27427-92-5

Usage

Uses

Used in Pharmaceutical Industry:
2-Pyrimidinecarboxaldehyde is used as a key intermediate for the synthesis of various pharmaceuticals, contributing to the development of new drugs and therapeutic agents. Its unique chemical structure allows for the creation of a wide range of medicinal compounds, enhancing the industry's ability to address diverse health concerns.
Used in Agrochemical Industry:
In the agrochemical sector, 2-Pyrimidinecarboxaldehyde serves as a crucial component in the synthesis of agrochemicals, including pesticides and herbicides. Its role in developing effective crop protection products highlights its importance in ensuring agricultural productivity and food security.
Used in Organic Synthesis:
As a building block in organic synthesis, 2-Pyrimidinecarboxaldehyde is utilized for the creation of a variety of heterocyclic compounds. Its versatility in forming different chemical structures makes it an essential component in the synthesis of complex organic molecules, contributing to advancements in material science and chemical research.
Used in Chemical Research:
2-Pyrimidinecarboxaldehyde is also employed in chemical research as a model compound for studying the properties and reactions of heterocyclic aldehydes. Its use in academic and industrial research facilitates a deeper understanding of chemical reactions and mechanisms, driving innovation in the chemical sciences.

Upstream product

• 34253-03-7 pyrimidine-2-carboxylic acid methyl ester 
• 14080-23-0 2-cyanopyrimidine 
• 31519-62-7 pyrimidine-2-carboxylic acid 
• 42839-09-8 2-pyrimidinemethanol 

Downstream Products

• 1202275-33-9 C₁₇H₁₅N₃O₂ 
• 1245750-96-2 2-(naphthalene-1-yloxy)-N-(2-(pyrimidin-2-yl)benzo[d]oxazol-5-yl)propanamide 
• 1094047-97-8 2-(1-bromopropyl)pyrimidine 
• 1352067-86-7 C₂₇H₂₇Cl₂N₃O₃ 
• 1183321-00-7 1-(pyrimidin-2-yl)propan-1-ol 
• 155191-69-8 1-phenyl-1-(2-pyrimidinyl)methanol 

Relevant academic research and scientific papers

Development of a new benzophenone-diketopiperazine-type potent antimicrotubule agent possessing a 2-pyridine structure

A new benzophenone-diketopiperazine-type potent antimicrotubule agent was developed by modifying the structure of the clinical candidate plinabulin (1). Although the right-hand imidazole ring with a branched alkyl chain at the 5-position in 1 was critical for the potency of the antimicrotubule activity, we successfully substituted this moiety with a simpler 2-pyridyl structure by converting the left-hand ring from a phenyl to a benzophenone structure without decreasing the potency. The resultant compound 6b (KPU-300) exhibited a potent cytotoxicity, with an IC50value of 7.0 nM against HT-29 cells, by strongly binding to tubulin (Kd= 1.3 μM) and inducing microtubule depolymerization.

Asymmetric zinc porphyrin derivatives bearing three pseudo-pyrimidine: Meso -position substituents and their photosensitization for H2evolution

Novel asymmetric zinc porphyrin derivatives (ZnPy-5 and ZnPy-6) with meso-positions bearing one benzoic acid and three pseudo-pyrimidines with two N atoms located at different positions were synthesized and utilized as sensitizers for Pt-loaded g-C3N4 (PCN). Compared to the analogue (ZnPy-1 bearing one benzoic acid and three phenyl meso-position substituents), ZnPy-5 and ZnPy-6 exhibit significantly enhanced photosensitization on PCN under visible light (λ ≥ 420 nm) illumination. In particular, ZnPy-5/PCN and ZnPy-6/PCN exhibit H2 evolution activities of 418 and 585 μmol h-1, corresponding to turnover numbers (TON) of 8845 and 12?381 h-1, respectively. Both of these values are much better that (316 μmol h-1) of ZnPy-1/PCN, which has a TON of 6687 h-1. In addition, ZnPy-5/PCN and ZnPy-6/PCN show apparent quantum yields of 32.6% and 33.1% at 420 nm monochromatic light, and these are much higher than that (10.6%) for ZnPy-1/PCN. Compared with ZnPy-5, the two N atoms of the pseudo-pyrimidines in ZnPy-6 are further away from the porphyrin macrocycle, which can more effectively combine with the sacrificial reagent and g-C3N4, thus promoting dye regeneration and the photoexcited charge transfer for delivering better photocatalytic performance. The present results demonstrate that the number and positions of the N atoms in the peripheral substituents of the porphyrin derivatives have a great influence on the photosensitization, and that the fine-tuning of molecular structures is crucial for improving the H2 evolution activity of the dye-sensitized semiconductors.

Screening Platform Based on Inductively Coupled Plasma Mass Spectrometry for β-Site Amyloid Protein Cleaving Enzyme 1 (BACE1) Inhibitors

β-Site amyloid protein cleaving enzyme 1 (BACE1) is a promising therapeutic target for developing inhibitors to alleviate Alzheimer's disease (AD). Herein, we established an inductively coupled plasma mass spectrometry (ICPMS)-based inhibitor screening platform. A biotin-labeled lanthanide-coded peptide probe (LCPP; biotin-PEG2-EVNLDAEC-DOTA-Ln) was designed to determine the activity of BACE1 and evaluate the degree of inhibition of inhibitors. The platform was first validated with two commercially available inhibitors (BSI I and BSI IV) in terms of IC50 values and then applied to two newly designed inhibitors (inhibitors II and III) based on the crystal structure of BACE1 interacting with inhibitor I, and each of them contained an acylguanidine core structure. We found that their inhibition effects were improved as evaluated by the sensitive and accurate LCPP-ICPMS platform, demonstrating its ability for new drug screening.

Synthesizing process of nitrogen-heterocyclic high-selectivity aldehyde

The invention relates to a synthesizing process of nitrogen-heterocyclic high-selectivity aldehyde. The synthesizing process is characterized in that when nitrogen-heterocyclic nitrogen atoms have hydrogen atoms, pyrrole, piperidine and pyrazole are used as the initial raw materials, and the pyrrole, the piperidine and the pyrazole are allowed to have reaction with piperidine-1-formaldehyde under nitrogen atom protection to obtain required nitrogen-atom ortho-position aldehyde; when nitrogen-heterocyclic nitrogen atoms have no hydrogen atoms, pyridine and pyrimidine are used to have reaction with the piperidine-1-formaldehyde to obtain the required nitrogen-atom ortho-position aldehyde. The synthesizing process is simple to operate, few in steps and high in selectivity and is a universal method using nitrogen heterocycle to synthesize the nitrogen ortho-position aldehyde.

Inhibition of the Cysteine Protease Human Cathepsin L by Triazine Nitriles: Amide???Heteroarene π-Stacking Interactions and Chalcogen Bonding in the S3 Pocket

We report an extensive “heteroarene scan” of triazine nitrile ligands of the cysteine protease human cathepsin L (hCatL) to investigate π-stacking on the peptide amide bond Gly67–Gly68 at the entrance of the S3 pocket. This heteroarene???peptide bond stacking was supported by a co-crystal structure of an imidazopyridine ligand with hCatL. Inhibitory constants (Ki) are strongly influenced by the diverse nature of the heterocycles and specific interactions with the local environment of the S3 pocket. Binding affinities vary by three orders of magnitude. All heteroaromatic ligands feature enhanced binding by comparison with hydrocarbon analogues. Predicted energetic contributions from the orientation of the local dipole moments of heteroarene and peptide bond could not be confirmed. Binding of benzothienyl (Ki=4 nm) and benzothiazolyl (Ki=17 nm) ligands was enhanced by intermolecular C?S???O=C interactions (chalcogen bonding) with the backbone C=O of Asn66 in the S3 pocket. The ligands were also tested for the related enzyme rhodesain.

Regioselectivity of Michael additions to 3-(pyridin-3-yl or pyrimidin-2-yl)-propenoates and their N-oxides - Experimental and theoretical studies

We demonstrate that nucleophilic addition to α,β-unsaturated carbonyl compounds can be redirected from the usual β-carbon (Michael) to an α-carbon regioselectivity by attaching a π-deficient aromatic substituent to the β-carbon atom. In particular, propanethiol addition to 3-(pyridin-3-yl or pyrimidin-2-yl)propenoate gives a β-carbon adduct, while addition to the corresponding more π-deficient N-oxides gives the α-adduct or a mixture of α- and β-adducts. This adds to the number of carbon-carbon bond-forming reactions at the α-position of Michael receptors documented recently. Density functional calculations reveal that the regioselectivity is due to a combination of reduction of the barrier for α-addition and increase of the barriers for β-addition and carbonyl addition as the π-deficient character of the aromatic substituent is increased. The calculations predict a significant solvent effect on the regioselectivity in some cases. The regioselectivity is also consistent with Hammett constants σ-. Wiley-VCH Verlag GmbH & Co. KGaA, 2005.

Chemokine receptor binding heterocyclic compounds with enhanced efficacy

The invention relates to heterocyclic compounds consisting of a core nitrogen atom surrounded by three pendant groups, wherein two of the three pendant groups are preferably benzimidazolyl methyl and tetrahydroquinolyl, and the third pendant group contains N and optionally contains additional rings. The compounds bind to chemokine receptors, including CXCR4 and CCR5, and demonstrate protective effects against infection of target cells by a human immunodeficiency virus (HIV).

1-cyclopropyl-4-pyridyl-quinolinones

Compounds of formula STR1 wherein R1 is hydrogen, lower-alkyl, or trifluoromethyl; R2 is lower-alkyl, trifluoromethyl or CH2 Z where Z is hydroxy, chloro, lower-alkylamino or dilower-alkylamino; R3 and R4 are each individually hydrogen or fluoro; and Ar is phenyl, an aromatic 5- or 6-membered heterocycle or any of these substituted at one or more positions with lower-alkyl, fluoro, chloro, hydroxy, amino, lower-alkylamino, dilower-alkylamino, carboxy, sulfonamido, lower alkylsulfonamido, methylenedioxy, trifluoroacetamido, lower-alkanoylamino, or carbamoyl; and their pharmaceutically acceptable acid addition salts are useful as anticancer agents.

2-Alkoxy(and 2-amino)-3-amino-2-heterocyclic-thiopropanamides

The compounds are 2-alkoxy(and 2-amino)-3-amino-2-heterocyclic-thiopropanamides, for example 2-methoxy-N-methyl-3-morpholino-2-(2-pyridyl)thiopropanamide, which are inhibitors of gastric acid secretion.