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5.10 References [1] Fusi F., Saponara S., Valoti M., Dragoni S., D'Elia P., Sgaragli T., Alderighi D., Kawase M., Shah A., Motohashi N., Sgaragli G. (2006)Curr. Drug Targets. 8, 949–959. [2] Bates, S.E., Regis, J.I., Robey, R.W., Zhan, Z., Scala, S., Meadows, B.J. (1994) Chemoresistance in the clinic: overview. Bull. Cancer 81 (suppl 2), 55–61. [3] Bellamy, W.T. (1996) Annu. Rev. Pharmacol. Toxicol. 36, 161–183 [4] Saponara S., Kawase M., Shah A., Motohashi N., Molnar J., Ugocsai K., Sgaragli G., Fusi F. (2004) Br. J. Pharm. 141, 415-422. [5] Saponara S., Ferrara A., Gorelli B., Shah A., Kawase M., Motohashi N., Molnar J., Sgaragli G., Fusi F. (2007) Eur. J. Pharmacol. 563, 160–163. [6] Guengerich, F.B., Brian, W.R., Iwasaki, M., Sari, M.A., Baarnhielm, C., Berntsson, P. (1991) J. Med. Chem. 34, 1838–1844. [7] Katoh, M., Nakajima, M., Shimada, N., Yamazaki, H., Yokoi, T. (2000) Eur. J. Clin. Pharmacol. 55, 843–852 [8] For synthesis and biological activity see (a) Paolo D'Elia , Francesco De Matteis , Stefania Dragoni , Anamik Shah ,Giampietro Sgaragli, Massimo Valoti. (2009) European Journal of Pharmacology. 614, 7–13 (b) Masami Kawase, Anamik Shah, Harsukh Gaveriya, Noboru Motohashi, Hiroshi Sakagami, Andreas Vargae, Joseph Molnar. (2002) Bioorganic & Medicinal Chemistry. 10, 1051–1055. (c) Prashant S. Kharkar, Bhavik Desai, Harsukh Gaveria, Bharat Varu, Rajesh Loriya, Yogesh Naliapara, Anamik Shah, Vithal M. Kulkarni. (2002) J. Med. Chem. 45, 4858-4867 [9] Otwinowski, Z. Minor, W. In: Methods in Enzymology, 276, Carter, C. W. Jr., Sweet, R. M., (1997) New York: Academic Press, 307-326. [10] Sheldrick, G.M. (2008) Acta Cryst., A64, 112-122. [11] Allen, F.H., Kennard, O., Watson, D.G., Brummer, L., Orpen, A.G., Taylor, R. (1987) J. Chem. Soc. Perkin Trans, II:S1. [12] Spek, A.L. (2003) J. Appl. Cryst. 36, 7-13. [13] Cremer, D., and Pople, J.A. (1975) J. Am. Chem. Soc. 97, 1354-1358.
SUMMARY The work represented in the thesis entitled “Synthesis and Characterization of New heterocyclic compounds & their application” is divided into five chapters which can be summarized as under. Chapter-1 covers basic introduction to Microwave assisted organic synthesis including comparison of conventional vs microwave assisted reaction and introduction of 2-aminoimidazole and their presence as naturally occurring marine alkaloids described. In this part various synthetic approaches toward 2aminoimidazole and short review on 2-aminoimidazole as pharmacophores also presented. Finally basic concept of anti biofilm activity described. Chapter-2 deals with microwave assisted one pot synthesis and Structure Activity Relationship of 2-Hydroxy-2-phenyl-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. Chapter-3 entitled “Structure Activity Relationship of N1-Substituted 2- Aminoimidazoles as Inhibitors of Biofilm Formation by Salmonella Typhimurium and Pseudomonas aeruginosa.” In this chapter a library of N1-substituted 4(5)-phenyl- 2-aminoimidazoles was synthesized and tested for the antagonistic effect against biofilm formation by Salmonella Typhimurium and Pseudomonas aeruginosa. The substitution pattern of the 4(5)-phenyl group and the nature of the N1-substituent were found to have a major effect on the biofilm inhibitory activity. The most active compounds of this series were shown to inhibit the biofilm formation at low micromolar concentrations. Chapter-4 deals with microwave-assisted Cu-catalyzed one pot protocol for the synthesis of 2-aminoimidazole-triazole framework via two consecutive steps of dimorth rearrangement and click reaction was demonstrated. Library of 22 compounds have been synthesized and were subjected to test for antibiofilm activity. However, the antibiofilm activities of these classes of compounds are under pipeline.
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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
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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),
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Yield: 52 %. 1 H NMR (300 MHz, CDCl
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5-(4-Chlorophenyl)-1-cyclooctyl-1H-
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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 and 164: 5.48 Hz, 2H), 3.59 (m, 2H), 3.16 (d
Page 165 and 166: 4.10 References [1] For a general r
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: 5.9.2 13 C spectra of bs-DP-7
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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