Molecule VI: Sulfonimide or Sulfonamide?

Lill, Sten O. Nilsson; Broo, Anders

doi:10.1021/cg500916u

Cited by 16 publications

(10 citation statements)

References 33 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…N ‐Heterocyclic sulfonamides are in equilibria with the tautomeric sulfonimides, a property that has been exploited in synthetic organic chemistry, which underlies the phenomena of tautomeric polymorphism . In the solid state, the environment favors in some cases the sulfonimides, which also become stabilized in polar solvents . The two tautomeric forms could presumably be important for therapeutic action.…”

Section: The Sulfonamidesmentioning

confidence: 99%

Antitubulin sulfonamides: The successful combination of an established drug class and a multifaceted target

Vicente‐Blázquez

González

Álvarez

et al. 2018

Medicinal Research Reviews

View full text Add to dashboard Cite

Tubulin, the microtubules and their dynamic behavior are amongst the most successful antitumor, antifungal, antiparasitic, and herbicidal drug targets. Sulfonamides are exemplary drugs with applications in the clinic, in veterinary and in the agrochemical industry. This review summarizes the actual state and recent progress of both fields looking from the double point of view of the target and its drugs, with special focus onto the structural aspects. The article starts with a brief description of tubulin structure and its dynamic assembly and disassembly into microtubules and other polymers. Posttranslational modifications and the many cellular means of regulating and modulating tubulin's biology are briefly presented in the tubulin code. Next, the structurally characterized drug binding sites, their occupying drugs and the effects they induce are described, emphasizing on the structural requirements for high potency, selectivity, and low toxicity. The second part starts with a summary of the favorable and highly tunable combination of physical-chemical and biological properties that render sulfonamides a prototypical example of privileged scaffolds with representatives in many therapeutic areas. A complete description of tubulin-binding sulfonamides is provided, covering the different species and drug sites. Some of the antimitotic sulfonamides have met with very successful Med Res Rev. 2019;39:775-830. wileyonlinelibrary.com/journal/med © 2018 Wiley Periodicals, Inc. | 775applications and others less so, thus illustrating the advances, limitations, and future perspectives of the field.All of them combine in a mechanism of action and a clinical outcome that conform efficient drugs. K E Y W O R D S molecular mechanisms, sulfonamides, tubulin binding drugs, tubulin binding sites 1 | INTRODUCTION Drugs targeting tubulin and the microtubules (tubulin binding drugs [TBDs]) are amongst the most successful antitumor, antifungal, antiparasitic, and herbicidal agents with applications in the clinic, in veterinary and in the agrochemical industry. Recently, the combination of computational methods, medicinal chemistry, biochemistry, structural biology, and cell biology is starting to unravel the intricacies of tubulin binding drugs and of the microtubules themselves, thus paving the way towards new and better TBDs. New methodological advances such as the high resolution cryo-electron microscopy, the imaging of individual microtubule dynamics, and the achievement of recombinant tubulin, altogether with more established methodologies for the study of the microtubules have combined to provide a sharper view of the structure and function of these essential cell components and their interactions with clinically important drugs. The sulfonamides are a prototypical example of privileged scaffolds, with representatives in many therapeutic areas, due to a combination of favorable and highly tunable physical-chemical and biological properties. The early discovery of the dinitroaniline herbicides, and mainly the seminal discovery o...

show abstract

Section: The Sulfonamidesmentioning

confidence: 99%

Antitubulin sulfonamides: The successful combination of an established drug class and a multifaceted target

Vicente‐Blázquez

González

Álvarez

et al. 2018

Medicinal Research Reviews

View full text Add to dashboard Cite

show abstract

“…Secondary sulfonamides can exist as amido-imidate tautomers [36,37]. The data of quantum-chemical calculations suggest that the amide tautomers of compounds I-III are ca.…”

Section: Methodsmentioning

confidence: 99%

Stereoelectronic structure and self-association of N-trimethylsilylsulfonamides RSO2NHSiMe3 (R = Me, CF3, Ph)

et al. 2015

View full text Add to dashboard Cite

The effect of trimethylsilyl group Me 3 Si on the intramolecular electronic interactions and acid-base properties of N-trimethylsilylmethanesulfonamide, N-trimethylsilyltriflamide, and N-trimethylsilylbenzenesulfonamide was studied by the methods of quantum chemistry (DFT/ B3LYP/6-311+G**, NBO-analysis). Structural effects of the О-and N-protonation of these N-trimethylsilylsulfonamides and their isostructural carbon analogs were investigated.

show abstract

“…For example, the dimensions of recently synthesized SBDs up to the G5 do not exceed 5 nm, as shown in Table 1 [20]. The properties of sulfonimide groups are not well understood, and they are described in the literature relative to a tautomer of a sulfonamide group [21,22].…”

Section: Structurementioning

confidence: 99%

“…To this extent, several sulfonimide-based isomers with different molecular weights and shapes have been evaluated. Several properties such as melting temperature, solubility, chromatographic separation, nuclear The properties of sulfonimide groups are not well understood, and they are described in the literature relative to a tautomer of a sulfonamide group [21,22].…”

Section: Isomeric Structuresmentioning

confidence: 99%

See 1 more Smart Citation

Sulfonimide-Based Dendrimers: Progress in Synthesis, Characterization, and Potential Applications

Bondareva

Evlashin

Lukin³

2020

Polymers

View full text Add to dashboard Cite

There are more than 50 families of dendrimers, and some of which, such as polyamidoamine PAMAM, are well studied, and some are just starting to attract the attention of researchers. One promising type of dendrimers is sulfonimide-based dendrimers (SBDs). To date, SBDs are used in organic synthesis as starting reagents for the convergent synthesis of higher generations dendrimers, in materials science as alternative electrolyte solutions for fuel cells, and in medicinal chemistry as potential substances for drug transfer procedures. Despite the fact that most dendrimers are amorphous substances among the SBDs, several structures are distinguished that are prone to the formation of crystalline solids with melting points in the range of 120–250 °C. Similar to those of other dendrimers, the chemical and physical properties of SBDs depend on their outer shell, which is formed by functional groups. To date, SBDs decorated with end groups such as naphthyl, nitro, methyl, and methoxy have been successfully synthesized, and each of these groups gives the dendrimers specific properties. Analysis of the structure of SBD, their synthesis methods, and applications currently available in the literature reveals that these dendrimers have not yet been fully explored.

show abstract

Molecule VI: Sulfonimide or Sulfonamide?

Cited by 16 publications

References 33 publications

Antitubulin sulfonamides: The successful combination of an established drug class and a multifaceted target

Antitubulin sulfonamides: The successful combination of an established drug class and a multifaceted target

Stereoelectronic structure and self-association of N-trimethylsilylsulfonamides RSO2NHSiMe3 (R = Me, CF3, Ph)

Sulfonimide-Based Dendrimers: Progress in Synthesis, Characterization, and Potential Applications

Contact Info

Product

Resources

About