Synthesis and Biological Evaluation of Benzo [4,5]- and Naphtho[2′,1′:4,5]imidazo[1,2-c]pyrimidinone Derivatives DOI Creative Commons

Polina N. Kamzeeva,

Nikolai Dagaev,

Sofia A. Lizunova

et al.

Biomolecules, Journal Year: 2023, Volume and Issue: 13(11), P. 1669 - 1669

Published: Nov. 20, 2023

Azacarbazoles have attracted significant interest due to their valuable properties, such as anti-pathogenic and antitumor activity. In this study, a series of structurally related tricyclic benzo[4,5]- tertacyclic naphtho[2′,1′:4,5]imidazo[1,2-c]pyrimidinone derivatives with one or two positively charged tethers were synthesized evaluated for anti-proliferative Lead tetracyclic derivative 5b amino-bearing arms inhibited the metabolic activity A549 lung adenocarcinoma cells CC50 value 3.6 μM, remarkable selectivity (SI = 17.3) over VA13 immortalized fibroblasts. Cell-cycle assays revealed that triggers G2/M arrest without signs apoptosis. A study its interaction various DNA G4s duplexes followed by dual luciferase intercalator displacement suggests intercalation, rather than modulation G4-regulated oncogene expression, might contribute observed Finally, water-soluble salt was shown cause no acute toxic effects, changes in mice behavior, any decrease body weight after 72 h treatment at concentrations up 20 mg/kg. Thus, is promising candidate studies vivo; however, further investigations are needed elucidate molecular target(s).

Language: Английский

The chemistry of heterocycles in the 21st century DOI
Valery N. Charushin, Egor V. Verbitskiy, О. Н. Чупахин

et al.

Russian Chemical Reviews, Journal Year: 2024, Volume and Issue: 93(7), P. RCR5125 - RCR5125

Published: July 1, 2024

The chemistry of heterocyclic compounds has traditionally been and remains a bright area chemical science in Russia. This is due to the fact that many heterocycles find widest application. These are key structural fragments most drugs, plant protection agents. Many natural also derivatives heterocycles. At present, more than half hundreds millions known collective review devoted achievements Russian chemists this field over last 15–20 years. presents leading heterocyclists representing both RAS institutes university science. It worth noting wide scope review, terms geography author teams, covering whole our large country, diversity research areas. Practically all major types represented review. special attention focused on practical applications design new drugs biologically active compounds, high-energy molecules, materials for organic electronics photovoltaics, ligands coordination chemistry, other rapidly developing advances would not be possible without development fundamental transformations chemistry.<br> Bibliography — 2237 references.

Language: Английский

Citations

37
[4 + 2] Cyclization or Lossen Rearrangement: Rhodium-Catalyzed Divergent Synthesis of Carboline Derivatives with Anticancer Activity DOI

Lijie Lv,

Jia Zheng,

Yijie Xiao

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(20), P. 4212 - 4217

Published: May 14, 2024

An unusual rhodium-catalyzed C–H activation/Lossen rearrangement/oxa-Michael addition tandem cyclization has been achieved along with a tunable well-known activation/[4 + 2] annulation, leading to regio-, chemo-, and diastereoselective access diverse pentacyclic α-carbolines β-carboline-1-one derivatives in moderate good yields significant anticancer activity.

Language: Английский

Citations

4
Synthesis of Substituted α-Carboline Derivatives by Base-Mediated Annulation of Azaindoles with Alkylidene Malononitriles DOI Creative Commons
Venkata Rao Kaki,

Aakansha Negi,

Harshini Gaddam

et al.

Synlett, Journal Year: 2025, Volume and Issue: unknown

Published: March 20, 2025

Abstract A new synthetic method has been established to synthesize α-carbolines through the reaction of electrophilic azaindoles with ambiphilic alkylidene malononitriles. The versatility this approach was explored by using various malononitriles, and also conducting nitrogen migration on azaindole. This enables simultaneous introduction diverse functional groups, such as amine, nitrile, aryl, onto benzene ring a carboline scaffold. As scaffold putatively shows antiproliferative other biological activities, is valuable in development chemical entities for drug discovery.

Language: Английский

Citations

0
New 9H‐pyrido[2,3‐b]Indoles, Synthesis, Photophysical/Theoretical Studies, and Application as the Fluorescence Probes DOI
Мaria I. Valieva, E. A. Kudryashova,

Svetlana S. Potapova

et al.

Chemistry - An Asian Journal, Journal Year: 2025, Volume and Issue: unknown

Published: May 9, 2025

Abstract Using the “1,2,4‐triazine” methodology, we have designed a series of new 9 H ‐pyrido[2,3‐ b ]indole‐based fluorophores/probes 4a‐e , 7a b, and 8a . Photophysical studies push‐pull fluorophores 8b revealed positive solvatochromic effect with Δμ > 15D Stokes shifts up to 270 nm. Experimental data theoretical calculations ground excited states compounds demonstrated that pyridoindoles 7a,b exhibit planarized intramolecular charge‐transfer (PLICT) state, which is accompanied by gradual increase in luminescence quantum yield for samples 4d 7b increasing solvent polarity. Probe 4b characterized an acid dissociation constant (p K ) 5.5, showed high sensitivity local pH changes microenvironment. A “turn‐off” acidochromic response was observed Stern–Volmer quenching constants 1.6 × 10 3 5.5 M −1 respectively, while “turn‐off‐on” detected during titration TFA. Fluorescence UV–vis absorption spectroscopy interaction between probe calf thymus DNA ( ct DNA) confirmed static mechanism formation 4b‐ complex, indicating binds helix via groove binding mode. These findings highlight potential this visual detection cellular imaging applications.

Language: Английский

Citations

0
Carboline Regioisomers Based on Unified Synthetic Approaches DOI
Ahmad Saifuddin Mohamad Arshad, Mohd Nizam Mordi

Advanced Synthesis & Catalysis, Journal Year: 2023, Volume and Issue: 365(13), P. 2126 - 2146

Published: May 31, 2023

Abstract Carbolines are a prominent class of tricyclic alkaloids omnipresent in natural products and bioactive compounds. Four different carboline regioisomers known (α‐, β‐, γ‐, δ‐carbolines), which can be classified according to the nitrogen atom position inside pyridine ring. As an emerging structural motif drug discovery, multitude synthetic methods have been established for construction frameworks, general requires customized approaches assembly each regioisomer. Distinguishingly, their frameworks also accessible from unified approaches, capable generating multiple regioisomers, thus suitable introducing diversity isomeric carbolines. In this review, carbolines based on is summarized.

Language: Английский

Citations

7
One-pot π-extension approach of iminoindoles-to-α-carbolines as blue-light emitters using the cooperative basic system DOI

Rajni Lodhi,

S Banuprakash Goud,

Sampak Samanta

et al.

New Journal of Chemistry, Journal Year: 2024, Volume and Issue: 48(32), P. 14163 - 14169

Published: Jan. 1, 2024

Efficient access to α-carbolines was achieved via a domino reaction between iminoindoles and arylidene malononitriles using DABCO/NaHCO 3 as cooperative basic system. The synthesized scaffolds display blue emissions with good quantum yields.

Language: Английский

Citations

2
Cascade Synthesis of New Indole‐Containing Pentacyclic Scaffolds Mediated by Aryl and Iminyl Radicals DOI
Rodrigo Abonı́a,

Andrés C. García,

E. HURTADO

et al.

Chemistry - An Asian Journal, Journal Year: 2024, Volume and Issue: 19(5)

Published: Jan. 13, 2024

A five-step approach, starting from simple 1,5-disubstituted indoles, has been implemented for the synthesis of diversely substituted indole-pyrido-indene pentacyclic compounds up to 54 % yield via domino radical-mediated processes in presence radical reagents DLP/TTMSS and AIBN/TTMSS. Reactions proceeded with diverse key cyano-precursors strategically synthesized which were subsequently transformed into target through an aryl/iminyl reactions sequence. In addition routine spectroscopic techniques, structure precursors, as well as, products unequivocally established by single crystal X-ray diffraction, confirming effectiveness proposed synthetic

Language: Английский

Citations

1
Ru(ii)-catalyzed synthesis of indolo[2,3-c]isoquinolines via [3+3] annulation of N,N′-cyclic azomethine ylides and 3-diazoindolin-2-imines DOI

Durgesh Gurukkala Valapil,

Priyanka Mishra,

Kalyani Jungare

et al.

New Journal of Chemistry, Journal Year: 2023, Volume and Issue: 47(37), P. 17586 - 17591

Published: Jan. 1, 2023

An efficient [3+3] annulation strategy for the synthesis of fused α-carboline or indolo[2,3- c ]isoquinoline frameworks from easily accessible N , ′-cyclic azomethine ylides and 3-diazoindolin-2-imines using an Ru( ii ) catalyst has been established.

Language: Английский

Citations

1
Synthesis and Biological Evaluation of Benzo [4,5]- and Naphtho[2′,1′:4,5]imidazo[1,2-c]pyrimidinone Derivatives DOI Creative Commons

Polina N. Kamzeeva,

Nikolai Dagaev,

Sofia A. Lizunova

et al.

Biomolecules, Journal Year: 2023, Volume and Issue: 13(11), P. 1669 - 1669

Published: Nov. 20, 2023

Azacarbazoles have attracted significant interest due to their valuable properties, such as anti-pathogenic and antitumor activity. In this study, a series of structurally related tricyclic benzo[4,5]- tertacyclic naphtho[2′,1′:4,5]imidazo[1,2-c]pyrimidinone derivatives with one or two positively charged tethers were synthesized evaluated for anti-proliferative Lead tetracyclic derivative 5b amino-bearing arms inhibited the metabolic activity A549 lung adenocarcinoma cells CC50 value 3.6 μM, remarkable selectivity (SI = 17.3) over VA13 immortalized fibroblasts. Cell-cycle assays revealed that triggers G2/M arrest without signs apoptosis. A study its interaction various DNA G4s duplexes followed by dual luciferase intercalator displacement suggests intercalation, rather than modulation G4-regulated oncogene expression, might contribute observed Finally, water-soluble salt was shown cause no acute toxic effects, changes in mice behavior, any decrease body weight after 72 h treatment at concentrations up 20 mg/kg. Thus, is promising candidate studies vivo; however, further investigations are needed elucidate molecular target(s).

Language: Английский

Citations

0