Chloramine-T (N-chloro-p-toluenesulfonamide sodium salt), a versatile reagent in organic synthesis and analytical chemistry: An up to date review

Nayak, Yogeesha N.; Gaonkar, Santosh L.; Harshitha, None

doi:10.1016/j.jscs.2021.101416

Cited by 7 publications

(5 citation statements)

References 175 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

Section: Resultsmentioning

confidence: 99%

“…Following hydrazinide 8A conjugation, iminolate 8B was formed, which was then converted into target 6 via an intramolecular nucleophilic substitution to give intermediate 9, followed by hydrogen chloride molecule removal (see Scheme 5). [43,44] The study was expanded to investigate the synthesis of another series of pyrrole-linked bis(1,3,4oxadiazole) hybrids 11 using a similar tandem protocol. The condensation step was carried out in ethanol at 80 °C for 2.5 -3.5 h using the pyrrole-linked benzohydrazide 10.…”

Section: Chemistrymentioning

confidence: 99%

See 1 more Smart Citation

Chloramine Trihydrate‐Mediated Tandem Synthesis of New Pyrrole and/or Arene‐Linked Mono‐ and Bis(1,3,4‐Oxadiazole) Hybrids as Potential Bacterial Biofilm and MRSA Inhibitors

Mekky

El-Idreesy

Sanad

2022

Chemistry & Biodiversity

View full text Add to dashboard Cite

A two-step tandem protocol was used to prepare new pyrrole and/or arene-linked bis(1,3,4-oxadiazoles) as well as their mono-analogs. The appropriate aldehydes and benzohydrazides were first condensed in ethanol at 80 °C to yield the corresponding N-benzoylhydrazones. Without isolation, the previous intermediates were subjected to a chloramine trihydrate-mediated oxidative cyclization in DMSO at 180 °C to yield the target molecules. The antibacterial potency of the (pyrrole-arene)-linked hybrids exceeded the arene-linked hybrids, and the bis(1,3,4-oxadiazoles) exceeded their mono-analogs against six different ATCC strains. Furthermore, the antibacterial efficacy of bis(1,3,4-oxadiazoles) 11c, and 11f, which are linked to pyrrole, and (p-tolylthio)methyl units, was highest against S. aureus, E. coli, and P. aeruginosa strains. Their MIC ranged between 3.8 and 3.9 μM, while their MBC values ranged between 7.7 and 15.8 μM. Additionally, they showed promising bacterial biofilm inhibitory activity against the same strains tested, with IC 50 values ranging from 4.7 to 5.3 μM. They were also effective against MRSA ATCC : 33591, and ATCC : 43300 strains, with MIC, and MBC values ranging from 3.8-7.9 and 7.7 -15.8 μM, respectively. When tested against the MCF-10A cell lines, hybrids 11c, and 11f are cytotoxic at concEntrations that are more than 6 and 13-fold higher than their MIC values against the S. aureus, E. coli, and P. aeruginosa strains, respectively. This lends support to both hybrids' potential as safe antibacterial agents.

show abstract

Section: Resultsmentioning

confidence: 99%

Section: Chemistrymentioning

confidence: 99%

Chloramine Trihydrate‐Mediated Tandem Synthesis of New Pyrrole and/or Arene‐Linked Mono‐ and Bis(1,3,4‐Oxadiazole) Hybrids as Potential Bacterial Biofilm and MRSA Inhibitors

Mekky

El-Idreesy

Sanad

2022

Chemistry & Biodiversity

View full text Add to dashboard Cite

show abstract

“…Following hydrazinide 6A conjugation, iminolate 6B was formed, which was then converted into target 4 via intramolecular nucleophilic substitution to give intermediate 7 , followed by the removal of a hydrogen chloride molecule (see Scheme 4). [ 72,73 ]…”

Section: Resultsmentioning

confidence: 99%

Tandem synthesis, cytotoxicity, and in silico study of new 1,3,4‐oxadiazoles as potential thymidylate synthase inhibitors

Sanad

Mekky

Ahmed

2022

Archiv der Pharmazie

View full text Add to dashboard Cite

A new series of pyrrole-linked mono-and bis(1,3,4-oxadiazole) hybrids, attached to various arene units, was prepared using a two-step tandem protocol. Therefore, a benzohydrazide derivative was condensed with the appropriate aldehydes in ethanol at 80°C for 60-150 min to give the corresponding N-(benzoylhydrazones). Without isolation, the previous intermediates underwent intramolecular oxidative cyclization in dimethyl sulfoxide at 180°C for 90-200 min in the presence of chloramine trihydrate to afford the target hybrids. The cytotoxicity of all hybrids was examined in vitro against the MCF-7, HEPG2, and Caco2 cell lines. Arene-linked hybrids 4i and 4j, attached to p-nitro and pacetoxy units, were the most potent ones, with IC 50 values ranging from 5.47 to 8.80 and 12.75 to 21.22 μM, respectively, when tested on the above cell lines. At the tested concentrations of 5 and 7.5 μM, hybrid 4i inhibited thymidylate synthase (TS) with the best inhibition percentages of 72.3 and 91.3, whereas hybrid 4j displayed comparable inhibitory activity to the reference pemetrexed. Hybrid 4j had inhibition percentages of 62.7 and 82.6, whereas pemetrexed had inhibition percentages of 59.2 and 80.2, respectively. The capability of hybrids 4i and 4j as potential TS inhibitors is supported by molecular docking studies, while SwissADME predicts their efficacy as drug-like scaffolds.

show abstract

“…On the other hand, heterocyclic chemistry is one of the most sought out areas of organic chemistry research [23][24][25][26]. Heterocycles have been primarily used in many bioactive compounds [27].…”

Section: Introductionmentioning

confidence: 99%

Chalcones: Versatile intermediates in heterocyclic synthesis

Nayak

Gaonkar

Sabu

2023

Journal of Heterocyclic Chem

Self Cite

View full text Add to dashboard Cite

Chalcones are a fascinating and well‐studied group of organic molecules. Synthesis of chalcones has been one of the essential areas of organic synthesis over the last few decades because of their immense therapeutic and excellent photophysical properties. Furthermore, these chalcone derivatives can be utilized to make a variety of heterocyclic compounds, especially five‐ and six‐membered heterocycles. Heterocyclic compounds have a long history in chemistry, primarily in pharmaceuticals. However, synthesizing some specific heterocyclic molecules remains challenging and requires multistep processes with few possible intermediates. Chalcones can be considered as one of the most useful, readily available intermediates in heterocyclic synthesis. Herein, the synthesis of various potential heterocyclic compounds using chalcones as an intermediate is elaborated. This review shows the untapped potential of chalcones in organic synthesis. Also, it will assist the chemist in designing new heterocycles by adopting these strategies.

show abstract

Chloramine-T (N-chloro-p-toluenesulfonamide sodium salt), a versatile reagent in organic synthesis and analytical chemistry: An up to date review

Cited by 7 publications

References 175 publications

Chloramine Trihydrate‐Mediated Tandem Synthesis of New Pyrrole and/or Arene‐Linked Mono‐ and Bis(1,3,4‐Oxadiazole) Hybrids as Potential Bacterial Biofilm and MRSA Inhibitors

Chloramine Trihydrate‐Mediated Tandem Synthesis of New Pyrrole and/or Arene‐Linked Mono‐ and Bis(1,3,4‐Oxadiazole) Hybrids as Potential Bacterial Biofilm and MRSA Inhibitors

Tandem synthesis, cytotoxicity, and in silico study of new 1,3,4‐oxadiazoles as potential thymidylate synthase inhibitors

Chalcones: Versatile intermediates in heterocyclic synthesis

Contact Info

Product

Resources

About