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CONTENTS CHAPTER – 1 Microwave Assisted Organic Synthesis 1. Microwave Assisted Organic Synthesis 1 1.1 Introduction 1 1.2 Microwave Frequency 2 1.3 Principle 2 1.4 Heating Mechanism 3 1.4.1 Dipolar Polarisation 3 1.4.2. Conduction Mechanism 4 1.5 Effects of solvents 5 1.6 Conventional vs Microwave Heating 6 1.7 Application of microwave in organic synthesis 7 1.8 Studies on 2-Aminoimidazoles 8 1.9 2-Aminoimidazole Alkaloids 11 1.10 Methods for the preparation of 2-aminoimidazoles 15 1.11 The 2-Aminoimidazole as a Pharmacophore 21 1.11.1 Antibiotics Activity 21 1.11.2 Sodium Hydrogen Exchanger-1 (NHE-1) Antagonists. 22 1.11.3 Anti HIV Activity 22 1.11.4 α-adrenoreceptor agonists. 24 1.11.5 Anti Cancer Activity 24 1.11.6 BACE-1 Inhibitors 25 1.11.7 Anti Biofilm Activity 26 1.12 Introduction to Biofilm 29 1.12.1 Properties of biofilms 30 1.12.2 Biofilm Growth Cycle 31 1.12.3 Biofilm Drug Resistance 31 1.13 Recent Publications on 2-aminoimidazoles 33 1.14 Conclusion 33 1.15 References 34
CHAPTER – 2 Microwave Assisted Synthesis & Structure Activity Relationship of 2-Hydroxy-2phenyl-2,3-dihydro-imidazo[1,2-a]pyrimidinium Salts and 2N-Substituted 4(5)- Phenyl-2-Amino-1H-imidazoles as Inhibitors of the Biofilm Formation by Salmonella Typhimurium and Pseudomonas aeruginosa 2.1 Introduction 40 2.2 Reaction scheme 41 2.3 Proposed Mechanism 42 2.4 Results and discussion 43 2.5 Biofilm activity 50 2.5.1 2N-substituted 2-aminopyrimidines 48 2.5.2 2-hydroxy-2,3-dihydro-imidazopyrimidinium salts 48 2.5.2.1 n-Alkyl or iso-alkyl substituents at 1-position 48 2.5.2.2 Further Modification in the most active core structure 51 2.5.2.3 Cyclo-alkyl substituents at 1-position 53 2.5.3 2N-substituted 2-aminoimidazoles 54 2.6 Conclusion 56 2.7 Experimental 57 2.8 Biological Assays 58 2.9 Experimental Protocols 60 2.10 Spectral Characterization 62 2.11 Representative NMR spectra 87 2.12 References 90 CHAPTER – 3 Structure Activity Relationship of N1-Substituted 2-Aminoimidazoles as Inhibitors of Biofilm Formation by Salmonella Typhimurium and Pseudomonas aeruginosa 3.1 Introduction 93 3.2 Reaction scheme 94 3.3 Proposed Mechanism 95 3.4 Results and discussion 96
Page 1 and 2: Saurashtra University Re - Accredit
Page 3: JANUARY-2011 Statement under O. Ph.
Page 7 and 8: Acknowledgment This thesis arose in
Page 9: since I was a child. My Mother Hans
Page 13 and 14: 5.5 Results and discussion 156 5.6
Page 15 and 16: Ms Mesyl MW Microwave NBS N-bromosu
Page 17 and 18: 1. Microwave Assisted Organic Synth
Page 19 and 20: 1.4 Heating Mechanism In microwave
Page 21 and 22: 1.5. Effects of solvents Every solv
Page 23 and 24: 1.7 Application of microwave in org
Page 25 and 26: aromatic amines, Lancini’s group
Page 27 and 28: 1.9 2-Aminoimidazole Alkaloids The
Page 29 and 30: Recently group of Erik 83 described
Page 31 and 32: 1.10 Methods for the preparation of
Page 33 and 34: R 1 O X R 2 NH 2 H 2N NAc R 1 HN R
Page 35 and 36: this manifold, was reported in 1925
Page 37 and 38: Another route to 4(5)-acyl-2-amino-
Page 39 and 40: this series of compounds against th
Page 41 and 42: documented. Extra care is needed be
Page 43 and 44: Very recently the research group of
Page 45 and 46: OH a,b O N H2N N Boc N 3 H N R N N
Page 47 and 48: 1.12.2 Biofilm Growth Cycle 1) Plan
Page 49 and 50: can survive both the onslaught of a
Page 51 and 52: [26] Leadbeater, N. E. (2004) Chemi
Page 53 and 54: [86] Kreutzberger, A. (1962) J. Org
Page 55 and 56: Microwave Assisted Synthesis & Stru
Page 57 and 58: 2.1 Introduction As described in ch
Page 59 and 60: 2.3 Proposed Mechanism: Regarding t
Page 61 and 62:
No. 12 60 120 traces 84 a All react
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the development of biofilm related
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In first instance, a series of 2-hy
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Br N N N R 1 OH Br N N N R 1 OH Fig
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do have a very strong effect agains
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2.6 Conclusion In the present study
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2.8 Biological assays 2.8.1 Static
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2.9 Experimental protocol: 2.9.1 Ge
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temperature of 80 °C and a maximum
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29.5,29.4, 29.2, 27.0, 22.6, 14.1.
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Yield: 78 %. 1 H NMR (300 MHz, CDCl
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N Br N N C 14H 29 OH Yield: 72 %. 1
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(75.5 MHz, CDCl3): δ = 167.7, 154.
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N Br N N C 14H 29 OH Cl Yield: 90 %
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2-(3,4-Dichlorophenyl)-2-hydroxy-1-
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N Br N N C 8H 17 OH NO 2 Yield: 49
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C3H7 HN N N H Cl Cl Yield : 70 %. 1
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(s, 1H), 3.16 (s, 3H), 1.80 (m, 2H)
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5-(4’-Nitrobiphenyl-4-yl)-N-octyl
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2.11 Representative NMR spectra 2.1
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2.11.3 10.4329 0.7429 151.5720 10.0
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[21] Matz C, McDougald D, Moreno A.
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Chapter-3 Structure Activity Relati
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imidazoles, where the addition of a
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3.4 Result and Discussion It was fo
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No. H 2N Compound Code N N C8H17 R1
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medium used in the set-up to monito
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H 2N N N N H2N N R R Figure-1 Effec
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3.5.3 Cyclo-alkyl 2-aminoimidazoles
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3.6. Conclusion In the present stud
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3.8. Experimental protocols 3.8.1 G
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122.6, 54.6, 33.3(×2), 27.3 (×2),
Page 125 and 126:
Page 127 and 128:
5-(4-Chlorophenyl)-1-cyclooctyl-1H-
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Yield: 50 %. Mp: 76-78 ° C. 1 H NM
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5-(4-Chlorophenyl)-1-cyclobutyl-1H-
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Yield: 66%. 1 H NMR (300 MHz, CDCl3
Page 135 and 136:
3.10 Representative NMR spectra 3.1
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3.11 References [1] (a) Alvi K. A,
Page 139 and 140:
Copper Catalyzed Microwave Assisted
Page 141 and 142:
4.1 Introduction There are only a f
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(Table-1, No- 6). Next reaction tem
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No. Product, Yield b (%) No. Produc
Page 147 and 148:
4.4 Possible Mechanism Regarding th
Page 149 and 150:
4.7 Experimental protocols 4.7.1 Ge
Page 151 and 152:
Page 153 and 154:
1-(3-Azidopropyl)-2-(3,4-dichloroph
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Yield: 84 %. 1 H NMR (300 MHz, DMSO
Page 157 and 158:
Page 159 and 160:
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1H), 1.66 (m, 6H), 1.70 (m, 2H). 13
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5.48 Hz, 2H), 3.59 (m, 2H), 3.16 (d
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4.10 References [1] For a general r
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Crystal and Molecular Structure Ana
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5.1 Introduction The membrane efflu
Page 171 and 172:
oscillation range of 5˚ and proces
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C12-C13 1.372(4) C32-C37 1.390(3) C
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Fig.-3: Packing of the molecules wh
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1 H NMR (400 MHz CDCl3): δ = 7.57-
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5.9.2 13 C spectra of bs-DP-7
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SUMMARY The work represented in the
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CONFERENCES/SEMINARS/WORKSHOPS ATTE
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PUBLICATIONS [1] One-Pot Microwave-
Page 200 and 201:
Scheme 2 Competitive formation of 1
Page 202 and 203:
Table 2 continued 9 10 11 12 N hydr
Page 204:
8. Colson G, Raboult L, Lavelle F,
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