180001-34-7

Usage

Uses

Used in Pharmaceutical Industry:
1400W is used as a selective inducible nitric oxide synthase (iNOS) inhibitor for its ability to modulate the production of nitric oxide, which plays a crucial role in various physiological and pathological processes.
Used in Cardiovascular Applications:
1400W is used as a cardioprotective agent for its potential to prevent cardiotoxicity induced by chemotherapeutic drugs such as Doxorubicin and Trastuzumab. By inhibiting iNOS, 1400W may help reduce the harmful effects of these drugs on the heart, improving patient outcomes and quality of life.
Used in Research Applications:
1400W is used as a research tool for studying the role of inducible nitric oxide synthase in various biological processes and disease states. Its selective inhibition of iNOS allows researchers to investigate the specific functions and consequences of nitric oxide production in different experimental models.

Biological Activity

Slow, tight binding, potent and highly selective inhibitor of inducible nitric oxide synthase (K d = 7 nM). Selective over nNOS and eNOS (K i values are 2 and 50 μ M respectively). Cell-permeable and active in vivo .

InChI:InChI=1/C10H15N3.2ClH/c1-8(12)13-7-10-4-2-3-9(5-10)6-11;;/h2-5H,6-7,11H2,1H3,(H2,12,13);2*1H

Upstream product

• 108467-99-8 1-(N-Boc-aminomethyl)-3-(aminomethyl)benzene 
• 180001-98-3 N-(3-(N-Boc-aminomethyl)benzyl)acetimidine hydrochloride 

Relevant academic research and scientific papers

Screening of NOS activity and selectivity of newly synthesized acetamidines using RP-HPLC

Nitric Oxide Synthase (NOS) inhibitors could play a powerful role in inflammatory and neurodegenerative diseases. In this work, novel acetamidine derivatives of NOS were synthesized and the inhibitor activity was evalued. To screen the activity and selectivity, the l-citrulline residue, after the enzymatic NOS assay, was derivatized with o-phthaldialdehyde/N-acetyl cysteine (OPA/NAC) and then evaluated by RP-HPLC method with fluorescence detection.All compounds did not affect the activity of endothelial and neuronal isoforms, while nine of them possessed a percentage of iNOS activity at 10 μM lower than 50%, and were selected for IC50 evaluation. Among them, a compound emerged as a very potent (IC50 of 53 nM) and selective iNOS inhibitor.

Mechanism of inactivation of inducible nitric oxide synthase by amidines. Irreversible enzyme inactivation without inactivator modification

Nitric oxide synthases (NOS) are hemoproteins that catalyze the reaction of L-arginine to L-citrulline and nitric oxide. N-(3-(Aminomethyl)benzyl) acetamidine (1400W) was reported to be a slow, tight-binding, and highly selective inhibitor of iNOS in vitr

Acetamidine derivatives and their use as inhibitors for the nitric oxide synthase

A class of acetamidine derivatives of general formula (I) STR1 wherein R1 is hydrogen, C1-6 hydrocarbyl group optionally substituted by halo, halo, nitro, cyano or a group XR3 wherein X is oxygen, C(O)m wherein m is 1 or 2, S(O)n wherein n is 0, 1 or 2, or a group NR4 wherein R4 is hydrogen or C1-6 alkyl; and R3 is hydrogen, C1-6 alkyl, or a group NR5 R6 wherein R5 and R6 are independently hydrogen or C1-6 alkyl, provided that R3 is not NR5 R6 when X is oxygen or S(O)n; R1a and R1b are independently selected from hydrogen and halo; R2 is a C1-14 hydrocarbyl group which may optionally contain one or two heteroatoms, the group R2 being optionally substituted by one or more groups independently selected from halo; N3 ; nitro; CF3 ; ZR7 wherein Z is oxygen, C(O)m' wherein m' is 1 or 2, S(O)n' wherein n' is 0, 1 or 2, or a group NR8 wherein R8 is hydrogen or C1-6 alkyl and R7 is hydrogen, C1-6 alkyl or a group NR9 R10 wherein R9 and R10 are independently hydrogen or C1-6 alkyl; or R2 is substituted by a group (a) STR2 wherein R11 has a definition the same as for R1 ; with the proviso that when R1 is a C1-6 alkyl group and R2 is a C1-14 hydrocarbyl substituted by two groups ZR7 wherein one group ZR7 is CO2 H, the other group ZR7 is not NH2; and salts thereof, methods for the manufacture thereof, and therapies, particularly inhibtion of nitric oxide synthase, is disclosed.