108857-18-7

Basic information

• Product Name: IMidazo[2,1-b]quinazolin-2(3H)-one, 1,5-dihydro-7-iodo-
• Synonyms: IMidazo[2,1-b]quinazolin-2(3H)-one, 1,5-dihydro-7-iodo-;7-Iodo-3,5-dihydroimidazo[2,1-b]quinazolin-2(1H)-one
• CAS NO: 108857-18-7
• Molecular Formula: C₁₀H₈IN₃O
• Molecular Weight: 313.09449
• Mol File: 108857-18-7.mol
• Article Data: 2

Chemical Properties

• Melting Point: >300 °C
• Appearance: /
• Density: 2.18±0.1 g/cm3(Predicted)
• Storage Temp.: 2-8°C
• PKA: 12.44±0.20(Predicted)
• CAS DataBase Reference: IMidazo[2,1-b]quinazolin-2(3H)-one, 1,5-dihydro-7-iodo-(CAS DataBase Reference)
• NIST Chemistry Reference: IMidazo[2,1-b]quinazolin-2(3H)-one, 1,5-dihydro-7-iodo-(108857-18-7)
• EPA Substance Registry System: IMidazo[2,1-b]quinazolin-2(3H)-one, 1,5-dihydro-7-iodo-(108857-18-7)

Safety Data

• Hazardous Substances Data: 108857-18-7(Hazardous Substances Data)

Upstream product

• 16353-27-8 6-Iodo-1H-quinazoline-2,4-dione 
• 116027-11-3 N-<4-iodo-2-(methoxycarbonyl)phenyl>urea 
• 74173-76-5 2,4-dichloro-6-iodoquinazoline 
• 5326-47-6 2-amino-5-iodobenzoic acid 
• 116027-12-4 2-chloro-6-iodo-3,4-dihydroquinazoline 
• 77317-55-6 methyl 2-amino-5-iodobenzoate 
• 116027-10-2 5-iodoisatoic anhydride 
• 50794-16-6 (2-amino-benzylamino)-acetic acid ethyl ester 
• 116027-13-5 ethyl (2-chloro-6-iodo-3,4-dihydroquinazolin-3-yl)acetate 
• 506-68-3 bromocyane 
• 108857-21-2 ethyl N-<(2-amino-5-iodophenyl)methyl>glycinate 

Downstream Products

• 108857-06-3 7-(2,6-dimethylpyridin-3-yl)-1,2,3,5-tetrahydroimidazo<2,1-b>quinazoline-2(1H)-one 

Relevant articles and documents

7-Heteroaryl-1,2,3,5-tetrahydroimidazoquinazolin-2(1H)-one Derivatives with Cardiac Stimulant Activity

A series of 7-heteroaryl-1,2,3,5-tetrahydroimidazoquinazolin-2(1H)-ones was synthesized and evaluated in dogs for cardiac stimulant activity.Compounds were obtained by a palladium-catalyzed cross-coupling reaction between a heteroarylzinc chloride and a 7-iodo-1,2,3,5-tetrahydroimidazoquinazolin-2(1H)-one or by cyclization of an N-glycinate with cyanogen bromide.Compared to the parent ring system (3), introduction of a 2,6-dimethylpyridin-3-yl (6), 2,4-dimethylimidazol-1-yl (7), or 1,2,4-triazol-1-yl (8) moiety at the 7-position led to a 13-17-fold increase in positive inotropic activity (percentage increase in dP(dtmax) in anesthetized dogs.Potency could be further enhanced with a 9-methyl substituent (10-12).The most potent member of the series, 7-(2,4-dimethylimidazol-1-yl)-9-methyl-1,2,3,5-tetrahydroimidazoquinazolin-2(1H)-one (11) (23percent increase in dP/dtmax, 2 μg/kg), was 80 times more active than 3 and displayed a 5-fold advantage over milrinone.In conscious dogs, 6 elicited marked and sustained positive inotropic activity (decrease in QA interval) after oral administration (1 mg/kg), whereas 10-12 were 10 times more potent. 11 produced an obvious increase in cardiac contractility (20percent increase in dP/dtmax) at low dose levels (25 μg/kg) while, after 100 μ/kg, the marked response (50percent increase in dP/dtmax) was maintained for the whole 7-h test period.In these experiments, 11 had no effect on heart rate, and the compound also displayed exceptional selectivity for increasing the force rather than the rate of cardiac contraction (> 150percent increase in dP/dtmax) in the Starling heart-lung preparation.These studies demonstrate that the tetrahydroimidazoquinazolinone nucleus is an effective bioisostere for the 2(1H)-quinolinone system and that 11 displays improved cardiac stimulant activity and duration of action when compared to milrinone.