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Usage

Uses

Used in Pharmaceutical Industry:
3-chloro-N-(3-methoxyphenyl)propanamide is used as an antimalarial agent for its ability to inhibit DOXP-reductoisomerase (DXR), a key enzyme in the isoprenoid biosynthesis pathway of Plasmodium falciparum. By targeting DXR, 3-chloro-N-(3-methoxyphenyl)propanamide can potentially disrupt the parasite's life cycle and contribute to the development of novel treatments for malaria.
Additionally, if there are other applications in different industries, they can be listed as follows:
Used in Chemical Research Industry:
3-chloro-N-(3-methoxyphenyl)propanamide is used as a research compound for studying the mechanisms of action and potential applications of inhibitors targeting DOXP-reductoisomerase (DXR) in the context of antimalarial drug development. This application aids in understanding the compound's interactions with the enzyme and its implications for malaria treatment.
Used in Drug Development Industry:
3-chloro-N-(3-methoxyphenyl)propanamide is utilized as a lead compound in the development of new antimalarial drugs. Its effectiveness in inhibiting DXR makes it a valuable starting point for designing and synthesizing more potent and selective inhibitors that can be used in the fight against malaria.

InChI:InChI=1/C10H12ClNO2/c1-14-9-4-2-3-8(7-9)12-10(13)5-6-11/h2-4,7H,5-6H2,1H3,(H,12,13)

Upstream product

• 536-90-3 m-Anisidine 
• 625-36-5 2-chloropropionyl chloride 
• 19565-19-6 3-chloropropionylisothiocyanate 

Downstream Products

• 73863-49-7 2-Chloro-3-chloromethyl-7-methoxy-quinoline 
• 22246-18-0 7-hydroxy-3,4-dihydro-2-(1H)-quinolinone 
• 1194459-28-3 6-bromo-7-hydroxy-3,4-dihydro-1H-quinolin-2-one 
• 1224927-77-8 6-bromo-7-methoxy-3,4-dihydroquinolin-2(1H)-one 
• 1392223-87-8 6-bromo-7-ethoxy-3,4-dihydro-1H-quinolin-2-one 
• 1392223-84-5 6-bromo-7-ethoxy-1-methyl-3,4-dihydro-1H-quinolin-2-one 
• 1392223-89-0 7-benzyloxy-6-bromo-3,4-dihydro-1H-quinolin-2-one 
• 1444511-80-1 diethyl [N-(3-methoxyphenyl)carbamoyl]ethylphosphonate 
• 1444512-25-7 [N-(3-methoxyphenyl)carbamoyl]ethylphosphonic acid 
• 1444512-73-5 sodium hydrogen [N-(3-methoxyphenyl)carbamoyl]ethylphosphonate 
• 952308-47-3 7-(4-iodobutoxy)-3,4-dihydroquinolin-2(1H)-one 
• 30389-33-4 5-hydroxycarbostyril 
• 129722-34-5 7-(4-bromobutoxy)-3,4-dihydro-2(1H)-quinolinone 

Relevant academic research and scientific papers

Rigid: Versus flexible anilines or anilides confirm the bicyclic ring as the hydrophobic portion for optimal σ2 receptor binding and provide novel tools for the development of future σ2 receptor PET radiotracers

Despite their uncertain identification, σ2 receptors are promising targets for the development of diagnostics and therapeutics for tumor diseases. Among the σ2 ligands developed, the class of the flexible benzamides furnished an opti

Design of a Chemical Probe for the Bromodomain and Plant Homeodomain Finger-Containing (BRPF) Family of Proteins

The bromodomain and plant homeodomain finger-containing (BRPF) family are scaffolding proteins important for the recruitment of histone acetyltransferases of the MYST family to chromatin. Here, we describe NI-57 (16) as new pan-BRPF chemical probe of the bromodomain (BRD) of the BRPFs. Inhibitor 16 preferentially bound the BRD of BRPF1 and BRPF2 over BRPF3, whereas binding to BRD9 was weaker. Compound 16 has excellent selectivity over nonclass IV BRD proteins. Target engagement of BRPF1B and BRPF2 with 16 was demonstrated in nanoBRET and FRAP assays. The binding of 16 to BRPF1B was rationalized through an X-ray cocrystal structure determination, which showed a flipped binding orientation when compared to previous structures. We report studies that show 16 has functional activity in cellular assays by modulation of the phenotype at low micromolar concentrations in both cancer and inflammatory models. Pharmacokinetic data for 16 was generated in mouse with single dose administration showing favorable oral bioavailability.

Exploring DOXP-reductoisomerase binding limits using phosphonated N-aryl and N-heteroarylcarboxamides as DXR inhibitors

DOXP-reductoisomerase (DXR) is a validated target for the development of antimalarial drugs to address the increase in resistant strains of Plasmodium falciparum. Series of aryl- and heteroarylcarbamoylphosphonic acids, their diethyl esters and disodium salts have been prepared as analogues of the potent DXR inhibitor fosmidomycin. The effects of the carboxamide N-substituents and the length of the methylene linker have been explored using in silico docking studies, saturation transfer difference NMR spectroscopy and enzyme inhibition assays using both EcDXR and PfDXR. These studies indicate an optimal linker length of two methylene units and have confirmed the importance of an additional binding pocket in the PfDXR active site. Insights into the constraints of the PfDXR binding site provide additional scope for the rational design of DXR inhibitors with increased ligand-receptor interactions.

Selective dual inhibitors of CYP19 and CYP11B2: Targeting cardiovascular diseases hiding in the shadow of breast cancer

Postmenopausal women are at high risk for cardiovascular diseases because of the estrogen deficiency. As for postmenopausal breast cancer patients, this risk is even higher due to inhibition of estrogens biosyntheses in peripheral tissue by the aromatase (CYP19) inhibitors applied. Because estrogen deficiency results in significantly elevated aldosterone levels, which are a major cause of cardiovascular diseases, dual inhibition of CYP19 and CYP11B2 (aldosterone synthase) is a promising treatment for breast cancer and the coinstantaneous cardiovascular diseases. By combination of important structural features of known CYP19 and CYP11B2 inhibitors, we succeeded in obtaining compounds 3 and 5 as selective dual inhibitors with IC50 values around 50 and 20 nM toward CYP19 and CYP11B2, respectively. These compounds showed also good selectivity toward CYP11B1 (selectivity factors (IC50 CYP11B1/IC 50 CYP11B2) around 50) and CYP17 (no inhibition).

Synthesis of novel 3,4-dihydroquinolin-2(1H)-one guanidines as potential antihypertensive agents

Hydroxy-3,4-dihydroquinolin-2(1H)-ones (4a-c) were synthesized by intramolecular Friedel Craft alkylation of N-(methoxyphenyl)-3- chloropropionamides (3a-c), obtained by acylation of anisidine with chloropropionyl chloride. The hydroxy-3,4-dihydro quinolin-2(1H)- ones (4a-c) were treated with various dibromo alkanes under phase transfer catalyst conditions at room temperature to give bromoalkyloxy- 3,4-dihydroquinolin-2(1H)- ones (5a-l) which on further reaction with guanidine hydrochloride in dimethyl formamide afforded N-{4- [(2-oxo-1,2,3,4-tetrahydroquinolin-5-yl)oxy]alkyl} guanidines (6a-l). These compounds were synthesized as potential antihypertensive agents.

A NOVEL PROCESS FOR PREPARATION OF ARIPIPRAZOLE AND ITS INTERMEDIATES

A process for the preparation of 7-hydroxy-3,4-dihydro carbostyril (II) by intramolecular Fridel-Craft alkylation of N-(3-methoxyphenyl)-3-chloropropionamide (I) in which an equivalent of N-(3-methoxyphenyl)-3-chloropropionamide (I) is contacted with a Lewis acid (e.g. aluminium chloride) in dimethyl acetamide (DMA), at an elevated temperature of from about 120°C to about 160°C, is provided. The process produces 7-hydroxy-3,4- dihydro carbostyril (II) in high yield and a high state of purity such that it may be used in subsequent .reaction towards the preparation of aripiprazole (IV). Thus 7-hydroxy-3,4- dihydro carbostyril (II) was treated with l-bromo-4-chlorobutane under phase transfer catalyst (PTC) conditions using solvents like acetone or n-butanol at temperature ranging 25°C to 45°C to afford 7-(4-chlorobutoxy)-3,4-dihydro carbostyril (III). The PTC conditions described in this patent afford 7-(4-chlorobutoxy)-3,4-dihydro carbostyril (III) in high purity and high yield with the corresponding dimmer formation is considerably low as compared with the other literature methods of preparing 7-(4-chlorobutoxy)-3,4- dihydro carbostyril (III). Compound (III) was treated with l-(2,3-dichlorophenyl)piperazine, at temperature ranging from 50°C to 100°C, and sodium iodide, potassium carbonate, dimethyl formamide (DMF) as a solvent to afford aripiprazole in high purity and high yield.

Synthesis and biological activities of novel furo[2,3,4-jk][2]benzazepin- 4(3H)-one derivatives

A novel seven-membered lactam formation method has been established by intramolecular ring closure reaction of 4-bromo-(E)-3-[(2-alkylvinyl) carbonylamino]benzo[b]furans (17) under Heck coupling conditions. A number of furo[2,3,4-jk][2]benzazepin-4(3H)-on

Synthesis and bioactivity of aripiprazole derivatives

Ten aripirazole (CAS 129722-12-9) derivatives were prepared and examined for dopamine receptor antagonist activity. The structures of these newly synthesized compounds were confirmed by their elemental analyses and by IR, 1H-NMR and mass spectra. It was demonstrated that all the new compounds have dopamine receptor antagonist activity to a certain extent. Three compounds showed more potent activity than aripiprazole. ECV · Editio Cantor Verlag.

Benzoamide piperidine containing compounds and related compounds

The present invention relates to certain benzoamide piperidine containing compounds and related compounds that exhibit activity as NK-1 receptor antagonists, (e.g., substance P receptor antagonists), to pharmaceutical compositions containing them, and to their use in the treatment and prevention of central nervous system disorders, inflammatory disorders, cardiovascular disorders, ophthalmic disorders, gastrointestinal disorders, disorders caused by helicobacter pylori, disorders of the immune system, urinary incontinence, pain, migraine, emesis, angiogenesis and other disorders.

Aluminium chloride-catalyzed intermolecular vs intramolecular friedel-crafts reaction of acrylanilides and 3-chloropropanamides

3-Phenylpropionanilide (4a) is obtained in a yield of 89% from acrylanilide by the treatment with AlCl3/ benzene, compared with a yield of 39% by the 1,4-conjugate addition of phenyllithium. The formation of 4a indicated that an intermolecular Friedel-Crafts reaction occurred, rather than the relatively more facile intramolecular ring cyclization, and provided a more efficient route than a conjugate addition of phenyllithium for the preparation of 3-phenylpropionanilide and its derivatives. Although the methoxy group is an activator of the nucleophilic substitution, introduction of a methoxy substituent at N-phenyl did not increase the competitive capability of the intramolecular cyclization because of AlCl3-catalyzed demethylation to form the ArOAlCl2 complex which decreased the availability of the π-electron in the N-phenyl aromatic system.