Simple isoquinoline and benzylisoquinoline alkaloids as potential antimicrobial, antimalarial, cytotoxic, and anti-HIV agents

• Published in: Bioorganic & medicinal chemistry Vol. 9; no. 11; pp. 2871 - 2884
• Main Authors: IWASA, Kinuko, MORIYASU, Masataka, TACHIBANA, Yoko, KIM, Hye-Sook, WATAYA, Yusuke, WIEGREBE, Wolfgang, BASTOW, Kenneth F, COSENTINO, L. Mark, KOZUKA, Mutsuo, LEE, Kuo-Hsiung
• Format: Journal Article
• Language: English
• Published: Oxford Elsevier Science 01.11.2001
• Subjects: Alkaloids - chemical synthesis; Alkaloids - chemistry; Alkaloids - pharmacology; Animals; Anti-Bacterial Agents; Anti-HIV Agents - chemical synthesis; Anti-HIV Agents - chemistry; Anti-HIV Agents - pharmacology; Anti-Infective Agents - chemical synthesis; Anti-Infective Agents - chemistry; Anti-Infective Agents - pharmacology; Antibiotics. Antiinfectious agents. Antiparasitic agents; Antimalarials - chemical synthesis; Antimalarials - chemistry; Antimalarials - pharmacology; Antineoplastic Agents - chemical synthesis; Antineoplastic Agents - chemistry; Antineoplastic Agents - pharmacology; Biological and medical sciences; Candida albicans - drug effects; Cell Division - drug effects; Crystallization; Drug Evaluation, Preclinical; Gram-Negative Bacteria - drug effects; Gram-Positive Bacteria - drug effects; HIV-1 - drug effects; Humans; Isoquinolines - chemical synthesis; Isoquinolines - chemistry; Isoquinolines - pharmacology; Magnetic Resonance Spectroscopy; Medical sciences; Mice; Microbial Sensitivity Tests; Miscellaneous. Antibiotics with multiple activities; Pharmacology. Drug treatments; Plasmodium falciparum - drug effects; Structure-Activity Relationship; Tumor Cells, Cultured - drug effects; Antineoplastic agent; Antimalarial; Organic cation; Nitrogen heterocycle; Cytotoxicity; Screening test; Antimicrobial agent; Plasmodium falciparum; Alkaloid; Structure activity relation; Benzylic compound; Parasiticid; Bicyclic compound; Antiviral; Aromatic compound; Chemical synthesis; Protozoa; Apicomplexa; Isoquinoline derivatives; Iminium compounds; Retroviridae; Lentivirus; In vitro; Virus; Phenols; Human immunodeficiency virus
• ISSN: 0968-0896; 1464-3391
• DOI: 10.1016/S0968-0896(01)00154-7

Twenty-six simple isoquinolines and 21 benzylisoquinolines were tested for antimicrobial, antimalarial, cytotoxic, and anti-HIV activities. Some simple isoquinoline alkaloids were significantly active in each assay, and may be useful as lead compounds for developing potential chemotherapeutic agents. These compounds include 13 (antimicrobial), 25, 26, and 42 (antimalarial), 13 and 25 (cytotoxic), and 28 and 29 (anti-HIV). A quaternary nitrogen atom of isoquinolium or dihydroisoquinolinium type may contribute to enhanced potency in the first three types of activities. In contrast, anti-HIV activity was found with tetrahydroisoquinoline and 6,7-dihydroxyisoquinolium salts.