1, 3-Dipolar cycloaddition of cycloimmonium salts and 4-(trimethylsilyl)-3-butyn-2-one to access new functionalized indolizines with potential cytostatic activity. (23rd January 2023)

• Record Type: Journal Article
• Authors: Zubaş, Andreea; Ghinet, Alina; Shova, Sergiu; Bîcu, Elena
• Is Part Of: New journal of chemistry. Volume 47:Number 8(2023)
• Page Start: 3758
• Page End: 3772
• Publication Date: 2023-01-23
• Subjects: Chemistry -- Periodicals; Chimie -- Périodiques; 540
• DOI: 10.1039/d2nj05257a
• Languages: English
• ISSNs: 1144-0546

Abstract

Abstract : 4-(Trimethylsilyl)-3-butyn-2-one is an effective dipolarophile in the [3+2] cycloaddition reaction with cycloimmonium salts to obtain bioactive non-silicon adducts, namely 1-acetylindolizines, but also trimethylsilyl-containing adducts. Abstract : This study revealed that 4-(trimethylsilyl)-3-butyn-2-one was an effective dipolarophile in the [3+2] cycloaddition reaction with cycloimmonium salts to obtain non-silicon adducts, namely 1-acetylindolizines. In some cases, two possible isomeric trimethylsilyl-containing adducts were also obtained. The structure of these silylated adducts has been found by X-ray crystallography to be 1-acetyl-2-trimethylsilyl-indolizines and 1-trimethylsilyl-2-acetylindolizines. The performance of 4-(trimethylsilyl)-3-butyn-2-one was compared to that of 3-butyn-2-one in the [3+2] cycloaddition reaction. The resulting 1-acetyl or 2-acetylindolizines were compared to previously described 3-acetyl or 1-carboxyethylindolizines in terms of biological potential to inhibit the NCI-60 cancer cell growth in vitro .