bond Acceptors (Hbond Acceptor) mainly control the bioactivity. The validation of the model was done by the full cross-validation tests, randomization tests, and external test set prediction. Molecular Field Analysis (MFA) investigated the substitutional requirements for the favorable receptor -drug interaction and constructed the best 3D-QSAR model using Genetic Partial Least Squares (G/PLS) method, showing that the electrostatic fields contribute significantly toward bioactivity. The results obtained by combining both methodologies give insight into the key features for designing more potent analogs against HIV-1(IIIB).

show abstract

“…Further, synthetic constituents selected for investigation possess i) a carbonyl group in conjugation with a double bond as this is reported to have a profound effect on the activity of various pharmacologically important compounds, 17,18) and ii) a basic chalcone nucleus (1c-1i), as several naturally occurring and synthetic compounds with chalcone as the core nucleus have been reported to have broad spectrum biological activity, 19) such as insecticidal, 20) antifungal, 21) antioxidant, [22][23][24] tyrosinase inhibitory, antimitotic, 26) and antibacterial activity. 27,28) In addition, all of the compounds can be synthesized easily at ambient temperature and pressure with minimum use of hazardous chemicals.…”

Section: Introductionmentioning

confidence: 99%

Synergistic fungicidal efficacy of formulations of neem oil, nicotinic acid and Ferula asafoetida with .ALPHA., .BETA.-unsaturated carbonyl compounds against Sclerotium rolfsii ITCC 5226 & Macrophomina phaseolina ITCC 0482

2009

View full text Add to dashboard Cite

Ninety formulations of neem oil (Azadirachta indica), N1; nicotinic acid, N2; and Ferula asafoetida, N3 at different concentrations with a, b-unsaturated carbonyl compounds (1a-1i), were screened in vitro against Sclerotium rolfsii ITCC 5226 and Macrophomina phaseolina ITCC 0482 following the Food Poisoning Method. Formulation 3 : 1,1a-N2(Ϫ) was found to be the most effective against S. rolfsii, enhancing the activity of 1a 2.7 times at 66 ppm, whereas 3 : 1,1f-N3 was found to be 5 times more active against M. phaseolina than 1f alone. A number of other formulations also showed significant synergistic effect in increasing fungicidal activity. The current study showed that the combination of synthetic and natural products may be an effective novel alternate approach to control pathogenic fungi.

show abstract

Synthesis, antimycobacterial activity evaluation, and QSAR studies of chalcone derivatives

Cited by 105 publications

References 27 publications

N-Aroyl-3,5-bis(benzylidene)-4-piperidones: A novel class of antimycobacterial agents

N-Aroyl-3,5-bis(benzylidene)-4-piperidones: A novel class of antimycobacterial agents

Quantitative Structure–Activity Relationship Analysis of Some Thiourea Derivatives with Activities Against HIV‐1 (IIIB)

Synergistic fungicidal efficacy of formulations of neem oil, nicotinic acid and Ferula asafoetida with .ALPHA., .BETA.-unsaturated carbonyl compounds against Sclerotium rolfsii ITCC 5226 & Macrophomina phaseolina ITCC 0482

Contact Info

Product

Resources

About