Benzofused tricycles based on 2-quinoxalinol

Area of Science:

• Medicinal Chemistry
• Organic Synthesis
• Drug Discovery

Background:

• Privileged structures are molecular frameworks known to bind to multiple biological targets.
• 2-Quinoxalinol is a versatile scaffold with diverse biological activities.
• Combining privileged structures can lead to novel compounds with enhanced therapeutic potential.

Purpose of the Study:

• To synthesize novel benzofused tricyclic compounds by integrating 2-quinoxalinol with various privileged structures.
• To explore the substituent diversity of these novel scaffolds.
• To evaluate the potential of these compounds as lead compounds in drug discovery.

Main Methods:

• Chemical synthesis of novel benzofused tricyclic scaffolds.
• Integration of 2-quinoxalinol with six different privileged structures: 1,3-dihydro-benzoimidazol-2-one, 1,3-dihydro-benzoimidazole-2-thione, 3-hydroxy-1H-quinoxalin-2-one, 2H-benzo[1,4]oxazin-3-ol, 2H-benzo[1,4]thiazin-3-ol, and 1,3,4,5-tetrahydro-benzo[1,4]diazepin-2-one.
• Characterization of the synthesized compounds.

Main Results:

• Successfully synthesized eight novel benzofused tricyclic compounds.
• These compounds include pyrazino[2,3-g]quinoxaline-2,8-diol (I) and 3-hydroxy-6,8,9,10-tetrahydro-1,4,6,10-tetraaza-cyclohepta[b]naphthalen-7-one (II), among others.
• Demonstrated substituent diversity points within the synthesized scaffolds.

Conclusions:

• The strategy of integrating two benzofused privileged structures into a single molecule is effective for generating novel compound scaffolds.
• This approach increases the likelihood of discovering new lead compounds for therapeutic applications.
• The synthesized novel benzofused tricycles represent a promising starting point for further drug development efforts.