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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
Online Access:http://psasir.upm.edu.my/id/eprint/67448/1/FS%202018%2033%20IR.pdf
http://psasir.upm.edu.my/id/eprint/67448/
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spelling my.upm.eprints.674482019-03-14T02:56:50Z http://psasir.upm.edu.my/id/eprint/67448/ Synthesis of 2-aryldihydrobenzofuran neolignans and 2-arylbenzofuran neolignans and their larvicidal activities 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. 2018-01 Thesis NonPeerReviewed text en http://psasir.upm.edu.my/id/eprint/67448/1/FS%202018%2033%20IR.pdf Juhan, Siti Fadilah (2018) Synthesis of 2-aryldihydrobenzofuran neolignans and 2-arylbenzofuran neolignans and their larvicidal activities. PhD thesis, Universiti Putra Malaysia.
institution Universiti Putra Malaysia
building UPM Library
collection Institutional Repository
continent Asia
country Malaysia
content_provider Universiti Putra Malaysia
content_source UPM Institutional Repository
url_provider http://psasir.upm.edu.my/
language English
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
author Juhan, Siti Fadilah
spellingShingle Juhan, Siti Fadilah
Synthesis of 2-aryldihydrobenzofuran neolignans and 2-arylbenzofuran neolignans and their larvicidal activities
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
publishDate 2018
url http://psasir.upm.edu.my/id/eprint/67448/1/FS%202018%2033%20IR.pdf
http://psasir.upm.edu.my/id/eprint/67448/
_version_ 1643838908831629312
score 13.211869

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