Synthesis of DNA‐Intercalating 6H‐Benzo[c]chromen‐6‐one Derivatives through a Strategic Combination of Garratt–Braverman and Minisci Acyloxylation Reactions

Abstract

A new strategy for the synthesis of 6H‐benzo[c]chromen‐6‐ones through judicious use of Garratt–Braverman (GB) Cyclization and Minisci acyloxylation reactions in moderate to good yield is reported. The uniqueness of the GB reaction is exemplified in providing the required biaryl esters, which could be successfully converted into the target skeleton by means of Minisci reaction on the free carboxylates. Ethidium bromide displacement and UV‐based assay on the final molecules established them as DNA intercalators with binding constants in the range of about 104.

Intracellular Fluorometric Recognition of Explosive and Mutagenic Nitroaromatics by a Luminescent Phenanthrene‐Naphthalene Sulfone

“…With our previous expertise, the suitable chemosensor has been synthesized by GB cyclization reaction of bis-propargyl sulfones with γ-substitution. [11][12][13][14] Emphasis was given towards distinguishable sensing of explosive and pollutant nitroaromatics (epNACs) and nitroaliphatics (NALs) by luminescence spectroscopy owing to the ease of handling, portability and safety [15][16][17][18][19][20][21][22][23] The detection would be of enormous importance for the homeland security and significantly for environmental perspective. [24][25] Interestingly, as a real day application, the in vitro detection of TNP was performed using a wide range of living organisms such as pollens of Tecoma Stans, Peperomia roots and Candida Albicans (a diploid fungus).…”

Oxidant-free, three-component synthesis of 7-amino-6H-benzo[c]chromen-6-ones under green conditions

“…Other signicant activities of 6H-benzo[c]chromen-6-one derivatives include anti-inammatory, estrogenic activity, DNA gyrase inhibitory activity, casein kinase 2 (CK2) inhibitory activity, DNA intercalative activity, and many others. 1,6 Owing to the biological signicance of 6H-benzo[c]chromen-6ones, the synthesis of derivatives of this framework remain an attractive goal for synthetic chemists. 7 Surprisingly, however, most of the existing approaches for the synthesis of 6H-benzo[c] chromen-6-ones involve the construction of the B ring (lactone ring) from biphenyl derivatives via lactonization reactions, CO insertion etc.…”

Anticancer Activity and DNA Binding Studies of Novel 3,7‐Disubstituted Benzopyrones

“…Due to the potential applications of coumarins in medicinal chemistry, many efforts have been made on the design and synthesis of new coumarin derivatives with improved biological activities. Coumarins exhibited antitumor activities at different stages of cancer formation through various mechanisms, for example blocking cell cycle, inducing cell apoptosis, modulating estrogen receptor (ER), or inhibiting the DNA‐associated enzymes, such as topoisomerase …”