The rhodium(ii)-catalyzed one-pot three-component reaction of 3-diazooxindole, benzyl alcohol and isatin or ninhydrin or acenaphthenequinone was explored to synthesize 3-bisoxindoles, 2-oxindolyl-2-hydroxyindan-1,3-diones and 2-oxindolyl-2-hydroxyacenaphthylen-1-ones with vicinal stereo centres, respectively through oxonium ylides. Their antibacterial activities against Staphylococcus aureus NCIM 5021, Escherichia coli NCIM 2931, Pseudomonas aeruginosa NCIM 5029, Salmonella typhimurium NCIM 2501 and Proteus vulgaris NCIM 2813 were evaluated by a microdilution method. Group-based quantitative structure activity relationships (GQSAR) for all antibacterial activities were developed. The statistical measures namely r2 (0.66-0.85), r 2 adj (0.63-0.84), q2 (0.54-0.79) and F-ratio (11.63-34.17) were found to be satisfactory. All of the test and training set compounds were found to be within a 99% confidence level. Descriptors pertaining to hydrophobicity, topology and electrostatic interactions of the substitutions were found to contribute to their activities. © 2013 The Royal Society of Chemistry.

Mukesh Doble

Department Of Biotechnology

Ponnurengan Malliappan Sivakumar

ACENAPHTHENEQUINONE

Anti-bacterial activity

benzyl alcohol

Confidence levels

Descriptors

F-RATIO

GROUP-BASED

MICRODILUTION

NINHYDRIN

One pot

OXONIUM

PROTEUS VULGARIS

Pseudomonas aeruginosa

QUANTITATIVE STRUCTURE ACTIVITY RELATIONSHIP

Salmonella typhimurium

Staphylococcus aureus

STATISTICAL MEASURES

THREE COMPONENT REACTIONS

TRAINING SETS

Escherichia coli

Molecular graphics

Rhodium

Salmonella

Synthesis (chemical)

Fulltext

IIT Madras is a public technical and research university located in Chennai, Tamil Nadu. Founded in 1959, it is recognised as an Institute of National Importance.

IIT Madras has been ranked as the top engineering institute in India for four years in a row by the National Institutional Ranking Framework of the MHRD

It currently offers undergraduate, postgraduate and research degrees across 16 disciplines in Engineering, Sciences, Humanities and Management. About 596 faculty belonging to science and engineering departments and centres of the Institute are engaged in teaching, research and industrial consultancy.

IIT Madras

RSC Advances

Sixteen 1,3,5-triphenyl-2-pyrazolines were synthesized and their anti-infective activities (against Mycobacterium tuberculosis H37Rv, six bacterial and four fungal strains) were tested. Only compound with SO2CH3 in the para position of the A-ring was active against the tubercular strain at 100 μg/ml concentration. All compounds showed good anti infective activity against Escherichia coli and poor activity against Staphylococcus aureus. Compounds 4, 12, 13 and 14 exhibited reasonable activity against all the organisms tested (&lt;0.309 μM except against S. aureus. The activity of these compounds correlated with their lipophilic/hydrophilic nature. Compounds 4, 10 and 16 showed very good activity (&gt;88% reduction) against four fungi studied at 2 mg/ml. All these compounds possess halogen substitutions. Compound 11 showed very high activity (&gt;90%) against three fungi. Majority of the compounds showed more than 90% inhibition against one or two fungi. Since pyrazolines are reported to inhibit the activity of p-glycoprotein, they may prevent drug resistance developed by microorganism. © 2010 Elsevier Ltd. All rights reserved.

Bioorganic and Medicinal Chemistry Letters

Novel 1,3,5-triphenyl-2-pyrazolines as anti-infective agents

In order to develop relatively small molecules as antimycobacterial agents, twenty-five chalcones were synthesized, their activity was evaluated, and quantitative structure-activity relationship (QSAR) was developed. The synthesis was based on the Claisen-Schimdt scheme and the resultant compounds were tested for antitubercular activity by luciferase reporter phage (LRP) assay. Compound C24 was found to be the most active (∼99%) in this series based on the percentage reduction in Relative Light Units at both 50 and 100 μg/ml levels, followed by compound C21. Four compounds at the 50 μg/ml and eight compounds at the 100 μg/ml showed activity above 90% level. QSAR model was developed between activity and spatial, topological, and ADME descriptors for the 50 μg/ml data. The statistical measures such as r, r2, q2, and F values obtained for the training set were in acceptable range and hence this relationship was used for the test set. The predictive ability of the model is satisfactory (q2 = 0.56) and it can be used for designing similar group of compounds. © 2007 Elsevier Ltd. All rights reserved.

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

Chemical Biology & Drug Design

10.1111/cbdd.2014.84.issue-6

Journal of Molecular Graphics and Modelling

A comprehensive structure–activity analysis of protein kinase B-alpha (Akt1) inhibitors

ChemInform

ChemInform Abstract: InCl3-Catalyzed Efficient One-Pot Synthesis of 2-Pyrrolo-3′-yloxindoles.

Expeditious synthesis, antibacterial activity evaluation and GQSAR studies of 3-bisoxindoles, 2-oxindolyl-2-hydroxyindan-1,3-diones and 2-oxindolyl-2-hydroxyacenaphthylen-1-ones

Journal	RSC Advances
ISSN	20462069
Open Access	No