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ADDENDUM
PAGELIST OF 1H-NMR AND 13C-NMR SPECTRA. 119
LIST OF IR SPECTROSCOPY DATA. 136
LIST OF MS SPECTROMETRY DATA. 141
LIST OF HPLC DATA. 146
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LIST OF 1H-NMR AND 13C-NMR SPECTRA.
(2E)-1-(5-chlorothiophen-2-yl)-3-[4-(trifluoromethyl)phenyl]-prop-2-en-1-one (10a) 1H-NMR (10a) 13C-NMR (10a) S Cl O CF3 4 3 6' 5' 3' 2' 3 2 1 " "
P ag e
120
(2E)-3-(3-chlorophenyl)-1-(1H-pyrrol-2-yl)prop-2-en-1-one (10b) 13C-NMR (10b) 1H-NMR (10b) O Cl N H 5 4 3 6' 5' 4' 2' 3 2 1 " " "P ag e
121
(2E)-3-(3-chlorophenyl)-1-(6-methoxypyridin-3-yl)prop-2-en-1-one (10c) 1H-NMR (10c) 13C-NMR (10c) N O H3C O Cl 6' 5' 4' 2' 3 2 1 5 4 2 " " "P ag e
122
(2E)-3-(5-chlorothiophen-2-yl)-1-(2-hydroxy-4-methoxyphenyl)prop-2-en-1-one (10d) 1H-NMR(10d) 13C-NMR (10d) S Cl O OH O H3C 6 5 3 4' 3' 3 2 1 " " "P ag e
123
(2E)-3-(3-bromo-4-fluorophenyl)-1-(1H-pyrrol-2-yl)prop-2-en-1-one (10e) 1H-NMR (10e) 13C-NMR (10e) N O Br F H 5 4 3 6' 5' 2' 3 2 1 " " "P ag e
124
DEPT 90 (10e) COSY (10e)P
ag
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125
P ag e
126
(2E)-1-(1H-pyrrol-2-yl)-3-[4-(trifluoromethyl)phenyl]prop-2-en-1-one (10f) 1H-NMR (10f) 13C-NMR (10f) N O CF3 H 5 4 3 3 2 1 6' 5' 3' 2' " " "P ag e
127
DEPT 90 (10f) HSQC (10f)P ag e
128
(2E)-1-(1H-pyrrol-2-yl)-3-[3-(trifluoromethyl)phenyl]prop-2-en-1-one (10g) 1H-NMR (10g) 13C-NMR (10g) N O CF3 H 5 4 3 6' 5' 4' 2' 3 2 1 " " "P ag e
129
DEPT 135 (10g) COSY (10g)P ag e
130
HSQC (10g) HMBC (10g)P ag e
131
(2E)-3-(3-bromo-4-fluorophenyl)-1-(5-chlorothiophen-2-yl)prop-2-en-1-one (10h) 1H-NMR (10h) 13C-NMR (10h) S O Cl Br F 4 3 6' 5' 2' 3 2 1 " "P ag e
132
DEPT 90 (10h) COSY (10h)P ag e
133
HSQC (10h) HMBC (10h)P ag e
134
(2E)-3-(3-bromo-4-fluorophenyl)-1-(5-methylthiophen-2-yl)prop-2-en-1-one (10i) 1H-NMR (10i) 13C-NMR (10i) S O H3C Br F 1 2 3 2' 5' 6' 3 4" "P ag e
135
(2E)-3-(4-chlorophenyl)-1-(2-hydroxy-4-methoxyphenyl)-prop-2-en-1-one (8) 1H-NMR (8) 13C-NMR (8) O O OH Cl H3C 6' 5' 3' 2' 3 2 1 6 5 3" " "P
ag
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136
LIST OF IR SPECTROSCOPY DATA.
(2E)-1-(5-chlorothiophen-2-yl)-3-[4-(trifluoromethyl)phenyl]-prop-2-en-1-one (10a) (2E)-3-(3-chlorophenyl)-1-(1H-pyrrol-2-yl)prop-2-en-1-one (10b) S Cl O CF3 4 3 6' 5' 3' 2' 3 2 1 " " O Cl N H 5 4 3 6' 5' 4' 2' 3 2 1 " " "
P ag e
137
(2E)-3-(3-chlorophenyl)-1-(6-methoxypyridin-3-yl)prop-2-en-1-one (10c) (2E)-3-(5-chlorothiophen-2-yl)-1-(2-hydroxy-4-methoxyphenyl)prop-2-en-1-one (10d) N O H3C O Cl 6' 5' 4' 2' 3 2 1 5 4 2 " " " S Cl O OH O H3C 6 5 3 4' 3' 3 2 1 " " "P ag e
138
(2E)-3-(3-bromo-4-fluorophenyl)-1-(1H-pyrrol-2-yl)prop-2-en-1-one (10e) (2E)-1-(1H-pyrrol-2-yl)-3-[4-(trifluoromethyl)phenyl]prop-2-en-1-one (10f) N O Br F H 5 4 3 6' 5' 2' 3 2 1 " " " N O CF3 H 5 4 3 3 2 1 6' 5' 3' 2' " " "P ag e
139
(2E)-1-(1H-pyrrol-2-yl)-3-[3-(trifluoromethyl)phenyl]prop-2-en-1-one (10g) (2E)-3-(3-bromo-4-fluorophenyl)-1-(5-chlorothiophen-2-yl)prop-2-en-1-one (10h) N O CF3 H 5 4 3 6' 5' 4' 2' 3 2 1 " " " S O Cl Br F 4 3 6' 5' 2' 3 2 1 " "P ag e
140
(2E)-3-(3-bromo-4-fluorophenyl)-1-(5-methylthiophen-2-yl)prop-2-en-1-one (10i) (2E)-3-(4-chlorophenyl)-1-(2-hydroxy-4-methoxyphenyl)-prop-2-en-1-one (8) S O H3C Br F 1 2 3 2' 5' 6' 3 4" " O O OH Cl H3C 6' 5' 3' 2' 3 2 1 6 5 3" " "P
ag
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141
LIST OF MS SPECTROMETRY DATA.
(2E)-1-(5-chlorothiophen-2-yl)-3-[4-(trifluoromethyl)phenyl]-prop-2-en-1-one (10a) Meas.m/z 315.9928 # 2 Formula C14H8ClF3OS Score 41.16 m/z 315.9931 err [mDa] 0.3 err [ppm] 0.9 mSigma 479.7 rdb 9.0 N-Rule ok e ̅ Conf odd (2E)-3-(3-chlorophenyl)-1-(1H-pyrrol-2-yl)prop-2-en-1-one (10b) Meas.m/z 231.0439 # 1 Formula C13H10ClNO Score 100 m/z 231.0445 err [mDa] 0.6 err [ppm] 2.7 mSigma 457.7 rdb 9.0 N-Rule ok e ̅ Conf odd
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142
(2E)-3-(3-chlorophenyl)-1-(6-methoxypyridin-3-yl)prop-2-en-1-one (10c) Meas.m/z 273.0551 # 1 Formula C15H12ClNO2 Score 100 m/z 273.0551 err [mDa] 0.1 err [ppm] 0.2 mSigma 437.7 rdb 10.0 N-Rule ok e ̅ Conf odd (2E)-3-(5-chlorothiophen-2-yl)-1-(2-hydroxy-4-methoxyphenyl)prop-2-en-1-one (10d) Meas.m/z 294.0109 # 2 Formula C14H11ClO3S Score 1.59 m/z 294.0112 err [mDa] 0.3 err [ppm] 1.1 mSigma 428.1 rdb 9.0 N-Rule ok e ̅ Conf oddP ag e
143
(2E)-3-(3-bromo-4-fluorophenyl)-1-(1H-pyrrol-2-yl)prop-2-en-1-one (10e) Meas.m/z 292.9847 # 1 Formula C13H9BrFNO Score 100 m/z 292.9846 err [mDa] -0.1 err [ppm] -0.2 mSigma 538.5 rdb 9.0 N-Rule ok e ̅ Conf odd (2E)-1-(1H-pyrrol-2-yl)-3-[4-(trifluoromethyl)phenyl]prop-2-en-1-one (10f) Meas.m/z 265.0705 # 1 Formula C14H10F3NO Score 100 m/z 265.0709 err [mDa] 0.4 err [ppm] 1.5 mSigma 540.2 rdb 9.0 N-Rule ok e ̅ Conf oddP ag e
144
(2E)-1-(1H-pyrrol-2-yl)-3-[3-(trifluoromethyl)phenyl]prop-2-en-1-one (10g) Meas.m/z 265.0714 # 1 Formula C14H10F3NO Score 100 m/z 265.0709 err [mDa] -0.5 err [ppm] -1.9 mSigma 501.4 rdb 9.0 N-Rule ok e ̅ Conf odd (2E)-3-(3-bromo-4-fluorophenyl)-1-(5-chlorothiophen-2-yl)prop-2-en-1-one (10h) Meas.m/z 343.9067 # 1 Formula C13H7BrClFOS Score 100 m/z 343.9068 err [mDa] 0.1 err [ppm] 0.2 mSigma 467.9 rdb 9.0 N-Rule ok e ̅ Conf oddP ag e
145
(2E)-3-(3-bromo-4-fluorophenyl)-1-(5-methylthiophen-2-yl)prop-2-en-1-one (10i) Meas.m/z 323.9609 # 1 Formula C14H10BrFOS Score 100 m/z 323.9614 err [mDa] 0.5 err [ppm] 1.5 mSigma 512.5 rdb 9.0 N-Rule ok e ̅ Conf odd (2E)-3-(4-chlorophenyl)-1-(2-hydroxy-4-methoxyphenyl)-prop-2-en-1-one (8) Meas.m/z 288.0543 # 1 Formula C16H13ClO3 Score 100 m/z 288.0548 err [mDa] 0.5 err [ppm] 1.8 mSigma 403.5 rdb 10.0 N-Rule ok e ̅ Conf oddP ag e
146
LIST OF HPLC DATA. (2E)-1-(5-chlorothiophen-2-yl)-3-[4-(trifluoromethyl)phenyl]-prop-2-en-1-one (10a) (2E)-3-(3-chlorophenyl)-1-(1H-pyrrol-2-yl)prop-2-en-1-one (10b)P ag e
147
(2E)-3-(3-chlorophenyl)-1-(6-methoxypyridin-3-yl)prop-2-en-1-one (10c) (2E)-3-(5-chlorothiophen-2-yl)-1-(2-hydroxy-4-methoxyphenyl)prop-2-en-1-one (10d)P ag e
148
(2E)-3-(3-bromo-4-fluorophenyl)-1-(1H-pyrrol-2-yl)prop-2-en-1-one (10e) (2E)-1-(1H-pyrrol-2-yl)-3-[4-(trifluoromethyl)phenyl]prop-2-en-1-one (10f)P ag e
149
(2E)-1-(1H-pyrrol-2-yl)-3-[3-(trifluoromethyl)phenyl]prop-2-en-1-one (10g) (2E)-3-(3-bromo-4-fluoro-phenyl)-1-(5-chlorothiophen-2-yl)prop-2-en-1-one (10h)P ag e
150
(2E)-3-(3-bromo-4-fluorophenyl)-1-(5-methylthiophen-2-yl)prop-2-en-1-one (10i) (2E)-3-(4-chlorophenyl)-1-(2-hydroxy-4-methoxyphenyl)-prop-2-en-1-one (8)P
ag
e
151
LIST OF DOCKING RESULTS. Compound 10a
Compound 10b
P ag e
152
Compound 10d Compound 10e Compound 10fP ag e
153
Compound 10g Compound 10h Compound 10iP
ag
e
154
P
ag
e
155
ACKNOWLEDGEMENTS
I would like to thank the following people for assisting me with my master’s degree; your help and guidance were valuable and much appreciated.
My supervisor Dr. A.C.U. Lourens
My co-supervisors Prof. J.P. Petzer and Dr. A. Petzer Mr. A Joubert Dr. J. Jordaan Prof J. Du Preez Miss. M. Geldenhuys Mr. S.J. Robinson Miss. J. Kleynhans Miss. M. Hoon Miss. L. Meiring NRF for funding MRC for funding
NWU for funding and facilities provided.
All my friends & family for their support and love.
And lastly for God for giving me the strength and opportunities to follow my dreams.
A last word….
There are two sayings that come to mind, when I think about my Master’s degree:
The first one - try and try again, in the end you will succeed - is absolutely applicable to a post graduate degree and all the effort that comes with it. The second, but most important - with God anything is possible, look to Him, He will guide you – reminds us that we all need some extra help and guidance sometimes, God will always be there for His children.
