A new way to do an old reaction: highly efficient reduction of organic azides by sodium iodide in the presence of acidic ion exchange resin

Suthagar, Kajitha; Fairbanks, Antony J.

doi:10.1039/c6cc08574a

Cited by 12 publications

(6 citation statements)

References 25 publications

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“…[26][27][28][29] As shown in Scheme 7, starting from thymidine 1, using literature conditions, we converted the 5′-OH group into an amino group through an iodination/displacement/reduction sequence in 71% yield over 3 steps. [30][31][32] Using literature conditions, 13 coupling of amine 32 with diethyl squarate under basic conditions provided the squarate ester 33 in 61% yield. This material was subsequently converted into the squaramide 34 in 74% yield.…”

Section: Resultsmentioning

confidence: 99%

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A hydroxamic-acid-containing nucleoside inhibits DNA repair nuclease SNM1A

et al. 2019

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Section: Resultsmentioning

confidence: 99%

“…All the other inhibitors (5,6,26,28,31,33 and 34) in this assay show virtually no inhibition of SNM1A. Formyloxyamide 6 does show marginal levels of enzyme inhibition but given the relatively weak inhibitory potential of this compound, we opted not to pursue this for further analysis.…”

Section: Resultsmentioning

confidence: 99%

A hydroxamic-acid-containing nucleoside inhibits DNA repair nuclease SNM1A

et al. 2019

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“…The 5’‐squaryl monoamide phosphoramidite 15 was synthesized in five steps, giving moderate to excellent yields, using modified literature procedures (Scheme a) . Intermediate iodothymidine 12 was prepared from thymidine ( 7 ) using an Appel reaction before reaction with sodium azide and Staudinger reduction to give amine 13 . This monomer was reacted with diethyl squarate to give squaryl monoamide 14 , which was successfully phosphitylated.…”

Section: Resultsmentioning

confidence: 99%

Squaramide‐Based 5’‐Phosphate Replacements Bind to the DNA Repair Exonuclease SNM1A

et al. 2018

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Phosphate groups are often crucial to biological activity and interactions of oligonucleotides, but confer poor membrane permeability. In addition, the group's lability to enzymatic hydrolysis is an obstacle to its use in therapeutics and in biological tools. We present the synthesis of N ‐oxyamide and squaramide modifications at the 5’‐end of oligonucleotides as phosphate replacements and their biological evaluation using the 5’‐exonuclease SNM1A. The squaryl diamide modification showed minimal recognition as a 5’‐phosphate mimic; however, modest inhibition of SNM1A, postulated to occur through metal coordination at the active site, was observed. Their facile incorporation after solid‐phase synthesis and recognition by the exonuclease makes squaryl diamides attractive neutral 5’‐phosphate replacements for oligonucleotides. This work is the first example of squaryl diamide modifications at the 5’‐terminal position of oligonucleotides and of the potential use of modified oligonucleotides to bind to the metal center of SNM1A.

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“…Evolution of HCl and formation of disulfonylation products are suppressed using other sulfonyl derivatives, such as sulfonyl pyridinium (X=pyr + ) or DBN (X=DBN + ) salts, pentafluorophenyl (X=OC 6 F 5 ), 2,4,6‐trichlorophenyl (X=OC 6 H 2 Cl 3 ) and benzotriazole (X=OC 6 H 5 N 3 ) sulfonates or sulfonyl hydrazides . An alternative is the reduction of sulfonyl azides or other nitrogenated derivatives . In many cases, the conversion of the sulfonic acids into their highly reactive and unstable chloro derivatives is required (Figure ; Route 1, X=OH to X=Cl), a reaction that is accomplished with phosphorus/sulfur halides or other halogenating reagents .…”

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

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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...

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A new way to do an old reaction: highly efficient reduction of organic azides by sodium iodide in the presence of acidic ion exchange resin

Cited by 12 publications

References 25 publications

A hydroxamic-acid-containing nucleoside inhibits DNA repair nuclease SNM1A

A hydroxamic-acid-containing nucleoside inhibits DNA repair nuclease SNM1A

Squaramide‐Based 5’‐Phosphate Replacements Bind to the DNA Repair Exonuclease SNM1A

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

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