Synthesis and biological evaluation of hydroxylcoumarin derivatives as antioxidant agents

Chen, Chen; Wang, Ping; Zou, Li-Wei; Yang, Ling; Ye, Fan; Wen-zhong, HU; Ge, Guang-Bo

doi:10.1007/s40242-017-6411-8

Cited by 5 publications

(2 citation statements)

References 22 publications

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“…Wang et al designed and synthesized a series of C-4 and C-8 substituted esculetin derivatives by perchloric acid catalyzed von Pechmann reaction and Mannich reaction, respectively. [270] 6,7-Dihydroxy-4-trifluoromethyl-coumarin 487, obtained by treatment of 1,2,4-phenenyl triacetate 486 and ethyl 4,4,4trifluoro-3-oxobutanoate 1 in the presence of perchloric acid, reacted with aqueous formaldehyde and pyrrolidine to furnish C-8 substituted coumarin 488 (Scheme 169). Notably, compound 488 having trifluoromethyl and pyrrolidinyl group displayed most potent antiproliferative activity against B16 and A549 cell lines with IC 50 values of 3.8 μM and 1.9 μM, respectively which was more than 20-fold higher than the parent compound esculetin.…”

Section: Coumarin and Isocoumarin Derivativesmentioning

confidence: 99%

“…Wang et al. designed and synthesized a series of C‐4 and C‐8 substituted esculetin derivatives by perchloric acid catalyzed von Pechmann reaction and Mannich reaction, respectively [270] . 6,7‐Dihydroxy‐4‐trifluoromethyl‐coumarin 487 , obtained by treatment of 1,2,4‐phenenyl triacetate 486 and ethyl 4,4,4‐trifluoro‐3‐oxobutanoate 1 in the presence of perchloric acid, reacted with aqueous formaldehyde and pyrrolidine to furnish C‐8 substituted coumarin 488 (Scheme 169).…”

Section: Trifluoromethyl‐β‐dicarbonyls Based Synthesis Of Heterocyclesmentioning

confidence: 99%

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Trifluoromethyl‐β‐dicarbonyls as Versatile Synthons in Synthesis of Heterocycles

Sumran,

Jain,

Kumar

et al. 2024

Chemistry A European J

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Trifluoromethyl group relishes a privileged position in the realm of medicinal chemistry because its incorporation into organic molecules often enhances the bioactivity by altering pharmacological profile of molecule. Trifluoromethyl‐β‐dicarbonyls have emerged as pivotal building blocks in synthetic organic chemistry due to their facile accessibility, stability and remarkable versatility. Owing to presence of nucleophilic and electrophilic sites, they offer multifunctional sites for the reaction. This review covers a meticulous exploration of their multifaceted role, encompassing an in‐depth analysis of mechanism, extensive scope, limitations and wide‐ranging applications in diverse organic synthesis, covering the literature from the 21st century. This comprehensive review encapsulates the applications of trifluoromethyl‐β‐dicarbonyls and their synthetic equivalents as precursors of complex and diverse heterocyclic scaffolds, fused heterocycles and spirocyclic compounds having medicinal and material importance. Their potent synthetic utility in cyclocondenation reactions with binucleophiles, cycloaddition reactions, C‐C bond formations, asymmetric multicomponent reactions using classical/solvent‐free/catalytic synthesis have been presented. Influence of unsymmetrical trifluoromethyl‐β‐diketones on regioselectivity of transformation is also reviewed. This review will benefit the synthetic and pharmaceutical communities to explore trifluoromethyl‐β‐dicarbonyls as trifluoromethyl building blocks for fabrication of heterocyclic scaffolds having implementation into drug discovery programs in the imminent future.

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Section: Coumarin and Isocoumarin Derivativesmentioning

confidence: 99%

Section: Trifluoromethyl‐β‐dicarbonyls Based Synthesis Of Heterocyclesmentioning

confidence: 99%

Trifluoromethyl‐β‐dicarbonyls as Versatile Synthons in Synthesis of Heterocycles

Sumran,

Jain,

Kumar

et al. 2024

Chemistry A European J

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Overview on developed synthesis procedures of coumarin heterocycles

2020

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Considering highly valuable biological and pharmaceutical properties of coumarins, the synthesis of these heterocycles has been considered for many organic and pharmaceutical chemists. This review includes the recent research in synthesis methods of coumarin systems, investigating their biological properties and describing the literature reports for the period of 2016 to the middle of 2020. In this review, we have classified the contents based on co-groups of coumarin ring. These reported methods are carried out in the classical and non-classical conditions particularly under green condition such as using green solvent, catalyst and other procedures.

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Synthesis and structure-activity relationship of coumarins as potent Mcl-1 inhibitors for cancer treatment

Xia

Wang

Li³

et al. 2021

Bioorganic & Medicinal Chemistry

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Synthesis and biological evaluation of hydroxylcoumarin derivatives as antioxidant agents

Cited by 5 publications

References 22 publications

Trifluoromethyl‐β‐dicarbonyls as Versatile Synthons in Synthesis of Heterocycles

Trifluoromethyl‐β‐dicarbonyls as Versatile Synthons in Synthesis of Heterocycles

Overview on developed synthesis procedures of coumarin heterocycles

Synthesis and structure-activity relationship of coumarins as potent Mcl-1 inhibitors for cancer treatment

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