52687-97-5

Usage

Uses

Used in Pharmaceutical Research:
2-chloro-N-pyrimidin-2-yl-acetamide is used as a research compound for the development of new drugs and medications. Its role in targeting specific receptors and pathways in the human body makes it a valuable asset in the creation of targeted therapies for various diseases and conditions.
Used in Medicinal Applications:
2-chloro-N-pyrimidin-2-yl-acetamide is used as a potential anticonvulsant and anti-inflammatory agent. Its ability to modulate specific biological processes and pathways contributes to its potential effectiveness in treating conditions such as epilepsy and inflammation.
Used in Drug Development:
2-chloro-N-pyrimidin-2-yl-acetamide is used in the development of new drugs and medications that address unmet medical needs. Its potential use in the treatment of various diseases and conditions highlights its importance in the field of pharmaceutical research and development.

InChI:InChI=1/C6H6ClN3O/c7-4-5(11)10-6-8-2-1-3-9-6/h1-3H,4H2,(H,8,9,10,11)

Upstream product

• 109-12-6 2-aminopyrimidine 
• 79-04-9 chloroacetyl chloride 

Downstream Products

• 1316196-87-8 2-methoxy-N-(2-(2-oxo-2-(pyrimidin-2-ylamino)ethylthio)benzo[d]thiazol-6-yl)benzamide 
• 1316196-71-0 2-chloro-N-(2-(2-oxo-2-(pyrimidin-2-ylamino)ethylthio)benzo[d]thiazol-6-yl)acetamide 
• 1316196-26-5 C₁₃H₁₁N₅OS₂ 
• 17802-65-2 pyrimidin-2-ylamine; hydrochloride 
• 1196091-71-0 (R)-3-(1-Phenyl-cycloheptanecarbonyloxy)-1-(pyrimidin-2-ylcarbamoylmethyl)-1-azonia-bicyclo[2.2.2]octane chloride 

Relevant academic research and scientific papers

Synthesis and Structure–Activity Relationship of Thioacetamide-Triazoles against Escherichia coli

Infections due to Gram-negative bacteria are increasingly dangerous due to the spread of multi-drug resistant strains, emphasizing the urgent need for new antibiotics with alternative modes of action. We have previously identified a novel class of antibacterial agents, thioacetamide-triazoles, using an antifolate targeted screen and determined their mode of action which is dependent on activation by cysteine synthase A. Herein, we report a detailed examination of the anti-E. coli structure–activity relationship of the thioacetamide-triazoles. Analogs of the initial hit compounds were synthesized to study the contribution of the aryl, thioacetamide, and triazole sections. A clear structure–activity relationship was observed generating compounds with excellent inhibition values. Substitutions to the aryl ring were generally best tolerated, including the introduction of thiazole and pyridine heteroaryl systems. Substitutions to the central thioacetamide linker section were more nuanced; the introduction of a methyl branch to the thioacetamide linker substantially decreased antibacterial activity, but the isomeric propionamide and N-benzamide systems retained activity. Changes to the triazole portion of the molecule dramatically decreased the antibacterial activity, further indicating that 1,2,3-triazole is critical for potency. From these studies, we have identified new lead compounds with desirable in-vitro ADME properties and in-vivo pharmacokinetic properties.

Synthesis method for pyrimidine derivative quaternary ammonium salt cationic surfactant

The invention provides a synthesis method for a pyrimidine derivative quaternary ammonium salt cationic surfactant and relates to synthesis methods for quaternary ammonium salt cationic surfactants. The synthesis method is used for solving the technical problems of the existing quaternary ammonium salt cationic surfactants that the critical micelle concentration is high, the surface activity is low and the biodegradability is poor. The synthesis method comprises the steps of adding chloracetyl-2-amino pyrimidine and N,N-dimethylalkyl tertiary amine into a three-mouthed flask, carrying out a heated and stirred reaction, and then, carrying out recrystallization by using a solvent, thereby obtaining the pyrimidine derivative quaternary ammonium salt cationic surfactant. The critical micelle concentration of the pyrimidine derivative quaternary ammonium salt cationic surfactant is 0.3mmol/L to 5.4mmol/L, the surface activity is relatively high, the synthesis method for the product is simple, the reaction is easy to control, the product is easy to purify, and the yield is high. The pyrimidine derivative quaternary ammonium salt cationic surfactant can be applied to the fields of petroleum, chemical industry, sterilization and pharmacy.

Synthesis and trypanocidal activity of novel benzimidazole derivatives

The present work reports the synthesis and biological activity of a series of 14 benzimidazole derivatives designed to act on the enzyme triosephosphate isomerase of Trypanosoma cruzi (TcTIM). This enzyme is involved in the metabolism of glucose, the only source of energy for the parasite. In this study, we found four compounds that inhibit TcTIM moderately and lack inhibitory activity against human TIM (HsTIM). In vitro studies against T. cruzi epimastigotes showed two compounds that were more active than the reference drug nifurtimox, and these presented a low cytotoxic effect in mouse macrophages (J744 cell line).

Design and development of novel Mycobacterium tuberculosis l-alanine dehydrogenase inhibitors

In the present study, we used crystal structure of MTB L-AlaDH protein complex with N6-methyl adenosine for structure based virtual screening of in house database to identify new small molecule inhibitors for MTB-L-AlaDH. Two molecules identified as better leads and were modified synthetically to obtain thirty novel analogues belonging to 2-iminothiazolidine-4-ones and 4,5,6,7-tetrahydrothieno[2,3-c]pyridine-3-carboxamides. Among the screened compounds four (4n, 4o, 12 and 14) emerged as potent inhibitors displaying IC50 values ranging from 0.58 ± 0.02 to 1.74 ± 0.03 μM against MTB-L-AlaDH and were non-cytotoxic at 50 μM. Some of these synthesized compounds also exhibited good activity against nutrient starved dormant MTB cells. The most potent inhibitors were found to stabilize the protein which was confirmed biophysically through differential scanning fluorimetry.

A facile and efficient method for the selective deacylation of N-arylacetamides and 2-chloro-Narylacetamides catalyzed by SOCl2

Thionyl chloride efficiently and selectively promoted the deacylation of N-arylacetamides and 2-chloro-N-arylacetamides, under anhydrous conditions, without effecting the ester group, aminosulfonyl group, or benzyloxyamide group. This method, which has been successfully applied to a variety of substrates including different N-arylacetamides and 2-chloro-N-arylacetamides, has the attractive advantages of inexpensive reagents, satisfactory selectivity, excellent yields, short reaction time, and convenient workup. This new method can probably be used to selectively deacylate between aromatic amides and alkyl amides. Springer Science+Business Media B.V. 2011.

Synthesis and biological evaluation of novel benzothiazole-2-thiol derivatives as potential anticancer agents

A series of novel benzothiazole-2-thiol derivatives were synthesized and their structures determined by 1H-NMR, 13C-NMR and HRMS (ESI). The effects of all compounds on a panel of different types of human cancer cell lines were investigated. Among them, pyridinyl-2-amine linked benzothiazole-2-thiol compounds 7d, 7e, 7f and 7i exhibited potent and broad-spectrum inhibitory activities. Compound 7e displayed the most potent anticancer activity on SKRB-3 (IC50 = 1.2 nM), SW620 (IC50 = 4.3 nM), A549 (IC50 = 44 nM) and HepG2 (IC50 = 48 nM) and was found to induce apoptosis in HepG2 cancer cells.

QUINUCLIDINE DERIVATIVES AS MUSCARINIC M3 RECEPTOR ANTAGONISTS

The invention provides named compounds of formula (I), wherein R4 is a N-substituted quinuclidine (I) pharmaceutical compositions containing them and a process for preparing the pharmaceutical compositions. Their use in therapy for’ the treatment of conditions mediated by M3 muscarinic receptors, such as chronic obstructive pulmonary disease is also disclosed.

QUINUCLIDINE DERIVATIVES AS MUSCARINIC M3 RECEPTOR ANTAGONISTS

The invention provides named compounds of formula (I ), wherein R4 is a N- sustituted quinuclidine ( I ) pharmaceutical compositions containing them and a process for preparing the pharmaceutical compositions. Their use in therapy for' the treatment of conditions mediated by M3 muscarinic receptors, such as chronic obstructive pulmonary disease is also disclosed.

Evaluation of glycolamide esters of indomethacin as potential cyclooxygenase-2 (COX-2) inhibitors

A number of novel indomethacin glycolamide esters were synthesized and tested for their cyclooxygenase (COX-1 and COX-2) inhibition properties in vitro. Many of these compounds proved to be selective COX-2 inhibitors, and subtle structural changes in the substituents on the glycolamide ester moiety altered the inhibitory properties as well as potencies significantly. Their in vitro data were rationalized through molecular modeling studies. Few of them displayed anti-inflammatory activity in vivo. Compound 32, [1-(4-chlorobenzoyl)-5-methoxy-2-methyl-1H-indol-3-yl]acetic acid 2-morpholin-4-yl-2-oxo ethyl ester, was identified as a promising compound in this class and its good anti-inflammatory activity was demonstrated in the in vivo model.

Synthesis of some new pyrimidine derivatives incorporated into other heterocycles for biological evaluation

Chloroacetyl pyrimidine was synthesized and reacted with both aromatic amines and hydrazine hydrate. Hydrazide was reacted with β-dicarbonyl compounds and also with different acid anhydrides. 2-Amino-pyrimidine afforded new Schiff's bases which were cyclized with thioglycolic acid and thiolactic acid. Thiosemicarbazido derivatives were cyclized to give thiadiazole which gave Mannich bases. Some of the newly prepared compounds were biologically tested as antimicrobials.