Synthesis of Uracil-, Coumarin- and Quinolone-Fused Benzosultams and Benzosultones

Debnath, Sudarshan; Pal, Subhajit; Das, Arko

doi:10.1055/s-0034-1378734

Cited by 18 publications

(9 citation statements)

References 23 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The benzosultam, 4,7-dimethyl-3,4,7,8-tetrahydro-3λ 6 -[1,2]thiazino[4,3- f ]quinoline-3,3,8-trione ( 8l ) was synthesized from its precursor quinolone (6-amino-5-bromo quinolone derivative) with the reaction of 2-chloroethylsulfonyl chloride at 0 o C followed by Heck cyclization as described in our earlier report 20 . After synthesis of the compound 8l , the product was purified by column chromatography using silica gel (60–120 mesh size) as column matrix and eluted with 30% ethyl acetate–petroleum ether to afford the compound 8l as a white solid.…”

Section: Methodsmentioning

confidence: 99%

“…coumarin and quinolone fused benzosultam, which may serve as a potential antifilarial drug. Based on this postulation, a series of twelve coumarin and quinolone fused benzosultams were synthesized 20 and tested for their efficacy in inducing mortality in the filarial parasite Setaria cervi as reported previously 21 . Amongst the tested compounds, a novel quinolone-fused cyclic sulfonamide (4,7-dimethyl-3,4,7,8-tetrahydro-3λ 6 -[1,2]thiazino[4,3- f ]quinoline-3,3,8-trione) was found to exhibit the highest efficacy with a low degree of toxicity on non-targeted cells and tissues 21 .…”

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

Quinolone-fused cyclic sulfonamide as a novel benign antifilarial agent

Mukherjee

Joardar

Schiefer

et al. 2018

Sci Rep

Self Cite

View full text Add to dashboard Cite

Search of potent antifilarial drugs has been a major thrust area in tropical medicine research over the decades. Herein, we report 4,7-dimethyl-3,4,7,8-tetrahydro-3λ6-[1,2]thiazino[4,3-f]quinoline-3,3,8-trione (8l) as a new class of antifilarial agent which is extremely potent, with lethality against all the developmental stages (oocyte, microfilaria and adult) of the filarial parasite Setaria cervi. Molecular investigation on its mode of action revealed that 8l is a typical inducer of reactive oxygen species that triggers oxidative stress inside the filarid and further signals induction of apoptosis by activating both intrinsic and extrinsic pathways. Moreover, 8l is also active against Wolbachia, the essential endosymbiont of several human infectious filarids. Selective toxicity against filarial parasites and non-toxic nature in rat model were found as unique traits of 8l to be a future medicine. Taken en masse, this maiden report on a novel quinolone fused cyclic sulfonamide presents a promising therapeutic lead for lymphatic filariasis in future.

show abstract

Section: Methodsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Quinolone-fused cyclic sulfonamide as a novel benign antifilarial agent

Mukherjee

Joardar

Schiefer

et al. 2018

Sci Rep

Self Cite

View full text Add to dashboard Cite

show abstract

“…It should be noted that the Z -bromoalkenes can be easily synthesized from the nucleophilic addition of N -alkyl- p -toluenesulfonamides to bromoacetylenes [ 50 ]. Later, Mondal and co-workers further applied this strategy into an intramolecular cyclization of aryl bromides for the regioselective formation of uracil-, coumarin-, and quinolone-fused benzosultams [ 51 ]. Using three equivalents of AgOAc as the efficient oxidant, in 2014, Laha et al demonstrated a Pd-promoted intramolecular oxidative coupling reaction of sulfonanilides, which offers a facile access to a range of biaryl sultams [ 52 ].…”

Section: Transition Metal-catalyzed Benzosultam Synthesismentioning

confidence: 99%

Recent Advances in Catalytic Synthesis of Benzosultams

Zhao

2020

Molecules

View full text Add to dashboard Cite

Benzosultams represent one category of multi-heteroatom heterocyclic scaffolds, which have been frequently found in pharmaceuticals, agricultural agents, and chiral catalysts. Given the diversely significant functions of these compounds in organic and medicinal chemistry, great efforts have been made to develop novel catalytic systems for the efficient construction of benzosultam motifs over the past decades. Herein, in this review, we mainly summarize the recent advances in the field of catalytic synthesis of benzosultams from 2017 to August of 2020, with an emphasis on the scopes and mechanisms of representative reactions.

show abstract

“…We have also applied Pd‐catalyzed intramolecular cyclization for the preparation of uracil‐, coumarin‐, and quinolone‐fused benzosultams 9.2a – h (Scheme ) . In this method regioselectivity in the cyclization step in the cases of the coumarin and quinolone substrates led predominantly to C‐5 cyclized products.…”

Section: Synthesis Of Sultamsmentioning

confidence: 99%

Sultams: Recent Syntheses and Applications

Debnath¹,

Mondal²

2018

Eur J Org Chem

Self Cite

View full text Add to dashboard Cite

Sultams are very important scaffolds both in medicinal chemistry and in synthetic organic chemistry. Very important methodologies for the asymmetric and non‐asymmetric synthesis of sultams, including asymmetric synthesis with memory of chirality (MOC), have recently been developed. Nowadays sultams are tremendously widely applied both in the medicinal field and in the synthetic field for the synthesis of different natural and non‐natural heterocycles. This review covers the recent development (2011–June 2017) of powerful methodologies for the synthesis of sultams and their applications in various fields during this period. A critical view of the mechanisms of the developed methodologies together with the scope and limitations of these methods add an extra dimension to the text.

show abstract

Synthesis of Uracil-, Coumarin- and Quinolone-Fused Benzosultams and Benzosultones

Cited by 18 publications

References 23 publications

Quinolone-fused cyclic sulfonamide as a novel benign antifilarial agent

Quinolone-fused cyclic sulfonamide as a novel benign antifilarial agent

Recent Advances in Catalytic Synthesis of Benzosultams

Sultams: Recent Syntheses and Applications

Contact Info

Product

Resources

About