Synthesis, Antimicrobial, and Anticoagulant Activities of 2-(Arylsulfonyl)indane-1,3-diones

Abstract

2-(Arylsulfonyl)indane-1,3-diones, earlier synthesized by Claisen condensation involving diethyl phthalate and aryl methyl sulphones, are found to be potent blood anticoagulants. In search of improved analogs of 2-(arylsulfonyl)indane-1,3-dione, we have synthesized them (7 a-f) by a different route involving Knoevenagel reaction between phthalic anhydride and arylsulfonylacetates in the presence of pyridine-piperidine medium for the first time. The synthesized 2-(arylsulfonyl)indane-1,3-diones were evaluated for antimicrobial and anticoagulant activities and all of them registered significant activity.

Leishmanicidal and cytotoxic activities and 4D‐QSAR of 2‐arylidene indan‐1,3‐diones

“…[ 19 ] Indan‐1,3‐dione derivatives present several biological activities such as antitumoral, [ 20 ] anticoagulant, [ 21 ] anti‐inflammatory, [ 22,23 ] neuroprotective, [ 24 ] and antimicrobial. [ 25 ] Besides, compounds presenting the indan‐1,3‐dione core have been isolated from nature. [ 26,27 ] For instance, the fredericamycin A is a natural spiro indan‐1,3‐dione presenting antitumor antibiotic activity.…”

Indanyl Analogs as Potential Antimicrobial Agents

“…Therefore, there is an urgent need to develop new classes of therapeutic agents to treat microbial infections. Indanyl derivatives have already drawn some attention as one of the templates for synthesizing compounds of varying biological activities such as antimicrobial [1][2][3][4][5][6][7], antitubercular [8][9][10], antimalarial [11], anti-inflammatory [12][13][14][15][16], anticancer 1 [17,18], antiviral [19], monoamine oxidase inhibitor [20], and anti-Alzheimer [21]. In search of newer antimicrobial agents, I have discovered and evaluated a series of substituted indanyl acids [(5-ethoxy-6-methoxy-3-oxo-2,3-dihydro-1H-inden-l-yl)acetic acid, (5,6-dimethoxy-3-oxo-2,3-dihydro-1H-inden-l-yl) acetic acid, and (6-chloro-3-oxo -2, 3-dihydro-1H-inden-l-yl) acetic acid] and their esters [(5-ethoxy-6-methoxy-3-oxo-2,3-dihydro-1H-inden-lyl)acetic acid esters, (5,6-dimethoxy-3-oxo-2,3-dihydro-1H-inden-l-yl) acetic acid esters, and (6-chloro-3-oxo -2, 3-dihydro-1H-inden-l-yl) acetic acid esters] against various pathogenic microorganisms.…”

Synthesis of Some New Fused and Spiro Heterocyclic Compounds under Phase Transfer Catalysis (PTC) Conditions

“…The great importance of 1,3-indandione derivatives can be referred to a wide range of their biological and medical effects as anti-inflammatory drugs (1)(2)(3) , antitumor agents (4) , acetylcholinesterase inhibitors (5) , anticoagulant activity (6) , in embryotoxic and teratogenic activities (7) , inhibitors of tyrosine kinase (8) , antimalarial activity (9) , antiallergic activity (10) and antimicrobial activity (11,12) . 1,3-Indandione, as well as, its derivatives serve as a synthon for the preparation of more structurally complex compounds, via condensation, decomposition, reduction, cyclization and rearrangements due to the presence of β-dicarbonyl moiety.…”