I= INVESTIGATION OF THE CHEMICAL CONSTITUENTS OF PROSOPIS JULIFLORA AND CIRCULAR DICHROISMIC STUDIES OF CHOLESTANQUINOXALINES
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Title of Thesis
INVESTIGATION OF THE CHEMICAL CONSTITUENTS OF PROSOPIS JULIFLORA AND CIRCULAR DICHROISMIC STUDIES OF CHOLESTANQUINOXALINES

Author(s)
Nadeem Bin Zia
Institute/University/Department Details
University of Karachi/ HEJ Research Institute of Chemistry
Session
1992
Subject
Number of Pages
220
Keywords (Extracted from title, table of contents and abstract of thesis)
prosopis juliflora, cholestanquinoxalines, prosoflorine, prosinine, namely juliprosine, isojulprosine, genus prosopis, coninine, aliphatic chain

Abstract
The present work represented in this thesis consists of two parts. The first part (PART-1) is entitled as “Investigation of chemical constituents of Prosopis juliflora” and the second part (PART-2) is related to the “Circular dichroismic studies of cholestanoquinoxalines”.

The first part (PART-1) is related to natural product chemistry. This work involved isolation of two new piperidine alkaloids from a pharmacologically active plant Prosopis juliflora. The names given to these alkaloids were prosoflorine and prosinine. The structure elucidationof these alkaloids involved spectroscopic techniques like UV, IR, Mass, 1H-NMR and 13C-NMR etc. Two already known alkaloids from the same plants namely juliprosine and isojulprosine were the isolated but not included in this thesis.

The second part (PART-2) of this thesis was carried out in Lehrstuhl fur Struktur Chemie, Ruhr Universitaet 4630, Bochum, W. Germany. This part of work was assigned to me by Prof. Dr. Dr. Guenther Snatzke (Late). After him unfortunately no body was there to supervise me for the interpretation of CD-spectra of cholestanoquinoxalines. All the cholestanoquinoxalines were synthesized an determined on the basis of spectroscopy. Their CD spectra were examined on the basis of all the available rules. But the CD spectra of cholestanoquinoxalines most nearly followed the helicity rule. The helicity rule includes P-helicity and M-helicity. All the cholestanoquinoxalines revealed 1La, 1Lb and 1Bb band in CD spectra as well as in UV-spectra of Cholestanoqinoxalines which followed P-helicity gave positive Cotton effects and those which followed M-elicity rule revealed negative Cotton effect. With the interpretation of the CD-spectra it was possible to determine the exact configuration of cholestane. Ultimately this work was strongly and positively supported by Prof. Dr. Hans Georg Kuball, Fachbereich Chemie der Universitaet Kaiserslautern, 6750 Kaiserslauterm. W. Germany.

Download Full Thesis
1285.11 KB
S. No. Chapter Title of the Chapters Page Size (KB)
1 0 Contents
65.01 KB
2 1 PART - 1: Investigation Of Chemical Constituents Of Prosopis Juliflora : Introduction 3
103.01 KB
  1.1 Genus Prosopis 4
  1.2 Chemical Constituents 12
3 2 Biosynthesis of Piperidine Alkaloids 18
84.82 KB
  2.1 Piperidine Alkaloids with short aliphatic side chain 28
  2.2 Biosynthesis of coninine 28
  2.3 Piperidine Alkaloids with long aliphatic chain 30
4 3 Plant Material 31
40.58 KB
  3.1 General Method of Extraction of crude alkaloids 31
5 4 Present Work 37
89.52 KB
  4.1 Prosoflorine (Isolation and Structure ) 39
  4.2 Prosinine (Isolation and Structure ) 44
6 5 Experimental 49
36.6 KB
  5.1 General Experimental Details 49
  5.2 Isolation and Spectroscopic Date of prosoflorine and prosinine 50
  5.3 Prosoflorine 51
  5.4 Prosinine 52
7 6 References
49.42 KB
8 7 PART - 2: Circular Dichroismic Studies Of Cholestanoquinoxalines : Introduction 58
29.81 KB
9 8 Theoretical Details of Work 61
196 KB
  8.1 UN Spectra of aromatic compounds 62
  8.2 Quinoxaline Chrompore 69
  8.3 Effect of substitution on aromatics 74
  8.4 CD and ORD Techniques 77
10 9 Synthesis 97
79.18 KB
  9.1 Synthesis Schemes followed for (2 ,3 ) and (3,4) condensation products, Schemes - 1,2,3,4,5,6 and 7 97
  9.2 Synthesis schemes followed for (6 ,7 ) condensation products, Schemes - 8,9,10 and 11 104
11 10 NMR Techniques 107
86.33 KB
  10.1 Chemical Shifts of (Me-18) and (Me-19) in cholestane 10
  10.2 Chemical Shifts of protons on substituted and Unsubstituted quinoxaline Condensed with cholestane 110
  10.3 Lanthanide shift measurements 111
12 11 UV Data of the Compounds 116
30.66 KB
13 12 CD Data of the Compounds 121
105.58 KB
  12.1 CD Spectra of the Compounds 129
14 13 Results and Discussion 140
191.3 KB
15 14 Experimental 166
313.66 KB
16 15 References 216
42.18 KB