103687-94-1

Basic information

• Product Name: ethyl 3-(2-methoxyphenylamino)propanoate
• Synonyms: ethyl 3-(2-methoxyphenylamino)propanoate
• CAS NO: 103687-94-1
• Molecular Weight: 223.272
• Mol File: 103687-94-1.mol

Chemical Properties

• CAS DataBase Reference: ethyl 3-(2-methoxyphenylamino)propanoate(CAS DataBase Reference)
• NIST Chemistry Reference: ethyl 3-(2-methoxyphenylamino)propanoate(103687-94-1)
• EPA Substance Registry System: ethyl 3-(2-methoxyphenylamino)propanoate(103687-94-1)

Safety Data

• Hazardous Substances Data: 103687-94-1(Hazardous Substances Data)

Upstream product

• 90-04-0 2-methoxy-phenylamine 
• 140-88-5 ethyl acrylate 

Downstream Products

• 103687-95-2 ethyl β-(N-tosyl-o-anisidino)propionate 
• 3536-04-7 2,3-dihydro-8-methoxy-1-tosyl-4(1H)-quinoline 
• 6295-94-9 N-tosyl-2-anisidine 
• 103687-96-3 β-(N-tosyl-o-anisidino)propionic acid 

Relevant articles and documents

Arylamino containing hydroxamic acids as potent urease inhibitors for the treatment of Helicobacter pylori infection

A novel series of aniline-containing hydroxamic acids were designed, synthesized and evaluated as anti-virulence agents for the treatment of gastritis and gastric ulcer caused by Helicobacter pylori. In vitro enzyme-based screen together with in vivo assays and structure?activity relationship (SAR) studies led to the discovery of three potent urease inhibitors 3-(3,5-dichlorophenylamino)–N-hydroxypropanamide (3a), 3-(2-chlorophenylamino)–N-hydroxypropanamide (3d) and 3-(2,4-dichlorophenylamino)–N-hydroxypropanamide (3n). Compounds 3a, 3d and 3n showed excellent urease inhibition with IC50 values 0.043 ± 0.005, 0.055 ± 0.008 and 0.018 ± 0.002 μM, and significantly depressed gastritis developing at the dose of 32 mg/kg b. i.d with eradication rates of H. pylori reaching 92.3, 84.6 and 100%, respectively. Preliminary safety studies (acute toxicity in mice) disclosed that 3a, 3d and 3n was well-tolerated in KM mice with LD50s of 2982.8, 3349.4 and 3126.9 mg/kg, respectively. Collectively, the data obtained in this study indicate that 3a, 3d and 3n, in particular 3n, could considered as promising candidates for the potential treatment of H. pylori caused gastritis and gastric ulcer, and hence merit further studies.

Reductive debromination of 1,2-dibromides with anisidines

vic-Dibromides containing the α-bromocarbonyl or α-bromoaromatic moieties were reductively debrominated to furnish alkenes in high yields. o- and m-anisidines but not p-anisidine were found to be effective debrominating agents. The reductive debrominations were found to be trans-stereospecific.

Design, synthesis and bioactivity evaluation of novel dabigatran derivatives as potential thrombin inhibitors

With the help of computer-aided drug design approach, five dabigatran derivatives were designed and synthesized. The structures of these compounds were elucidated by 1H NMR, 13C NMR, HRMS analyses. All the compounds were evaluated fo

Synthesis and biological evaluation of some new 2,5-Substituted 1-Ethyl-1H-benzoimidazole fluorinated derivatives as direct thrombin Inhibitors

A new series of fluorinated 2,5-substituted 1-ethyl-1H-benzimidazole derivatives were synthesized from starting compounds 3a-i, which were prepared from acrylic acid ethyl ester and the appropriate amines using trifluoromethanesulfonic acid as a catalyst. A total of 9 novel derivatives were synthesized through 9 steps. All of them were evaluated for thrombin inhibition activity in vitro for the first time. We have altered their structures using different substituents on the amines to assess their structure-activity relationships as direct thrombin inhibitors. All the compounds were effective thrombin inhibitors, with IC50 values ranging from 3.39 to 23.30nM. Among the compounds synthesized, compounds 14a, 14b, 14d, 14e, and 14h exhibited greater anticoagulant activity than argatroban (IC50=9.36nM). Furthermore, compound 14h synthesized starting with 2-amino-pyridine was the most potent thrombin inhibitor with an IC50 value of 3.39nM. Molecular modeling studies were performed to determine the probable interactions of the most potent compounds 14a, 14e, and 14h with their protein receptor (PDB ID: 1KTS). Docking data show that the active compounds inhibit thrombin in a similar mode to that of the potent anticoagulant dabigatran. A new series of fluorinated derivatives were evaluated for their in vitro thrombin inhibition activities. 3-({2-[(4-Carbamimidoyl-2-fluoro-phenylamino)-methyl]-1-ethyl-1H-benzoimidazole-5-carbonyl}-pyridin-2-yl-amino)-propionic acid 14h shows the most potent antithrombin activity (IC50=3.39nM). Molecular docking revealed that its inhibition mode was similar to that of dabigatran.

Aza-Michael reaction promoted by aqueous sodium carbonate solution

A general and efficient aza-Michael reaction promoted by aqueous sodium carbonate solution has been developed. The reaction has complete mono-alkylation selectivity and proceeds with complete chirality retention for chiral amino esters. With a broad substrate scope, a well-common catalyst and simple operation, the catalytic approach provides a facile, practicable, economical, and environmentally benign method for the synthesis of β-amino carbonyl compounds.

6,7-dihydropyrrol[3,4-c]pyrido[2,3-d]pyrimidine derivatives

The present invention concerns compounds of the formula: STR1 wherein R is a lower alkyl group, an aryl group or an alkylaryl group and X and Y are the same or different, and each is OH, NH2, or SH. The aryl group or the aryl moiety of the alkylaryl group may be unsubstituted, monosubstituted, disubstituted or trisubstituted. If substituted, each substituent may independently be an alkyl group, an alkyloxy group or a halogen. The present invention also provides methods for synthesizing the compounds described above.

Antifertility Agents: Part XLIII - Synthesis of 3-Aryl-4,5-dihydro-2-substituted-5-tosyl-2H-pyrazoloquinolines and 2,4-Dihydro-3-phenylbenzopyranopyrazoles and Their Derivatives

2,3-Dihydro-1-tosyl-4(1H)-quinolones (5-7) on formylation give the corresponding 3-hydroxymethylene derivatives (11-13) of which 12 and 13 react with piperazine to afford N,N-bis-substituted piperazines (15 and 16).Refluxing of 11-13 with substituted hydr