433226-06-3

Usage

Uses

Used in Pharmaceutical Industry:
ETHYL 2-AMINO-5-BROMONICOTINATE is used as a pharmaceutical intermediate for the development of new drugs and pharmaceutical products. Its unique chemical structure and potential biological activities contribute to its role in enhancing the therapeutic efficacy of various medications.
Used in Medicinal Chemistry Research:
ETHYL 2-AMINO-5-BROMONICOTINATE serves as a valuable compound in the field of organic chemistry and pharmaceutical sciences. Its properties and potential applications make it a subject of interest for further research, enabling the discovery of novel therapeutic agents and advancing our understanding of chemical-bioactivity relationships.

Upstream product

• 13362-26-0 2-aminopyridine-3-carboxylic acid ethyl ester 
• 14667-47-1 methyl 2-aminonicotinate 
• 114078-88-5 5-bromo-1,2,3-triazine 
• 105-56-6 ethyl 2-cyanoacetate 
• 5345-47-1 2-aminopyridin-3-carboxylic acid 

Downstream Products

• 1801262-20-3 6-bromo-[1,2,4]triazolo[1,5-a]pyridine-8-carboxylic acid methyl ester 
• 1215787-31-7 6-bromo-4-chloropyrido[2,3-d]pyrimidine 
• 155690-79-2 6-bromo-3H,4H-pyrido[2,3-d]pyrimidin-4-one 

Relevant academic research and scientific papers

Synthesis of 5H-pyrido[3,2-b]pyrrolizin-5-one tripentone analogs with antitumor activity

Pyrrolizinones represent an interesting class of compounds with varied degrees of structural complexity and pharmacological activity. Among these, 9H-pyrido[2,3-b]pyrrolizin-9-one, tripentone analogs, recently reported by us, showed significant antiproliferative activity against human tumor cell lines, inducing apoptosis and not affecting viability of Caco-2 differentiated in normal intestinal-like cells. Considering their interesting biological activity, their 5H-pyrido[3,2-b]pyrrolizin-5-one analogs were efficiently synthesized in good to excellent yields (61–91%). All tripentone derivatives were tested to assess their cytotoxicity against two human tumor cell lines, HCT-116 (human colorectal carcinoma) and MCF-7 (human breast cancer). The most active derivatives, with IC50 ranging from 0.11 to 16.11 μM, did not affect viability of Caco-2 differentiated in normal intestinal-like cells, suggesting tumor cells as the main target of their cytotoxic action. The same compounds, further investigated, showed that they did not exert necrotic effects, while induced a clear shift of viable cells towards early apoptosis confining the cells in the mitotic phases.

SYNTHESIS, X-RAY STRUCTURE ANALYSIS, AND VIBRATIONAL SPECTRAL STUDIES OF 1-(3-((6-BROMOPYRIDO[2,3-d]PYRIMIDIN-4-YL) OXY)PHENYL)-3-CYCLOPENTYLUREA

Abstract: A new pyrido[2,3-d]pyrimidine derivative 1-(3-((6-bromopyrido[2,3-d]pyrimidin-4-yl)oxy)phenyl)-3-cyclopentylurea is designed and synthesized. The final structure is characterized by 1H, 13C, and 2D NMR, MS, FTIR. In addition, the crystal structure of the title compound is determined by X-ray diffraction. With the 6-311G(2d,p) basis set, the molecule is further explored using density functional theory (DFT) by the B3LYP method. The final results show that the DFT optimized structure of the title molecule is consistent with the crystal structure determined by X-ray diffraction. The Hirshfeld surface analysis and the 2D fingerprint plot are given to support the quantitative analysis of intermolecular interactions and contacts generated by supramolecular accumulation in crystals. The interactions of the title molecule are analyzed by the natural bond orbital analysis. Finally, the molecular electrostatic potential and frontier molecular orbitals are further investigated using DFT. [Figure not available: see fulltext.]

Synthesis, crystal structure, and DFT study of a new pyrido[2,3-d]pyrimidine compound 1-(4-((6-bromopyrido[2,3-d]pyrimidin-4-yl)oxy) phenyl)-3-(2,4-difluorophenyl)urea

In this study, 1-(4-((6-bromopyrido[2,3-d]pyrimidin-4-yl)oxy)phenyl)-3- (2,4-difluorophenyl) urea was synthesized. The structure of the compound was determined by mass spectrometry and 1H NMR, 13C NMR and FT-IR spectroscopy. The solid-state structure of the title compound was determined using single-crystal X-ray diffraction and the optimized molecular structure was determined using density functional theory calculations. The conformation of the most stable isomer that was calculated at room temperature was consistent with the conformation derived from X-ray diffraction. Hirshfeld surface analysis and 2D fingerprints were used to quantitatively analyze the intermolecular interactions and contacts in the crystal structure.

Pyrido[2,3-d]pyrimidine compound as well as preparation method and application thereof

The present invention discloses a pyrido[2,3-d]pyrimidine compound represented by a general formula I or a pharmaceutically acceptable salt thereof. The general formula I is shown as the specification, wherein R1 is selected from one of an alkylamine group of C1-C6, an alicyclic amine group of C1-C6, a heterocyclic amine group of C1-C6, and an aromatic amine group of C6-C8, and X represents a hydrogen atom or a halogen atom. According to the invention, in-vitro cell activity tests prove that the compound provided by the invention has antitumor activity and can be used for preparing medicines for treating and/or preventing various cancers caused by BRaf kinase mutation, such as melanoma, thyroid cancer, breast cancer, liver cancer, kidney cancer, colorectal cancer, pancreatic cancer, ovarian cancer, etc.

Synthesis and antitumor activity of novel pyridino[2,3-d]pyrimidine urea derivatives

A series of novel N-(3-((6-bromopyrido[2,3-d]pyrimidin-4-yl)oxy)phenyl)pyrrolidine-1-carboxamide and 1-(3-((6-bromopyrido[2,3-d]pyrimidin-4-yl)oxy)phenyl)-3-propylurea derivatives were synthesized. Their antitumor activities against human breast carcinoma cells (MCF-7) and human colon cancer cells (HCT-116) in vitro were evaluated, using sorafenib as a positive control drug. Anticancer bioassays indicated that several compounds exhibited appreciable anticancer activity against MCF-7 and HCT-116 cells. Particularly, compounds 9g and 8b demonstrated the most significant inhibitory effect against HCT-116 and MCF-7 cells, with inhibition ratios of 25.56% and 26.46%, respectively. Additionally, the synthesized pyridine[2,3-d]pyrimidine derivatives containing a urea group moieties exhibited antitumor activities against MCF-7 and HCT-116 cells in vitro.

Synthesis, Crystal Structure, and DFT Study of a New Derivative of Pyrido[2,3-d]pyrimidine

Abstract: N-{4-[(6-bromopyrido[2,3-d]pyrimidin-4-yl)oxy]phenyl}morpholine-4-carboxamide has been synthesized as a derivative of pyrido[2,3-d]pyrimidine that demonstrates antitumor, antibacterial, anti-inflammatory, and antimicrobial activities. Synthesis of the target compound based on 2-aminonicotinic acid as the starting material has included its esterification, bromination, cyclization, and substitution reactions. Structure of the product is confirmed by 1H and 13C NMR, FT-IR, and single-crystal X-ray diffraction (XRD). The optimized structure, electrostatic potential and frontier molecular orbitals (FMO) of the compound have been approached by DFT calculations. The compound demonstrates antiproliferative activity on A375 cells.

Access to pyridines via cascade nucleophilic addition reaction of 1,2,3-triazines with activated ketones or acetonitriles

We studied the cascade nucleophilic addition reactions of 1,2,3-triazines with activated acetonitriles or ketones, which were used to construct highly substituted pyridines that are not easily accessed by conventional methods. The strategy addressed some structural diversity issues currently facing medicinal chemistry, and the resulting pyridines could be used as convenient precursors for the synthesis of related pharmaceuticals. In particular, our method was applied to the syntheses of the marketed drug etoricoxib and several biologically important molecules in a few steps.

Synthesis method and applications of polysubstituted 2-aminopyridine derivative

The invention belongs to the field of organic synthetic chemistry, and relates to a synthetic method and applications of a polysubstituted 2-aminopyridine derivative. According to the method, a 1,2,3-triazine compound and a cyanomethyl compound are used as substrates and are subjected to a one-step cycloaddition reaction under an alkaline condition to obtain a polysubstituted 2-aminopyridine derivative, wherein the reaction does not involve in danger and control reagents and medicines, and a simple, safe, efficient and environment-friendly strategy is provided for synthesizing the polysubstituted 2-aminopyridine derivative. According to the present invention, the obtained product is subjected to further derivatization, such that the active molecule or the drug molecule containing the 2-aminopyridine structure can be synthesized, such as active molecule SC-53606, drug molecule apatinib and nevirapine.

INHIBITORS OF PLASMA KALLIKREIN AND USES THEREOF

The present invention provides compounds and compositions thereof which are useful as inhibitors of plasma kallikrein and which exhibit desirable characteristics for the same.

A 3-aldehyde-6-polybromide imidazo [1,2-a] pyridine-8-carboxylic acid ethyl ester synthetic method (by machine translation)

The invention relates to a synthetic method of ethyl 3-aldehyde-6-bromoimidazo[1,2-a]pyridine-8-formate. The method comprises the following steps: carrying out a substitution reaction on ethyl 2-aminonicotinate and N-bromosuccinimide in a certain solvent at normal temperature to prepare ethyl 2-amino-5-bromonicotinate; and reacting2-amino-5-bromonicotinate with N,N-dimethylformamide dimethyl acetal at 30-150DEG C to prepare an intermediate, reacting the intermediate with chloroacetaldehyde in a certain solvent at 60-160DEG C without purifying the intermediate, cooling, and drying to obtain ethyl 3-aldehyde-6-bromoimidazo[1,2-a]pyridine-8-formate. The method has the advantages of easily available reaction raw materials, reasonable price, mild reaction conditions, easy operation, easy control and simple post-treatment, and the above obtained product has the advantages of stable quality and high purity.