Abstract
The tetracyclic indolo[3,2-b]quinoline ring system constitutes an important structural moiety in natural products exhibiting numerous biological activities. In particular, indolo [3, 2-b]quinoline, commonly known as linear quindoline is of particular interest, because of its rigid structure and scope of derivatization. Although the core linear quindoline skeleton shows little or no activity in several biological systems, introduction of a methyl group on the N-5 atom leading to cryptolepine induces remarkable activity against a broad spectrum of biological targets. A number of analogs of quindoline and cryptolepine have been synthesized, incorporating various functional groups on the core quindoline skeleton leading to improved biological activities. In this review, we describe various synthetic methodologies leading to the quindoline scaffold, the biological activities and the structure activity relationships (SAR) of quindoline derivatives toward different disease states to give a better picture of the importance of this moiety in medicinal chemistry.
Publication types
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Research Support, N.I.H., Extramural
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Research Support, Non-U.S. Gov't
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Review
MeSH terms
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Alkaloids* / chemical synthesis
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Alkaloids* / chemistry
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Alkaloids* / pharmacology
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Animals
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Anti-Bacterial Agents / chemical synthesis
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Anti-Bacterial Agents / chemistry
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Anti-Bacterial Agents / pharmacology
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Antifungal Agents / chemical synthesis
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Antifungal Agents / chemistry
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Antifungal Agents / pharmacology
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Antineoplastic Agents / chemical synthesis
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Antineoplastic Agents / chemistry
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Antineoplastic Agents / pharmacology
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Antiprotozoal Agents / chemical synthesis
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Antiprotozoal Agents / chemistry
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Antiprotozoal Agents / pharmacology
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Humans
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Hypoglycemic Agents / chemical synthesis
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Hypoglycemic Agents / chemistry
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Hypoglycemic Agents / pharmacology
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Indoles* / chemical synthesis
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Indoles* / chemistry
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Indoles* / pharmacology
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Quinolines* / chemical synthesis
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Quinolines* / chemistry
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Quinolines* / pharmacology
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Structure-Activity Relationship
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Vasodilator Agents / chemical synthesis
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Vasodilator Agents / chemistry
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Vasodilator Agents / pharmacology
Substances
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Alkaloids
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Anti-Bacterial Agents
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Antifungal Agents
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Antineoplastic Agents
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Antiprotozoal Agents
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Hypoglycemic Agents
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Indoles
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Quinolines
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Vasodilator Agents
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quindoline