6H-Indolo[2,3-b]quinoxalines: DNA and protein interacting scaffold for pharmacological activities.

doi:10.2174/13895575113139990005

Paper

6H-Indolo[2,3-b]quinoxalines: DNA and protein interacting scaffold for pharmacological activities.

Published Jul 31, 2013 · N. Moorthy, E. Manivannan, C. Karthikeyan

Mini reviews in medicinal chemistry

Q2 SJR score

41

Citations

0

Influential Citations

Full textSemantic Scholar

Abstract

6H-Indolo[2,3-b]quinoxaline, a planar fused heterocyclic compound exhibits a wide variety of pharmacological activities. The mechanism of pharmacological action exerted by these compounds is predominantly DNA intercalation. The thermal stability of the intercalated complex (DNA and 6H-indolo[2,3-b]quinoxaline derivatives) is an important parameter for the elucidation of anticancer, antiviral and other activities. This thermal stability of the 6H-indolo[2,3- b]quinoxaline-DNA complex depends on the type of substituents and side chains attached to the 6H-indolo[2,3- b]quinoxaline nucleus and also the orientation of the side chain towards the GC rich minor groove of the DNA. Highly active 6H-indolo[2,3-b]quinoxaline derivatives such as NCA0424, B-220 and 9-OH-B-220 have shown good binding affinity to DNA as evident from high thermal stability of compound-DNA complex. Interestingly, these compounds possessed poor inhibitory activity on topoisomerase II enzyme but have significant MDR modulating activity. This review establishes '6H-indolo[2,3-b]quinoxaline' as a valuable template for design and development of novel molecules with different biological activities.

Study Snapshot

6H-indolo[2,3-b]quinoxaline is a valuable template for designing and developing novel molecules with diverse biological activities, primarily through DNA intercalation.

PopulationOlder adults (50-71 years)

Sample size24

MethodsObservational

OutcomesBody Mass Index projections

ResultsSocial networks mitigate obesity in older groups.

Sign up to use Study Snapshot

Consensus is limited without an account. Create an account or sign in to get more searches and use the Study Snapshot.

Create an account

Paper

6H-Indolo[2,3-b]quinoxalines: DNA and protein interacting scaffold for pharmacological activities.

Sign up to use Study Snapshot

References

Solution processable indoloquinoxaline derivatives containing bulky polyaromatic hydrocarbons: synthesis, optical spectra, and electroluminescence.

New hybrid materials with 6H-indolo[2,3-b]quinoxaline and bulky polyaromatic hydrocarbons show promising properties for organic light-emitting diodes.

Synthesis and biological activity of 7H-benzo[4,5]indolo[2,3-b]-quinoxaline derivatives.

7H-benzo[4,5]indolo[2,3-b]quinoxalines show stronger DNA binding and reduced anti-viral activity compared to their predecessors.

Design, synthesis, cytotoxic evaluation, and QSAR study of some 6H-indolo[2,3-b]quinoxaline derivatives

6H-indolo[2,3-b]quinoxaline derivatives show significant in vitro activity against human leukemia cells, with potential for increased cytotoxic potency by incorporating cyclic or primary carbon atoms.

Synthesis, cytotoxicity, antiviral activity and interferon inducing ability of 6-(2-aminoethyl)-6H-indolo[2,3-b]quinoxalines.

6-(2-aminoethyl)-6H-indolo[2,3-b]quinoxalines are low-toxic potent interferon inducers and antivirals, with Morpholine and 4-methyl-piperidine derivatives being the most active and least cytotoxic.

Synthesis, anticancer and cytostatic activity of some 6H-indolo[2,3-b]quinoxalines

Compounds 5b, 5d, 5g, and 5l show significant anticancer activity and cytostatic activity against various human tumor cell lines and murine L1210 leukemia cells.

Citations

4-Alkyl-4H-thieno[2′,3′:4,5]pyrrolo[2,3-b]quinoxaline Derivatives as New Heterocyclic Analogues of Indolo[2,3-b]quinoxalines: Synthesis and Antitubercular Activity

Novel 4-alkyl-4H-thieno[2′,3′:4,5]pyrrolo[2,3-b]quinoxaline derivatives show promising antimycobacterial activity against Mycobacterium tuberculosis H37Rv, including drug-resistant strains.

Thiourea Dioxide Catalyzed Sustainable Synthesis of Diverse Quinoxaline and Pyrazine Derivatives in Aqueous Medium at Ambient Temperature

This eco-friendly, metal-free method for synthesizing diverse quinoxaline and pyrazine derivatives uses thiourea dioxide as a catalyst, resulting in higher yields, shorter reaction times, and easy reusability.

Design, synthesis and antimicrobial studies of novel imine derivatives of 2-(6H-indolo[2,3-b]quinoxalin-6-yl)-1-phenylethan-1-ones

Compound 4a, a novel imine derivative, shows greater antimicrobial activity than Rivanol against gram-negative bacteria Escherichia coli and Proteus Vulgaris and a fungal strain of Candida albicans.

Regioselective Synthesis of Trisubstituted Quinoxalines Mediated by Hypervalent Iodine Reagents.

Hypervalent iodine reagents enable the regioselective synthesis of trisubstituted quinoxalines, an important motif in medicinal chemistry and materials sciences.

One-Pot Construction of Indolo[2,3-b]quinoxalines through Ruthenium-Catalyzed Ortho C-H Bond Functionalization of 2-Arylquinoxalines with Sulfonyl Azides.

This one-pot method efficiently synthesizes biologically relevant 6H-indolo[2,3-b]quinoxaline derivatives with up to 94% yield, offering a broad substrate scope applicability.

Propargylamines in Pd/Cu-catalyzed tandem coupling-cyclization-N-deprotection in a single pot: Construction of N-unsubstituted vs N-sulfonyl indole ring

Propargylamines can be used to synthesize N-unsubstituted and N-sulfonyl indoles under environmentally friendly conditions, potentially benefiting anti-tubercular agents.