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Modular synthesis of annonaceous ace...

Paige, Mikell Atkin.

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Modular synthesis of annonaceous acetogenins and their activity against H-116 human solid colon tumor cells.

紀錄類型:	書目-電子資源 : Monograph/item
正題名/作者:	Modular synthesis of annonaceous acetogenins and their activity against H-116 human solid colon tumor cells./
作者:	Paige, Mikell Atkin.
面頁冊數:	250 p.
附註:	Source: Dissertation Abstracts International, Volume: 64-04, Section: B, page: 1737.
Contained By:	Dissertation Abstracts International64-04B.
標題:	Chemistry, Organic. -
電子資源:	http://pqdd.sinica.edu.tw/twdaoapp/servlet/advanced?query=3087138

Modular synthesis of annonaceous acetogenins and their activity against H-116 human solid colon tumor cells.
Paige, Mikell Atkin.

Modular synthesis of annonaceous acetogenins and their activity against H-116 human solid colon tumor cells. - 250 p.

Source: Dissertation Abstracts International, Volume: 64-04, Section: B, page: 1737.

Thesis (Ph.D.)--University of Virginia, 2003.

A 4-pronged approach enabling the syntheses of all 256 possible stereoisomers of bis-THF Annonaceous acetogenins is described. In this approach, the acetogenins are divided into 4 major segments, an aliphatic terminus, a core sub-unit, a spacer sub-unit, and a butenolide terminus. The aliphatic terminus and the spacer sub-unit are joined to the core sub-unit utilizing well-precedented alpha-oxygenated allylic stannane chemistry, which also serves to set key stereocenters. The final butenolide fragment is attached by Sonogashira coupling. Completion of the synthesis involves reduction of multiple bonds and deprotection of hydroxyl groups. The generality of the 4-pronged approach is illustrated by the syntheses of three acetogenins: (30S)-bullanin, (10R)-asimin, and an unnatural acetogenin, (4S)-asimicin. The efficiency of the 4-pronged approach is further exemplified in the synthesis of (30 S)-hydroxybullatacin in 3 steps from a previously synthesized intermediate. The four aforementioned acetogenins were found to be highly cytotoxic toward H-116 human solid tumor cells with IC50 values in the 10 -3 to 10-4 muM range. Differential cytotoxicity studies against CFU-GM human bone marrow cell lines were also performed to determine the best candidate for in vivo studies. A summary and comparison of structure-activity relationships from the literature and bioactivity data of our synthesized acetogenins is given.Subjects--Topical Terms:

516206
Chemistry, Organic.

Modular synthesis of annonaceous acetogenins and their activity against H-116 human solid colon tumor cells.
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100 1 $a Paige, Mikell Atkin. $3 1948130
245 1 0 $a Modular synthesis of annonaceous acetogenins and their activity against H-116 human solid colon tumor cells.
300 $a 250 p.
500 $a Source: Dissertation Abstracts International, Volume: 64-04, Section: B, page: 1737.
500 $a Adviser: James A. Marshall.
502 $a Thesis (Ph.D.)--University of Virginia, 2003.
520 $a A 4-pronged approach enabling the syntheses of all 256 possible stereoisomers of bis-THF Annonaceous acetogenins is described. In this approach, the acetogenins are divided into 4 major segments, an aliphatic terminus, a core sub-unit, a spacer sub-unit, and a butenolide terminus. The aliphatic terminus and the spacer sub-unit are joined to the core sub-unit utilizing well-precedented alpha-oxygenated allylic stannane chemistry, which also serves to set key stereocenters. The final butenolide fragment is attached by Sonogashira coupling. Completion of the synthesis involves reduction of multiple bonds and deprotection of hydroxyl groups. The generality of the 4-pronged approach is illustrated by the syntheses of three acetogenins: (30S)-bullanin, (10R)-asimin, and an unnatural acetogenin, (4S)-asimicin. The efficiency of the 4-pronged approach is further exemplified in the synthesis of (30 S)-hydroxybullatacin in 3 steps from a previously synthesized intermediate. The four aforementioned acetogenins were found to be highly cytotoxic toward H-116 human solid tumor cells with IC50 values in the 10 -3 to 10-4 muM range. Differential cytotoxicity studies against CFU-GM human bone marrow cell lines were also performed to determine the best candidate for in vivo studies. A summary and comparison of structure-activity relationships from the literature and bioactivity data of our synthesized acetogenins is given.
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