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Usage

Uses

Used in Pharmaceutical Industry:
6-Bromoquinoline-2-carbaldehyde is used as a reagent for the synthesis of histone deacetylase (HDAC) inhibitors, which are a class of anti-cancer agents. These inhibitors have the potential to modulate gene expression and cell cycle regulation, thereby exhibiting anti-proliferative effects on cancer cells. The development of HDAC inhibitors using 6-Bromoquinoline-2-carbaldehyde as a starting material has shown promise in the treatment of various types of cancer, including solid tumors and hematological malignancies.

Upstream product

• 877-42-9 6-Bromo-2-methyl-quinoline 
• 1080-92-8 6-bromo-4-ethoxy-2-methyl-1,2,3,4-tetrahydro-quinoline 
• 106-40-1 4-bromo-aniline 

Relevant academic research and scientific papers

Synthesis and optical properties of new 2-(5-arylpyridine-2-yl)-6-(het)arylquinoline-based “push-pull” fluorophores

2-(5-Arylpyridine-2-yl)-6-(het)arylquinoline-based “push-pull” fluorophores were synthesized by means of the heterocyclization reaction between the corresponding isonitrosoacetophenone hydrazones and 6-bromoquinoline-2-carboxaldehyde followed by an aza-Diels-Alder/Suzuki cross-coupling reaction sequence. The optical properties of the obtained fluorophores were studied and the non-linear optic behavior for the two most representative ones were confirmed based on the solvatochromic experiments.

A Quninolylthiazole Derivatives as an ICT-Based Fluorescent Probe of Hg(II) and its Application in Ratiometric Imaging in Live HeLa Cells

As a structural analogue of pyridylthiazole, 2-(2-benzothiazoyl)-phenylethynylquinoline (QBT) was designed as a fluorescent probe for Hg(II) based on an intramolecular charge transfer (ICT) mechanism. The compound was synthesized in three steps starting from 6-bromo-2-methylquinoline, with moderate yield. Corresponding studies on the optical properties of QBT indicate that changes in the fluorescence ratio of QBT in response to Hg(II) could be quantified based on dual-emission changes. More specifically, the emission spectrum of QBT before and after interactions with Hg(II) exhibited a remarkable red shift of about 120?nm, which is rarely reported in ICT-based fluorescent sensors. Finally, QBT was applied in the two-channel imaging of Hg(II) in live HeLa cells.

Chalcone Analogue as New Candidate for Selective Detection of α-Synuclein Pathology

Deposition of α-synuclein (α-syn) aggregates is one of the neuropathological hallmarks of synucleinopathies including Parkinson’s disease, dementia with Lewy bodies, and multiple-system atrophy. In vivo detection of α-syn aggregates with SPECT or PET may be an effective tool for medical intervention against synucleinopathy. In the present study, we designed and synthesized a series of chalcone analogues with different aryl groups to evaluate their potential as α-syn imaging probes. In competitive inhibition assays, aryl groups markedly affected binding affinity and selectivity for recombinant α-syn aggregates. Chalcone analogues with a 4-(dimethylamino)phenyl group bound to both α-syn and amyloid β (Aβ) aggregates while ones with a 4-nitrophenyl group displayed α-syn-selective binding. In fluorescent staining, only chalcone analogues with a 4-nitrophenyl group succeeded in selective detection of human α-syn against Aβ aggregates in patients’ brain samples. Among them, PHNP-3 exhibited the most promising binding characteristics for α-syn aggregates (Ki = 0.52 nM), encouraging us to further evaluate its utility. Then, a 125I-labeling reaction was performed to obtain [125I]PHNP-3. In a binding saturation assay, [125I]PHNP-3 bound to α-syn aggregates with high affinity (Kd = 6.9 nM) and selectivity. In a biodistribution study, [125I]PHNP-3 exhibited modest uptake (0.78% ID/g at 2 min after intravenous injection) into a normal mouse brain. Although there is room for improvement of its pharmacokinetics in the brain, encouraging in vitro results in the present study indicate that further structural optimization based on PHNP-3 might lead to the development of a clinically useful probe targeting α-syn aggregates in the future.

A class of two-photon fluorescent probes for the design of fluorescent probes for epilepsy brain hypochlorous acid characteristic imaging and its synthesis method

The present invention belongs to the field of molecular biology, medicine, etc., in particular to the present invention relates to a class of fluorescent probes with quinoline as the parent nucleus for epilepsy brain hypochlorous acid dynamic change characteristic imaging and synthesis method. The structure of the fluorescent probe compound is shown in the following formula: .

Iodine-imine Synergistic Promoted Povarov-Type Multicomponent Reaction for the Synthesis of 2,2′-Biquinolines and Their Application to a Copper/Ligand Catalytic System

An efficient iodine-imine synergistic promoted Povarov-type multicomponent reaction was reported for the synthesis of a practical 2,2′-biquinoline scaffold. The tandem annulation has reconciled iodination, Kornblum oxidation, and Povarov aromatization, where the methyl group of the methyl azaarenes represents uniquely reactive input in the Povarov reaction. This method has broad substrate scope and mild conditions. Furthermore, these 2,2′-biquinoline derivatives had been directly used as bidentate ligands in metal-catalyzed reactions.

Synthesis and biological evaluation of 2-quinolineacrylamides

A series of C6-substituted N-hydroxy-2-quinolineacrylamides (3–15), with four types of bridging groups have been synthesized. Most of these compounds exhibit antiproliferative activity against A549 and HCT116 cells and Western blot analysis revealed that they are able to inhibit HDAC. Measurement of the HDAC isoform activity of ether-containing compounds showed that compound 9 has distinct HDAC6 selectivity, more than 300-fold over other isoforms. This paper describes the development of 6-aryloxy-N-hydroxy-2-quinolineacrylamides as potential HDAC6 inhibitors.

Imaging of formaldehyde fluxes in epileptic brains with a two-photon fluorescence probe

A two-photon (TP) fluorescence probe has been developed for imaging endogenous FA fluxes during metabolic and epigenetic processes in animal models, especially in live brains.

Facile synthesis of 1,3,4-oxadiazoles via iodine promoted oxidative annulation of methyl-azaheteroarenes and hydrazides

An oxidative sp3 C–H bond of methyl-azaheteroarenes protocol was reported for the synthesis of 1,3,4-oxadiazoles via [4 + 1] annulation with hydrazides. This protocol enables 1,3,4-oxadiazole and quinoline linked diheterocycles via selective oxidation of sp3 C–H bond of methyl-azaheteroarenes in the presence of I2-DMSO. The reaction has a broad substrate scope and good functional group tolerance for methyl-azaheteroarenes and hydrazides.

Metal- and radical-free aerobic oxidation of heteroaromatic methanes: An efficient synthesis of heteroaromatic aldehydes

A metal-free and radical-free synthesis of heteroaromatic aldehydes was developed through aerobic oxidation of methyl groups in an I2/DMSO/O2 catalytic system. Under the reaction conditions, various functional groups such as methoxy, aldehyde, ester, nitro, amide, and halo (F, Cl, Br) groups were well tolerated. The bioactive compounds like chlorchinaldin derivative and papaverine were also oxidized to the corresponding aldehydes and ketones. This reaction provided an efficient method for preparing the valuable heteroaromatic aldehydes.

Synthesis of a class of fluorescent mother nuclei containing quinoline ring

The invention relates to a class of fluorescent mother nuclei containing a quinoline ring, wherein the fluorescent mother nuclei have a structure represented by the following general formula I. The invention discloses a synthesis method of a class of novel fluorescent mother nuclei containing a quinoline ring, and applications of the fluorescent mother nuclei in fluorescent probe design.