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A facile stereoselective synthesis of dispiro-indeno pyrrolidine/pyrrolothiazole–thiochroman hybrids and evaluation of their antimycobacterial, anticancer and AchE inhibitory activities
- Source :
- Bioorganic & Medicinal Chemistry. 24:5873-5883
- Publication Year :
- 2016
- Publisher :
- Elsevier BV, 2016.
-
Abstract
- A facile stereoselective synthesis of novel dispiro indeno pyrrolidine/pyrrolothiazole–thiochroman hybrids has been achieved by 1,3-dipolar cycloaddition of azomethine ylides, generated in situ from ninhydrin and sarcosine/thiaproline, on a series of 3-benzylidenethiochroman-4-ones. The synthesised compounds were screened for their antimycobacterial, anticancer and AchE inhibition activities. Compound 4l (IC50 1.07 μM) has been found to exhibit the most potent antimycobacterial activity compared to cycloserine (12 times), pyrimethamine (37 times) and ethambutol (IC50
- Subjects :
- Models, Molecular
Pyrrolidines
Sarcosine
Cell Survival
medicine.drug_class
Stereochemistry
Clinical Biochemistry
Pharmaceutical Science
Antineoplastic Agents
Microbial Sensitivity Tests
010402 general chemistry
Antimycobacterial
01 natural sciences
Biochemistry
Pyrrolidine
Structure-Activity Relationship
chemistry.chemical_compound
Cell Line, Tumor
Drug Discovery
medicine
Humans
Spiro Compounds
Molecular Biology
Cell Proliferation
Dose-Response Relationship, Drug
Molecular Structure
010405 organic chemistry
Chemistry
Organic Chemistry
Cycloserine
Stereoisomerism
Mycobacterium tuberculosis
Cycloaddition
Anti-Bacterial Agents
0104 chemical sciences
Thiazoles
Indenes
Chromones
Ninhydrin
1,3-Dipolar cycloaddition
Acetylcholinesterase
Molecular Medicine
Stereoselectivity
Cholinesterase Inhibitors
Drug Screening Assays, Antitumor
medicine.drug
Subjects
Details
- ISSN :
- 09680896
- Volume :
- 24
- Database :
- OpenAIRE
- Journal :
- Bioorganic & Medicinal Chemistry
- Accession number :
- edsair.doi.dedup.....b2586640a1917d068fd7d805ebdf7af0