Biologically active quinoline and quinazoline alkaloids part I

Abstract

Quinoline and quinazoline alkaloids, two important classes of N-based heterocyclic compounds, have attracted tremendous attention from researchers worldwide since the 19th century. Over the past 200 years, many compounds from these two classes were isolated from natural sources, and most of them and their modified analogs possess significant bioactivities. Quinine and camptothecin are two of the most famous and important quinoline alkaloids, and their discoveries opened new areas in antimalarial and anticancer drug development, respectively. In this review, we survey the literature on bioactive alkaloids from these two classes and highlight research achievements prior to the year 2008 (Part I). Over 200 molecules with a broad range of bioactivities, including antitumor, antimalarial, antibacterial and antifungal, antiparasitic and insecticidal, antiviral, antiplatelet, anti-inflammatory, herbicidal, antioxidant and other activities, were reviewed. This survey should provide new clues or possibilities for the discovery of new and better drugs from the original naturally occurring quinoline and quinazoline alkaloids.

Quinoline‐Conjugated Ruthenacarboranes: Toward Hybrid Drugs with a Dual Mode of Action

“…We chose to combine an [( η 6 ‐arene)Ru] 2+ ‐carborane unit with a 1‐aza‐naphtalene‐based organic residue, commonly known as quinoline (Figure ). Quinoline derivatives possess a plethora of biological activities, which have prompted the development of numerous drugs, ranging from antiparasitic (e. g. chloroquine and its ferrocene analogue ferroquine), to antiviral (e. g. saquinavir), antibacterial (e. g. ciprofloxacin), anti‐inflammatory (e. g. quinoline alkaloids), antioxidant (e. g. quinoline glycoconjugates), antineoplastic (e. g. irinotecan), and many others –. The specific type and position of substituents on the heterocycle influence the physicochemical and pharmacologic properties of the quinoline‐containing molecules, and thus modulate the activity of the drug, as reported for example by Natarajan et al.…”

Topoisomerase 1B poisons: Over a half‐century of drug leads, clinical candidates, and serendipitous discoveries

“…Polymers and delivery systems have also been covalently linked to 1 or derivatives, usually at the E‐ring hydroxyl. For more comprehensive information about noncovalent delivery systems and conjugates for/of CPTs, the reviews of Venditto and Shang are highly recommended. Several notable examples have progressed into human clinical trials.…”

4-Hydroxy-3-methyl-2(1H)-quinolone, originally discovered from a Brassicaceae plant, produced by a soil bacterium of the genus Burkholderia sp.: determination of a preferred tautomer and antioxidant activity

“…4-Hydroxy-2(1H)-quinolone is a unique structural motif mostly found in alkaloids from rutaceous plants (family Rutaceae) [1,2]. This motif has several tautomeric forms including 2,4-dihydroxyquinoline [3], although which tautomer to be taken seems not always be identified in some of the studies.…”