35691-20-4

Usage

Uses

Used in Pharmaceutical Industry:
4-azetidin-1-yl-2-chloropyrimidine is used as a reagent for the preparation of pyrimidinyl biphenylureas, which are allosteric modulators of the cannabinoid receptor 1 (CB1). These modulators have potential applications in the treatment of various conditions, such as obesity, metabolic disorders, and neurological diseases, by selectively modulating the CB1 receptor's activity without directly activating it.

InChI:InChI=1/C8H10ClN3/c9-8-10-4-3-7(11-8)12-5-1-2-6-12/h3-4H,1-2,5-6H2

Upstream product

• 123-75-1 pyrrolidine 
• 3934-20-1 2,6-Dichloropyrimidine 

Relevant academic research and scientific papers

Synthesis and in vitro study of platelet antiaggregant activity of 2(4)-imidazol-1-yl-4(2)-cycloalkylamino pyrimidines

The synthesis of some 2(4)-imidazol-1-yl-4(2)-cycloalkylaminopyrimidines are reported. The compounds demonstrated a marked antiaggregating activity superior to dipyridamole, ASA, ticlopidine and similar to that of indobufen.

Design, synthesis, docking, molecular dynamics and bioevaluation studies on novel N-methylpicolinamide and thienopyrimidine derivatives with inhibiting NF-κB and TAK1 activities: Cheminformatics tools RDKit applied in drug design

Using cheminformatics tools RDKit and literature investigation, four series of 24 thienopyrimidine/N-methylpicolinamide derivatives substituted with pyrimidine were designed, synthesized and evaluated for activities against three cancer cell lines (MDA-MB-231, HCT116 and A549), TAK1 kinase and NF-κB signaling pathway. Almost all compounds showed selectivity toward the A549 cell lines and the most promising compound 38 could inhibit TAK1 kinase and NF-κB signaling pathway with the IC50 values of 0.58 and 0.84 μM. Moreover, 38 can induce cell cycle arrest of A549 cells at the G2/M checkpoint with 30.57% and induce apoptosis (34.94%) in a concentration-dependent manner. And western blot showed that compound 38 could inhibit TNF-α-induced IκBα phosphorylation, IκBα degradation, p65 phosphorylation and TAK1 phosphorylation, and reduce the expression of p65. What's more, the studies of docking, molecular dynamics, MM/PBSA and frequency analysis theoretically supported the conclusions of the bioevaluation.

Pyrimidyl piperazine urea TRPV1 antagonistic/MOR agonistic double-target compound as well as preparation method and application thereof

The invention discloses a pyrimidinyl piperazine urea TRPV1 antagonistic/MOR agonistic double-target compound or a pharmaceutically acceptable salt thereof, the compound has a structural general formula I, and a drug taking the compound as an active component not only shows obvious inhibitory activity on TRPV1, but also can show obvious agonistic activity on MOR. The invention also discloses a preparation method of the compound or the pharmaceutically acceptable salt thereof. The preparation method has the characteristic of mild reaction conditions. The invention also discloses application of the compound or the pharmaceutically acceptable salt thereof in preparation of a medicine for treating and/or preventing TRPV1 and/or MOR mediated diseases, the medicine not only can block pain transmission of peripheral and central nervous systems, but also can reduce side effects related to single targeting, such as nausea, sleepiness and respiratory depression caused by an MOR agonist and nociceptive thermal inductance weakening and obvious body temperature rise caused by a TRPV1 antagonist, and has a good application prospect.

Discovery and SAR studies of novel 2-anilinopyrimidine-based selective inhibitors against triple-negative breast cancer cell line MDA-MB-468

Triple-negative breast cancers (TNBCs) are characterized as an invasive and intractable subtype of breast cancers. Overexpression of epidermal growth factor receptor (EGFR) has been considered to be an important target for TNBC therapy, but efficacies of

SAR optimization studies on a novel series of 2-anilinopyrimidines as selective inhibitors against triple-negative breast cancer cell line MDA-MB-468

Triple-negative breast cancers (TNBCs) account for approximately 15% of breast cancer cases and exhibit an aggressive clinical behavior. In this study, we designed and synthesized two series of 2-anilinopyrimidines based on the structure of our previously

Pd/PTABS: Catalyst for Room Temperature Amination of Heteroarenes

A mild and highly efficient catalytic amination procedure for chloroheteroarenes at ambient temperature using the Pd/PTABS catalytic system is reported. The protocol is selective for the amination of chloroheteroarenes using secondary amines such as piperidine, pyrrolidine, and several others. The exceptional mildness of the developed protocol is beneficial for the synthesis of a crucial Buparlisib intermediate as well as the formal synthesis of Alogliptin in competitive yields.

Novel Derivatives of 2-Anilinopyrimidine and Composition Comprising the Same

The present invention relates to a 2-anilinopyrimidine derivative represented by chemical formula 1 and a composition containing the 2-anilinopyrimidine derivative as an active ingredient for preventing or treating cancer. According to the present inventi

Pyrimidinyl Biphenylureas: Identification of New Lead Compounds as Allosteric Modulators of the Cannabinoid Receptor CB1

The allosteric modulator 1-(4-chlorophenyl)-3-(3-(6-(pyrrolidin-1-yl)pyridin-2-yl)phenyl)urea (PSNCBAM-1, 2) bound the cannabinoid receptor 1 (CB1) and antagonized G protein coupling. This compound demonstrated potent anorectic effects similar to the CB1 antagonist rimonabant that once was marketed for the treatment of obesity, suggesting a new chemical entity for the discovery of antiobesity drugs. To increase structural diversity of this class of CB1 ligands, we designed and synthesized two classes of novel analogues, in which the pyridine ring of 2 was replaced by a pyrimidine ring. These positively modulate the binding of the CB1 orthosteric agonist CP55,940 while exhibiting an antagonism of G-protein coupling activity. Interestingly, compounds 7d and 8d demonstrated ERK1/2 phosphorylation mediated via β-arrestin unlike the orthosteric CP55,940 that does so in a G protein-dependent manner. These can serve as new lead compounds for the future development of CB1 allosteric modulators that show biased agonism and potentially antiobesity behavior via a new mechanism.

Selective mono-amination of dichlorodiazines

A mild, easy-to-perform, and versatile method for the formation of aminochlorodiazines from reaction of several types of dichlorodiazines (i.e., pyridazines, pyrimidines, and pyrazines) with primary or secondary amines in ethanol in the presence of trieth

DIARYLAMINE-SUBSTITUTED QUINOLONES USEFUL AS INDUCIBLE NITRIC OXIDE SYNTHASE INHIBITORS

Novel diarylamine-substituted quinolone compounds and pharmaceutical compositions, certain of which have been found to inhibit inducible NOS synthase have been discovered, together with methods of synthesizing and using the compounds including methods for the treatment of iNOS-mediated diseases in a patient by administering the compounds.