Trifluoromethyl-substituted 1,6-naphthyridines and pyrido[4,3-d]pyrimidines

Васильев, Л. Л.; Surzhikov, F. E.; Baranin, S. V.; Dorokhov, V. A.

doi:10.1007/s11172-013-0173-3

Cited by 5 publications

(3 citation statements)

References 10 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Dioxaborines were synthesized by directly borylating 1,3-dicarbonyls ( Bally et al., 1965 ) ( Figure 3 C). Reaction of BC23 with a range of alkyl amines yielded diazaborines ( Figure 3 D) adapted from Vasil'ev et al. (2013) .…”

Section: Resultsmentioning

confidence: 99%

Boron-Based Inhibitors of the NLRP3 Inflammasome

Baldwin

Rivers-Auty

Daniels

et al. 2017

Cell Chemical Biology

View full text Add to dashboard Cite

SummaryNLRP3 is a receptor important for host responses to infection, yet is also known to contribute to devastating diseases such as Alzheimer's disease, diabetes, atherosclerosis, and others, making inhibitors for NLRP3 sought after. One of the inhibitors currently in use is 2-aminoethoxy diphenylborinate (2APB). Unfortunately, in addition to inhibiting NLRP3, 2APB also displays non-selective effects on cellular Ca2+ homeostasis. Here, we use 2APB as a chemical scaffold to build a series of inhibitors, the NBC series, which inhibit the NLRP3 inflammasome in vitro and in vivo without affecting Ca2+ homeostasis. The core chemical insight of this work is that the oxazaborine ring is a critical feature of the NBC series, and the main biological insight the use of NBC inhibitors led to was that NLRP3 inflammasome activation was independent of Ca2+. The NBC compounds represent useful tools to dissect NLRP3 function, and may lead to oxazaborine ring-containing therapeutics.

show abstract

Section: Resultsmentioning

confidence: 99%

Boron-Based Inhibitors of the NLRP3 Inflammasome

Baldwin

Rivers-Auty

Daniels

et al. 2017

Cell Chemical Biology

View full text Add to dashboard Cite

show abstract

“…In the case of the synthesis of 1,6-naphthyridine derivatives, the method presented in the literature [ 31 ] involves a procedure different from the one described by Conrad and Limpach. Pyridine with an active α-methyl function ( 4 ), which can be regarded as an acetophenone derivative [ 32 ], is reacted with dimethyl oxalate in the presence of excess MeONa needed to shift the reaction toward the ring closure ( Scheme 2 ).…”

Section: Synthesis Of Functionalized and Heteroatom Containing Kyna Derivativesmentioning

confidence: 99%

“…Dorokhov et al, besides synthesizing the pyridine- and pyrimidine-fused derivatives with the use of acetophenones [ 31 , 32 ], also achieved the synthesis of pyranone derivatives. Pyranones 102a–c bearing the crucial active α-methyl function, similar to the ones used for pyridine- and pyrimidine-fused derivatives synthesized previously, were reacted with diethyl oxalate in the presence of sodium ethoxide ( Scheme 34 ) [ 89 ].…”

Section: Synthesis Of Functionalized and Heteroatom Containing Kyna Derivativesmentioning

confidence: 99%

KYNA Derivatives with Modified Skeleton; Hydroxyquinolines with Potential Neuroprotective Effect

Lőrinczi

Szatmári

2021

IJMS

View full text Add to dashboard Cite

Kynurenic acid (KYNA) is an endogenous neuroprotective agent of increasing importance. Several derivatives have already been synthesized, bearing an abundance of functional groups attached to the main skeleton in different positions. Several of these compounds have already been tested in biological evaluations, with several of them targeting the same receptors and biological effects as KYNA. However, these modified compounds build upon the unmodified KYNA skeleton leaving a possible route for the synthesis of new, potentially neuroprotective derivatives with heteroatom-containing ring systems. The aim of this review is to summarize the syntheses of KYNA derivatives with altered skeletons and to pinpoint an appealing transformation for future medicinal lead molecules.

show abstract

Four-coordinate six-membered ketiminate and diketiminate boron complexes. Synthesis, structure, reactivity, and application in the design of nitrogen heterocycles

Baranin

Заварзин

2017

Russ Chem Bull

View full text Add to dashboard Cite

Trifluoromethyl-substituted 1,6-naphthyridines and pyrido[4,3-d]pyrimidines

Cited by 5 publications

References 10 publications

Boron-Based Inhibitors of the NLRP3 Inflammasome

Boron-Based Inhibitors of the NLRP3 Inflammasome

KYNA Derivatives with Modified Skeleton; Hydroxyquinolines with Potential Neuroprotective Effect

Four-coordinate six-membered ketiminate and diketiminate boron complexes. Synthesis, structure, reactivity, and application in the design of nitrogen heterocycles

Contact Info

Product

Resources

About