SYNTHESIS OF A BIOLOGICALLY PERTINENT MOLECULE, AURONES –AN EXTENSIVE REVIEW (original) (raw)
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Medicinal Chemistry Research, 2015
Two new series of aurone compounds were synthesized via an oxidative cyclization reaction of 2 0 -hydroxy-chalcones. Series (A) consists of 1a-3a aurones with different substitutions on a B-ring at position 4 0 , and series (B) is made up of 1b-3b aurones that have different substitutions at position 2 0 of a B-ring. Structures of the synthesized compounds were characterized and confirmed by FTIR (1D and 2D NMR) and EI mass spectral studies. The molecular structure of 2b was further confirmed by the X-ray crystallographic technique, with the compound found to be in Z-isomeric form. The compounds of both series were tested for their antiproliferative activity against human colorectal tumor (HCT 116), human chronic myelogenous leukemia (K562) and hormone-dependent breast cancer (MCF-7) cell lines according to an MTT assay. Series (B) exhibited a higher cytotoxic effect on the cancer cell lines compared to series (A). Selectively, the most promising results have been shown by the two most active compounds, 1b (Z-5,7, 2 0 -trichloro-aurone), which resulted in IC 50 values of 36, 23 and 23 lM against HCT 116, MCF-7 and K562 cancer cells, respectively. Compound 3a (Z-5, 7-dichloro-4 0 -methyl-aurone) exhibited the highest activity against the K562 cell line (IC 50 = 20 lM), which can be compared to that of the standard drug, betulinic acid, with an IC 50 value of 15 lM. The results of the present study suggested that aurone derivatives emerged as a potential candidate for the development of future chemotherapeutic agents.
ChemInform, 2012
Aurones [2-benzylidenebenzofuran-3(2H)-ones] are either natural or synthetic compounds, belonging to the flavonoid family. They are isomeric to flavones and provide a bright yellow color to the plants in which they occur. Today, a literature survey indicates that the related flavonoids have been studied not only for their physiological properties and effects on Nature, but also for their therapeutic potential. Aurones are recently attracting the interest of an increasing number of research groups, and, since the last review, some interesting advances have been made in understanding the aurones.
Aurones: interesting natural and synthetic compounds with emerging biological potential
Natural product communications, 2012
Aurones [2-benzylidenebenzofuran-3(2H)-ones] are either natural or synthetic compounds, belonging to the flavonoid family. They are isomeric to flavones and provide a bright yellow color to the plants in which they occur. Today, a literature survey indicates that the related flavonoids have been studied not only for their physiological properties and effects on Nature, but also for their therapeutic potential. Aurones are recently attracting the interest of an increasing number of research groups, and, since the last review, some interesting advances have been made in understanding the aurones. In this review, we report the recent advances made on the synthetic routes towards aurones. We also highlight their activity in different biological areas, as well as applied genetic plant modifications to produce these colored compounds. Their synthesis, structure-activity relationships and the importance of the substitution pattern will also be mentioned. Finally, some aspects regarding the...
THERAPEUTIC ACTIVITIES OF AURONE, AN APPOSITELY ACTIVE MOLECULE-A REVIEW
Aurone is a heterocyclic benzofuranone molecule which is isolated from a natural source, aurone and its derivatives add a new dimension to drug discovery and development due to its anticancer, antidiabetic, antiviral, anti-malarial, anti-hepatitis, antihormonal, anti-diabetic, anti-obesity, anti-cholinesterase inhibitor and anti-inflammatory activity, which inspired chemist due to its incomparable properties. In this review we have compiled various pharmacological activity of aurone molecule in an effort to pave a way for development in this area of research.
Russian Journal of General Chemistry, 2019
Synthesis of some new multi-functional analogues of 2'-hydroxy chalcone containing isoxazole and pyrazole functions were synthesized, and their pharmacological activity was tested. Chalcone derivatives were synthesized by the reaction of 2'-hydroxy acetophenone with various substituted benzaldehydes in a basic medium. Aurones were isolated upon treatment with mercuric acetate. Synthesized chalcones and aurones were converted into the corresponding isoxazole and pyrazole derivatives upon their reaction with hydroxylamine hydrochloride or hydrazine hydrate, respectively. Structures of the compounds were confi rmed by spectroscopic methods. All synthesized compounds were tested for antioxidant and antibacterial potential. Some of those demonstrated excellent antioxidant activity, and one product was identifi ed as a promising antimicrobial candidate.
Versatile and Expeditious Synthesis of Aurones via Au I -Catalyzed Cyclization
Aurones are conveniently formed in a three-step procedure including a goldI-catalyzed cyclization of 2-(1-hydroxyprop- 2-ynyl)phenols as a highly regio- and stereoselective key step. A wide diversity of derivatives can be obtained starting from substituted salicylaldehydes. Synthesis of natural 4,6,3¢,4¢-tetramethoxyaurone and structure revision of two natural products (dalmaisione D and 4¢-chloroaurone) were achieved.
Construction of some cytotoxic agents with aurone and furoaurone scaffolds
Future Medicinal Chemistry, 2018
In spite of the availability of different chemotherapies for cancer treatment, there is still a need for new candidates with higher efficacy and lower toxicity. Methodology: Aurones 7a-f, 8a-f and furoaurones 13a-f, 16a-c were synthesized. Some compounds were selected by the National Cancer Institute, USA, for cytotoxicity screening. Results & discussion: The furoaurone derivative, 13a was the most active one exhibiting promising growth inhibition against leukemia, K562 and melanoma, MDA-MB-435 cells at concentration of 10 μM. It induced apoptosis in both cell lines by activation of CASP3 and inhibition of CDK2. Additionally, 13a showed good selectivity over normal kidney and liver cells. Simulation docking study was undertaken to gain insight into the possible binding mode of 13a in the CDK2 enzyme. Conclusion: The furoaurone 13a can be considered as a scaffold for further optimization to obtain more active hits.
Green synthesis of aurones and related compounds under solvent-free conditions
Journal of chemical research, 2016
3-Coumaranones were condensed with aldehydes on alumina or alumina-potassium fluoride without solvent under microwave irradiation or classical heating. Novel aurones and analogues bearing ferrocenyl, benzodioxole or benzodioxane groups were obtained in good yields without use of heavy metal reagents.