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

Claisen Condensation. Behaviour of Esters Towards 3-Acetyl-1,2,3,4-tetrahydro-2,4-dioxo-1-phenylquinoline.

Les (dialkylamino-3' propionyl-2) indanediones-1,3 sont preparees a partir de l'acetyl-2 indanedione-1,3. Leur reactivite vis-a-vis de l'aniline, la glycine, la piperazine, la phenyl hydrazine et l'hydroxylamine est examinee

Synthesis and some reactions of 2-(3-aminopropionyl)-1,3-indandiones

1-azabicyclo[2.2.2]octan-3-one. HCI (1) reacts with ylidene nitrile through photo- thermal reaction conditions to give 4-benzyl-5-imino-3-phenyl-6-oxa-1-aza-tricyclo[6.2.2.0 2 , 7 ]dodec-2(7)-ene-4-carbonitrile. (3) via intermolecular double Micheal reaction, whereas, 5-imino-3-phenyl-6-oxa-1-azatricyclo[6.2.2.0 2 , 7 ]dodec-2(7)-ene-4-carbonitrile (4) was achieved via thermal conditions only.

Intermolecular double Michael reaction to construct 4-benzyl-5-imino-3-phenyl-6-oxa-1-aza-tricyclo[6.2.2.02,7]dodec-2(7)-ene-4-carbonitrile

The new thiopyrano[2,3- b ]pyridines 4 – 9 could be synthesized from the nicotinonitrile derivative 1 . The cytotoxicity activity of the selected compounds 5 , 6 and 8 was tested against MCF-7 and HCT -116 cell lines. The compound 5 ( TP 5 ) exhibited significant inhibitory activity and displayed the most potent activity, more than 6 and 8 . The compound 5 with potent inhibitory activity in tumor growth inhibition would be a potential anticancer agent. In the light of this result, the labeled 125 I-compound 5 ( 125 I -TP 5 ) was prepared and its cytotoxicity against ascites tumor in mice has been evaluated. The results show that compound 5 ( TP 5 ) may be potentially used as a radiopharmaceutical for tumor diagnosis when labeled with 125 I.

/pdf/synthesis-labeling-and-biological-evolution-of-new-3dl72zq78u.pdf

Wafaa S. Hamama

Papers

Claisen Condensation. Behaviour of Esters Towards 3-Acetyl-1,2,3,4-tetrahydro-2,4-dioxo-1-phenylquinoline.

Synthesis and some reactions of 2-(3-aminopropionyl)-1,3-indandiones

Intermolecular double Michael reaction to construct 4-benzyl-5-imino-3-phenyl-6-oxa-1-aza-tricyclo[6.2.2.02,7]dodec-2(7)-ene-4-carbonitrile

Synthesis, Labeling and Biological Evolution of New Thiopyrano[2,3-b]Pyridine Derivatives as Potential Anticancer Agents.

Highlights on the chemistry of 2-amino-3-cyano-quinoxaline 1, 4-dioxides and their derivatives