61310-33-6

Usage

InChI:InChI=1/C10H8ClN3/c1-7-6-9(11)14-10(13-7)8-2-4-12-5-3-8/h2-6H,1H3

Upstream product

• 824-72-6 P,P-dichlorophenylphosphine oxide 
• 59341-68-3 6-methyl-2-(pyridin-4'-yl)pyrimidin-4(3H)-one 
• 100-48-1 pyridine-4-carbonitrile 
• 1570-45-2 isonicotinic acid ethylester 
• 6345-27-3 4-amidinopyridine hydrochloride 
• 59341-68-3 6-methyl-2-(pyridin-4-yl)pyrimidin-4(3H)-one 

Downstream Products

• 61310-35-8 4-amino-6-methyl-2-(4-pyridyl)pyrimidine 

Relevant academic research and scientific papers

4-Anilino-2-pyridylquinazolines and -pyrimidines as Highly Potent and Nontoxic Inhibitors of Breast Cancer Resistance Protein (ABCG2)

Multidrug resistance (MDR) mediated by ATP-binding cassette (ABC) transport proteins remains a major problem in the chemotherapeutic treatment of cancer and might be overcome by inhibition of the transporter. Because of the lack of understanding, the complex mechanisms involved in the transport process, in particular for breast cancer resistance protein (BCRP/ABCG2), there is a persistent need for studies of inhibitors of ABCG2. In this study, we investigated a systematic series of 4-substituted-2-pyridylquinazolines in terms of their inhibitory potency as well as selectivity toward ABCG2. For comparison, the quinazoline scaffold was reduced to the significantly smaller 4-methylpyrimidine basic structure. Furthermore, the cytotoxicity and the ability to reverse MDR was tested with the chemotherapeutic agents SN-38 and mitoxantrone (MX). Interaction of the compounds with ABCG2 was investigated by a colorimetric ATPase assay. Enzyme kinetic studies were carried out with Hoechst 33342 as fluorescent dye and substrate of ABCG2 to elucidate the compounds binding modes.

Synthesis and evaluation of 2-pyridinylpyrimidines as inhibitors of HIV-1 structural protein assembly

In an effort to identify an HIV-1 capsid assembly inhibitor with improved solubility and potency, we synthesized two series of pyrimidine analogues based on our earlier lead compound N-(4-(ethoxycarbonyl)phenyl)-2-(pyridine-4-yl)quinazoline-4-amine. In vitro binding experiments showed that our series of 2-pyridine-4-ylpyrimidines had IC50values higher than 28 μM. Our series of 2-pyridine-3-ylpyrimidines exhibited IC50values ranging from 3 to 60 μM. The congeners with a fluoro substituent introduced at the 4-N-phenyl moiety, along with a methyl at C-6, represent potent HIV capsid assembly inhibitors binding to the C-terminal domain of the capsid protein.

N-[2-(pyridinyl)-4-pyrimidinyl]ureas

Compounds useful as anti-allergic agents are N-R3 -N-R4 -N'-R-N'-(2-Q-5-R1 -6-R2 -4-pyrimidinyl)ureas (I), where Q is 4- or 3- or 2-pyridinyl or 4- or 3- or 2-pyridinyl having one or two lower-alkyl substituents or N-oxide thereof, R is hydrogen or lower-alkyl, R1 is hydrogen, lower-alkyl or cyano, R2 is hydrogen or lower-alkyl, R3 is hydrogen, lower-alkyl or lower-hydroxyalkyl, R4 is hydrogen, lower-alkyl, lower-hydroxyalkyl, lower-alkenyl or lower-cycloalkyl. Said ureas are prepared by reacting 2-Q-4-RNH-5-R1 -6-R2 -pyrimidine (II) with a carbamylating agent selected from an R4 '-isocyanate of the formula R4 'N=C=O to produce N-R4 '-N'-R-N'-(2-Q-5-R1 -6-R2 -4-pyrimidinyl)urea (IA), an N-R3 '-N-R4 '-carbamyl halide of the formula R3 'R4 'NC(=O)-halide to produce N-R3 '-N-R4 'N'-R-N'-(2-Q-5-R1 -6-R2 -4-pyrimidinyl)urea (IB) or 1,1'-carbonyldiimidazole to produce N-(2-Q-5-R1 -6-R2 -4-pyrimidinyl)-N-R-imidazole-1-carboxamide and then reacting said 1-carboxamide with R3 R4 NH to produce I.

N-(2-(pyridinyl)-4-pyrimidinyl)-aminomethylenemalonates and analogs

Compounds useful as anti-allergic agents are 2-Q-4-[XZC=C(R)NH]-5-R1 -6-R2 -pyrimidines (I), where Q is 4- or 3- or 2-pyridinyl or 4- or 3- or 2-pyridinyl having one or two lower-alkyl substituents or N-oxide thereof, R is hydrogen or lower-alkyl, R1 is hydrogen, lower-alkyl or cyano, R2 is hydrogen, lower-alkyl, hydroxy or halo, X and Z are the same or different and are each selected from lower-carbalkoxy, lower-alkanoyl, carbamyl and cyano, or STR1 where R3 and R4 are each lower-alkyl, or X is hydrogen, are prepared by reacting 4-amino-2-Q-5-R1 -6-R2 -pyrimidine (II where Q' is amino) with R'O-C-(R)=CXZ (III). Preparations of II are given. Also shown as intermediates and/or anti-allergic agents are 4-(AcNH)-2-Q-5-R1 -6-R2 -pyrimidines (IV) and 4-(R5 R6 N)-2-Q-5-R1 -6-R2 -pyrimidines (V) where Ac is lower-alkanoyl or lower-carbalkoxy, R5 is hydrogen, lower-alkyl or lower-hydroxyalkyl, and R6 is lower-alkyl or lower-hydroxyalkyl.

5,8-Dihydro-5-oxo-2-(4-or 3-pyridinyl)pyrido[2,3-d]pyrimidine-6-carboxylic acids and esters

Antibacterial 5,8-dihydro-8-(lower-alkyl)-5-oxo-2-Q-4-R2 -6-Z-pyrido[2,3-d]pyrimidine (I) where Z is carboxy or lower-carbalkoxy, R2 is hydrogen or lower-alkyl and Q is 4(or 3)-pyridinyl or 4(or 3)-pyridinyl having one or two lower-alkyl substituents is prepared by heating di-(lower-alkyl) N-(2-Q-6-R2 -4-pyrimidinyl)aminomethylenemalonate (III) to produce 5,8-dihydro-5-oxo-2-Q-4-R2 -6-Z-pyrido[2,3-d]pyrimidine (II) which is tautomeric with 5-hydroxy-2-Q-4-R2 -6-Z-pyrido[2,3-d]pyrimidine (IIA) where Q and R2 are the same as in I above and Z is lower-carbalkoxy, reacting II(or IIA) with a lower-alkylating agent to produce I where Z is lower-carbalkoxy and hydrolyzing this ester (I) to produce I where Z is carboxy. Alternatively, the acid (II or IIA where Z is COOH) can be alkylated after first hydrolyzing the ester (II or IIA where Z is lower-carbalkoxy). The preparations of the intermediate III and intermediates used in its preparation are given.