Synthesis of 2-aryldihydrobenzofuran neolignans and 2-arylbenzofuran neolignans and their larvicidal activities

2-Aryldihydrobenzofuran neolignans (tomentosanan A, ficusal, tomentosanan B) and 2- arylbenzofuran neolignans (zanthocapensole, zanthocapensate) have been isolated from the plants were synthesized and evaluated for their larvicidal activities against Crocidolimia binotalis. Two Heck coupling meth...

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Main Author:	Juhan, Siti Fadilah
Format:	Thesis
Language:	English
Published:	2018
Subjects:	Microbiological synthesis Plants Microtubules
Online Access:	http://psasir.upm.edu.my/id/eprint/67448/1/FS%202018%2033%20IR.pdf
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id	my-upm-ir.67448
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spelling	my-upm-ir.674482019-03-14T02:56:50Z Synthesis of 2-aryldihydrobenzofuran neolignans and 2-arylbenzofuran neolignans and their larvicidal activities 2018-01 Juhan, Siti Fadilah 2-Aryldihydrobenzofuran neolignans (tomentosanan A, ficusal, tomentosanan B) and 2- arylbenzofuran neolignans (zanthocapensole, zanthocapensate) have been isolated from the plants were synthesized and evaluated for their larvicidal activities against Crocidolimia binotalis. Two Heck coupling methods have been developed are using an activated C-I bond of iodovanillin or non-activated C-H bond of vanillin and alkene of cinnamic acid derivatives or methyl cinnamate derivatives. Heck coupling reaction between iodovanillin or vanillin with a series of cinnamic acid derivatives lead to the formation of eleven new compounds and four known compounds are 2- aryldihydrobenzofuran neolignan, 3-arylbenzofuran neolignans, 2-arylbenzofuran neolignans and stilbenes. The reaction involves a series of methyl cinnamate derivatives has resulted in the formation of five new compounds and three known compounds are lignans, neolignans, 2,3-diarylbenzofuran neolignan and coumarins. Both methods have been developed then have applied to the synthesis of five natural products of 2- arydihydrobenzofuran neolignans and 2-arylbenzofuran neolignans. All the targeted dihydrobenzofuran neolignans have synthesized as a single enantiomer form namely (+)- tomentosanan A, (+)-ficusal and (+)-tomentosanan B. Two routes have utilized to synthesize zanthocapensole and zanthocapensate and only their derivatives have been obtained from both routes. The selected compounds have been obtained from the Heck methods development and syntheses part have tested for larvicidal activity by using Crocidolomia binotalis larvae and azadirachtin as the commercial standard (LD50 = 2.818). The results indicate some of the compounds have significant activity such as dihydrobenzofuran neolignan, benzofuran neolignans, lignans, neolignans, stilbene and coumarin. Among all active compounds, (2E,3E)-dimethyl 2,3-bis(4-hydroxy-3,5- dimethoxybenzylidene)succinate (lignan) and methyl-3-(4-hydroxy-3-methoxyphenyl)-2- {2-methoxy-4[(E)-3-methoxy-3-oxo-prop-1-enyl]phenoxy}-prop-2-enoate (neolignan) have showed the strongest activity with LD50=1.678 mg/L and LD50=2.218 mg/L, respectively. Microbiological synthesis Plants Microtubules 2018-01 Thesis http://psasir.upm.edu.my/id/eprint/67448/ http://psasir.upm.edu.my/id/eprint/67448/1/FS%202018%2033%20IR.pdf text en public doctoral Universiti Putra Malaysia Microbiological synthesis Plants Microtubules
institution	Universiti Putra Malaysia
collection	PSAS Institutional Repository
language	English
topic	Microbiological synthesis Plants Microtubules
spellingShingle	Microbiological synthesis Plants Microtubules Juhan, Siti Fadilah Synthesis of 2-aryldihydrobenzofuran neolignans and 2-arylbenzofuran neolignans and their larvicidal activities
description	2-Aryldihydrobenzofuran neolignans (tomentosanan A, ficusal, tomentosanan B) and 2- arylbenzofuran neolignans (zanthocapensole, zanthocapensate) have been isolated from the plants were synthesized and evaluated for their larvicidal activities against Crocidolimia binotalis. Two Heck coupling methods have been developed are using an activated C-I bond of iodovanillin or non-activated C-H bond of vanillin and alkene of cinnamic acid derivatives or methyl cinnamate derivatives. Heck coupling reaction between iodovanillin or vanillin with a series of cinnamic acid derivatives lead to the formation of eleven new compounds and four known compounds are 2- aryldihydrobenzofuran neolignan, 3-arylbenzofuran neolignans, 2-arylbenzofuran neolignans and stilbenes. The reaction involves a series of methyl cinnamate derivatives has resulted in the formation of five new compounds and three known compounds are lignans, neolignans, 2,3-diarylbenzofuran neolignan and coumarins. Both methods have been developed then have applied to the synthesis of five natural products of 2- arydihydrobenzofuran neolignans and 2-arylbenzofuran neolignans. All the targeted dihydrobenzofuran neolignans have synthesized as a single enantiomer form namely (+)- tomentosanan A, (+)-ficusal and (+)-tomentosanan B. Two routes have utilized to synthesize zanthocapensole and zanthocapensate and only their derivatives have been obtained from both routes. The selected compounds have been obtained from the Heck methods development and syntheses part have tested for larvicidal activity by using Crocidolomia binotalis larvae and azadirachtin as the commercial standard (LD50 = 2.818). The results indicate some of the compounds have significant activity such as dihydrobenzofuran neolignan, benzofuran neolignans, lignans, neolignans, stilbene and coumarin. Among all active compounds, (2E,3E)-dimethyl 2,3-bis(4-hydroxy-3,5- dimethoxybenzylidene)succinate (lignan) and methyl-3-(4-hydroxy-3-methoxyphenyl)-2- {2-methoxy-4[(E)-3-methoxy-3-oxo-prop-1-enyl]phenoxy}-prop-2-enoate (neolignan) have showed the strongest activity with LD50=1.678 mg/L and LD50=2.218 mg/L, respectively.
format	Thesis
qualification_level	Doctorate
author	Juhan, Siti Fadilah
author_facet	Juhan, Siti Fadilah
author_sort	Juhan, Siti Fadilah
title	Synthesis of 2-aryldihydrobenzofuran neolignans and 2-arylbenzofuran neolignans and their larvicidal activities
title_short	Synthesis of 2-aryldihydrobenzofuran neolignans and 2-arylbenzofuran neolignans and their larvicidal activities
title_full	Synthesis of 2-aryldihydrobenzofuran neolignans and 2-arylbenzofuran neolignans and their larvicidal activities
title_fullStr	Synthesis of 2-aryldihydrobenzofuran neolignans and 2-arylbenzofuran neolignans and their larvicidal activities
title_full_unstemmed	Synthesis of 2-aryldihydrobenzofuran neolignans and 2-arylbenzofuran neolignans and their larvicidal activities
title_sort	synthesis of 2-aryldihydrobenzofuran neolignans and 2-arylbenzofuran neolignans and their larvicidal activities
granting_institution	Universiti Putra Malaysia
publishDate	2018
url	http://psasir.upm.edu.my/id/eprint/67448/1/FS%202018%2033%20IR.pdf
_version_	1747812475949023232

Synthesis of 2-aryldihydrobenzofuran neolignans and 2-arylbenzofuran neolignans and their larvicidal activities

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