892502-09-9

Usage

Uses

Used in Pharmaceutical Research and Development:
3-(1H-PYRAZOL-1-YLMETHYL)ANILINE is used as a key intermediate in the synthesis of pharmaceutical compounds for various therapeutic areas. Its unique structure allows it to be a versatile building block in the creation of new drug candidates.
Used in Organic Synthesis:
In the field of organic synthesis, 3-(1H-PYRAZOL-1-YLMETHYL)ANILINE is used as a reagent or a precursor for the preparation of a wide range of organic compounds, including those with potential applications in material science and specialty chemicals.
Used in Agrochemical Development:
3-(1H-PYRAZOL-1-YLMETHYL)ANILINE is also utilized in the development of agrochemicals, where its unique properties may contribute to the creation of new pesticides or herbicides with improved efficacy and selectivity.
Used in Medicinal Chemistry:
3-(1H-PYRAZOL-1-YLMETHYL)ANILINE is used as a starting material for the design and synthesis of new molecules with potential pharmacological properties. Its pyrazole ring may offer specific binding affinities or interactions with biological targets, making it a valuable component in the development of novel therapeutic agents.

InChI:InChI=1/C10H11N3/c11-10-4-1-3-9(7-10)8-13-6-2-5-12-13/h1-7H,8,11H2

Upstream product

• 3958-57-4 1-bromomethyl-3-nitrobenzene 
• 1026901-09-6 1-(3-Nitro-benzyl)-1H-pyrazole 

Downstream Products

• 1114591-86-4 6-[(cyclopropylmethyl)(propyl)amino]-N-[3-(1H-pyrazol-1-ylmethyl)phenyl]pyrimidine-4-carboxamide 
• 188263-55-0 6-tert-Butyl-8-isocyanato-4-oxo-4H-chromene-2-carboxylic acid (3-pyrazol-1-ylmethyl-phenyl)-amide 

Relevant academic research and scientific papers

N-phenylamidines as selective inhibitors of human neuronal nitric oxide synthase: Structure-activity studies and demonstration of in vivo activity

Selective inhibition of the neuronal isoform of nitric oxide synthase (NOS) compared to the endothelial and inducible isoforms may be required for treatment of neurological disorders caused by excessive production of nitric oxide. Recently, we described N-(3-(aminomethyl)benzyl)acetamidine (13) as a slow, tight-binding inhibitor, highly selective for human inducible nitric oxide synthase (iNOS). Removal of a single methylene bridge between the amidine nitrogen and phenyl ring to give N-(3- (aminomethyl)phenyl)acetamidine (14) dramatically altered the selectivity to give a neuronal selective nitric oxide synthase (nNOS) inhibitor. Part of this large shift in selectivity was due to 14 being a rapidly reversible inhibitor of iNOS in contrast to the essentially irreversible inhibition of iNOS observed with 13. Structure-activity studies revealed that a basic amine functionality tethered to an aromatic ring and a sterically compact amidine are key pharmacophores for this class of NOS inhibitors. Maximal nNOS inhibition potency was achieved with N-(3-(aminomethyl)phenyl)-2- furanylamidine (77) (K(i-nNOS) = 0.006 μM; K(i-eNOS) = 0.35 μM; K(i-iNOS) = 0.16 μM). Finally, α-fluoro-N-(3-(aminomethyl)phenyl)acetamidine (74) (K(i- nNOS) = 0.011 μM; K(i-eNOS) = 1.1 μM; K(i-iNOS) = 0.48 μM) had excellent brain penetration and inhibited nNOS in a rat brain slice assay as well as in the rat brain (cerebellum) in vivo. Thus, N-phenylamidines should be useful in validating the role of nNOS in neurological disorders.