99844-02-7

Usage

Uses

Used in Pharmaceutical Industry:
4-(4-Methoxyphenyl)pyrimidin-2-amine is used as a key building block for the synthesis of various biologically active molecules, primarily for the development of kinase inhibitors. Its unique structure and properties make it instrumental in creating compounds that can modulate cellular processes and target specific pathways implicated in disease mechanisms.
Used in Cancer Treatment Research:
In the field of oncology, 4-(4-Methoxyphenyl)pyrimidin-2-amine is studied for its potential therapeutic effects in the treatment of cancer. Its ability to inhibit kinases, which are often dysregulated in cancer cells, positions it as a candidate for developing targeted cancer therapies that can selectively affect tumor growth and progression while minimizing damage to healthy cells.
Used in Inflammation Treatment Research:
Beyond cancer, 4-(4-Methoxyphenyl)pyrimidin-2-amine is also being investigated for its potential in treating inflammatory conditions. Kinase inhibitors, which 4-(4-METHOXYPHENYL)PYRIMIDIN-2-AMINE can help synthesize, are known to play a role in regulating inflammatory responses, offering a promising avenue for developing anti-inflammatory drugs.
Used in Medicinal Chemistry Research:
4-(4-Methoxyphenyl)pyrimidin-2-amine serves as a valuable tool in medicinal chemistry research, where it aids in the exploration of new chemical entities and the optimization of drug candidates. Its structural attributes and reactivity make it a versatile component in the design and synthesis of novel therapeutic agents.
Overall, 4-(4-Methoxyphenyl)pyrimidin-2-amine's multifaceted applications across different areas of pharmaceutical and medical research highlight its significance in advancing our understanding of disease mechanisms and in the development of more effective treatments.

InChI:InChI=1/C11H11N3O/c1-15-9-4-2-8(3-5-9)10-6-7-13-11(12)14-10/h2-7H,1H3,(H2,12,13,14)

Upstream product

• 50-01-1 guanidine hydrochloride 
• 100-07-2 4-methoxy-benzoyl chloride 
• 1066-54-2 trimethylsilylacetylene 
• 100-06-1 1-(4-methoxyphenyl)ethanone 
• 3993-78-0 2-amino-4-chloropyrimidine 
• 5720-07-0 4-methoxyphenylboronic acid 
• 14063-79-7 (Z)-3-chloro-3-(4-methoxyphenyl)acrylaldehyde 
• 593-87-3 guanidine acetic acid 
• 18096-70-3 3-(dimethylamino)-1-(4-methoxyphenyl)prop-2-en-1-one 
• 506-93-4 guanidine nitrate 
• 18096-70-3 3-dimethylamino-4'-methoxyacrylophenone 
• 99048-48-3 1‐(4‐methoxyphenyl)‐3‐(trimethylsilyl)prop‐2‐yn‐1‐one 

Relevant academic research and scientific papers

Discovery of coumarin derivatives as potent and selective cyclin-dependent kinase 9 (CDK9) inhibitors with high antitumour activity

Specific inhibition of CDK9 is considered a promising strategy for developing effective anticancer therapeutics. However, most of the reported CDK9 inhibitors are still at an early stage of development and lack selectivity against other CDKs. Herein, we discovered coumarin derivative 30i as a potent CDK9 inhibitor with high selectivity (8300-fold over CDK7). Binding mode analysis illustrated that the substituent coumarin moiety is a critical group for CDK9 selectivity by occupying a flexible hinge/αD region, which is sterically hindered in other CDKs. Compound 30i showed excellent cellular antiproliferative activity, moderate pharmacokinetic property and low hERG inhibition. Moreover, 30i significantly induced tumour growth inhibition in a dose-dependent manner without causing an obvious loss of body weight in an MV4-11 xenograft mice model. Altogether, these results suggest that 30i may serve as a potential acute myeloid leukaemia (AML) therapeutics by selectively targeting CDK9.

Efficient synthesis of 4- And 5-substituted 2-aminopyrimidines by coupling of β-Chlorovinyl Aldehydes and Guanidines

A general, practical, and simple synthesis of functionalized 2-aminopyrimidines starting from β-chlorovinyl aldehydes and amidines is reported. In the presence of potassium carbonate, various ketones have been efficiently transformed into the pyrimidine derivatives by a two-step sequence involving the Vilsmeier-Haack reaction followed by a condensation reaction with guanidines. The protocol is distinguished by operational simplicity, inexpensive reagents, and functional-group tolerance. In many cases, pure solid products can be obtained in high to excellent yields without using column chromatography. The synthetic value of the method was demonstrated by the efficient synthesis of steroidal pyrimidines and a precursor of the antitumor agents Imatinib and Mocetinostat.

Synthesis of C5-tethered indolyl-3-glyoxylamide derivatives as tubulin polymerization inhibitors

A series of C5-tethered Indolyl-3-glyoxylamide derivatives were synthesized and evaluated for their in?vitro cytotoxic activity against DU145 (prostate), PC-3 (prostate), A549 (lung) and HCT-15 (colon) cancer cell lines by employing the 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) assay. Among all the synthesized compounds, compound 7f displayed cytotoxicity of IC50?=?140?nM towards DU145 cancer cell line. The treatment of DU145?cells with 7f led to inhibition of cell migration ability. Futher, the detailed studies such as acridine orange/ethidium Bromide (AO/EB), DAPI, annexin V-FITC/propidium iodide staining assay suggested that the compound 7f induced apoptosis in DU145?cells. The influence of the cytotoxic compound 7f on the cell cycle distribution was assessed on the DU145?cell line, exhibiting a cell cycle arrest at the G2/M phase (hallmark of tubulin polymerization) and next inhibited tubulin polymerization with IC500.40?μM. Furthermore, the treatment with compound 7f caused collapse of mitochondrial membrane potential and elevated intracellular superoxide ROS levels in DU145?cells. Western blotting was performed to examine the levels of apoptotic proteins (Bcl-2 and Bax); the study confirmed that compound 7f induced apoptosis through apoptosis-related protein expression. Thus, these studies provided a new molecular scaffold for the further development of anticancer agents that target tubulin.

Synthesis and biological evaluation of oxindole linked indolyl-pyrimidine derivatives as potential cytotoxic agents

In our endeavor towards the development of effective cytotoxic agents, a series of oxindole linked indolyl-pyrimidine derivatives were synthesized and characterized by IR, 1H NMR, 13C NMR and Mass spectral analysis. All the newly synthesized target compounds were assessed against PA-1 (ovarian), U-87MG (glioblastoma), LnCaP (prostate), and MCF-7 (Breast) cancer cell lines for their cytotoxic potential, with majority of them showing inhibitory activity at low micro-molar concentrations. Significantly, compound 8e was found to be most potent amongst all the tested compounds with an IC50 value of (2.43 ± 0.29 μM) on PA-1 cells. The influence of the most active cytotoxic compound 8e on the cell cycle distribution was assessed on the PA-1 cell line, exhibiting a cell cycle arrest at the G2/M phase. Moreover, acridine orange/ethidium bromide staining and annexin V binding assay confirmed that compound 8e can induce cell apoptosis in PA-1 cells. These preliminary results persuade further investigation on the synthesized compounds aiming to the development of potential cytotoxic agents.

New Entry to a Three-Component Pyrimidine Synthesis by TMS-Ynones via Sonogashira Coupling

(Equation presented) TMS-ynones are versatile synthetic equivalents of β-keto aldehydes and can be readily synthesized in an atom-economical fashion by coupling (het)aroyl chlorides and (TMS)-acetylene with only one equiv (!) of triethylamine under Sonogashira conditions. This mild ynone synthesis is also a suitable entry to 2,4-disubstituted pyrimidines in the sense of a one-pot three-component reaction, i.e., a coupling-addition- cyclocondensation sequence.

Straightforward Novel One-Pot Enaminone and Pyrimidine Syntheses by Coupling-Addition-Cyclocondensation Sequences

The coupling of acid chlorides 1 with terminal alkynes 2 using only one equivalent (!) of triethylamine under Sonogashira conditions followed by subsequent addition of primary or secondary amines 4 to the intermediate alkynones 3 represents a straight-for