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4.9.2 1 H and 13 C NMR spectra of bs-304 Integral 160 11.0 10.6535 0.7987 150.5865 146.5318 150 10.0 140 134.0549 131.0403 130 9.0 125.4219 122.0327 120 Br 117.4725 Br 7.8767 7.6231 7.5139 7.4857 0.9951 1.8738 1.9716 8.0 110 7.1731 N H 0.9264 N 7.0 N N H 100 N H N H 6.0069 5.9887 5.9705 90 N N N 0.9433 6.0 (ppm) N N N C 3H7 80 (ppm) C 3H 7 5.0 4.5890 4.5689 4.5488 70 1.9449 60 3.6965 3.6764 3.6569 3.6368 4.0 1.9690 3.0 2.6414 2.6169 2.5918 1.9586 48.9026 42.9570 40.3132 39.7568 39.4805 39.2005 38.6441 50 40 2.0 30 27.0764 1.6773 1.6528 1.6283 1.6032 0.9724 0.9479 0.9235 1.9563 22.2144 20 3.0000 1.0 13.6286 10 0.0 0
4.10 References [1] For a general review of the synthesis and activity of 2-aminoimidazole alkaloids, see: (a) S. M. Weinreb, (2007) Nat. Prod. Rep. 24, 931–948. (b) H. Hoffmann, T. Lindel, (2003) Synthesis. 1753–1783. (c) J. D. Sullivan, R. L. Giles, R. E. Looper. (2009) Curr. Bioactive Cmpds. 5, 39-78. [2] For the anti-biofilm activity of 2-aminoimidazoles, see: (a) R. W. Huigens III, J. J. Richards, G. Parise, T. E. Ballard, W. Zeng, R. Deora, C. Melander, (2007) J. Am. Chem. Soc. 129, 6966–6967. (b) S. A. Rogers, C.Melander, (2008) Angew. Chem. 120, 5307–5309., (2008) Angew. Chem. Int. Ed. 47, 5229–5231. (c) T. E. Ballard, J. J. Richards, A. L. Wolf, C. Melander, (2008) Chem. Eur. J. 14, 10745–10761. [3] (a) M. S. Malamas, J. Erdei, I. Gunawan, J. Turner, Y. Hu, E. Wagner, K. Fan, R.Chopra, A. Olland, J. Bard, S. Jacobsen, R. L. Magolda, M. Pangalos, A. J. Robi- chaud. (2010) J. Med. Chem. 53, 1146–1158. (b) M. S. Malamas, J. rdei, I. Gunawan, K. Barnes, M. Johnson, Y. Hui, J. Turner, Y.Hu, E. Wagner, K. Fan, A. Olland, J. Bard,A. J. Robichaud. (2009) J. Med. Chem. 52, 6314–6323. [4] (a) R. S. Coleman, E. L. Campbell, D. J. Carper. (2009) Org. Lett. 11, 2133–2136. (b) M. Nodwell, A. Pereira, J. L. Riffell, C. Zimmermann, B. O. Patrick, M. Roberge, R. J. Andersen. (2009) J. Org. Chem. 74, 995–1006. [5] (a) A. G. Beaman, W. Tautz, T. Gabriel, R. Duschinsky. (1966) J. Am. Chem. SOC. 87, 389. (b) G. C. Lancini, E. Lazzari, V. Arioli, P. Bellani. (1969) J. Med. Chem. 12, 775 [6] (a) A. Lawson. (1956) J. Am. Chem. Soc. 307–310. (b) B. T. Storey, W. W. Sullivan, C. L. Moyer. (1964) J. Org. Chem. 29, 3118–3120. (c) G. C. Lencini,; E. Lazzari. (1966) J. Heterocycl. Chem. 3, 152–154. [7] (a) N. S. Aberle, L. Guillaume, K. G. Watson. (2006) Org. Lett. 8, 419–421. (b) N. Aberle, J. Catimel, E. C. Nice, K. G. Watson. (2007) Bioorg. Med. Chem. Lett. 17,3741–3744. [8] C. H. Soh, W. K. Chui, Y. Lam. (2008) J.Comb.Chem. 10,118. [9] P. Molina, P. Fresneda, M. Sanz. (1999) J. Org. Chem. 64, 2540–2544. [10] T. Moschny, H. Hartmann. (1999) Helv. Chim. Acta 82, 1981–1993. [11] S. Ohta, N. Tsuno, S. Nakamura, N. Taguchi, M. Yamashita, I. Kawasaki, M. Fujieda. (2000) Heterocycles. 53, 1939–1955. [12] (a) H. C. Kolb, M. G. Finn, K. B. Sharpless. (2001) Angew. Chem., Int. Ed. 40, 2004-2021. (b) H. C. Kolb, K. B. Sharpless. (2003) Drug Discovery Today. 8, 1128 1137. (c) C. W. Tornøe, C. Christensen, M. Meldal. (2002) J. Org. Chem., 67, 3057-3064. [13] (a) E. Lieber, T. S. Chao, C. N. R. Rao. (1963) Organic Syntheses. Coll. Vol. 4, 380., 1957. Vol. 37, 26. (b) El. Ashry, Y. El Kilany, N. Rashed, H. Assafir, (1999) Adv. Heterocycl. Chem. 75, 79. (c) D. J. Brown, Mechanisms of Molecular Migrations. Thyagarajan, B. S., (1968) Wiley-Interscience: New York, Vol. 1, 209. [14] For synthesis and anti biofilm activity see (a) D. S. Ermolat’ev, J. B. Bariwal, H. P. L. Steenackers, S. C. J. De Keersmaecker, E. V. Van der Eycken, (2010) Angew. Chem. Int. Ed.
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Saurashtra University Re - Accredit
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JANUARY-2011 Statement under O. Ph.
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Acknowledgment This thesis arose in
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since I was a child. My Mother Hans
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CHAPTER - 2 Microwave Assisted Synt
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5.5 Results and discussion 156 5.6
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Ms Mesyl MW Microwave NBS N-bromosu
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1. Microwave Assisted Organic Synth
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1.4 Heating Mechanism In microwave
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1.5. Effects of solvents Every solv
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1.7 Application of microwave in org
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aromatic amines, Lancini’s group
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1.9 2-Aminoimidazole Alkaloids The
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Recently group of Erik 83 described
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1.10 Methods for the preparation of
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R 1 O X R 2 NH 2 H 2N NAc R 1 HN R
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this manifold, was reported in 1925
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Another route to 4(5)-acyl-2-amino-
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this series of compounds against th
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documented. Extra care is needed be
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Very recently the research group of
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OH a,b O N H2N N Boc N 3 H N R N N
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1.12.2 Biofilm Growth Cycle 1) Plan
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can survive both the onslaught of a
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[26] Leadbeater, N. E. (2004) Chemi
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[86] Kreutzberger, A. (1962) J. Org
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Microwave Assisted Synthesis & Stru
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2.1 Introduction As described in ch
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2.3 Proposed Mechanism: Regarding t
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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
Page 113 and 114: medium used in the set-up to monito
Page 115 and 116: H 2N N N N H2N N R R Figure-1 Effec
Page 117 and 118: 3.5.3 Cyclo-alkyl 2-aminoimidazoles
Page 119 and 120: 3.6. Conclusion In the present stud
Page 121 and 122: 3.8. Experimental protocols 3.8.1 G
Page 123 and 124: 122.6, 54.6, 33.3(×2), 27.3 (×2),
Page 125 and 126: Yield: 52 %. 1 H NMR (300 MHz, CDCl
Page 127 and 128: 5-(4-Chlorophenyl)-1-cyclooctyl-1H-
Page 129 and 130: Yield: 50 %. Mp: 76-78 ° C. 1 H NM
Page 131 and 132: 5-(4-Chlorophenyl)-1-cyclobutyl-1H-
Page 133 and 134: Yield: 66%. 1 H NMR (300 MHz, CDCl3
Page 135 and 136: 3.10 Representative NMR spectra 3.1
Page 137 and 138: 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
Page 143 and 144: (Table-1, No- 6). Next reaction tem
Page 145 and 146: 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: Yield: 69 %. 1 H NMR (300 MHz, CDCl
Page 153 and 154: 1-(3-Azidopropyl)-2-(3,4-dichloroph
Page 155 and 156: Yield: 84 %. 1 H NMR (300 MHz, DMSO
Page 161 and 162: 1H), 1.66 (m, 6H), 1.70 (m, 2H). 13
Page 163: 5.48 Hz, 2H), 3.59 (m, 2H), 3.16 (d
Page 167 and 168: Crystal and Molecular Structure Ana
Page 169 and 170: 5.1 Introduction The membrane efflu
Page 171 and 172: oscillation range of 5˚ and proces
Page 173 and 174: C12-C13 1.372(4) C32-C37 1.390(3) C
Page 175 and 176: Fig.-3: Packing of the molecules wh
Page 177 and 178: 1 H NMR (400 MHz CDCl3): δ = 7.57-
Page 179 and 180: 5.9.2 13 C spectra of bs-DP-7
Page 181 and 182: SUMMARY The work represented in the
Page 183 and 184: CONFERENCES/SEMINARS/WORKSHOPS ATTE
Page 185: 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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