51674-33-0

Upstream product

• 33543-62-3 2-(3-methoxyphenyl)-N-methylethan-1-amine 
• 52059-50-4 2-(3-hydroxyphenyl)ethyl bromide 
• 74-89-5 methylamine 
• 220299-54-7 N-methyl-(3-hydroxyphenyl)acetamide 
• 2146-61-4 3-methoxyphenethyl bromide 
• 1798-09-0 m-methoxyphenylacetic acid 
• 2039-67-0 2-(3-methoxyphenyl)-1-ethanamine 
• 621-37-4 m-hydroxyphenylacetic acid 
• 53102-68-4 N-methyl-(3-methoxyphenyl)acetamide 
• 42058-59-3 3-hydroxy-benzeneacetic acid, methyl ester 
• 18927-05-4 methyl (3-methoxyphenyl)acetate 

Downstream Products

• 132513-31-6 tert-butyl (3-hydroxyphenethyl)(methyl)carbamate 
• 293756-94-2 N-methyl-N-[2-(2,4,6-tribromo-3-hydroxy-phenyl)-ethyl]-formamide 
• 294210-58-5 lutamide C 
• 1057214-74-0 C₁₁H₁₅NO₂ 
• 209546-50-9 3-(N-methyl,N-n-propylcarbamyloxy)-N-Boc,N-methylphenethylamine 
• 209546-55-4 {2-[3-(ethyl-methyl-carbamoyloxy)-phenyl]-ethyl}-methyl-carbamic acid tert-butyl ester 
• 209546-53-2 [2-(3-dimethylcarbamoyloxy-phenyl)-ethyl]-methyl-carbamic acid tert-butyl ester 

Relevant academic research and scientific papers

Phenyl ether- and aniline-containing 2-aminoquinolines as potent and selective inhibitors of neuronal nitric oxide synthase

Excess nitric oxide (NO) produced by neuronal nitric oxide synthase (nNOS) is implicated in neurodegenerative disorders. As a result, inhibition of nNOS and reduction of NO levels is desirable therapeutically, but many nNOS inhibitors are poorly bioavailable. Promising members of our previously reported 2-aminoquinoline class of nNOS inhibitors, although orally bioavailable and brain-penetrant, suffer from unfavorable off-target binding to other CNS receptors, and they resemble known promiscuous binders. Rearranged phenyl ether- and aniline-linked 2-aminoquinoline derivatives were therefore designed to (a) disrupt the promiscuous binding pharmacophore and diminish off-target interactions and (b) preserve potency, isoform selectivity, and cell permeability. A series of these compounds was synthesized and tested against purified nNOS, endothelial NOS (eNOS), and inducible NOS (iNOS) enzymes. One compound, 20, displayed high potency, selectivity, and good human nNOS inhibition, and retained some permeability in a Caco-2 assay. Most promisingly, CNS receptor counterscreening revealed that this rearranged scaffold significantly reduces off-target binding.

Synthesis and biological activities of the marine bryozoan alkaloids convolutamines A, C and F, and lutamides A and C

Synthesis of convolutamines and lutamides, new 2,4,6-tribromo-3-methoxyphenethylamine alkaloids isolated from Floridian marine bryozoan Amathia convoluta, was accomplished by a sequence of reactions starting from 3-hydroxyphenethylamines. Cytotoxities of the synthetic lutamides, convolutamines and their de-O-methyl derivatives were examined using drug-sensitive and -resistant P388 as well as KB cell lines. The bioassay suggests that the 2,4,6-tribromo-3-methoxyphenethylamine is an indispensable unit for detection of the activities. Additionally, a reversal of drug resistance by those alkaloids is recognized. Copyright (C) 2000 Elsevier Science Ltd.