57004-60-1

Usage

Uses

Used in Pharmaceutical Industry:
N-(3-Methoxy-phenyl)-guanidine is used as an anti-inflammatory agent for its ability to reduce inflammation and alleviate pain. This makes it a valuable component in the development of medications aimed at treating various inflammatory conditions.
Used in Research Applications:
In the field of scientific research, N-(3-Methoxy-phenyl)-guanidine serves as a valuable compound for studying the structure and function of guanidine-containing molecules. It can be used to investigate the interactions of guanidine groups with other molecules, providing insights into their potential applications in drug design and development.

InChI:InChI=1/C8H11N3O/c1-12-7-4-2-3-6(5-7)11-8(9)10/h2-5H,1H3,(H4,9,10,11)

Upstream product

• 536-90-3 m-Anisidine 
• 420-04-2 CYANAMID 
• 1026732-19-3 C₂₃H₂₀N₂O₃S 

Downstream Products

• 692733-41-8 furan-2-carboxylic acid {3-[2-(3-methoxy-phenylamino)-pyrimidin-4-yl]-phenyl}-amide 
• 692733-40-7 furan-2-carboxylic acid {3-[2-(3-methoxy-phenylamino)-pyrimidin-4-yl]-phenyl}-methyl-amide 
• 1011297-66-7 C₂₁H₂₁N₅O₂ 
• 1038386-76-3 C₂₂H₂₂N₄O₂ 
• 1612217-68-1 C₁₇H₁₄BrN₃O 
• 1612217-72-7 C₁₇H₁₃Cl₂N₃O 
• 1612217-76-1 C₁₇H₁₃Cl₂N₃O 
• 1612217-62-5 C₁₈H₁₇N₃O₂ 
• 1550369-55-5 2-amino-1-(3-methoxyphenyl)-1H-benzo[d]imidazol-6-ol 
• 1610886-22-0 5-(2-(3-methoxyphenylamino)pyrimidin-4-yl)-3,4-dimethylthiazol-2(3H)-one 
• 229617-63-4 N-[3-methoxy-phenyl]-4-(2-chloro-4-pyridyl)-2-pyrimidineamine 

Relevant academic research and scientific papers

Discovery of CDK5 Inhibitors through Structure-Guided Approach

Specific abrogation of cyclin-dependent kinase 5 (CDK5) activity has been validated as a viable approach for the development of anticancer agents. However, no selective CDK5 inhibitor has been reported to date. Herein, a structure-based in silico screenin

DERIVATIVES OF MACROCYCLIC N-ARYL-TRICYCLOPYRIMIDINE-2-AMINE POLYETHERS AS INHIBITORS OF FTL3 AND JAK

The present invention relates to a compound with the following formula (I): (I) or a salt and/or a pharmaceutically acceptable solvate thereof, in particular for use as a drug, in particular in the treatment of cancer, as well as to the pharmaceutical compositions that contain same and to the methods for preparing same.

One-Pot Evolution of Ageladine A through a Bio-Inspired Cascade towards Selective Modulators of Neuronal Differentiation

A bio-inspired cascade reaction has been developed for the construction of the marine natural product ageladine A and a de novo array of its N1-substituted derivatives. This cascade features a 2-aminoimidazole formation that is modeled after an arginine post-translational modification and an aza-electrocyclization. It can be effectively carried out in a one-pot procedure from simple anilines or guanidines, leading to structural analogues of ageladine A that had been otherwise synthetically inaccessible. We found that some compounds out of this structurally novel library show a significant activity in modulating the neural differentiation. Namely, these compounds selectively activate or inhibit the differentiation of neural stem cells to neurons, while being negligible in the differentiation to astrocytes. This study represents a successful case in which the native biofunction of a natural product could be altered by structural modifications.

Discovery of 5-(2-(phenylamino)pyrimidin-4-yl)thiazol-2(3H)-one derivatives as potent Mnk2 inhibitors: Synthesis, SAR analysis and biological evaluation

Phosphorylation of eIF4E by human mitogen-activated protein kinase (MAPK)-interacting kinases (Mnks) is crucial for human tumourigenesis and development. Targeting Mnks may provide a novel anticancer therapeutic strategy. However, the lack of selective Mnk inhibitors has so far hampered pharmacological target validation and clinical drug development. Herein, we report, for the first time, the discovery of a series of 5-(2-(phenylamino) pyrimidin-4-yl)thiazole-2(3H)-one derivatives as Mnk inhibitors. Several derivatives demonstrate very potent Mnk2 inhibitory activity. The most active and selective compounds were tested against a panel of cancer cell lines, and the results confirm the cell-type-specific effect of these Mnk inhibitors. Detailed cellular mechanistic studies reveal that Mnk inhibitors are capable of reducing the expression level of anti-apoptotic protein Mcl-1, and of promoting apoptosis in MV4-11 acute myeloid leukaemia cells. Highly active Mnk2 inhibitors: Mnk-related cancer biology is an area of intensive research, but its inhibitor discovery has lagged behind due to a lack of understanding of the protein structure. Herein we report the discovery of Mnk2 inhibitors (e.g. 8 e). These potent and selective inhibitors are extremely valuable for target validation and drug discovery.

Reaction of quinones and guanidine derivatives: Simple access to bis-2-aminobenzimidazole moiety of benzosceptrin and other benzazole motifs

A new strategy for the synthesis of 2-aminobenzimidazol-6-ols via a reaction of quinones with guanidine derivatives is reported. Sequential application of this methodology provided a simple access to the first benzosceptrin analogue bearing a bis-2-aminoimidazole moiety. A concomitant addition of two guanidines to the naphtho[1′,2′:4,5]imidazo[1,2-a] pyrimidine-5,6-dione, which includes the redox neutral debenzylation and guanidine-assisted cleavage of the 2-aminopyrimidine part resulted in the synthesis of the free challenging contiguous bis-2-aminoimidazole moiety of benzosceprins in one step.

Design and synthesis of a novel series of N,4-diphenylpyrimidin-2-amine derivatives as potent and selective PI3Kγ inhibitors

Due to the increasing evidence linking the PI3Kγ pathway to various disease states, PI3Kγ is becoming an important target for cancer treatment. Herein we designed and synthesized a novel series of N,4-diphenylpyrimidin-2-amine derivatives with low CDOCKER-INTERACTION-ENERGY and then evaluated their PI3Kγ in vitro inhibitory activities and in vitro antiproliferation assays against four human cancer cells. Among the compounds we synthesized, compound C8 (IC50 = 65 nM) demonstrated the most potent inhibitory activity against PI3Kγ kinase as well as at the cellular level, compared to the control drug TG100713 (IC50 = 127 nM). Moreover, molecular docking analysis was also performed to determine possible binding modes between PI3Kγ and the target compounds.

Identification of pyrimidine derivatives as hSMG-1 inhibitors

hSMG-1 kinase plays a dual role in a highly conserved RNA surveillance pathway termed nonsense-mediated RNA decay (NMD) and in cellular genotoxic stress response. Since deregulation of cellular responses to stress contributes to tumor growth and resistance to chemotherapy, hSMG-1 is a potential target for cancer treatment. From our screening efforts, we have identified pyrimidine derivatives as hSMG-1 kinase inhibitors. We report structure-based optimization of this pan-kinase scaffold to improve its biochemical profile and overall kinome selectivity, including mTOR and CDK, to generate the first reported selective hSMG-1 tool compound.

Novel heterocycle-substituted pyrimidines as inhibitors of NF-κB transcription regulation related to TNF-α cytokine release

Novel heterocyclic ring-substituted pyrimidines have been designed as inhibitors of glycogen synthase kinase-3β (GSK-3β) from the modification of known inhibitors. Several potent inhibitors exhibiting nanomolar activities were discovered against GSK-3β kinase as well as in an NF-κB reporter gene assay. Based on the results from in vitro TNF-α release inhibition and in vivo endotoxima, these inhibitors are expected to be useful candidates for treatment of inflammation-related diseases.

Solid-phase synthesis of N-aryl-N′-carboalkoxy guanidines by the mitsunobu reaction of Fmoc-guanidines

A new method for the solid-phase synthesis of N-aryl-N′-carboalkoxy guanidines is described. Aromatic amines were reacted with Fmoc-isothiocyanate to provide Fmoc-thioureas, which were coupled with Rink amide resin to provide the corresponding resin-bound Fmoc-guanidines. Subsequent Mitsunobu alkylation with a variety of alcohols delivered N-aryl-N′ carboalkoxy guanidines in good to high purity after resin cleavage.

Cardiovascular activity of aromatic guanidine compounds.

A series of aromatic guanidines and several 1-phenylbiguanides was prepared and tested for cardiovascular (CV) effects in anesthetized dogs measuring heart rate, blood pressure, carotid artery blood flow, and myocardial force changes. The predominant CV effect at minimally effective dose was vasoconstriction unassociated with cardiac stimulation. The structure-activity relationships of the compounds were discussed comparing their structural similarities to the beta-phenylethylamines. The most potent members of the series were phenylguanidines substituted in the 3 and 4 positions on the aromatic nucleus with hydroxy or chloro groups. Preliminary mechanism studies indicated that the 3,4-dihydroxyphenylguanidines act at least partially by a direct alpha-adrenergic mechanism