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1. Synthesis and biological evaluati...
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Ragains, Justin R.
1. Synthesis and biological evaluation of Manzamine analogs. 2. Applications of the intramolecular crossed [2+2] photocycloaddition of vinylogous amides with olefins.
紀錄類型:
書目-電子資源 : Monograph/item
正題名/作者:
1. Synthesis and biological evaluation of Manzamine analogs. 2. Applications of the intramolecular crossed [2+2] photocycloaddition of vinylogous amides with olefins.
作者:
Ragains, Justin R.
面頁冊數:
544 p.
附註:
Adviser: Jeffrey D. Winkler.
附註:
Source: Dissertation Abstracts International, Volume: 67-03, Section: B, page: 1450.
Contained By:
Dissertation Abstracts International67-03B.
標題:
Chemistry, Organic.
電子資源:
http://pqdd.sinica.edu.tw/twdaoapp/servlet/advanced?query=3211137
ISBN:
9780542597435
1. Synthesis and biological evaluation of Manzamine analogs. 2. Applications of the intramolecular crossed [2+2] photocycloaddition of vinylogous amides with olefins.
Ragains, Justin R.
1. Synthesis and biological evaluation of Manzamine analogs. 2. Applications of the intramolecular crossed [2+2] photocycloaddition of vinylogous amides with olefins.
- 544 p.
Adviser: Jeffrey D. Winkler.
Thesis (Ph.D.)--University of Pennsylvania, 2006.
*Please refer to dissertation for diagrams.
ISBN: 9780542597435Subjects--Topical Terms:
193634
Chemistry, Organic.
1. Synthesis and biological evaluation of Manzamine analogs. 2. Applications of the intramolecular crossed [2+2] photocycloaddition of vinylogous amides with olefins.
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1. Synthesis and biological evaluation of Manzamine analogs. 2. Applications of the intramolecular crossed [2+2] photocycloaddition of vinylogous amides with olefins.
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544 p.
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Adviser: Jeffrey D. Winkler.
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Source: Dissertation Abstracts International, Volume: 67-03, Section: B, page: 1450.
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Thesis (Ph.D.)--University of Pennsylvania, 2006.
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*Please refer to dissertation for diagrams.
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The second part of this dissertation describes the development of the intramolecular crossed [2+2] photocycloaddition of vinylogous amides with olefins. We set out to synthesize a photosubstrate which, upon irradiation, would provide a photoproduct that could be elaborated to the structure of the naturally-occurring alkaloid peduncularine. Initial efforts at synthesizing a model system were directed toward photosubstrates with allene coupling partners. Later efforts involved the use of allene surrogates of varying complexity. A rationale for the stereochemical outcome of the photocycloaddition is presented. A solution to a stereochemical problem incurred during the course of these studies exploiting the pseudosymmetry of derived photoproducts is also presented.*
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This dissertation describes two independent research projects. The first part discusses the synthesis and biological evaluation of four compounds based on the structure of Manzamine A. The parent structure Manzamine A has been shown to have both in vitro and in vivo activity against the malaria-causing pathogen Plasmodium falciparum . Because of the complexity and limited availability of Manzamine A, we set out to synthesize and evaluate four analogs as the initial effort in an ongoing project to develop a structure-activity relationship (SAR) for the antimalarial activity of Manzamine A. The analogs were synthesized via the Suzuki coupling of 1-bromo-beta-carboline and the appropriate boronate esters. The boronate esters were synthesized by short and straightforward syntheses. Biological screening of the B, BC and AB ring system analogs of Manzamine A against P. falciparum showed greatly attenuated activity relative to Manzamine A, suggesting that more complex analogs would be necessary to approach the activity of the parent structure.*
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