The chemical syntheses of final compounds 1-48 are outlined in Schemes 1-3. As shown in Scheme 1, the alkyne region analogues were synthesized from commercially available indole 49 using Sonogashira or Suzuki coupling conditions. Indole region analogues 7-18 were synthesized as shown in Scheme 2. Preparation of 55 began from commercially available bromoindole 52, which was refluxed with Bredereck's reagent and then cyclized to the corresponding aminopyrimidine 58. Similar routes were used to prepare intermediates 59 and 60 from indole 53 and carboxamide 54, respectively. As shown in the middle of Scheme 2, both 53 and 54 required a Fischer indole synthesis for their preparation. Final Sonogashira and Suzuki cross coupling reactions were conducted to obtain compounds 7-14. Next, we synthesized aminopyrimidine region analogues as shown in Scheme 3. Starting from 5-bromoindole 64, a Friedel-Crafts acylation reaction was employed to generate 65. A basemediated nucleophilic substitution reaction with 2-methoxyethanol provided 66, which was refluxed with Bredereck's reagent and then cyclized to aminopyrimidine 67. Finally, Sonogashira coupling conditions were used to convert 67 to analogues 19-20.