63365-23-1

Usage

Synthesis Reference(s)

Journal of Medicinal Chemistry, 24, p. 742, 1981 DOI: 10.1021/jm00138a020

InChI:InChI=1/C7H5N3O2/c8-4-5-6(9)2-1-3-7(5)10(11)12/h1-3H,9H2

Upstream product

• 606-21-3 1-chloro-2,6-dinitrobenzene 
• 35213-00-4 2,6-dinitrobenzonitrile 

Downstream Products

• 63404-53-5 (3-nitro-2-cyanophenylamino) oxoacetic acid ethyl ester 
• 77326-60-4 N-(2-cyano-3-nitrophenyl)acetamide 
• 77326-44-4 N-(3-Amino-2-cyano-phenyl)-acetamide 
• 77326-35-3 N-(3-Acetylamino-2-cyano-phenyl)-oxalamic acid ethyl ester 
• 77326-62-6 2-amino-6-bromobenzonitrile 
• 123241-50-9 2-amino-6-iodobenzonitrile 
• 119584-75-7 5-bromo-2,4-diaminoquinazoline 
• 123241-51-0 2-amino-6-(phenylethynyl)benzonitrile 
• 123241-52-1 2-amino-6-(phenylethyl)benzonitrile 
• 119584-76-8 2,4-diamino-5-iodoquinazoline 
• 123242-02-4 5-Phenethyl-quinazoline-2,4-diamine 
• 79603-05-7 2-iodo-6-nitrobenzonitrile 
• 79603-02-4 2-bromo-6-nitrobenzonitrile 

Relevant academic research and scientific papers

NEW BRAF INHIBITORS AS PARADOX BREAKERS

The invention provides a novel compound having the general formula (I) (I) wherein R1-R3 and X are as defined in the description and in the claims. The compound of formula (I) can be used as a medicament.

PYRROLOPYRIMIDINE DERIVATIVES AS MODULATORS OF MULTI-DRUG RESISTANCE (MDR)

A compound which is a pyrrolopyrimidine of formula (I) wherein R1 is selected from H, Cl-C6 alkyl which is unsubstituted or substituted, (CH2)nAr1, (CH2)pNR4R5, halogen and (CH2)pX; R2 is CH2)pArl; R3 is selected from H, Cl -C6 alkyl which is unsubstituted or substituted, (CH2)pZ and (CH2)pArl; P is an unsaturated 5, 6, or 7 membered carbocyclic or heterocyclic ring which is unsubstituted or substituted; R4 and R5 which are the same or different are selected from H, Cl -C6 alkyl which is unsubstituted or substituted, (CH2)nC3-C10 cycloalkyl, (CH2)nAr1 , and (CH2)nOR6, or R4 and R5 together with the nitrogen atom to which they are attached, form a saturated five or six membered nitrogen containing heterocyclic ring which may contain one extra heteroatom selected from 0, N and S and which is unsubstituted or substituted; R6 is selected from H, Cl -C6 alkyl which is unsubstituted or substituted, C3-C10 cycloalkyl, (CH2)nOC1-C6alkyl which is unsubstituted or substituted, (CH2)nO(CH2)nAr1 , (CH2)nCO2C1-C6,alkyl which is unsubstituted or substituted and (CH2)nAr1; X is selected from CN, azide, (CH2)nNHSO2R6 and (CH2)nNHCOR6; Z is selected from CN, CO2R6 and CONR4R5; Ar1 is the same or different when more than one is present within a given substituent group and is an unsaturated C6-C10 membered carbocylic group or an unsaturated 5-11 membered heterocycle, either of which is unsubstituted or substituted; p is an integer of 1 to 6; n is the same or different when more than one is present within a given substituent group and is 0 or an integer of 1 to 6; with the proviso that the pyrrolepyrimidine compound of formula (I) is other than 1-(4-benzyl-piperazin-1-yl)-9H-2,4,9-triaza-fluorene; and the pharmaceutically acceptable salts thereof, have activity as inhibitors of MRP (multidrug resistant protein) and may thus be used to modulate multidrug resistance, for instance in potentiating the cytotoxicity of a chemotherapeutic agent.

Antifolate and Antibacterial Activities of 5-Substituted 2,4-Diaminoquinazolines

A series of 5-substituted 2,4-diaminoquinazolines (3) has been synthesized and evaluated as inhibitors of the enzyme dihydrofolate reductase (DHFR) from both bacterial and mammalian sources.The best compounds (e.g. 53) show good activity against Escherichia coli DHFR, but there is no significant selectivity for the bacterial over the mammalian enzyme.The structure-activity relationships for enzyme inhibition appear to be complex and not amenable to simple analysis; a hypotesis to explain the observed qualitative structure-activity relationships is proposed.The inhibitory activities of the compounds against the growth of intact bacterial cells in vitro closely parallel those for the inhibition of the isolated bacterial enzymes, suggesting that their antifolate action is responsible for their antibacterial effects.Five of the compounds were tested for their ability to cure a systemic E. coli infection in the mouse, but they showed no therapeutic effects at their maximum tolerated doses.

N-(Aminophenyl)oxamic Acids and Esters as Potent, Orally Active Antiallergy Agents

A series of N-(2-cyano-substituted-phenyl)oxamates was prepared by acylation of the appropriate anthranilonitrile with ethyloxalyl chloride.Hydrolysis with sodium hydroxide gave the corresponding oxamic acid sodium salts.These compounds were extremely potent when tested in the rat passive cutaneous anaphylaxis (PCA assay either by the ip or the po route of administration).One of the sodium salts, oxoacetic acid sodium salt (11a, Wy-41 195), has ED50 value of 0.07 mg/kg po and has been selected for further evaluation.

Antisecretory oxamic acid esters

Variously substituted oxanilic acid esters possessing anti-secretory activity are useful anti-ulcer agents.

Antisecretory oxamic acid esters

Variously substituted oxanilic acid esters possessing anti-secretary activity are useful anti-ulcer agents.