Chemoenzymatic biotransformation of some dihydroindole derivatives by lipase enzymes


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Çalışkan Z., Garipcan Z.

1. International Advances in Molecular Biology Congress, İstanbul, Turkey, 19 - 22 September 2022, pp.103

  • Publication Type: Conference Paper / Summary Text
  • City: İstanbul
  • Country: Turkey
  • Page Numbers: pp.103
  • Yıldız Technical University Affiliated: Yes

Abstract

Indole is a nitrogenous heterocyclic aromatic compound found in various alkaloids and phytohormones as well as in many foods consumed daily. This compound, which has an important place in the pharmaceutical industry and is used as a pharmacological drug precursor, has a wide range of biological activities such as antitumor, antimicrobial, antiviral, anti-inflammatory, antidepressant, anticholinergic, antimigraine, antiemetic and antihypertensive. Due to these properties, indole compound is used in the pharmaceutical field to synthesize active drug substances by using enzymatic and microbial biotransformation methods. Many compounds that are difficult or impossible to synthesize by classical methods can be obtained cheaply, quickly and efficiently with biotransformation reactions performed using enzymes and biological systems. In the synthesis made by this method, the stereochemical properties of the compounds are preserved and the racemic forms are obtained as enantiopure. In this study, it was aimed to obtain high enantiopurity indole derivatives, which are very difficult to synthesize synthetically, under cheap and mild synthesis conditions. In the first step, 1-benzyl-6,7-dihydro-6-phenyl-1H-indol-4(5H)one compound was synthesized as a result of various synthesis[1] steps using commercially purchased 5-phenyl-1,3-cyclohexadione starting material. Subsequently, α-acetoxy-1-benzyl-6,7-dihydro-6-phenyl-1H-indol-4(5H) one was synthesized by the regioselective acetoxylation reaction of the synthesized compound 1-benzyl-6,7-dihydro-6-phenyl-1H-indol-4(5H)one.