Supramolecular synthon hierarchy in sulfonamide cocrystals with syn-amides and N-oxides

Geetha Bolla, Ashwini Nangia

Research output: Contribution to journalArticlepeer-review

10 Scopus citations

Abstract

Sulfonamide drugs are well known antibacterial and antimicrobial molecules for pharmaceutical development. Building a library of suitable supramolecular synthons for the sulfonamide functional group and understanding their crystal structures with partner coformer molecules continues to be a challenge in crystal engineering. Although a few sulfonamide cocrystals with amides and N-oxides have been reported, the body of work on sulfonamide synthons is limited compared with those that have carboxylic acids and carboxamides. To address this structural gap, the present work is primarily focused on sulfonamide-lactam and sulfonamide-syn-amide synthons with drugs such as celecoxib, hydrochlorothiazide and furosemide. Furthermore, the electrostatic potential of previously reported cocrystals has been recalculated to show that the negative electrostatic potential on the lactam and syn-amide O atom is higher compared with the charge on carboxamide and pyridine N-oxide O atoms. The potential of sulfonamide molecules to form cocrystals with syn-amides and lactams are evaluated in terms of the electrostatic potential energy for the designed supramolecular synthons..

Original languageEnglish
Pages (from-to)751-760
Number of pages10
JournalIUCrJ
Volume6
DOIs
StatePublished - 1 Jul 2019
Externally publishedYes

Keywords

  • cocrystals
  • crystal engineering
  • sulfonamides
  • supramolecular synthons
  • syn-amides

ASJC Scopus subject areas

  • General Chemistry
  • Biochemistry
  • General Materials Science
  • Condensed Matter Physics

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