Sulfondiimidamides as new functional groups for synthetic and medicinal chemistry

نویسندگان

چکیده

•Efficient three-component assembly of sulfondiimidamides; new analogs sulfonamides•Use unsymmetrical sulfurdiimide reagents is key to success the synthesis•Broad variation at all three nitrogen atoms and carbon substituent•Preparation enantiomerically enriched, chiral sulfur, examples A functional group an arrangement that defines topology reactivity a molecule. The ability modify these two parameters in useful predictive ways foundation synthetic organic chemistry accounts for wide-ranging applications enjoyed by molecules. For example, medicinal chemists often tune substituents attached specific groups as they explore chemical space, searching biologically active Sulfonamides have long history chemistry, with first important examples, “sulfa drugs,” being described 1930s. Here, we report group, sulfondiimidamides, which are double aza sulfonamides. We show molecules stable, can be efficiently prepared, precise manipulation functionalization possible. Sulfondiimidamides provide exciting scaffold exploring space. Due their three-dimensional structure, metabolic stability, polarity, hydrogen-bonding ability, sulfonamides occupy privileged position among used design bioactive mono variants, sulfonimidamides, known since 1930s, possess extra atom, delivers additional point diversity introduces chirality sulfur. However, analogs, elusive severely limited accessibility. sulfondiimidamides viable using linchpin, combination organometallic amines, Variation substrates, controlled functionality, allows broad range introduced carbon. discovery drug,” Prontosil,1Domagk G. Chemotherapie der Streptokokken-Infektionen.Klin Wochenschr. 1936; 15: 1585-1590https://doi.org/10.1007/BF01780820Crossref Scopus (8) Google Scholar 1930s predated isolation naturally occurring sulfonamide some 50+ years.2Takahashi A. Ikeda D. Nakamura H. Naganawa Kurasawa S. Okami Y. Takeuchi T. IitakaY Altemicidin, acaricidal antitumor substance. II. 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ژورنال

عنوان ژورنال: Chem

سال: 2022

ISSN: ['2451-9308', '2451-9294']

DOI: https://doi.org/10.1016/j.chempr.2022.02.013