The Combinatorial Synthesis of Bicyclic Privileged Structures or Privileged Substructures

Abstract

I. Introduction 893 A. The Drug Discovery Process 895 B. Characteristics of Privileged Substructures 896 C. Scope of the Review 897 II. Phenyl-Substituted Monocycles 898 A. Biphenyls 898 B. Arylpiperidines 899 C. Arylpiperazines 901 D. 1,4-Dihydropyridines 901 E. Dihydropyrimidones 902 III. Fused [7−6] Ring Systems 904 A. 1,4-Benzodiazepin-2-ones 904 B. 1,5-Benzodiazepin-2-ones 905 C. 1,4-Benzodiazepin-2,5-diones and Pyrrolo-[2,1-c][1,4]benzodiazepin-5,11-diones 906 D. 1,4-Benzothiazepin-5-ones 907 E. 5,11-Dihydro-benzo[e]pyrido[3,2-b][1,4]diazepin-6-ones 907 IV. Fused [6−6] Ring Systems 908 A. Benzopyrans, Chromones, Coumarins, and Pyranocoumarins 908 1. Benzopyrans 908 2. Chromones 909 3. Coumarins 911 4. Pyranocoumarins 911 B. Quinoxalines/Quinazolines 913 1. 3,4-Dihydroquinoxalin-2-ones (Benzopiperazinones) 913 2. Quinazolinones 915 3. Quinazolindiones 916 4. Imidazoquinoxalines 917 V. Fused [5−6] Ring Systems 919 A. Indoles 919 B. Benzimidazoles 921 C. Benzofurans 922 D. Benzothiophenes 924 VI. Conclusions 925 VII. Acknowledgments 925 VIII. References 925

Bifunctional Asymmetric Catalysis: Cooperative Lewis Acid/Base Systems

“…The products of these reactions may have significant biological applications. Quinoxalinones have structural similarities to benzodiazepines 35 but have not been investigated as thoroughly. To demonstrate the utility of this method, we synthesized two biologically active compounds: compound 12, an inhibitor of cholesterol ester transfer protein, 36 and compound 13, which exhibits strong antiviral activity against HIV 37 (Scheme 10).…”

Synthesis of New 2-Substituted Phenyl-1H-Indoles via Fischer Indole Reaction

“…While indole that have functional substituent at C-2 and C-3 position are capable of binding to many receptors with high affinity especially for electron withdrawing substituent at C-2 position [19][20] . Herein we report the results on synthesis of new 2-substituted phenyl-1H-indole derivatives via sulfuric acid catalyzed Fischer indole reaction.…”

In Search of the Antimicrobial Potential of Benzimidazole Derivatives

“…This ring system is present in numerous antiparasitic, fungicidal anthelmintic, anti-inflamatory and antiviral drugs (Pedini et al, 1994;Martin, 1997;Zacny et al, 1999;Gaba et al, 2014). Some benzimidazoles show also cytotoxicity against diverse cancer cell lines (Horton et al, 2003;Padmavathi et al, 2008;Karpińska et al, 2012). Recently, we found that polyhalogenated benzimidazoles are potent inhibitors of casein kinase 2 (CK2), probably the most pleiotropic protein kinase in more than 300 known eukaryotic organisms (Pagano et al, 2004;Gianoncelli et al, 2009;Janeczko et al, 2012).…”