Synthesis of Sulfonamides and Evaluation of Their Histone Deacetylase (HDAC) Activity

Oh, Seikwan; Moon, Hyung‐In; Son, Ilhong; Jung, Jae‐Chul; Avery, Mitchell A.

doi:10.3390/12051125

Cited by 18 publications

(2 citation statements)

References 26 publications

(7 reference statements)

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Diazomethane was prepared by reacting compound 4 (Diazald) with potassium hydroxide and 2‐(2‐ethoxyethoxy)‐ethanol in dichloromethane at 65 °C for 1 h on an oil bath. An alcohol‐free dichloromethane solution of diazomethane gas was condensed through diazomethane generator (12) and N ‐methylmorpholine polystyrene, isobutyl chloroformate in dichloromethane to yield N‐protected diazo compounds 5 and 6 , which were treated with HBr/AcOH with purification in dichloromethane to give bromides 7 and 9 in 85% and 88% yields, respectively (13). Compounds 7 and 9 were treated with LiOH in tetrahydrofuran (THF)/H 2 O at −78 to 0 °C for 20 min to yield primary alcohols 8 and 10 , which were readily subjected to acetylation with acetyl chloride in dichloromethane to generate N‐protected acetates 11 and 12 in 54% and 50%, two step yields, respectively.…”

Section: Resultsmentioning

confidence: 99%

Synthesis, Structural Characterization and Biological Evaluation of N‐Protected Cyclopropylethylcarbamates as Potential Histone Deacetylase Inhibitor

Jung¹,

Moon

Oh³

2008

Chem Biol Drug Des

Self Cite

View full text Add to dashboard Cite

A simple synthesis involving a key coupling reaction and biological activity of N-protected cyclopropylethylcarbamates (18-21) are described. The key fragments are amine.HCl salt (13) and acids (16 and 17) which were smoothly coupled by using 2-(7-aza-1H-benzotriazol-1-yl)-1,1,3,3-tetramethyluroniumhexafluorophosphate in high yield. We have found that the in vitro growth inhibitory potency of new compound 19 exhibited good histone deacetylase activity.

show abstract

Section: Resultsmentioning

confidence: 99%

Synthesis, Structural Characterization and Biological Evaluation of N‐Protected Cyclopropylethylcarbamates as Potential Histone Deacetylase Inhibitor

Jung¹,

Moon

Oh³

2008

Chem Biol Drug Des

Self Cite

View full text Add to dashboard Cite

show abstract

“…3 Piperazinyl linked ciprofloxacin dimers reported as potent antibacterial agents against resistant strains. 4 Sulfonamide and substituted sulfonamide derivatives are important category of pharmacophores that have a wide spectrum of biological and pharmacological applications such as antimalarial, 5 antimicrobial, 6 antibacterial, 7,8 anticancer, 9 antifungal, 10 antihelmintic, 10 antioxidant, 11 antiHIV, 12 antitumor, 12 antiplasmodial, 13 antineoplastic, 14 antiproliferative 15 activities and additionally known to act as 5-HT 6 , 5-HT 7 receptor antagonists, 16,17 A2B and CXCR3 antagonists, 18,19 11b-HSD, 20 histone deacetylase (HDAC) inhibitors, 21 b-secretase (BACE1) inhibitors 22 and dual PI3K/mTOR inhibitors. 23 In recent years, literature reveals that the research interest and applications of antioxidants have constantly gathered high importance to eradicate the oxidative stress in humans.…”

Section: Introductionmentioning

confidence: 99%

Synthesis, Spectral Characterization and Antioxidant Activity of Novel Zafirlukast Sulfonyl Derivatives

Donka

Srinivasulu

Sridhar

et al. 2016

J Chinese Chemical Soc

View full text Add to dashboard Cite

A new series of cyclopentyl 3-(2-methoxy-4-(piperazine-1-carbonyl)benzyl)-1-methyl-1H-indol-5-ylcarbamate sulfonyl derivatives were synthesized by the reaclion of 4-((5-(cyclopentyloxycarbonylamino)-1-methyl-1H-indol-3-yl)methyl)-3-methoxybenzoic acid (ZAK drug intermediate) with Boc piperazine in the presence of EDC.HCl, HOBt, TEA in DMF followed by deboxylation by using 2N HCl or 35% HCl in acetone to get an intermediate compound. Further, this compound was treated with various substituted benzene sulfonyl chlorides in the presence of TEA in THF to afford title compounds. All the title compounds were characterized by 1 HNMR, 13 CNMR, IR and mass spectral data. The title compounds and starting material were evaluated for their antioxidant activity by using the DPPH, H 2 O 2 and NO methods. The results revealed that some of the compounds have shown significant antioxidant activity.

show abstract

Schwefel(VI)‐fluorid‐Austausch (SuFEx): Eine weitere gute Anwendung für die Click‐Chemie

et al. 2014

View full text Add to dashboard Cite

Arylsulfonylchloride (z. B. Ts‐Cl) sind die am häufigsten eingesetzten SVI‐Elektrophile in der organischen Synthesechemie, und auch die Stammverbindung, das Sulfurylchlorid (O2SVICl2), wurde zur Synthese von Sulfaten und Sulfamiden genutzt. Allerdings wird die gewünschte Halogenidsubstitution oftmals durch die Zersetzung des Schwefelelektrophils in SIV‐Spezies und Cl− verhindert, denn die SVI‐Cl‐Bindung ist äußerst reduktionsanfällig. Mit Schwefel(VI)‐fluoriden (z. B. R‐SO2‐F und SO2F2) verläuft die Umsetzung hingegen ausschließlich über den Substitutionsweg. Wie es bei der Click‐Chemie zumeist der Fall ist, wurden viele entscheidende Aspekte der Reaktivität von Schwefel(VI)‐fluoriden vor langer Zeit in Deutschland entdeckt.6a Überraschenderweise gerieten diese außerordentlichen Arbeiten in der Mitte des 20. Jahrhunderts ziemlich abrupt aus dem Blickfeld. In diesem Aufsatz versuchen wir, dieser Chemie neues Leben einzuhauchen. Insbesondere stützen wir uns dabei auch auf John Hyatts unbeachtet gebliebene Veröffentlichung über CH2CH‐SO2‐F aus dem Jahr 1979.98 Wir tragen mehrere neue Beobachtungen bei, einschließlich dem Befund, dass das ansonsten sehr stabile Gas SO2F2 eine exzellente Reaktivität unter den richtigen Umständen aufweist. Wir zeigen auch, dass Protonen oder Siliciumzentren den Austausch von S‐F‐Bindungen gegen S‐O‐Bindungen aktivieren können und dass der Sulfat‐Konnektor überraschend hydrolysestabil ist. Anwendungen dieser kontrollierbaren Ligationschemie auf kleine Moleküle, Polymere und Biomoleküle werden diskutiert.

show abstract

Synthesis of Sulfonamides and Evaluation of Their Histone Deacetylase (HDAC) Activity

Cited by 18 publications

References 26 publications

Synthesis, Structural Characterization and Biological Evaluation of N‐Protected Cyclopropylethylcarbamates as Potential Histone Deacetylase Inhibitor

Synthesis, Structural Characterization and Biological Evaluation of N‐Protected Cyclopropylethylcarbamates as Potential Histone Deacetylase Inhibitor

Synthesis, Spectral Characterization and Antioxidant Activity of Novel Zafirlukast Sulfonyl Derivatives

Schwefel(VI)‐fluorid‐Austausch (SuFEx): Eine weitere gute Anwendung für die Click‐Chemie

Contact Info

Product

Resources

About