40941-53-5

Usage

InChI:InChI=1/C10H8ClN/c1-7-4-5-12-10-6-8(11)2-3-9(7)10/h2-6H,1H3

Upstream product

• 6607-66-5 1,3,3-trimethoxybutane 
• 141-85-5 3-chloroaniline hydrochloride 
• 78-94-4 methyl vinyl ketone 
• 108-42-9 3-chloro-aniline 
• 121714-78-1 iron(III) chloride hexahydrate 
• 86-98-6 4,7-dichloroquinoline 
• 75-16-1 methylmagnesium bromide 
• 18826-95-4 1.3-butanediol 

Downstream Products

• 476472-18-1 2-(7-chloro-quinolin-4-yl)-1-pyridin-2-yl-ethanone 
• 476472-19-2 2-(7-chloro-quinoline-4-yl)-1-(6-methyl-pyridin-2-yl)-ethanone 
• 13337-66-1 7-chloroquinoline-4-carboxylic acid 
• 476473-27-5 1-[2-(7-Chloro-quinolin-4-yl)-1-(6-methyl-pyridin-2-yl)-eth-(E)-ylideneamino]-pyrrolidin-2-one 
• 476473-26-4 1-[2-(7-Chloro-quinolin-4-yl)-1-pyridin-2-yl-eth-(E)-ylideneamino]-pyrrolidin-2-one 

Relevant academic research and scientific papers

Metal-Free Chemoselective Oxidation of 4-Methylquinolines into Quinoline-4-Carbaldehydes

A convenient protocol for the synthesis of quinoline-4-carbaldehydes via chemoselective oxidation of 4-methylquinolines using hypervalent iodine(III) reagents as oxidant is described. This method highlights metal-free and mild reaction conditions, nice yield, good functional group tolerance, and high chemoselectivity.

Synthesis and biological evaluation of benzhydryl-based antiplasmodial agents possessing Plasmodium falciparum chloroquine resistance transporter (PfCRT) inhibitory activity

Due to the surge in resistance to common therapies, malaria remains a significant concern to human health worldwide. In chloroquine (CQ)-resistant (CQ-R) strains of Plasmodium falciparum, CQ and related drugs are effluxed from the parasite's digestive vacuole (DV). This process is mediated by mutant isoforms of a protein called CQ resistance transporter (PfCRT). CQ-R strains can be partially re-sensitized to CQ by verapamil (VP), primaquine (PQ) and other compounds, and this has been shown to be due to the ability of these molecules to inhibit drug transport via PfCRT. We have previously developed a series of clotrimazole (CLT)-based antimalarial agents that possess inhibitory activity against PfCRT (4a,b). In our endeavor to develop novel PfCRT inhibitors, and to perform a structure-activity relationship analysis, we synthesized a new library of analogues. When the benzhydryl system was linked to a 4-aminoquinoline group (5a-f) the resulting compounds exhibited good cytotoxicity against both CQ-R and CQ-S strains of P. falciparum. The most potent inhibitory activity against the PfCRT-mediated transport of CQ was obtained with compound 5k. When compared to the reference compound, benzhydryl analogues of PQ (5i,j) showed a similar activity against blood-stage parasites, and a stronger in vitro potency against liver-stage parasites. Unfortunately, in the in vivo transmission blocking assays, 5i,j were inactive against gametocytes.

Dearomative Photocatalytic Construction of Bridged 1,3-Diazepanes

The construction of diverse sp3-rich skeletal ring systems is of importance to drug discovery programmes and natural product synthesis. Herein, we report the photocatalytic construction of 2,7-diazabicyclo[3.2.1]octanes (bridged 1,3-diazepanes) via a reductive diversion of the Minisci reaction. The fused tricyclic product is proposed to form via radical addition to the C4 position of 4-substituted quinoline substrates, with subsequent Hantzsch ester-promoted reduction to a dihydropyridine intermediate which undergoes in situ two-electron ring closure to form the bridged diazepane architecture. A wide scope of N-arylimine and quinoline derivatives was demonstrated and good efficiency was observed in the construction of sterically congested all-carbon quaternary centers. Computational and experimental mechanistic studies provided insights into the reaction mechanism and observed regioselectivity/diastereoselectivity.

Synthesis and antileishmanial evaluation of thiazole orange analogs

Cyanine compounds have previously shown excellent in vitro and promising in vivo antileishmanial efficacy, but the potential toxicity of these agents is a concern. A series of 22 analogs of thiazole orange ((Z)-1-methyl-4-((3-methylbenzo[d]thiazol-2(3H)-ylidene)methyl)quinolin-1-ium salt), a commercial cyanine dye with antileishmanial activity, were synthesized in an effort to increase the selectivity of such compounds while maintaining efficacy. Cyanines possessing substitutions on the quinolinium ring system displayed potency against Leishmania donovani axenic amastigotes that differed little from the parent compound (IC50 12–42 nM), while ring disjunction analogs were both less potent and less toxic. Changes in DNA melting temperature were modest when synthetic oligonucleotides were incubated with selected analogs (ΔTm ≤ 5 °C), with ring disjunction analogs showing the least effect on this parameter. Despite the high antileishmanial potency of the target compounds, their toxicity and relatively flat SAR suggests that further information regarding the target(s) of these molecules is needed to aid their development as antileishmanials.

Quinolines synthesis by reacting 1,3-butanediol with anilines in the presence of iron catalysts

2-, 4-, 6-, 7-, and 8-substituted quinolines were synthesized in 78–95% yield by the reaction of 1,3- butanediol with anilines in the presence of iron catalysts in carbon tetrachloride.

Chemoselective sp 2-sp3 cross-couplings: Iron-catalyzed alkyl transfer to dihaloaromatics

The chemoselective functionalization of a range of dihaloaromatics with methyl, cyclopropyl, and higher alkyl Grignard reagents via iron-catalyzed cross-coupling is described. The site selectivity of C-X (X = halogen) activation is determined by factors such as the position of the halogen on the ring, the solvent, and the nucleophile. A one-pot protocol for the chemoselective synthesis of mixed dialkyl heterocycles is achieved solely employing iron catalysis.

Asymmetric cyanine compounds, their preparation methods and their uses

Asymmetric cyanine compounds represented by general formula I are provided, wherein X, n, R1, R2, R3, R4 and Y? are as defined in the specification. They have a maximum absorption peak at about 640 nm which may not change with ambient temperature. When the compounds bind a nucleic acid to form a dye/nucleic acid complex, the fluorescence intensity of the complexes will increased rapidly, so that they can be used as a staining agent for nucleic acids in flow cytometers. Their spectra are in the near-infrared region, which can effectively reduce the interference from background fluorescence and improve the accuracy of detection. Moreover, the compounds provided can also be used as a staining agent for blood reticulocytes.

PIPERIDIN-4-YLPIPERAZINE COMPOUNDS FOR THE TREATMENT OF HCV INFECTION

The invention relates to new piperazine-pieridine compounds having anti-viral activity and particularly anti-HCV activity. The invention further relates to pharmaceutical compositions comprising compounds according to the invention.

ASYMMETRIC CYANINE COMPOUNDS, THEIR PREPARATION METHODS AND THEIR USES

Asymmetric cyanine compounds represented by general formula I are provided, wherein X, n, R1, R2, R3, R4 and Y? are as defined in the specification. They have a maximum absorption peak at about 640 nm which may not change with ambient temperature. When the compounds bind a nucleic acid to form a dye/nucleic acid complex, the fluorescence intensity of the complexes will increased rapidly, so that they can be used as a staining agent for nucleic acids in flow cytometers. Their spectra are in the near-infrared region, which can effectively reduce the interference from background fluorescence and improve the accuracy of detection. Moreover, the compounds provided can also be used as a staining agent for blood reticulocytes.

Clotrimazole scaffold as an innovative pharmacophore towards potent antimalarial agents: Design, synthesis, and biological and structure-activity relationship studies

We describe herein the design, synthesis, biological evaluation, and structure-activity relationship (SAR) studies of an innovative class of antimalarial agents based on a polyaromatic pharmacophore structurally related to clotrimazole and easy to synthesize by low-cost synthetic procedures. SAR studies delineated a number of structural features able to modulate the in vitro and in vivo antimalarial activity. A selected set of antimalarials was further biologically investigated and displayed low in vitro toxicity on a panel of human and murine cell lines. In vitro, the novel compounds proved to be selective for free heme, as demonstrated in the β-hematin inhibitory activity assay, and did not show inhibitory activity against 14-α-lanosterol demethylase (a fungal P450 cytochrome). Compounds 2, 4e, and 4n exhibited in vivo activity against P. chabaudi after oral administration and thus represent promising antimalarial agents for further preclinical development.