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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
https://ir.uitm.edu.my/id/eprint/59874/
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spelling my.uitm.ir.598742022-05-18T08:33:49Z https://ir.uitm.edu.my/id/eprint/59874/ Synthetic studies towards the total synthesis of quinolactacin B and its analogues / Putri Nur Arina Mohd Ariff 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 NonPeerReviewed text en https://ir.uitm.edu.my/id/eprint/59874/1/59874.pdf (2020) Synthetic studies towards the total synthesis of quinolactacin B and its analogues / Putri Nur Arina Mohd Ariff. Masters thesis, thesis, Universiti Teknologi MARA.
institution Universiti Teknologi Mara
building Tun Abdul Razak Library
collection Institutional Repository
continent Asia
country Malaysia
content_provider Universiti Teknologi Mara
content_source UiTM Institutional Repository
url_provider http://ir.uitm.edu.my/
language English
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
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
publishDate 2020
url https://ir.uitm.edu.my/id/eprint/59874/1/59874.pdf
https://ir.uitm.edu.my/id/eprint/59874/
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score 13.211869

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