104615-18-1

Basic information

• Product Name: CGS 15943
• Synonyms: CGS 15943;9-CHLORO-2-(2-FURYL)(1,2,4)TRIAZOLO(1,5-C)QUINAZOLIN-5-AMINE;9-CHLORO-2-(2-FURANYL)-[1,2,4]TRIAZOLO[1,5-C]QUINAZOLIN-5-AMINE;CGS-15943 ADENOSINE A1 RECEPTOR;9-chloro-2-(2-furyl)-(1,2,4)triazolo(1,5-c)quinazolin-5-imine;9-Chloro-2-(furan-2-yl)[1,2,4]triazolo[1,5-c]quinazolin-5-amine;9-Chloro-5,6-dihydro-2-(furan-2-yl)[1,2,4]triazolo[1,5-c]quinazolin-5-imine;CGS-15943A
• CAS NO: 104615-18-1
• Molecular Formula: C₁₃H₈ClN₅O
• Molecular Weight: 285.69
• Product Categories: Adenosine receptor
• Mol File: 104615-18-1.mol

Chemical Properties

• Melting Point: 278-279 °C
• Boiling Point: 566.6 °C at 760 mmHg
• Flash Point: 296.5 °C
• Appearance: white/solid
• Density: 1.728 g/cm³
• Vapor Pressure: 7.4E-13mmHg at 25°C
• Refractive Index: 1.84
• Storage Temp.: Store at RT
• Solubility: DMSO: >16 mg/mL
• PKA: 1.23±0.30(Predicted)
• CAS DataBase Reference: CGS 15943(CAS DataBase Reference)
• NIST Chemistry Reference: CGS 15943(104615-18-1)
• EPA Substance Registry System: CGS 15943(104615-18-1)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 104615-18-1(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
CGS 15943 is used as a potent adenosine receptor antagonist for its ability to block adenosine A1 and adenosine A2A receptors. This property makes it a valuable compound in the development of drugs targeting various conditions related to adenosine receptor activity.

Synthesis Reference(s)

Journal of Heterocyclic Chemistry, 27, p. 1549, 1990 DOI: 10.1002/jhet.5570270605

Biological Activity

Potent adenosine receptor antagonist (K i values are 3.5, 4.2, 16 and 51 nM for human A 1 , A 2A , A 2B and A 3 receptors respectively). Orally active in vivo .

Biochem/physiol Actions

CGS-15943 is a potent and non-selective adenosine receptor antagonist. It exhibits anti-carcinogenic and anti-apoptotic activity.

InChI:InChI=1/C13H8ClN5O/c14-7-3-4-9-8(6-7)12-17-11(10-2-1-5-20-10)18-19(12)13(15)16-9/h1-6H,(H2,15,16)

Upstream product

• 104615-77-2 9-chloro-2-(2-furyl)-5-(methylthio)<1,2,4>triazolo<1,5-c>quinazoline 
• 420-04-2 CYANAMID 
• 113686-04-7 4-Chloro-2-<3-(2-furanyl)-1H-1,2,4-triazol-5-yl>benzeneamine 
• 54610-73-0 furan-5-carboxamidine 
• 1885-29-6 anthranilic acid nitrile 
• 104615-49-8 (2-cyano-4-chloro-phenyl)-carbamic acid ethyl ester 
• 41534-70-7 (2-cyanophenyl)carbamic acid ethyl ester 
• 153488-30-3 6-chloro-3-(2-furoylamino)-4-imino-3,4-dihydroquinazoline 
• 153488-26-7 N-(4-Chloro-2-cyano-phenyl)-formimidic acid ethyl ester 
• 104615-78-3 4-chloro-2-cyanophenyl isothiocyanate 
• 113686-21-8 9-chloro-2-(3-furyl)-5-(methylthio)<1,2,4>triazolo<1,5-c>quinazoline 
• 104615-79-4 9-chloro-2-(2-furyl)<1,2,4>triazolo<1,5-c>quinazoline-5(6H)-thione 
• 104615-72-7 2-(2-furyl)-5-(methylthio)<1,2,4>triazolo<1,5-c>quinazoline 
• 104615-73-8 2-(2-furyl)<1,2,4>triazolo<1,5-c>quinazoline-5(6H)-thione 

Downstream Products

• 104615-00-1 9-chloro-2-(2-furyl)-[1,2,4]triazolo[1,5-c]quinazolin-5(6H)one 
• 210991-27-8 2-(4-Amino-phenyl)-N-(9-chloro-2-furan-2-yl-[1,2,4]triazolo[1,5-c]quinazolin-5-yl)-acetamide 

Relevant articles and documents

ARYL HYDROCARBON RECEPTOR (AHR) ACTIVATOR COMPOUNDS AS CANCER THERAPEUTICS

The present disclosure relates to compositions and methods for the diagnosis and treatment or prevention of cancers, particularly cancers that exhibit elevated expression of FOXA1 and/or FOXA1 gene targets, such as certain breast, liver and/or prostate cancers, including luminal and/or ER-positive forms of breast cancer. Three previously identified adenosine receptor antagonists, CGS-15943, MRS-1220 and SCH-58261, as well as furan ring moiety-possessing derivatives of CGS-15943 are specifically provided for killing cancer cells in a manner that appears to involve activation of the aryl hydrocarbon receptor (AHR) by such compounds. The instant disclosure therefore provides for selecting and/or administering CGS-15943, MRS-1220, SCH-58261 and/or a furan-possessing derivative of CGS-15943, MRS-1220 and/or SCH-58261 as a therapeutic agent to target a cancer cell and/or subject having or at risk of developing a cancer. Methods and compositions for therapies that include such compounds are also provided

Synthesis and evaluation of adenosine antagonist activity of a series of [1,2,4]triazolo[1,5-c]quinazolines

A series of [1,2,4]triazolo[1,5-c]quinazolines were prepared in satisfactory yields by reaction of some derivatives of 2-aminobenzohydrazide with several hydrochlorides of aromatic amidines, and their binding affinities for the recombinant human adenosine A2A and A2B receptors were determined. None of the new compounds showed noteworthy affinity for these receptors, though a very high affinity for the A2A receptor and, consequently, a high level of A2A/A2B selectivity was revealed for one of the synthesized compounds.

Synthesis of Triazoloquinazoline and Triazolo-1,4-benzodiazepine Derivatives

Some triazoloquinazolin-5(6H)-ones 7, the corresponding isomers triazoloquinazolin-5(6H)-ones and the 5-amino derivatives 8,9 and 11 have been synthesized starting from the acylamidrazones 5.The preparation of 5H-triazol

Structure-Activity Profile of a Series of Novel Triazoloquinazoline Adenosine Antagonists

During a search for benzodiazepine receptor modulators, a highly potent adenosine antagonist (CGS 15943) was discovered.The compound was defined as resonance-stabilized hybrid of the canonical structures 9-chloro-2-(2-furyl)triazoloquinazoli