Synthesis, antibacterial activity and QSAR studies of 1,2-disubstituted-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinolines

• Published in: European journal of medicinal chemistry 2006, Vol.41 (1), p.40-49
• Main Authors: Tiwari, Rakesh Kumar, Singh, Devender, Singh, Jaspal, Chhillar, Anil Kumar, Chandra, Ramesh, Verma, Akhilesh Kumar
• Format: Article
• Language: English
• Subjects: 1,2,3,4-Tetrahydroisoquinolines; Anti-Bacterial Agents - chemical synthesis; Anti-Bacterial Agents - chemistry; Anti-Bacterial Agents - pharmacology; Antibacterial activity; Antibacterial agents; Antibiotics. Antiinfectious agents. Antiparasitic agents; Biological and medical sciences; Gram-Negative Bacteria - drug effects; Gram-Positive Bacteria - drug effects; Linear free energy relationship (LFER); Medical sciences; Microbial Sensitivity Tests - statistics & numerical data; Pharmacology. Drug treatments; QSAR; Quantitative Structure-Activity Relationship; Tetrahydroisoquinolines - chemical synthesis; Tetrahydroisoquinolines - chemistry; Tetrahydroisoquinolines - pharmacology
• ISSN: 0223-5234; 1768-3254
• DOI: 10.1016/j.ejmech.2005.10.010

Some new substituted-tetrahydroisoquinoline derivatives were synthesized and evaluated for their in vitro antimicrobial activities against the standard Gram positive and Gram negative strains: Staphylococcus aureus (ATCC 25923), S. epidermidis (WHO-6), Escherichia coli (ATCC 25922), Pseudomonas aeruginosa (ATCC 27853), 1-aryl-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline 4a–c proved to be effective with MIC 3.5–20 (μg ml –1). Quantitative structure activity relationship (QSAR) studies with multiple linear regression analysis were applied to find correlation between different calculated molecular descriptors of the synthesized compounds and biological activity. Synthesis, QSAR and in vitro antimicrobial activity of new substituted-tetrahydroisoquinoline derivatives were describe against the standard Gram positive and Gram negative strains and compounds 4a-c were found to be most effective.