71130-60-4

Usage

Uses

Used in Pharmaceutical Industry:
2-[(Ethylamino)methyl]-4-nitrophenol is used as a key intermediate in the synthesis of novel amodiaquine analogs, which are being explored for their potential as antimalarial and antifilarial compounds. These analogs aim to provide more effective treatments for malaria and filariasis, two prevalent and life-threatening diseases.
Used in Chemical Synthesis:
As a bright-yellow solid, 2-[(Ethylamino)methyl]-4-nitrophenol can also be utilized in the chemical industry for the development of various dyes, pigments, and other colorants. Its unique chemical structure allows it to be a valuable component in the creation of new compounds with specific color properties and applications.

InChI:InChI=1/C9H12N2O3/c1-2-10-6-7-5-8(11(13)14)3-4-9(7)12/h3-5,10,12H,2,6H2,1H3

Upstream product

• 2973-19-5 2-hydroxy-5-nitrobenzyl chloride 
• 75-04-7 ethylamine 
• 147820-72-2 N-ethyl-3-nitro-5-tert-butylsalicylaldimine 
• 97-51-8 5-Nitrosalicylaldehyde 

Downstream Products

• 86177-06-2 4‐amino‐2‐((ethylamino)methyl)phenol dihydrochloride 
• 79352-80-0 4-amino-2-((ethylamino)methyl)phenol 
• 86177-44-8 N-(3,4-Dichloro-phenyl)-N'-[4-(3-ethylaminomethyl-4-hydroxy-phenylamino)-6-trifluoromethyl-pyrimidin-2-yl]-guanidine 

Relevant academic research and scientific papers

Synthesis of stable isotope–labeled chloroquine and amodiaquine and their metabolites

Anti-malaria drugs chloroquine and amodiaquine and their metabolites were synthesized to incorporate 13C and 15N starting from U-13C–labeled benzene to give M?+?7 isotopomers. Chloroquine and its metabolites were prepared

Antimalarial Pyrido[1,2- a]benzimidazole Derivatives with Mannich Base Side Chains: Synthesis, Pharmacological Evaluation, and Reactive Metabolite Trapping Studies

A novel series of pyrido[1,2-a]benzimidazoles bearing Mannich base side chains and their metabolites were synthesized and evaluated for in vitro antiplasmodium activity, microsomal metabolic stability, reactive metabolite (RM) formation, and in vivo antimalarial efficacy in a mouse model. Oral administration of one of the derivatives at 4 × 50 mg/kg reduced parasitemia by 95% in Plasmodium berghei-infected mice, with a mean survival period of 16 days post-treatment. The in vivo efficacy of these derivatives is likely a consequence of their active metabolites, two of which showed potent in vitro antiplasmodium activity against chloroquine-sensitive and multidrug-resistant Plasmodium falciparum (P. falciparum) strains. Rapid metabolism was observed for all the analogues with 40% of parent compound remaining after 30 min of incubation in liver microsomes. RM trapping studies detected glutathione adducts only in derivatives bearing 4-aminophenol moiety, with fragmentation signatures showing that this conjugation occurred on the phenyl ring of the Mannich base side chain. As with amodiaquine (AQ), interchanging the positions of the 4-hydroxyl and Mannich base side group or substituting the 4-hydroxyl with fluorine appeared to block bioactivation of the AQ-like derivatives though at the expense of antiplasmodium activity, which was significantly lowered.

Synthesis and antifilarial activity of N-[4-[[4-alkoxy-3-[(dialkylamino)methyl]phenyl]amino]-2-pyrimidinyl]-N'-ph enylguanidines

A series of N-[4-[[4-alkoxy-3-[(dialkylamino)methyl]phenyl]amino]-2-pyrimidinyl]-N' -phenylguanidines have been synthesized for antifilarial evaluation. Reaction of the appropriate benzenamines with N-cyanoguanidine, followed by condensation of the result