Synthetic studies towards the total synthesis of quinolactacin B and its analogues / Putri Nur Arina Mohd Ariff

Quinolactacin 1, was isolated from larvae mulberry pyralid (Margaronia pyloalis Welker) It has a unique N-methyl-quinolone moiety fused to a lactam ring and was found to contribute towards the activity against tumor necrosis factor production. In this study, a short method on synthesizing quinolacta...

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Main Author:	Mohd Ariff, Putri Nur Arina
Format:	Thesis
Language:	English
Published:	2020
Subjects:	Analytical chemistry
Online Access:	https://ir.uitm.edu.my/id/eprint/59874/1/59874.pdf
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spelling	my-uitm-ir.598742022-05-18T08:33:49Z Synthetic studies towards the total synthesis of quinolactacin B and its analogues / Putri Nur Arina Mohd Ariff 2020-07 Mohd Ariff, Putri Nur Arina Analytical chemistry Quinolactacin 1, was isolated from larvae mulberry pyralid (Margaronia pyloalis Welker) It has a unique N-methyl-quinolone moiety fused to a lactam ring and was found to contribute towards the activity against tumor necrosis factor production. In this study, a short method on synthesizing quinolactacins and their analogues was established by using 2,4-, and 2,3-pyrrolidinediones as the starting materials. In the first part, 2,4-pyrrolidinedione ring 7 which was also known as tetramic acid underwent amination and acylation reactions to produce two types of key lactam intermediates which are intermediates with enamine functionality (79 and 11) and intermediates with enol-ester functionality (87 and 92). The lactam intermediate with enamine functionality, 79 was synthesized from tetramic acid 7 using a stepwise reaction which includes condensation and reduction while enamine 11 was directly synthesized from tetramic acid 7 via amination reaction. Lactam intermediates with enol-ester functionality, 87 and 97 were then synthesized from tetramic acid 7 in the presence of sodium hydride in dry THF with different acyl halides which are 2-florobenzoyl chloride and 2-nitrobenzoyl chloride, respectively. The final part focused on synthesizing quinolactacin analogues using 2,3-pyrrolidinedione ring as the starting material. 2,3-Pyrrolidinediones 95, 96, and 97 were synthesized via a one-pot multicomponent reaction of sodium diethyl oxaloacetate salt, an aldehyde and a primary amine in ethanol. Consequently, 2,3-pyrrolidinedione rings 95, 96, and 97 were used to synthesize quinolactacin analogues via Conrad limpach reaction which consists of thermal condensation of the primary amine and intramolecular cyclization of enamine intermediates. Despite all the challenges and obstacles in synthesizing quinolactacin B, quinolactacin analogues of 101, 102, and 103 were successfully synthesized in short three steps with the yield of 64%, 71% and 70% respectively. 2020-07 Thesis https://ir.uitm.edu.my/id/eprint/59874/ https://ir.uitm.edu.my/id/eprint/59874/1/59874.pdf text en public masters Universiti Teknologi MARA Faculty of Applied Sciences Shaameri, Zurina (Assoc. Prof. Dr.)
institution	Universiti Teknologi MARA
collection	UiTM Institutional Repository
language	English
advisor	Shaameri, Zurina (Assoc. Prof. Dr.)
topic	Analytical chemistry
spellingShingle	Analytical chemistry Mohd Ariff, Putri Nur Arina Synthetic studies towards the total synthesis of quinolactacin B and its analogues / Putri Nur Arina Mohd Ariff
description	Quinolactacin 1, was isolated from larvae mulberry pyralid (Margaronia pyloalis Welker) It has a unique N-methyl-quinolone moiety fused to a lactam ring and was found to contribute towards the activity against tumor necrosis factor production. In this study, a short method on synthesizing quinolactacins and their analogues was established by using 2,4-, and 2,3-pyrrolidinediones as the starting materials. In the first part, 2,4-pyrrolidinedione ring 7 which was also known as tetramic acid underwent amination and acylation reactions to produce two types of key lactam intermediates which are intermediates with enamine functionality (79 and 11) and intermediates with enol-ester functionality (87 and 92). The lactam intermediate with enamine functionality, 79 was synthesized from tetramic acid 7 using a stepwise reaction which includes condensation and reduction while enamine 11 was directly synthesized from tetramic acid 7 via amination reaction. Lactam intermediates with enol-ester functionality, 87 and 97 were then synthesized from tetramic acid 7 in the presence of sodium hydride in dry THF with different acyl halides which are 2-florobenzoyl chloride and 2-nitrobenzoyl chloride, respectively. The final part focused on synthesizing quinolactacin analogues using 2,3-pyrrolidinedione ring as the starting material. 2,3-Pyrrolidinediones 95, 96, and 97 were synthesized via a one-pot multicomponent reaction of sodium diethyl oxaloacetate salt, an aldehyde and a primary amine in ethanol. Consequently, 2,3-pyrrolidinedione rings 95, 96, and 97 were used to synthesize quinolactacin analogues via Conrad limpach reaction which consists of thermal condensation of the primary amine and intramolecular cyclization of enamine intermediates. Despite all the challenges and obstacles in synthesizing quinolactacin B, quinolactacin analogues of 101, 102, and 103 were successfully synthesized in short three steps with the yield of 64%, 71% and 70% respectively.
format	Thesis
qualification_level	Master's degree
author	Mohd Ariff, Putri Nur Arina
author_facet	Mohd Ariff, Putri Nur Arina
author_sort	Mohd Ariff, Putri Nur Arina
title	Synthetic studies towards the total synthesis of quinolactacin B and its analogues / Putri Nur Arina Mohd Ariff
title_short	Synthetic studies towards the total synthesis of quinolactacin B and its analogues / Putri Nur Arina Mohd Ariff
title_full	Synthetic studies towards the total synthesis of quinolactacin B and its analogues / Putri Nur Arina Mohd Ariff
title_fullStr	Synthetic studies towards the total synthesis of quinolactacin B and its analogues / Putri Nur Arina Mohd Ariff
title_full_unstemmed	Synthetic studies towards the total synthesis of quinolactacin B and its analogues / Putri Nur Arina Mohd Ariff
title_sort	synthetic studies towards the total synthesis of quinolactacin b and its analogues / putri nur arina mohd ariff
granting_institution	Universiti Teknologi MARA
granting_department	Faculty of Applied Sciences
publishDate	2020
url	https://ir.uitm.edu.my/id/eprint/59874/1/59874.pdf
_version_	1783735065474236416

Synthetic studies towards the total synthesis of quinolactacin B and its analogues / Putri Nur Arina Mohd Ariff

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