- Library Home /
- Search Collections /
- Open Collections /
- Browse Collections /
- UBC Theses and Dissertations /
- The attempted synthesis of a thiazolidinedione-containing...
Open Collections
UBC Theses and Dissertations
UBC Theses and Dissertations
The attempted synthesis of a thiazolidinedione-containing ligand for vanadyl complexation : investigating potential synergistic insulin mimics Mitchell, Devin Paul
Abstract
Thiazolidinedione-containing compounds are a relatively recent class of oral hypoglycemic agents used today to treat type II diabetes mellitus. Vanadium is well known to be an effective agent for lowering blood-glucose levels. In this study, synthesis of the ligand precursors 5-[4-(3-hydroxypropoxy)benzyl]-2,4- thiazolidinedione (HPBT), 5-[4-(3-bromopropoxy)benzyl]-2,4-thiazolidinedione (BPBT), and 5-[4-(3-iodopropoxy)benzyl]-2,4-thiazolidinedione (IPBT) were accomplished at high purity in gram scale quantities. These were fully characterized by the methods mentioned below. Several synthetic pathways were examined, with varying success; 5-[4-(3-ptoluenesulfonylpropoxy) benzyl]-2,4-thiazolidinedione (TsPBT), N-BOC-5-[4-(3- hydroxypropoxy)benzyl]-2,4-thiazolidinedione (BocHPBT), N-BOC-5-[4-(3- iodopropoxy)benzyl]-2,4-thiazolidinedione (BocIPBT), and 5-[4-(3- sulfonylimidazolepropoxy)benzyl]-2,4-thiazolidinedione (ImPBT) were compounds on those pathways. 5-[4-(3-Acetyl-6-hexoxy-2-one)benzyl]-2,4-thiazolidinedione (APBT), was synthesized, but not successfully purified. The vanadium coordination complex, bis-(5-[4-(3-acetyl-6-hexoxy-2-one)benzyl]-2,4-thiazolidinedionato) oxovanadium VO(APBT)2) gave encouraging preliminary results, e.g., synthesis of the complex directly from IPBT and vanadyl acetylacetonate; however further purification of the ligand would be required to determine stability constants. The ligand precursors were characterized by ¹H NMR spectroscopy, mass spectrometry, elemental analyses, infrared spectroscopy and, in certain instances, ¹³C NMR spectroscopy and two dimensional NMR spectroscopy for HPBT and IPBT. BocHPBT was characterized as a pure compound with ¹H NMR spectroscopy. TsPBT, BocIPBT and ImPBT were not purified enough for complete characterization. LSIMS characterization of the thiazolidinedione oxovanadium(IV) complex, VO(APBT)₂, indicated that the synthetic pathway so far elucidated could ultimately be refined to yield this compound in greater purity and quantity.
Item Metadata
Title |
The attempted synthesis of a thiazolidinedione-containing ligand for vanadyl complexation : investigating potential synergistic insulin mimics
|
Creator | |
Publisher |
University of British Columbia
|
Date Issued |
2000
|
Description |
Thiazolidinedione-containing compounds are a relatively recent class of oral
hypoglycemic agents used today to treat type II diabetes mellitus. Vanadium is well
known to be an effective agent for lowering blood-glucose levels. In this study, synthesis
of the ligand precursors 5-[4-(3-hydroxypropoxy)benzyl]-2,4-
thiazolidinedione (HPBT), 5-[4-(3-bromopropoxy)benzyl]-2,4-thiazolidinedione (BPBT),
and 5-[4-(3-iodopropoxy)benzyl]-2,4-thiazolidinedione (IPBT) were accomplished at
high purity in gram scale quantities. These were fully characterized by the methods
mentioned below.
Several synthetic pathways were examined, with varying success; 5-[4-(3-ptoluenesulfonylpropoxy)
benzyl]-2,4-thiazolidinedione (TsPBT), N-BOC-5-[4-(3-
hydroxypropoxy)benzyl]-2,4-thiazolidinedione (BocHPBT), N-BOC-5-[4-(3-
iodopropoxy)benzyl]-2,4-thiazolidinedione (BocIPBT), and 5-[4-(3-
sulfonylimidazolepropoxy)benzyl]-2,4-thiazolidinedione (ImPBT) were compounds
on those pathways. 5-[4-(3-Acetyl-6-hexoxy-2-one)benzyl]-2,4-thiazolidinedione
(APBT), was synthesized, but not successfully purified. The vanadium coordination
complex, bis-(5-[4-(3-acetyl-6-hexoxy-2-one)benzyl]-2,4-thiazolidinedionato)
oxovanadium VO(APBT)2) gave encouraging preliminary results, e.g., synthesis of the
complex directly from IPBT and vanadyl acetylacetonate; however further purification of
the ligand would be required to determine stability constants.
The ligand precursors were characterized by ¹H NMR spectroscopy, mass
spectrometry, elemental analyses, infrared spectroscopy and, in certain instances, ¹³C
NMR spectroscopy and two dimensional NMR spectroscopy for HPBT and IPBT.
BocHPBT was characterized as a pure compound with ¹H NMR spectroscopy. TsPBT,
BocIPBT and ImPBT were not purified enough for complete characterization. LSIMS
characterization of the thiazolidinedione oxovanadium(IV) complex, VO(APBT)₂,
indicated that the synthetic pathway so far elucidated could ultimately be refined to yield
this compound in greater purity and quantity.
|
Extent |
2522503 bytes
|
Genre | |
Type | |
File Format |
application/pdf
|
Language |
eng
|
Date Available |
2009-07-07
|
Provider |
Vancouver : University of British Columbia Library
|
Rights |
For non-commercial purposes only, such as research, private study and education. Additional conditions apply, see Terms of Use https://open.library.ubc.ca/terms_of_use.
|
DOI |
10.14288/1.0061392
|
URI | |
Degree | |
Program | |
Affiliation | |
Degree Grantor |
University of British Columbia
|
Graduation Date |
2000-05
|
Campus | |
Scholarly Level |
Graduate
|
Aggregated Source Repository |
DSpace
|
Item Media
Item Citations and Data
Rights
For non-commercial purposes only, such as research, private study and education. Additional conditions apply, see Terms of Use https://open.library.ubc.ca/terms_of_use.