59394-26-2

Usage

Uses

Used in Pharmaceutical Industry:
6-Chloroquinoline-2-carbaldehyde is used as a reagent for the design, synthesis, and biological evaluation of 2-substituted quinoline libraries. These libraries consist of potential antileishmanial agents, which are crucial for the development of new treatments against Leishmaniasis, a vector-borne disease caused by protozoan parasites.
Used in Drug Discovery:
6-Chloroquinoline-2-carbaldehyde is also utilized in the synthesis and biological evaluation of quinoline derivatives as HDAC (Histone Deacetylase) class I inhibitors. HDAC inhibitors are a class of compounds that modulate gene expression by altering the acetylation state of histones, which can have therapeutic potential in various diseases, including cancer and neurodegenerative disorders. By targeting HDAC class I, these quinoline derivatives may offer novel therapeutic options for the treatment of these conditions.

InChI:InChI=1/C10H6ClNO/c11-8-2-4-10-7(5-8)1-3-9(6-13)12-10/h1-6H

Upstream product

• 92-46-6 6-chloro-2-methylquinoline 
• 106-47-8 4-chloro-aniline 
• 15644-86-7 6-chloro-2-methyl-quinolin-4-ol 

Relevant academic research and scientific papers

Iodine-catalyzed oxidative annulation: Facile synthesis of pyrazolooxepinopyrazolones: Via methyl azaarene sp3C-H functionalization

An iodine-catalyzed methyl azaarene sp3 C-H functionalization has been developed for the synthesis of a seven-membered O-heterocyclic architecture containing three different heterocyclic aromatic hydrocarbons. This method can be applied to a wide range of substituted methyl azaarenes and diverse 2,4-dihydro-3H-pyrazol-3-ones, and brings about the efficient preparation of 2,9-dihydrooxepino[2,3-c:6,5-c′]dipyrazol-3(7H)-ones in high yields with the merits of low catalyst loading, good functional group tolerance and metal-free conditions.

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.

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.

Discovery of fused heterocyclic carboxamide derivatives as novel α7-nAChR agonists: Synthesis, preliminary SAR and biological evaluation

The α7 nicotinic acetylcholine receptor (α7 nAChR) has emerged as a promising therapeutic target for schizophrenia. In our previous work, a novel series of α7-nAChR agonists bearing scaffold of indolizine were discovered. To explore the effect of aromaticity on the activity and find more active agents, herein, fused heterocyclic carboxamide derivatives were designed and synthesized in this study. Based on the evaluation by two-electrode voltage clamp in Xenopus oocytes, 27 of the synthesized compounds showed obvious agonism of α7 nAChR. Particularly, compounds 10a and 10e showed significantly higher Emax than EVP-6124. The result illustrated the importance of aromaticity to the activity of agonism. Compound 10a, which showed EC50 of 1.88 μM and Emax of 72.4%, was further characterized comprehensively, including co-application with type II positive allosteric modulator PNU-120596, selectivity with other closely related ligand-gated ion channel, etc. The results showed that 10a showed moderate selectivity over other subtypes such as α4β2 and α3β4 nAChR. 10a evoked α7-like currents that were inhibited by MLA and enhanced in the presence of the α7 PAM PNU-120596. The analysis of binding mode and understanding of structure-activity relationship provided insights to develop more potent novel α7-nAChR agonists.

Copper-Catalyzed Aerobic Oxidation of Azinylmethanes for Access to Trifluoromethylazinylols

A copper-catalyzed oxygenation of methylazaarenes was found to occur in the absence of both ligand and additive, and has been successfully employed for the synthesis of trifluoromethylazinylketols. This synthetic strategy incorporates aerobic oxidation and a trifluoromethylation in one-pot and provides a novel method for the trifluoromethylation of aliphatic C-H bond.

Metal-free C(sp3)–H oxidation of 2-methylquinolines with PIDA under microwave irradiation

An efficient metal-free protocol has been developed for the sp3C–H bond oxidation of 2-methylquinolines in the presence of PIDA under microwave irradiation, providing 2-quinolinecarboxaldehydes with moderate to high yields and excellent selectivities. A wide range of 2-quinolinecarboxaldehydes with different functional groups have been synthesized. A tentative mechanism has been presented to explain this highly selective oxidation process.

Chemical synthesis method of quinoline (oxaline)-2-carboxaldehyde compounds

The invention relates to a preparation method of quinoline (oxaline)-2-carboxaldehyde compounds. The preparation method comprises the following steps of dissolving 2-methylquinoline(oxaline) shown in a formula (II) into an organic solvent, adding iron salts, and completely reacting under the condition of 100 to 180DEG C with the assistance of microwave; performing after treatment on a reaction solution to obtain the quinoline (oxaline)-2-carboxaldehyde compounds shown in a formula (I), wherein the feed molar ratio of the iron salts to the quinoline (oxaline)-2-carboxaldehyde compounds is (0.5 to 3.5):1. R in the formula (I) and the formula (II) is hydrogen at the same time; or the hydrogen is monosubstituted or polysubstituted by alkyls of C1 to C8, alkoxys of C1 to C8, nitryl or halogen; the number of substituent groups is n; X in the formula (I) and the formula (II) is carbon or nitrogen at the same time. The preparation method disclosed by the invention has the advantages of short reaction time, low reaction temperature, wide application range of reaction, good reaction selectivity, low price and no toxicity of a used catalyst, and simplicity and convenience in operation; the preparation method meets the requirement of green chemistry. (The formulas are shown in the description).

Design, synthesis and preliminary bioactivity evaluations of substituted quinoline hydroxamic acid derivatives as novel histone deacetylase (HDAC) inhibitors

Inhibition of HDACs activity has become a promising therapeutic strategy in clinical practice to reverse the abnormal epigenetic states of cancer and other diseases. Therefore, HDAC inhibitors become a relatively new class of anti-cancer agent. In the present study, we reported the design and synthesis of a series of novel HDAC inhibitors using various substituted quinoline rings as the cap group. In vitro studies showed that some compounds have good inhibitory activities against HDACs and potent antiproliferative activities in some tumor cell lines. Especially, compound 9w (IC50 = 85 nM), exhibited better inhibitory effect compared with SAHA (IC50 = 161 nM).