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SYNTHESIS, CHARACTERIZATION AND PHARMACOLOGICAL STUDY OF SOME BIOACTIVE MOLECULES A THESIS SUBMITTED TO THE SAURASHTRA UNIVERSITY IN THE FACULTY OF SCIENCE FOR THE DEGREE OF DOCTOR OF PHILOSOPHY IN CHEMISTRY By Nikhil R. Vekariya UNDER THE GUIDANCE OF PROF. ANAMIK SHAH DEPARTMENT OF CHEMISTRY (DST-FIST Funded & UGC-SAP Sponsored) SAURASHTRA UNIVERSITY RAJKOT – 5 (GUJARAT, INDIA) SEPTEMBER – 2007
Statement under O.Ph.D.7 of <strong>Saurashtra</strong> <strong>University</strong> The work included in the thesis is done by me under the supervision of Prof. Anamik Shah and the contribution made thereof is my own work. Date: Place: Nikhil R. Vekariya
Page 1: Saurashtra University Re - Accredit
Page 5 and 6: To My Family, With Love
Page 7 and 8: I would like to thank my dear lab m
Page 9 and 10: Synthetic Aspects 55 QSAR Study 59
Page 11 and 12: CHAPTER-6 MICROWAVE ASSISTED SYNTHE
Page 13: Chapter-1 Introduction, Synthesis a
Page 16 and 17: 2 Their biological functions are as
Page 18 and 19: 4 5. The reaction of β-amino-α,
Page 20 and 21: 6 5. A general, highly flexible Cu-
Page 22 and 23: 8 11. A new microwave-assisted rear
Page 24 and 25: 10 Gaetano Dattolo 38 and his resea
Page 26 and 27: 12 -CONHOCH 3 O -CONHNH 2 Cl C N F
Page 28 and 29: 14 Molecular modeling and docking c
Page 30 and 31: 16 R 3 R 4 R 1 ,R 2 ,R 3 ,=H, alkyl
Page 32 and 33: 18 CH 3 CH 3 N C O NH H 3 CH 3 F N
Page 34 and 35: 20 Drug Name Chemical Structure : :
Page 36 and 37: 22 1.3 REACTION SCHEMES 1.3.1 Schem
Page 38 and 39: 24 1.4 Experimental Protocols Comme
Page 41 and 42: 27 1.7 SPECTRAL ANALYSIS 1.7.1 IR S
Page 43 and 44: 29 of phenyl ring from molecule, ba
Page 45 and 46: 31 Ethyl 3,5-dimethyl-4-[5-(3-nitro
Page 47 and 48: 33 C, H, N (in %): Found: 60.62(C),
Page 49 and 50: 35 IR (KBr) cm -1 : 3320, 3246 (-NH
Page 51 and 52: IR spectrum of Ethyl 4-[5-(4-methox
Page 53 and 54:
39 1 H NMR spectrum of Ethyl 3, 5-d
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41 1 H NMR spectrum of Ethyl 3, 5-d
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Mass spectrum of Ethyl 3, 5-dimethy
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45 Mass spectrum of Ethyl 3, 5-dime
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47 29. Ekkati A. R., Bates D. K., S
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Chapter-2 Introduction, Synthesis a
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50 with improved bioavailability, t
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52 combining Ca 2+ antagonism and t
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54 alpha1G, expressed in Xenopus oo
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56 3,5-Dibenzoyl-4-(3-phenoxyphenyl
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58 PAF, will have clinical utilitie
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60 According to the 3D QSAR study,
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62 2.3.3 Scheme 3 O O R HN CH 3 O H
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64 2.5 EXPERIMENTAL 2.5.1 N-(naphth
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66 2.6 PHYSICAL DATA TABLE 2.6.1 Ph
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68 2.7 SPECTRAL DISCUSSION 2.7.1 IR
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70 ionization chamber and resolved
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72 C, H, N (in %): Found: 78.10 (C)
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74 1,4- Dihydro -4- (4-hydroxy phen
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76 C, H, N (in %): Found: 69.87 (C)
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IR spectrum of 1,4- dihydro-4-(4-me
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1 H NMR spectrum of 1,4- dihydro-4-
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1 H NMR spectrum of 1,4- dihydro-4-
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84 REFERENCES 1. Alker, D.; Arrowsm
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86 51. Pickard, J. D.; Murray, G. D
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Chapter - 3 A mini review of Dihydr
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urea, is the first intermediate in
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91 A variety of substituted aromati
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93 first organocatalytic asymmetric
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95 one system in high yield and hig
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97 classical dihydropyridine calciu
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99 Atwal et al 58 examined a series
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101 biological activity. Biological
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103 Applying intramolecular Heck re
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105 furo[3,4-d]pyrimidines, pyrrolo
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107 Figure 2: The reaction of 2-ami
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109 O O O R 1 NH ClCH 2 COOH R 1 N
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111 A N B N O S R 1 3.6 Biginelli R
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113 3.7.1 Name reactions Following
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115 and urea or thiourea to afford
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117 3.8.1 Cycloaddition reaction Re
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119 3.8.5 Solid Phase Organic Synth
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121 Lusch and Tallarico 31 reported
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123 continuation of this work, it w
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124 INTRODUCTION A general introduc
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126 4.1.2 Scheme-2 R 2 O R 1 NH NH
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128 4.1.5 Reaction Mechanism O NH N
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130 4.3.2 N - (Substituted phenyl)-
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132 13. AKS- 562 4-F 2,3,5,6- 441.5
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134 14 AKS-583 4-F 3-OCH 3 397.46 1
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136 4.5 SPECTRAL ANALYSIS Spectral
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gave multiplet signal at similar re
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140 IR(KBr)cm -1 :3192 (-NH,str),31
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142 N - (4-Fluoro phenyl) -5- (3-me
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144 Mass: 435 (2), 431 (10), 416 (3
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IR spectrum of N,6-Bis(4-chlorophen
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1 H NMR Spectrum of 5-(2-Chlorophen
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150 1 H NMR Spectrum of N-(4-Chloro
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152 1 H NMR Spectrum of N,6-Bis(1-n
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Mass Spectrum of N-(4-Chlorophenyl)
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Mass Spectrum of 5-(2-Chlorophenyl)
Page 175 and 176:
Chapter-5 Synthesis and Characteriz
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159 5.1 REACTOIN SCHEMES 5.1.1 Sche
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161 5.2 Experimental 5.2.1 N-Substi
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163 5.3 PHYSICAL DATA 5.3.1 Physica
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165 AKS-916 2,4diCH 3 4-Cl 3,4,5-tr
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167 The supplementary characterizat
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169 IR(KBr,cm -1 ): 3292-3228 (-NH)
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171 IR(KBr,cm -1 ): 3312-3215 (-NH)
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173 N-(2,4-Di-methylphenyl)-N-(4-ch
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IR spectrum of 4-(phenyl)-N-(4-chlo
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IR spectrum of 4-(4-flourophenyl)-N
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1 H NMR spectrum of 4-(4-hydroxyphe
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1 H NMR spectrum of N-(3-methylphen
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Mass spectrum of 4-(2,3-benzophenyl
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184 INTRODUCTION The current chapte
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186 6.1.3 Scheme-3 CH 3 R NH O H 3
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188 6.2 EXPERIMENTAL N- (Substitute
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190 6.3.2 Physical data of 6-methyl
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192 at 7.59 δ ppm with J value 8.8
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194 N-(4-Flourophenyl)-6-methyl-2-o
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196 C, H, N (in %): Found: 71.72 (C
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198 C, H, N (in %): Found: 68.09 (C
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IR spectrum of N-( 4-Flouro phenyl)
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1 H NMR spectrum of N-(4-Fluorophen
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Mass spectrum of N-(2,3-Dimethylphe
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206 References 1. Kappe, C. O.; Acc
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208 54. Forray, C.; Bard, J. A.; We
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210 96. Manhi, M. and Abdel-Fattah,
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212 153. Trost, B. M.; Crawley, M.
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213 Biological Activity Study The p
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215 Incubation time and temperature
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217 34. AKS-904 -- - - - 100 100 35
Page 239 and 240:
234 SUMMARY OF WORK The work presen
Page 241 and 242:
236 Presentation of Paper & Confere
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