Preparation of Unsymmetrical Sulfonylureas from <i>N</i>,<i>N</i>‘-Sulfuryldiimidazoles

Beaudoin, Serge; Kinsey, Kenneth E.; Burns, James F.

doi:10.1021/jo026505k

Cited by 55 publications

(32 citation statements)

References 23 publications

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“…The nitro function was reduced with iron 66 or via catalytic hydrogenation 67 to provide the corresponding amines. Reaction of the amines with appropriate sulfonyl or acyl chlorides or 3-methyl-1-((4-phenylpiperazin-1-yl)sulfonyl)-1 H -imidazol-3-ium 68 provided the penultimate compounds ( 49 ), which were demethylated with BBr 3 followed by purification by trituration or reverse-phase HPLC to afford the target compounds ( 1 – 3 , 9 – 14 , 16 – 23 , 25 – 26 , 28 – 29 , 31 – 38 ) of >95% purity (Tables 1–3). In the case of analogues with an ester side chain, the BBr 3 step provided a convenient way to concomitantly hydrolyze the ester in a single pot.…”

Section: Resultsmentioning

confidence: 99%

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3-Substituted-N-(4-Hydroxynaphthalen-1-yl)arylsulfonamides as a Novel Class of Selective Mcl-1 Inhibitors: Structure-Based Design, Synthesis, SAR, and Biological Evaluation

Abulwerdi¹,

Liao²,

Mady³

et al. 2014

J. Med. Chem.

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Mcl-1, an antiapoptotic member of the Bcl-2 family of proteins, is a validated and attractive target for cancer therapy. Overexpression of Mcl-1 in many cancers results in disease progression and resistance to current chemotherapeutics. Utilizing high-throughput screening, compound 1 was identified as a selective Mcl-1 inhibitor and its binding to the BH3 binding groove of Mcl-1 was confirmed by several different, but complementary, biochemical and biophysical assays. Guided by structure-based drug design and supported by NMR experiments, comprehensive SAR studies were undertaken and a potent and selective inhibitor, compound 21, was designed which binds to Mcl-1 with a Ki of 180 nM. Biological characterization of 21 showed that it disrupts the interaction of endogenous Mcl-1 and biotinylated Noxa-BH3 peptide, causes cell death through a Bak/Bax-dependent mechanism, and selectively sensitizes Eμ-myc lymphomas overexpressing Mcl-1, but not Eμ-myc lymphoma cells overexpressing Bcl-2. Treatment of human leukemic cell lines with compound 21 resulted in cell death through activation of caspase-3 and induction of apoptosis.

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Section: Resultsmentioning

confidence: 99%

“…As reported previously, 68 to a solution of 1,1′-sulfonyldiimidazole (1.98 g, 10 mmol) in CH 2 Cl 2 (40 mL) was added methyl trifluoromethanesulfonate (1.64 g, 10 mmol) at 0 °C. The solvent was removed after 3 h stirring.…”

Section: Methodsmentioning

confidence: 99%

3-Substituted-N-(4-Hydroxynaphthalen-1-yl)arylsulfonamides as a Novel Class of Selective Mcl-1 Inhibitors: Structure-Based Design, Synthesis, SAR, and Biological Evaluation

Abulwerdi¹,

Liao²,

Mady³

et al. 2014

J. Med. Chem.

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“…To overcome this issue, Oehlrich and co‐workers introduced bench‐stable 2,3,5,6‐tetafluorophenyl ester 3 . We have turned our attention to other stable reagents used to prepare organosulfur(IV) derivatives, that is, compounds 4 – 7 (Figure ) . Being inspired by these results, herein, we report a novel stable and convenient reagent 8 for the synthesis of sulfonimidamides.…”

Section: Introductionmentioning

confidence: 99%

Sulfonimidamides and Imidosulfuric Diamides: Compounds from an Underexplored Part of Biologically Relevant Chemical Space

Zasukha

Тимошенко

Tolmachev

et al. 2019

Chemistry A European J

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Two novel solid reagents—1‐sulfonimidoyl‐ and 1‐sulfamimidoyl‐3‐methylimidazolium derivatives—for the synthesis of sulfonimidamides and imidosulfuric diamides, respectively, were developed. It is shown that these reagents are very effective in substitution reactions with various N‐ and O‐nucleophiles; therefore, they significantly extend the accessibility to the chemical space covered by organosulfur(VI) compounds with S=N bonds. In addition, previously unknown imidosulfuric diamides with free imino nitrogen groups were prepared, and their physical and chemical properties were characterized (including molecular geometry, pKa, Log P, microsomal stability, and reactivity towards typical electrophiles). Similar to other organosulfur(VI) derivatives with S=N bonds, these compounds can be considered as promising bioisosteres of amides, ureas, or sulfonamides.

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“…This synthetic methodology has been described for the synthesis of N , N ′ ‐bis(2‐phenylethyl)‐sulfamide ( 7 ) by Gavernet et al . A similar synthesis can also be carried out from the reaction of amines with sulfonyldiimidazole and catechol sulfate . In this study, the first synthetic methodology including the reaction of free amines with SO 2 Cl 2 was chosen for the synthesis of symmetric sulfamides with a slight modification.…”

Section: Resultsmentioning

confidence: 99%

Acetylcholinesterase Inhibitory and Antioxidant Activities of Novel Symmetric Sulfamides Derived from Phenethylamines

Aksu

Topal

Gülçın

et al. 2015

Archiv der Pharmazie

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The antioxidant and acetylcholinesterase inhibitory properties of novel symmetric sulfamides derived from phenethylamines were evaluated. Phenethylamines 8-11 were reacted with SO2Cl2 in the presence of Et3N to afford sulfamides in good yields. The synthesized sulfamides were converted to their phenolic derivatives with BBr3. We elucidated the antioxidant activity of novel symmetric sulfamides by using different bioanalytical assays. For this purpose, the radical scavenging activities of the novel symmetric sulfamides were assessed by DPPH(•), ABTS(•+), DMPD(•+), and O2(•-) radical scavenging tests. In addition, the reducing abilities of the novel symmetric sulfamides were evaluated by Fe(3+)-Fe(2+) reducing, Cu(2+)-Cu(+) reducing, and [Fe(3+)-(TPTZ)2](3+)-[Fe(2+)-(TPTZ)2](2+) reducing activity tests. Also, the Fe(2+) chelating activity by the pipyrdyl reagent and the acetylcholinesterase inhibitory activities of the novel symmetric sulfamides were studied. Especially, the novel phenolic and symmetric sulfamides 16-19 showed high antioxidant and acetylcholinesterase inhibitory properties. On the other hand, IC50 values were calculated for the DPPH(•), ABTS(•+), DMPD(•+), and O2(•-) scavenging, the metal chelating, and the acetylcholinesterase inhibition effects of the novel symmetric sulfamides.

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Preparation of Unsymmetrical Sulfonylureas from N,N‘-Sulfuryldiimidazoles

Cited by 55 publications

References 23 publications

3-Substituted-N-(4-Hydroxynaphthalen-1-yl)arylsulfonamides as a Novel Class of Selective Mcl-1 Inhibitors: Structure-Based Design, Synthesis, SAR, and Biological Evaluation

3-Substituted-N-(4-Hydroxynaphthalen-1-yl)arylsulfonamides as a Novel Class of Selective Mcl-1 Inhibitors: Structure-Based Design, Synthesis, SAR, and Biological Evaluation

Sulfonimidamides and Imidosulfuric Diamides: Compounds from an Underexplored Part of Biologically Relevant Chemical Space

Acetylcholinesterase Inhibitory and Antioxidant Activities of Novel Symmetric Sulfamides Derived from Phenethylamines

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