Synthesis and antimycobacterial evaluation of novel 5,6-dimethoxy-1-oxo-2,5-dihydro-1H-2-indenyl-5,4-substituted phenyl methanone analogues

Ali, Mohamed Ashraf; Samy, Jeyabalan Govinda; Elumalai, Manogaran; Velmurugan, Sellappan; Hasan, Mohamed Zaheen; Ahsan, Mohamed Jawed; Pandian, Suresh; Yar, Mohammad Shahar

doi:10.1016/j.bmcl.2009.10.034

Cited by 23 publications

(13 citation statements)

References 3 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…2-[(E)-1-(substituted aryl) methylidene]-1-indanones were synthesized by Claisen-Schmidt condensation according to the literature method (Ali et al, 2009), followed by synthesis of dispiropyrrolidines via 1,3-dipolar cycloaddition of azomethine ylides generated in situ from the decarboxylative condensation of ninhydrin or acenaphthenequinone and thiazolidine-4-carboxylic acid with appropriate dipolarophiles, 2-[(E)-1-arylmethylidene]-1-indanones (Schemes 1, 2). Purity of the newly synthesized dispiropyrrolidines was checked using NMR, CHN, and mass spectrometry.…”

Section: Resultsmentioning

confidence: 99%

Antimycobacterial activity and in silico study of highly functionalised dispiropyrrolidines

et al. 2014

Self Cite

View full text Add to dashboard Cite

Two series of novel and highly functionalised dispiropyrrolidines were synthesized using 1,3-dipolar cycloaddition reaction. The synthesized compounds were screened for their antimycobacterial activity against M. tuberculosis H 37 Rv using the Promega reagent BacTiter-Glo TM Microbial Cell Viability (BTG). Molecular docking analysis was carried out for the active compounds against the target enzyme enoyl-ACP reductase (InhA) to understand the possible binding mode. Of the 24 novel synthesized compounds, seven dispiropyrrolidines revealed inhibition with EC 50 \25 lM. Compound 5b 7 0 -(4-chlorophenyl)-5 0 ,6 0 ,7 0 ,7a 0 -tetrahydrodispiro[indan-2,5 0 -pyrrolo [1,2-c]-[1,3]thiazole-6 0 ,2 00 -indan]-1,3,1 00 -trione was found to be the most active with EC 50 of 10.52 lM, and was 2.2-fold more active than cycloserine. The docking result revealed that 5b had good affinity with the catalytic residues in InhA, forming hydrophobic and mild polar interactions with the important amino acids in the active site.

show abstract

Section: Resultsmentioning

confidence: 99%

Antimycobacterial activity and in silico study of highly functionalised dispiropyrrolidines

et al. 2014

Self Cite

View full text Add to dashboard Cite

show abstract

“…General method for the preparation of 2-[(E)-1-(substituted aryl) methylidene]- 5,6-dimethoxy-1-indanone (2a-2o) [6][7].…”

Section: General Proceduresmentioning

confidence: 99%

“…Based on the prevalence of disease and the availability of limited options of drugs for the treatment of AD, Continuation of our previous work [7] we planned to develop novel drugs for AD. In the present investigation potent heterocyclic compounds were developed targeting AChE.…”

Section: Introductionmentioning

confidence: 99%

Alzheimer Diseases: Substituted Spiro [2.3′] Oxindolespiro [3.2″]- 5, 6-Dimethoxy-Indane-1″-One- Indolizine Analogue as Inhibitors of Acetylcholinesterase

Ali¹,

Ismail²,

Choon³

et al. 2012

Med Chem

View full text Add to dashboard Cite

Indanone derivatives share vital pharmacological properties, considered useful in alzheimer's disease (AD).The aim of this study was synthesis and evaluate indolizine analogues if possess acetyl cholinesterase (AChE)inhibitory activity. The easily accessible three-step synthesis of these compounds resulted to be significantly less difficult and expensive than that of donepezil. Several compounds possess anti-cholinesterase activity in the order of micro and sub-micromolar. Particularly, compound 3k was the most potent inhibitors of the series. Compound 3k, showed potent inhibitory activity against acetyl cholinesterase enzyme with IC 50 0.10 µmol/L. Indolizine analogues might be potential acetyl cholinesterase agents for AD.

show abstract

“…However, highly effective new anti-TB drugs have not been developed in the last 40 years. Literature survey of novel chemotherapeutic agents reveals that the substituted pyrazoline derivatives are proved to be active against many mycobacterial species [8][9][10][11][12][13][14] . Based on these literatures, the current work was designed to synthesize novel indane substituted pyrazoline derivatives.…”

Section: Short Communicationmentioning

confidence: 99%

Synthesis and biological evaluation of novel 6, 7-dimethoxy-3-(4-pyridyl)-2,3,3a,4-tetrahydroindeno[1,2-c]pyrazol-2-yl-4-substituted phenylmethanone/ethanone derivatives

Ali

Ismail

Choon

et al. 2011

Journal of Enzyme Inhibition and Medicinal Chemistry

Self Cite

View full text Add to dashboard Cite

Synthesis and antimycobacterial evaluation of novel 5,6-dimethoxy-1-oxo-2,5-dihydro-1H-2-indenyl-5,4-substituted phenyl methanone analogues

Cited by 23 publications

References 3 publications

Antimycobacterial activity and in silico study of highly functionalised dispiropyrrolidines

Antimycobacterial activity and in silico study of highly functionalised dispiropyrrolidines

Alzheimer Diseases: Substituted Spiro [2.3′] Oxindolespiro [3.2″]- 5, 6-Dimethoxy-Indane-1″-One- Indolizine Analogue as Inhibitors of Acetylcholinesterase

Synthesis and biological evaluation of novel 6, 7-dimethoxy-3-(4-pyridyl)-2,3,3a,4-tetrahydroindeno[1,2-c]pyrazol-2-yl-4-substituted phenylmethanone/ethanone derivatives

Contact Info

Product

Resources

About