Synthesis of ring-A serjanic acid derivatives and their cytotoxic evaluation through the brine shrimp lethality assay (BSLA)

Abstract Sixteen serjanic acid derivatives were synthesized by modification of the A-ring of the triterpenoid skeleta. Fischer indolization of intermediate 2 with the requisite aromatic hydrazines afforded the indolo-triterpenes 8–13. Also, reaction of 2 with hydroxylamine hydrochloride in pyridine provided the desired C-3 oxime 14, while pyrazine 15 was obtained by condensation of 2 in the presence of ethylenediamine and sulphur in morpholine. Finally, the Claisen-Schmidt condensation of intermediate 2 with corresponding substituted benzaldehydes 16–23, afforded benzylidine ketones 24–31. All compounds were elucidated on the basis of NMR and HR-MS spectroscopic data and evaluated for their in-vitro cytotoxicity to the Brine Shrimp Lethality Assay (BSLA). As a result, the compounds exhibited medium to good cytotoxic potential and this activity was as high as eight times that of serjanic acid (1) on the tested zoophytes.

• Publication year

  2022

• Venue

  Zeitschrift für Naturforschung. B, A journal of chemical sciences

• Publication date

  2022-08-17

• Fields of study

  Not labeled

• Identifiers
  DOI 10.1515/znb-2022-0064
• External record

  Open on Semantic Scholar

• Source metadata

  Semantic Scholar

• No claims are published for this paper.

• No concepts are published for this paper.

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