Building a Sulfonamide Library by Eco-Friendly Flow Synthesis

Gioiello, Antimo; Rosatelli, Emiliano; Teofrasti, M; Filipponi, P; Pellicciari, Roberto

doi:10.1021/co400012m

Cited by 63 publications

(38 citation statements)

References 36 publications

(35 reference statements)

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“…The EI dissociation constant Ki was determined by the secondary plot of 1/V versus inhibitor concentration and the ESI dissociation constant Ki ′ was calculated from the intercept versus inhibitor concentrations. Urease activity was determined by measuring ammonia production using the indophenol method as reported previously [ 50 ]. The results (change in absorbance per min) were recorded at 625 nm using a microplate reader (Optimax Tunable, Sunnyvale, CA, USA).…”

Section: Methodsmentioning

confidence: 99%

Sulfonamide-Linked Ciprofloxacin, Sulfadiazine and Amantadine Derivatives as a Novel Class of Inhibitors of Jack Bean Urease; Synthesis, Kinetic Mechanism and Molecular Docking

et al. 2017

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Sulfonamide derivatives serve as an important building blocks in the drug design discovery and development (4D) process. Ciprofloxacin-, sulfadiazine- and amantadine-based sulfonamides were synthesized as potent inhibitors of jack bean urease and free radical scavengers. Molecular diversity was explored and electronic factors were also examined. All 24 synthesized compounds exhibited excellent potential against urease enzyme. Compound 3e (IC50 = 0.081 ± 0.003 µM), 6a (IC50 = 0.0022 ± 0.0002 µM), 9e (IC50 = 0.0250 ± 0.0007 µM) and 12d (IC50 = 0.0266 ± 0.0021 µM) were found to be the lead compounds compared to standard (thiourea, IC50 = 17.814 ± 0.096 µM). Molecular docking studies were performed to delineate the binding affinity of the molecules and a kinetic mechanism of enzyme inhibition was propounded. Compounds 3e, 6a and 12d exhibited a mixed type of inhibition, while derivative 9e revealed a non-competitive mode of inhibition. Compounds 12a, 12b, 12d, 12e and 12f showed excellent radical scavenging potency in comparison to the reference drug vitamin C.

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Section: Methodsmentioning

confidence: 99%

Sulfonamide-Linked Ciprofloxacin, Sulfadiazine and Amantadine Derivatives as a Novel Class of Inhibitors of Jack Bean Urease; Synthesis, Kinetic Mechanism and Molecular Docking

et al. 2017

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“…In 2013, Gioiello and coworkers reported their work on the synthesis of sulfonamides by employing flow-based chemistry [11]. This work could therefore support medicinal chemistry program at various stages as the hit-to-lead, lead-optimization and lead candidate scale-up (Fig.…”

Section: Synthesis Of Sulfonamidesmentioning

confidence: 99%

Sulfur Containing Scaffolds in Drugs: Synthesis and Application in Medicinal Chemistry

Feng¹,

Tang²,

Liang³

et al. 2016

CTMC

1,429

673

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The impact of the development of sulfur therapeutics is instrumental to the evolution of the pharmaceutical industry. Sulfur-derived functional groups can be found in a broad range of pharmaceuticals and natural products. For centuries, sulfur continues to maintain its status as the dominating heteroatom integrated into a set of 362 sulfur-containing FDA approved drugs (besides oxygen or nitrogen) through the present. Sulfonamides, thioethers, sulfones and Penicillin are the most common scaffolds in sulfur containing drugs, which are well studied both on synthesis and application during the past decades. In this review, these four moieties in pharmaceuticals and recent advances in the synthesis of the corresponding core scaffolds are presented.

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“…The inherent potential of this scaffold ( 2a – c ) for derivatization combined with the advantages of flow chemistry for library synthesis (including excellent heat exchange and fast mixing for better reaction control, automated small‐scale optimization and rapid automated compound‐library preparation) encouraged us to further develop a new class of urea derivatives in flow ( 5 and 6 ) based on scaffolds 2a – c (Scheme ).…”

Section: Introductionmentioning

confidence: 99%

Continuous Flow Synthesis of Urea‐Containing Compound Libraries Based on the Piperidin‐4‐one Scaffold

Riesco-Domínguez¹,

Blanco‐Ania²,

Rutjes³

2018

Eur J Org Chem

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The advantages of performing reactions in continuous flow vs. the classic batch processes render flow chemistry a suitable technique for library synthesis. Inspired by our recent work to create fluorine‐containing nitrogen heterocycles and by the potential of the urea group in drug design, we herewith describe the combination of both aspects in the continuous flow synthesis of two libraries of urea derivatives based on the piperidin‐4‐one scaffold.

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Building a Sulfonamide Library by Eco-Friendly Flow Synthesis

Cited by 63 publications

References 36 publications

Sulfonamide-Linked Ciprofloxacin, Sulfadiazine and Amantadine Derivatives as a Novel Class of Inhibitors of Jack Bean Urease; Synthesis, Kinetic Mechanism and Molecular Docking

Sulfonamide-Linked Ciprofloxacin, Sulfadiazine and Amantadine Derivatives as a Novel Class of Inhibitors of Jack Bean Urease; Synthesis, Kinetic Mechanism and Molecular Docking

Sulfur Containing Scaffolds in Drugs: Synthesis and Application in Medicinal Chemistry

Continuous Flow Synthesis of Urea‐Containing Compound Libraries Based on the Piperidin‐4‐one Scaffold

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