73742-07-1

Usage

Uses

Used in Organic Synthesis:
2-(3-CHLOROBENZOYL)PYRIDINE is used as a building block for the synthesis of various organic compounds. Its unique structure allows for the creation of a wide array of derivatives, making it a versatile component in the development of new chemical entities.
Used in Pharmaceutical Industry:
In the pharmaceutical sector, 2-(3-CHLOROBENZOYL)PYRIDINE is utilized as a key intermediate in the production of drugs. Its presence in the molecular structure of certain medications contributes to their therapeutic effects, highlighting its importance in drug discovery and development.
Used in Agrochemical Industry:
2-(3-CHLOROBENZOYL)PYRIDINE also finds application in the agrochemical industry, where it serves as a precursor for the synthesis of various agrochemicals. Its role in the creation of pesticides and other agricultural chemicals underscores its utility in enhancing crop protection and productivity.

InChI:InChI=1/C12H8ClNO/c13-10-5-3-4-9(8-10)12(15)11-6-1-2-7-14-11/h1-8H

Upstream product

• 109-04-6 2-bromo-pyridine 
• 1529-41-5 3-chloro-benzeneacetonitrile 
• 2905-65-9 methyl 3-chlorobenzoate 
• 75343-75-8 (3-chlorophenyl)-2-pyridylmethanol 
• 1121-60-4 pyridine-2-carbaldehyde 
• 36229-42-2 (3-chlorophenyl)magnesium bromide 
• 2524-52-9 ethyl-2-picolinate 
• 108-37-2 1-bromo-3-chlorobenzene 
• 694-59-7 pyridine N-oxide 
• 766-83-6 m-chlorophenylacetylene 
• 766-84-7 3-chloro-benzonitrile 
• 201230-82-2 carbon monoxide 
• 63503-60-6 3-chlorophenylboronic acid 

Downstream Products

• 928046-28-0 1-(3-chlorophenyl)-3-methyl-1-(2-pyridyl)-1-butanol 
• 928046-51-9 2-[1-(3-chlorophenyl)-3-methyl-1-butenyl]pyridine 
• 949934-47-8 (3-chlorophenyl)[4-(pyrrolidin-1-ylmethyl)phenyl](pyridin-2-yl)methanol 
• 1318776-83-8 C₁₉H₂₄ClNO 
• 75343-75-8 (3-chlorophenyl)-2-pyridylmethanol 
• 1585241-35-5 (3E)-4-(3-chlorophenyl)-N,N-dimethyl-4-(2-pyridyl)but-3-en-1-ammoniumtrifluoroacetate 
• 1585241-37-7 (3Z)-4-(3-chlorophenyl)-N,N-dimethyl-4-(2-pyridyl)but-3-en-1-ammonium trifluoroacetate 

Relevant academic research and scientific papers

Continuous flow as an enabling technology: a fast and versatile entry to functionalized glyoxal derivatives

We herein report two complementary strategies employing organolithium chemistry for the synthesis of glyoxal derivatives. Micro-mixer technology allows for the generation of unstable organometallic intermediates and their instantaneous in-line quenching with esters as electrophiles. Selective mono-addition was observedviaputative stabilized tetrahedral intermediates. Advantages offered by flow chemistry technologies facilitate direct and efficient access to masked 1,2-dicarbonyl compounds while mitigating undesired by-product formation. These two approaches enable the production of advanced and valuable synthetic building blocks for heterocyclic chemistry with throughputs of grams per minute.

Photoinduced Divergent Alkylation/Acylation of Pyridine N-Oxides with Alkynes under Anaerobic and Aerobic Conditions

Ortho-alkylated and ortho-acylated pyridines have been conveniently synthesized from pyridine N-oxides and alkynes under visible-light-mediation in a metal-free manner. The alkynes served as both alkylating and acylating agents via switching between anaerobic and aerobic conditions. The overall strategy accommodates a broad scope of substituted pyridine N-oxides and alkynes, with excellent regioselectivity in a number of cases.

Chlorpheniramine Analogues Reverse Chloroquine Resistance in Plasmodium falciparum by Inhibiting PfCRT

The emergence and spread of malaria parasites that are resistant to chloroquine (CQ) has been a disaster for world health. The antihistamine chlorpheniramine (CP) partially resensitizes CQ-resistant (CQR) parasites to CQ but possesses little intrinsic antiplasmodial activity. Mutations in the parasite's CQ resistance transporter (PfCRT) confer resistance to CQ by enabling the protein to transport the drug away from its site of action, and it is thought that resistance-reversers such as CP exert their effect by blocking this CQ transport activity. Here, a series of new structural analogues and homologues of CP have been synthesized. We show that these compounds (along with other in vitro CQ resistance-reversers) inhibit the transport of CQ via a resistance-conferring form of PfCRT expressed in Xenopus laevis oocytes. Furthermore, the level of PfCRT-inhibition was found to correlate well with both the restoration of CQ accumulation and the level of CQ resensitization in CQR parasites.

Synthesis and biological evaluation of a fluorescent analog of phenytoin as a potential inhibitor of neuropathic pain and imaging agent

Here we report on a novel fluorescent analog of phenytoin as a potential inhibitor of neuropathic pain with potential use as an imaging agent. Compound 2 incorporated a heptyl side chain and dansyl moiety onto the parent compound phenytoin and produced greater displacement of BTX from sodium channels and greater functional blockade with greatly reduced toxicity. Compound 2 reduced mechano-allodynia in a rat model of neuropathic pain and was visualized ex vivo in sensory neuron axons with two-photon microscopy. These results suggest a promising strategy for developing novel sodium channel inhibitors with imaging capabilities.

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.

Slow-onset, long-duration, alkyl analogues of methylphenidate with enhanced selectivity for the dopamine transporter

Methylphenidate analogues, in which the carbomethoxy has been replaced by an alkyl group and with different phenyl substituents, have been synthesized and tested in monoamine transporter assays. As predicted from a pharmacophore model, most of the RR/SS diastereomers showed high potency as dopamine reuptake inhibitors. Analogues with a 4-chlorophenyl group and an unbranched initial alkyl atom had consistently enhanced selectivity for the dopamine transporter. The most potent compounds were those with a three- or four-carbon chain. The "inactive" RS/SR diastereomers showed substantial activity when the phenyl substituent was 3,4-dichloro. On a locomotor assay, one compound was found to have a slow onset and a long duration of action. The activity of these compounds provides additional evidence for a conformational/superposition model of methylphenidate with cocaine-like structures. A ketone analogue, obtained by hydrogenating a previously described vinylogous amide, had activity similar to that of methylphenidate.

ANTIMALARIAL AGENTS HAVING POLYAROMATIC STRUCTURE

Antimalarial agents having a novel pharmacophore of formula (I) are herein described. These polycyclic compounds are able to inhibit chloroquine-sensitive and chloroquine-resistant strains ofPlasmodium falciparum (Pf). Furthermore, the synthesis of these compounds involves few steps from commercial products with low cost of production.Λa présente invention concerne des agents antimalariaux comportant un nouveau pharmacophore de formule (I). Ces composés polycycliques sont susceptibles d''inhiber les souches sensibles à la chloroquine et résistantes à la chloroquine de Plasmodium falciparum (Pf). En outre, la synthèse de ces composés est peu onéreuse et implique peu d''étapes à partir des produits commerciaux.

Palladium-N-heterocyclic carbene an efficient catalytic system for the carbonylative cross-coupling of pyridine halides with boronic acids

Carbonylative cross-coupling of different pyridyl halides with various boronic acids was studied using catalytic systems constituted of N-heterocyclic carbene type ligands and palladium. These systems easily obtained in situ from the corresponding imidazolium salt and palladium acetate appear more efficient toward bromopyridines than catalysts based on hindered and basic alkylphosphines such as tricyclohexylphosphine. Their higher efficiency was also evidenced by coupling using chloro- or dichloropyridines and chloroquinolines, which practically do not react with catalytic systems based on phosphines.

Synthesis of 2- and 3-pyridinyl(aryl)methanones

A procedure was developed for the preparation of 2- and 3-pyridinyl(aryl)methanones by the reactions of aryllithium with methyl pyridinecarboxylate and methyl esters of substituted phenylcarboxylic acids.

Synthesis and pharmacology of potential cocaine antagonists. 2. Structure-activity relationship studies of aromatic ring-substituted methylphenidate analogs

As part of a program, to develop medications which can block the binding of cocaine to the dopamine transporter, yet spare dopamine uptake, a series of aromatic ring-substituted methylphenidate derivatives was synthesized and tested for inhibitory potency in [3H]WIN 35,428 binding and [3H]dopamine uptake assays using rat striatal tissue. Synthesis was accomplished by alkylation of 2-bromopyridine with anions derived from various substituted phenylacetonitriles. In most cases, erythro compounds were markedly less potent than the corresponding (±)-threo-methylphenidate (TMP; Ritalin) derivatives. The ortho-substituted compounds were much less potent than the corresponding meta- and/or para-substituted derivatives. The most potent compound against [3H]WIN 35,428 binding, m-bromo-TMP, was 20-fold more potent than the parent compound, whereas the most potent compound against [3H]dopamine uptake, m,p-dichloro-TMP, was 32-fold more potent. Threo derivatives with m-or p-halo substituents were more potent than TMP, while electron-donating substituants caused little change or a small loss of potency. All of the derivatives had Hill coefficients approaching unity, except m,p-dichloro-TMP, which had an nH of 2.0. Although the potency of the (±)-methylphenidate derivatives in the two assays was highly correlated (R2 = 0.986), the compounds m-chloro-, m-methyl-, and p-iodo-TMP were 4-5-fold more potent at inhibiting [3H]-WIN 35,428 binding than [3H]dopamine uptake (cocaine has a ratio of 2.3). These and other compounds may be promising candidates for further testing as potential partial agonists or antagonists of cocaine.