Synthesis of halogensubstituted styryl lactones and their cytotoxic activity against T-jurkat cell line / Nik Salmah Nik Salleh

Styryl lactones are small organic compounds that possess interesting biological properties. A study was done in order to synthesise halogen substituted styryl lactones as only few of these derivatives have been reported. A new synthetic route has been established which consists of three steps only....

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Main Author:	Nik Salleh, Nik Salmah
Format:	Thesis
Language:	English
Published:	2014
Online Access:	http://ir.uitm.edu.my/id/eprint/16359/ http://ir.uitm.edu.my/id/eprint/16359/1/TM_NIK%20SALMAH%20NIK%20SALLEH%20PH%2014_5.pdf

id	uitm-16359
recordtype	eprints
spelling	uitm-163592019-02-20T07:05:07Z http://ir.uitm.edu.my/id/eprint/16359/ Synthesis of halogensubstituted styryl lactones and their cytotoxic activity against T-jurkat cell line / Nik Salmah Nik Salleh Nik Salleh, Nik Salmah Styryl lactones are small organic compounds that possess interesting biological properties. A study was done in order to synthesise halogen substituted styryl lactones as only few of these derivatives have been reported. A new synthetic route has been established which consists of three steps only. Commercially available 3,4-dihydro-2//-pyran-2-methanol was used as starting material and subjected to Swem oxidation to provide the corresponding aldehyde. This reaction was conducted at -78 °C in the presence of dimethyl sulfoxide (DMSO), oxalyl chloride (COCl)2 and triethylamine (EtjN). Phosphonium salts were synthesised through microwave irradiation. These phosphonium salts were subjected to a base to yield Wittig reagents. Wittig reactions were performed in a -40 °C bath by using tetrahydrofuran (THF) and sodium bis(trimethylsilyl)amide (NaHMDS) leading to (Z)-precursors of halogensubstituted styryl lactones. The oxidation of the styryl lactone precursors with tert-butyl hydroperoxide (/buBOOH) and pyridinium dichromate (PDC) in dichloromethane (CH2CI2) at -40 °C yielded the targeted products as well as two by-products with overall yields of main product ranging from 45 % to 67 %. The final products were purified by both column chromatography and preparative layer chromatography (PLC). The structures of the synthesised compounds were confirmed by nuclear magnetic resonance (NMR) and mass spectrometry analyses. The cytotoxic activity of the six final compounds was tested on E6.1 Jurkat-T cell line. All targeted compounds showed encouraging cytotoxic activity with IC50 ranging from 26 % to 120 % of that goniothalamin. 2014 Thesis NonPeerReviewed text en http://ir.uitm.edu.my/id/eprint/16359/1/TM_NIK%20SALMAH%20NIK%20SALLEH%20PH%2014_5.pdf Nik Salleh, Nik Salmah (2014) Synthesis of halogensubstituted styryl lactones and their cytotoxic activity against T-jurkat cell line / Nik Salmah Nik Salleh. Masters thesis, Universiti Teknologi MARA.
repository_type	Digital Repository
institution_category	Local University
institution	Universiti Teknologi MARA
building	UiTM Institutional Repository
collection	Online Access
language	English
description	Styryl lactones are small organic compounds that possess interesting biological properties. A study was done in order to synthesise halogen substituted styryl lactones as only few of these derivatives have been reported. A new synthetic route has been established which consists of three steps only. Commercially available 3,4-dihydro-2//-pyran-2-methanol was used as starting material and subjected to Swem oxidation to provide the corresponding aldehyde. This reaction was conducted at -78 °C in the presence of dimethyl sulfoxide (DMSO), oxalyl chloride (COCl)2 and triethylamine (EtjN). Phosphonium salts were synthesised through microwave irradiation. These phosphonium salts were subjected to a base to yield Wittig reagents. Wittig reactions were performed in a -40 °C bath by using tetrahydrofuran (THF) and sodium bis(trimethylsilyl)amide (NaHMDS) leading to (Z)-precursors of halogensubstituted styryl lactones. The oxidation of the styryl lactone precursors with tert-butyl hydroperoxide (/buBOOH) and pyridinium dichromate (PDC) in dichloromethane (CH2CI2) at -40 °C yielded the targeted products as well as two by-products with overall yields of main product ranging from 45 % to 67 %. The final products were purified by both column chromatography and preparative layer chromatography (PLC). The structures of the synthesised compounds were confirmed by nuclear magnetic resonance (NMR) and mass spectrometry analyses. The cytotoxic activity of the six final compounds was tested on E6.1 Jurkat-T cell line. All targeted compounds showed encouraging cytotoxic activity with IC50 ranging from 26 % to 120 % of that goniothalamin.
format	Thesis
author	Nik Salleh, Nik Salmah
spellingShingle	Nik Salleh, Nik Salmah Synthesis of halogensubstituted styryl lactones and their cytotoxic activity against T-jurkat cell line / Nik Salmah Nik Salleh
author_facet	Nik Salleh, Nik Salmah
author_sort	Nik Salleh, Nik Salmah
title	Synthesis of halogensubstituted styryl lactones and their cytotoxic activity against T-jurkat cell line / Nik Salmah Nik Salleh
title_short	Synthesis of halogensubstituted styryl lactones and their cytotoxic activity against T-jurkat cell line / Nik Salmah Nik Salleh
title_full	Synthesis of halogensubstituted styryl lactones and their cytotoxic activity against T-jurkat cell line / Nik Salmah Nik Salleh
title_fullStr	Synthesis of halogensubstituted styryl lactones and their cytotoxic activity against T-jurkat cell line / Nik Salmah Nik Salleh
title_full_unstemmed	Synthesis of halogensubstituted styryl lactones and their cytotoxic activity against T-jurkat cell line / Nik Salmah Nik Salleh
title_sort	synthesis of halogensubstituted styryl lactones and their cytotoxic activity against t-jurkat cell line / nik salmah nik salleh
publishDate	2014
url	http://ir.uitm.edu.my/id/eprint/16359/ http://ir.uitm.edu.my/id/eprint/16359/1/TM_NIK%20SALMAH%20NIK%20SALLEH%20PH%2014_5.pdf
first_indexed	2023-09-18T22:55:53Z
last_indexed	2023-09-18T22:55:53Z
_version_	1777417850676314112

Synthesis of halogensubstituted styryl lactones and their cytotoxic activity against T-jurkat cell line / Nik Salmah Nik Salleh

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