Coumarin compounds represent an important type of naturally occurring and synthetic oxygen-containing heterocycles with typical benzopyrone framework. This type of special benzopyrone structure enables its derivatives readily interact with a diversity of enzymes and receptors in organisms through weak bond interactions, thereby exhibit wide potentiality as medicinal drugs. So far, some coumarin-based drugs such as anticoagulant and antineurodegenerative agents have been extensively used in clinic. Coumarin-containing supramolecular medicinal agents as a new increasing expansion of supramolecular chemistry in pharmaceutical science have also been actively investigated in recent years. Coumarin-derived artificial ion receptors, fluorescent probes and biological stains are growing quickly and have a variety of potential applications in monitoring timely enzyme activity, complex biological events as well as accurate pharmacological and pharmacokinetic properties. This review provides a systematic summary and insight of the whole range of medicinal chemistry in the current developments of coumarin compounds as anticoagulant, antineurodegenerative, anticancer, antioxidative, antibacterial, antifungal, antiviral, antiparasitic, antiinflammatory and analgesic, antidiabetic, antidepressive and other bioactive agents as well as supramolecular medicinal drugs, diagnostic agents and pathologic probes, and biological stains. Some rational design strategies, structure-activity relationships and action mechanisms are discussed. The perspectives of the future development of coumarinbased medicinal chemistry are also presented.

Current Developments of Coumarin Compounds in Medicinal Chemistry

Further advances in the chemistry of mannich bases

Current developments of coumarin-based anti-cancer agents in medicinal chemistry

Coumarin heterocyclic derivatives: chemical synthesis and biological activity

The synthesis of complex organic compounds is largely a manual process that is often incompletely documented. To address these shortcomings, we developed an abstraction that maps commonly reported methodological instructions into discrete steps amenable to automation. These unit operations were implemented in a modular robotic platform using a chemical programming language which formalizes and controls the assembly of the molecules. We validated the concept by directing the automated system to synthesize three pharmaceutical compounds, Nytol, rufinamide, and sildenafil, without any human intervention. Yields and purities of products and intermediates were comparable to or better than those achieved manually. The syntheses are captured as digital code that can be published, versioned, and transferred flexibly between platforms with no modification, thereby greatly enhancing reproducibility and reliable access to complex molecules.

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Organic synthesis in a modular robotic system driven by a chemical programming language

3-Acetylcoumarin (1) was utilized as a key intermediate for the synthesis of 2-aminothiazole derivative 3
 via bromination of 1 followed by treatment of the formed acetylbromide 2 with thiourea or via Bignailli reaction of 1. Treatment of 3 with 2 afforded the bis-coumarin 4, whereas, cyanoacetylation of 3 followed by treatment of the formed cyanoacetamide 6 with salicyaldehyde give the bis-coumarin 7. Reaction of 6 with phenyl isothiocyanate in DMF/KOH produced the potassium salt 8, which cyclized with chloroacetyl chloride to give the thiazolidinone 9. Acidification of 8 with HCl afforded the thiocarbamoyl 10, which condensed with 2 in DMF to give the mercapto derivative 12, whereas in DMF/TEA gave the thiophene derivative 13. The thiophenes 15a–c were achieved via treatment of the thiocarbamoyls 14a–c with 2 in DMF/TEA, whereas, in DMF gave the corresponding thiazoles 16a–c. Treatment of the components 17a, b with carbon disulfide in DMF/KOH followed by addition of 2 afforded the dithioacetals 19a, b. Cyclization of 19b under alkaline condition gave the desired thiophene 20. Representative compounds of the synthesized products were evaluated as antitumor and antioxidant agents. 3-Acetylcoumarin (1) was utilized as a key intermediate for the synthesis of different coumarin derivatives. Newly synthesized compounds were elucidated by analytical and spectral data. Representative compounds of the synthesized products were evaluated as antitumor and antioxidant agents.

Synthesis, antitumor and antioxidant evaluation of some new thiazole and thiophene derivatives incorporated coumarin moiety

Recent advances in the chemistry of selenium-containing heterocycles: Five-membered ring systems

Pyrazolones as versatile precursors for the synthesis of fused and binary heterocycles

Chemistry of Pyrazolinones and their Applications

This review highlights the recently cited research data in the literature on the chemistry of 2-chloroquinoline-3-carbaldehyde and related analogs and their applications over the period from 2013 to 2017. It covers: synthesis of quinoline ring systems and reactions adopted to construct fused or binary quinoline-cord heterocyclic systems. The biological evaluation and the synthetic applications of the target compounds were illustrated.

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Wafaa S. Hamama

Papers

Synthesis, antitumor and antioxidant evaluation of some new thiazole and thiophene derivatives incorporated coumarin moiety

Recent advances in the chemistry of selenium-containing heterocycles: Five-membered ring systems

Pyrazolones as versatile precursors for the synthesis of fused and binary heterocycles

Chemistry of Pyrazolinones and their Applications

Recent advances in the chemistry of 2-chloroquinoline-3-carbaldehyde and related analogs