21261-76-7

Basic information

• Product Name: 3-CHLORO-N-(3-METHOXYPHENYL)PROPANAMIDE
• Synonyms: AKOS BBS-00003942;3-CHLORO-N-(3-METHOXYPHENYL)PROPANAMIDE;AURORA KA-4810;PROPANAMIDE, 3-CHLORO-N-(3-METHOXYPHENYL)-;3-chloro-N-(3-methoxyphenyl)propionamide;A3535/0149786;ZINC02379752
• CAS NO: 21261-76-7
• Molecular Formula: C₁₀H₁₂ClNO₂
• Molecular Weight: 213.66
• Product Categories: Pharmaceuticals, Intermediates & Fine Chemicals
• Mol File: 21261-76-7.mol
• Article Data: 12

Chemical Properties

• Melting Point: 93-95 °C(Solv: water (7732-18-5); ethanol (64-17-5))
• Boiling Point: 391.5°C at 760 mmHg
• Flash Point: 190.6°C
• Appearance: /
• Density: 1.225g/cm³
• Vapor Pressure: 2.45E-06mmHg at 25°C
• Refractive Index: 1.563
• Storage Temp.: Refrigerator
• Solubility: DMSO (Slightly), Methanol (Slightly)
• PKA: 13.74±0.70(Predicted)
• CAS DataBase Reference: 3-CHLORO-N-(3-METHOXYPHENYL)PROPANAMIDE(CAS DataBase Reference)
• NIST Chemistry Reference: 3-CHLORO-N-(3-METHOXYPHENYL)PROPANAMIDE(21261-76-7)
• EPA Substance Registry System: 3-CHLORO-N-(3-METHOXYPHENYL)PROPANAMIDE(21261-76-7)

Safety Data

• Hazardous Substances Data: 21261-76-7(Hazardous Substances Data)

Usage

Uses

3-Chloro-N-(3-methoxyphenyl)propanamide acts as an inhibitor towards DOXP-reductoisomerase (DXR), a primary target for antimalarial drugs.

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

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

Relevant articles and documents

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

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.

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.