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SYNTHETIC, CHEMICAL AND BIOLOGICAL STUDIES OF FR901464 ANALOGUES

Wang, Yanping (2010) SYNTHETIC, CHEMICAL AND BIOLOGICAL STUDIES OF FR901464 ANALOGUES. Master's Thesis, University of Pittsburgh. (Unpublished)

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Abstract

Since the total synthesis of FR901464 was achieved in our group, its structure-activity relationships were extensively studied through analogue syntheses. Here I described the syntheses and biological activities of two acetal analogues and two cyclopropane analogues. Although the acetal analogues were less potent than its parental analogue meayamycin, they retained nanomolar activity against MCF-7 cells. Meanwhile, the methyl groups on the acetal ring slightly influenced the activities of acetal analogues. The biological profiles of the two cyclopropane analogues suggested that FR901464 had no preference to bind to its targets with either face of the diene. I also developed an efficient strategy to synthesize the side chain with Ando's reagent. Subsequently, a convergent strategy was used to prepare acetal analogue, containing a total of 20 steps with 12 steps in the longest linear sequence.

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Details

Item Type: University of Pittsburgh ETD
Status: Unpublished
Creators/Authors:
CreatorsEmailPitt UsernameORCID
Wang, Yanpingwypman@hotmail.com
ETD Committee:
TitleMemberEmail AddressPitt UsernameORCID
Committee ChairKoide, Kazunorikoide@pitt.eduKOIDE
Committee MemberDay, Billybday@pitt.eduBDAY
Committee MemberWipf, Peterpwipf@pitt.eduPWIPF
Date: 20 September 2010
Date Type: Completion
Defense Date: 22 February 2010
Approval Date: 20 September 2010
Submission Date: 27 July 2010
Access Restriction: 5 year -- Restrict access to University of Pittsburgh for a period of 5 years.
Institution: University of Pittsburgh
Schools and Programs: Dietrich School of Arts and Sciences > Chemistry
Degree: MS - Master of Science
Thesis Type: Master's Thesis
Refereed: Yes
Uncontrolled Keywords: Analogue; Biology; FR901464; Structure-activity relationship
Other ID: http://etd.library.pitt.edu/ETD/available/etd-07272010-105250/, etd-07272010-105250
Date Deposited: 10 Nov 2011 19:54
Last Modified: 15 Nov 2016 13:47
URI: http://d-scholarship.pitt.edu/id/eprint/8667

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