Isolation And Selective Reduction Of Mitragynine, Synthesis And Characterization Of New Indole Derivatives And Their Selected Biological Activity Studies

Mitraginina (MGT) memiliki sifat analgesik yang poten tetapi ketoksikan MGT telah juga dilaporkan. Objektif utama tesis ini adalah untuk memencilkan MGT bagi pengubahsuaian lanjutan struktur dan juga untuk mensintesis terbitan indolnya bagi menilai aktiviti antiproliferatif, antioksida dan antinosis...

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Main Author:	Goh, Teik Beng
Format:	Thesis
Language:	English
Published:	2015
Subjects:	R735-854 Medical education Medical schools Research
Online Access:	http://eprints.usm.my/31812/1/Goh_Teik_Beng_%28HJ%29.pdf
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spelling	my-usm-ep.318122019-04-12T05:25:39Z Isolation And Selective Reduction Of Mitragynine, Synthesis And Characterization Of New Indole Derivatives And Their Selected Biological Activity Studies 2015-09 Goh, Teik Beng R735-854 Medical education. Medical schools. Research Mitraginina (MGT) memiliki sifat analgesik yang poten tetapi ketoksikan MGT telah juga dilaporkan. Objektif utama tesis ini adalah untuk memencilkan MGT bagi pengubahsuaian lanjutan struktur dan juga untuk mensintesis terbitan indolnya bagi menilai aktiviti antiproliferatif, antioksida dan antinosiseptif masing-masing. MGT telah dipencilkan daripada daun M. speciosa dengan menggunakan prosedur penulenan yang ringkas dan berkesan. Pelbagai silana telah digunakan untuk menurunkan kumpulan karbonil dan ikatan dubel indol bagi MGT tetapi hanya ikatan berkembar indol telah berjaya diturunkan kepada indolina [CDR80 ((E)-metil 2-((2S,3S,12bS)-3-etil-8-metoksi-1,2,3,4,6,7,7a,12,12a,12b-dekahidroindolo[2,3-a]quinolizin-2-il)-3-metoksiakrilat)]. Tindak balas Pictet-Spengler telah diubahsuai dengan menggunakan 5-metoksitriptamina dan asid trifluoroasetik dalam medium akueus untuk mensintesis terbitan indol yang baru yang telah dicirikan dan dikenalpastikan sebagai CDR81 (6- metoksi-1-fenil-2,3,4,9-tetrahidro-1H-pyrido[3,4-b]indol) , CDR83 (6-metoksi-1-metil-2,3,4,9-tetrahidro-1H-pirido[3,4-b]indol), CDR82 (6-metoksi-1-(4-metoksifenil)-2,3,4,9-tetrahidro-1H-pirido[3,4-b]indol) dan CDR84 (2-metoksi-4-(6-metoksi-2,3,4,9-tetrahidro-1H-pirido[3,4-b]indol-1-l) fenol). Mitragynine (MTG) possesses potent analgesic properties but the toxic effects of MTG have also been reported. The main objective of this thesis is to isolate MTG for further structural modification and also to synthesize its indole derivatives and evaluate their antiproliferative, antioxidant and antinociceptive activities. MTG was isolated from M. speciosa leaves using a simple and effective purification procedure. Various silanes were used to reduce the carbonyl and indole double bonds of MTG but only the indole double bond was successfully reduced to indoline [CDR80 ((E)-methyl 2-((2S,3S,12bS)-3-ethyl-8-methoxy-1,2,3,4,6,7,7a,12,12a,12b-decahydroindolo[2,3-a]quinolizin-2-yl)-3-methoxy acryl ate)]. The Pictet-Spengler reaction was modified using 5-methoxytryptamine and trifluoroacetic acid in an aqueous medium to synthesize new indole derivatives which were identified and characterized as CDR81 (6- methoxy-1-phenyl-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole), CDR82 (6-methoxy-1-(4-methoxyphenyl)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole), CDR83 (6-methoxy-1-methyl-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole) and CDR84 (2-methoxy-4-(6-methoxy-2,3,4,9-tetrahydro-1H-pyrido[3,4- b]indol-1-l)phenol). 2015-09 Thesis http://eprints.usm.my/31812/ http://eprints.usm.my/31812/1/Goh_Teik_Beng_%28HJ%29.pdf application/pdf en public phd doctoral Universiti Sains Malaysia Pusat Penyelidikan Dadah & Ubat-ubatan
institution	Universiti Sains Malaysia
collection	USM Institutional Repository
language	English
topic	R735-854 Medical education Medical schools Research
spellingShingle	R735-854 Medical education Medical schools Research Goh, Teik Beng Isolation And Selective Reduction Of Mitragynine, Synthesis And Characterization Of New Indole Derivatives And Their Selected Biological Activity Studies
description	Mitraginina (MGT) memiliki sifat analgesik yang poten tetapi ketoksikan MGT telah juga dilaporkan. Objektif utama tesis ini adalah untuk memencilkan MGT bagi pengubahsuaian lanjutan struktur dan juga untuk mensintesis terbitan indolnya bagi menilai aktiviti antiproliferatif, antioksida dan antinosiseptif masing-masing. MGT telah dipencilkan daripada daun M. speciosa dengan menggunakan prosedur penulenan yang ringkas dan berkesan. Pelbagai silana telah digunakan untuk menurunkan kumpulan karbonil dan ikatan dubel indol bagi MGT tetapi hanya ikatan berkembar indol telah berjaya diturunkan kepada indolina [CDR80 ((E)-metil 2-((2S,3S,12bS)-3-etil-8-metoksi-1,2,3,4,6,7,7a,12,12a,12b-dekahidroindolo[2,3-a]quinolizin-2-il)-3-metoksiakrilat)]. Tindak balas Pictet-Spengler telah diubahsuai dengan menggunakan 5-metoksitriptamina dan asid trifluoroasetik dalam medium akueus untuk mensintesis terbitan indol yang baru yang telah dicirikan dan dikenalpastikan sebagai CDR81 (6- metoksi-1-fenil-2,3,4,9-tetrahidro-1H-pyrido[3,4-b]indol) , CDR83 (6-metoksi-1-metil-2,3,4,9-tetrahidro-1H-pirido[3,4-b]indol), CDR82 (6-metoksi-1-(4-metoksifenil)-2,3,4,9-tetrahidro-1H-pirido[3,4-b]indol) dan CDR84 (2-metoksi-4-(6-metoksi-2,3,4,9-tetrahidro-1H-pirido[3,4-b]indol-1-l) fenol). Mitragynine (MTG) possesses potent analgesic properties but the toxic effects of MTG have also been reported. The main objective of this thesis is to isolate MTG for further structural modification and also to synthesize its indole derivatives and evaluate their antiproliferative, antioxidant and antinociceptive activities. MTG was isolated from M. speciosa leaves using a simple and effective purification procedure. Various silanes were used to reduce the carbonyl and indole double bonds of MTG but only the indole double bond was successfully reduced to indoline [CDR80 ((E)-methyl 2-((2S,3S,12bS)-3-ethyl-8-methoxy-1,2,3,4,6,7,7a,12,12a,12b-decahydroindolo[2,3-a]quinolizin-2-yl)-3-methoxy acryl ate)]. The Pictet-Spengler reaction was modified using 5-methoxytryptamine and trifluoroacetic acid in an aqueous medium to synthesize new indole derivatives which were identified and characterized as CDR81 (6- methoxy-1-phenyl-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole), CDR82 (6-methoxy-1-(4-methoxyphenyl)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole), CDR83 (6-methoxy-1-methyl-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole) and CDR84 (2-methoxy-4-(6-methoxy-2,3,4,9-tetrahydro-1H-pyrido[3,4- b]indol-1-l)phenol).
format	Thesis
qualification_name	Doctor of Philosophy (PhD.)
qualification_level	Doctorate
author	Goh, Teik Beng
author_facet	Goh, Teik Beng
author_sort	Goh, Teik Beng
title	Isolation And Selective Reduction Of Mitragynine, Synthesis And Characterization Of New Indole Derivatives And Their Selected Biological Activity Studies
title_short	Isolation And Selective Reduction Of Mitragynine, Synthesis And Characterization Of New Indole Derivatives And Their Selected Biological Activity Studies
title_full	Isolation And Selective Reduction Of Mitragynine, Synthesis And Characterization Of New Indole Derivatives And Their Selected Biological Activity Studies
title_fullStr	Isolation And Selective Reduction Of Mitragynine, Synthesis And Characterization Of New Indole Derivatives And Their Selected Biological Activity Studies
title_full_unstemmed	Isolation And Selective Reduction Of Mitragynine, Synthesis And Characterization Of New Indole Derivatives And Their Selected Biological Activity Studies
title_sort	isolation and selective reduction of mitragynine, synthesis and characterization of new indole derivatives and their selected biological activity studies
granting_institution	Universiti Sains Malaysia
granting_department	Pusat Penyelidikan Dadah & Ubat-ubatan
publishDate	2015
url	http://eprints.usm.my/31812/1/Goh_Teik_Beng_%28HJ%29.pdf
_version_	1747820492898697216

Isolation And Selective Reduction Of Mitragynine, Synthesis And Characterization Of New Indole Derivatives And Their Selected Biological Activity Studies

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