A chemoselective and continuous synthesis of <i>m</i>-sulfamoylbenzamide analogues

Verlee, Arno; Heugebaert, Thomas S. A.; Meer, Tom van der; Kerchev, Pavel; Breusegem, Frank Van; Stevens, Christian V.

doi:10.3762/bjoc.13.33

Cited by 6 publications

(2 citation statements)

References 31 publications

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“…The protocol typically includes activation with oxalyl chloride, [232,233] followed by base-promoted reaction with N-or O-nucleophile (Scheme 36). In this way, SO 2 Clcontaining amides derived from anilines [234][235][236] (including oaminophenol [237] ), heteroaromatic [238,239] and aliphatic [234,[240][241][242][243] amines, hydrazides, [244] and hydroxamic acids [245] were obtained. Analogously, SO 2 Cl-substituted esters were synthesized from alcohols, [246][247][248] phenols, [249][250][251] or heterocyclic hydroxy derivatives.…”

Section: Reactions Tolerating the So 2 CL Moietymentioning

confidence: 99%

Chemoselective Reactions of Functionalized Sulfonyl Halides

Liashuk,

Andriashvili,

Tolmachev

et al. 2023

The Chemical Record

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Chemoselective transformations of functionalized sulfonyl fluorides and chlorides are surveyed comprehensively. It is shown that sulfonyl fluorides provide an excellent selectivity control in their reactions. Thus, numerous conditions are tolerated by the SO2F group – from amide and ester formation to directed ortho‐lithiation and transition‐metal‐catalyzed cross‐couplings. Meanwhile, sulfur (VI) fluoride exchange (SuFEx) is also compatible with numerous functional groups, thus confirming its title of “another click reaction”. On the contrary, with a few exceptions, most transformations of functionalized sulfonyl chlorides typically occur at the SO2Cl moiety.

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Section: Reactions Tolerating the So 2 CL Moietymentioning

confidence: 99%

Chemoselective Reactions of Functionalized Sulfonyl Halides

Liashuk,

Andriashvili,

Tolmachev

et al. 2023

The Chemical Record

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“…Pakerine analogues were synthesized according to the method described by Verlee et al [34]. Briefly, a continuous-flow method was developed to increase the chemoselectivity and reduced production time allowing for quicker production of chemical libraries with higher purity.…”

Section: Structure-activity Relationship Analysismentioning

confidence: 99%

Chemical Genetics Approach Identifies Abnormal Inflorescence Meristem 1 as a Putative Target of a Novel Sulfonamide That Protects Catalase2-Deficient Arabidopsis against Photorespiratory Stress

Meer

Verlee

Willems

et al. 2020

Cells

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Alterations of hydrogen peroxide (H2O2) levels have a profound impact on numerous signaling cascades orchestrating plant growth, development, and stress signaling, including programmed cell death. To expand the repertoire of known molecular mechanisms implicated in H2O2 signaling, we performed a forward chemical screen to identify small molecules that could alleviate the photorespiratory-induced cell death phenotype of Arabidopsisthaliana mutants lacking H2O2-scavenging capacity by peroxisomal catalase2. Here, we report the characterization of pakerine, an m-sulfamoyl benzamide from the sulfonamide family. Pakerine alleviates the cell death phenotype of cat2 mutants exposed to photorespiration-promoting conditions and delays dark-induced senescence in wild-type Arabidopsis leaves. By using a combination of transcriptomics, metabolomics, and affinity purification, we identified abnormal inflorescence meristem 1 (AIM1) as a putative protein target of pakerine. AIM1 is a 3-hydroxyacyl-CoA dehydrogenase involved in fatty acid β-oxidation that contributes to jasmonic acid (JA) and salicylic acid (SA) biosynthesis. Whereas intact JA biosynthesis was not required for pakerine bioactivity, our results point toward a role for β-oxidation-dependent SA production in the execution of H2O2-mediated cell death.

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