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This dissertation describes the syntheses of indole and tryptamine derivatives via various synthetic strategies and screening of their biological activities. All synthetic compounds were characterized by different spectroscopic techniques such as 1H-, and 13C-NMR, EIMS/FAB-MS and EI-HRMS. This dissertation has been divided into three chapters and each chapter has its own numbering of compounds, figures, tables, schemes, and references. Chapter-1 comprises of the syntheses of Schiff bases of tryptamine 60-85 (Part A), urea and thiourea analogues of tryptamine 87-99 (Part B) and evaluation of their biological activities. Compound 78 (IC50 = 206.90 ± 0.88 μM) showed a potent activity against antiglycation activity, while, other thirteen compounds showed good to moderate activity. Chapter-2 describes the broad literature survey regarding the general introduction of indole, its biological importance and various synthetic schemes. It includes synthetic strategies of indole-3-acetamides 55-81 (Part A) and Knoevengal condensates of indole 83-118 (Part B) and evaluation of their biological activities. Eight compounds 84, 85, 88, 94, 106, 111, 115, and 118 were found to be weakly active against antiepileptic activity. Compound 83 (IC50 = 4.03 ± 0.05 μM) and 91 (IC50 = 4.89 ± 0.05 μM) were found to be the most active members of the series. Chapter-3 deals with the syntheses of bis(indolyl)methanes derivatives 38-92. The synthesized analogues were subjected for the random screening and were found to be active against anticancer and anti-inflammatory activities. Five analogues 64 (IC50 = 2.7 ± 0.1 μM), 47 (IC50 = 5.4 ± 0.8 μM), 52 (IC50 = 6.7 ± 0.6 μM), 78 (IC50 = 7.1 ± 1.3 μM), and 42 (IC50 = 7.2 ± 1.2 μM) were found to have potent activity as compared to standard ibuprofen (IC50 = 11.2 ± 1.9 μM), while compounds 45 (IC50 = 17.1 ± 0.2 μM) and 41 (IC50 = 26.6 ± 2.4 μM) possess weak antiinflammatory activity. However, seventeen compounds showed a weak anticancer activity.
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