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5-Chloro-2-thiophenyl-1,2,3-triazolylmethyldihydroquinolines as dual inhibitors of Mycobacterium tuberculosis and influenza virus: Synthesis and evaluation
- Source :
- Bioorganic & Medicinal Chemistry Letters. 29:2664-2669
- Publication Year :
- 2019
- Publisher :
- Elsevier BV, 2019.
-
Abstract
- This study describes synthesis and evaluation of novel 5-Chloro-2-thiophenyl-1,2,3-triazolylmethyldihydroquinolines 7a-o as dual inhibitors of Mycobacterium tuberculosis and influenza virus. Huisgen’s [3+2] dipolar cycloaddition of 6-(azidomethyl)-5-chloro-2-(thiophen-2-yl)-7,8-dihydroquinoline 5 with various alkynes 6a-o using sodium ascorbate and copper sulphate gave new dihydroquinoline-1,2,3-triazoles 7a-o in good to excellent yields. The new compounds were evaluated for in vitro antimycobacterial against M. tuberculosis H37Rv (Mtb) and antiviral activity against influenza virus A/Puerto Rico/8/34 (H1N1). Among the fifteen new analogs, compounds 7a (MIC: 3.12 µg/mL), 7j and 7k (MIC: 6.25 µg/mL) were identified as potent antitubercular agents. The virus-inhibiting activity of all the fifteen compounds was found to be moderate, and among them the compound 7l, bearing thiophene moiety appeared the most active with good selectivity index (IC50 = 19.5 µg/mL; SI = 15). The results presented here will help developing newer dual inhibitors of tuberculosis and influenza virus.
- Subjects :
- Sodium ascorbate
Tuberculosis
medicine.drug_class
Stereochemistry
Clinical Biochemistry
Antitubercular Agents
Triazole
Pharmaceutical Science
Microbial Sensitivity Tests
Antimycobacterial
Antiviral Agents
01 natural sciences
Biochemistry
Virus
Mycobacterium tuberculosis
Structure-Activity Relationship
chemistry.chemical_compound
Drug Discovery
medicine
Moiety
Molecular Biology
Dose-Response Relationship, Drug
Molecular Structure
biology
010405 organic chemistry
Organic Chemistry
Orthomyxoviridae
medicine.disease
biology.organism_classification
Cycloaddition
0104 chemical sciences
010404 medicinal & biomolecular chemistry
chemistry
Molecular Medicine
Subjects
Details
- ISSN :
- 0960894X
- Volume :
- 29
- Database :
- OpenAIRE
- Journal :
- Bioorganic & Medicinal Chemistry Letters
- Accession number :
- edsair.doi.dedup.....00be46294ecdfeb39d5b61aa7861a2f9