1,4,6-Trisubstituted imidazo[4,5-c]pyridines as inhibitors of Bruton’s tyrosine kinase

Krajčovičová, Soňa; Jorda, Radek; Vanda, David; Soural, Miroslav; Kryštof, Vladimı́r

doi:10.1016/j.ejmech.2020.113094

Cited by 14 publications

(23 citation statements)

References 19 publications

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“…The imidazopyridine scaffold has been reported in the structures of various kinase inhibitors, such as KDR kinase, calmodulin-dependent kinase II (CaMKII), Glycogen Synthase Kinase-3, cyclin-dependent kinase (CDK), Bruton's tyrosine kinase, AKT Kinase, c-Met kinase, VEGFR2 kinase, FLT3 kinase, Pan-JAK, Aurora-A kinase, phosphatidylinositol-3-kinase (PI3K) and apoptosis signal-regulating kinase 1 (ASK1) [182][183][184][185][186][187][188][189][190][191][192][193][194][195].…”

Section: Imidazopyridinesmentioning

confidence: 99%

Fused Pyridine Derivatives: Synthesis and Biological Activities

Istanbullu¹,

Bayraktar²,

Saylam³

2023

Exploring Chemistry With Pyridine Derivatives

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Five-membered heteroaromatic ring fused pyridine derivatives are of increasing interest in drug design and medicinal chemistry. The structural similarity of many drugs (especially antiviral and anticancer ones) with DNA bases such as adenine and guanine is a key factor to explain their effectiveness. Apart from these, it is also found in the structures of substances with antituberculosis, antibacterial, antifungal, anti-inflammatory, and antimalarial activities. Another advantage of this group of compounds is their positive contribution to solubility, polarity, lipophilicity, and hydrogen bonding capacity properties of the compounds they are incorporated into. In this chapter, various bioactivities of fused pyridine derivatives will be categorized and summarized.

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Section: Imidazopyridinesmentioning

confidence: 99%

Fused Pyridine Derivatives: Synthesis and Biological Activities

Istanbullu¹,

Bayraktar²,

Saylam³

2023

Exploring Chemistry With Pyridine Derivatives

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“…They demonstrated that the imidazo[4,5- c ]pyridine core exhibited a significantly higher activity against BTKs compared to the imidazo[4,5- b ]pyridine one, and that imidazo[4,5- c ]pyridine compounds had a remarkably high tolerance on the C6 position for both hydrophobic and hydrophilic substituents, representing an interesting starting point for the further development of BTKIs that could be useful after Ibrutinib failure. The most active compounds are compounds 30a , b ( Figure 9 ) with IC 50 values in the nanomolar range (25 and 27 nM, respectively) [ 103 ].…”

Section: Recent Advances In Btkismentioning

confidence: 99%

The Development of BTK Inhibitors: A Five-Year Update

et al. 2021

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Bruton’s tyrosine kinase (BTK) represented, in the past ten years, an important target for the development of new therapeutic agents that could be useful for cancer and autoimmune disorders. To date, five compounds, able to block BTK in an irreversible manner, have been launched in the market, whereas many reversible BTK inhibitors (BTKIs), with reduced side effects that are more useful for long-term administration in autoimmune disorders, are under clinical investigation. Despite the presence in the literature of many articles and reviews, studies on BTK function and BTKIs are of great interest for pharmaceutical companies as well as academia. This review is focused on compounds that have appeared in the literature from 2017 that are able to block BTK in an irreversible or reversible manner; also, new promising tunable irreversible inhibitors, as well as PROTAC molecules, have been reported. This summary could improve the knowledge of the chemical diversity of BTKIs and provide information for future studies, particularly from the medicinal chemistry point of view. Data reported here are collected from different databases (Scifinder, Web of Science, Scopus, Google Scholar, and Pubmed) using “BTK” and “BTK inhibitors” as keywords.

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“…Pyridine ring plays a role in the formation of a discontinuous silver film on a polymer composite using its derivative poly (4‐vinyl pyridine) P4VP. Due to its beneficial and extensive biological properties, pyridine derivatives are used in the treatment of various diseases such as cancer, diabetes, hyperpigmentation, tuberculosis, hyperplasia and ulcers 1‐8 …”

Section: Introductionmentioning

confidence: 99%

Quantum chemical, spectroscopic and molecular docking investigations of potential pulmonary fibrosis drug methyl 2‐chloro 4‐iodonicotinate

Pandimeena¹,

Mathavan²,

Samuel

et al. 2022

J of Molecular Recognition

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In this work, the methyl 2-chloro 4-iodonicotinate (MCIN) was investigated to study the structural, spectroscopic and electronic properties using density functional theory (DFT) quantum chemical calculations. The most stable structure of MCIN was optimized by DFT/B3LYP method with a LanLD2Z basis set. The optimized parameters and vibrational wavenumbers were determined. The vibrational task of the molecule was done by potential energy distribution calculations. The 13 C NMR spectrum of the MCIN molecule was simulated by the Gauge-Invariant-Atomic Orbital method using a dimethyl sulfoxide solution and the isotropic chemical shift values of the molecule were calculated and observed. Ultraviolet-visible spectra were simulated and observed. The pharmaceutical activity was predicted using frontier molecular orbital and natural bond orbital analysis. The reactive sites of the MCIN molecule were determined using Mulliken atomic charge distribution, molecular electrostatic potential surface and the local reactivity analysis. The molecular docking analysis confirms that the title molecule can be used in drug design for the treatment of pulmonary fibrosis.

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1,4,6-Trisubstituted imidazo[4,5-c]pyridines as inhibitors of Bruton’s tyrosine kinase

Cited by 14 publications

References 19 publications

Fused Pyridine Derivatives: Synthesis and Biological Activities

Fused Pyridine Derivatives: Synthesis and Biological Activities

The Development of BTK Inhibitors: A Five-Year Update

Quantum chemical, spectroscopic and molecular docking investigations of potential pulmonary fibrosis drug methyl 2‐chloro 4‐iodonicotinate

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