77414-24-5

Basic information

• Product Name: sulmazole sulfone
• Synonyms: sulmazole sulfone
• CAS NO: 77414-24-5
• Molecular Formula: C₁₄H₁₃N₃O₃S
• Molecular Weight: 303.33632
• Mol File: 77414-24-5.mol

Chemical Properties

• Boiling Point: 600.8°C at 760 mmHg
• Flash Point: 317.2°C
• Appearance: /
• Density: 1.382g/cm³
• Vapor Pressure: 2.15E-14mmHg at 25°C
• Refractive Index: 1.632
• CAS DataBase Reference: sulmazole sulfone(CAS DataBase Reference)
• NIST Chemistry Reference: sulmazole sulfone(77414-24-5)
• EPA Substance Registry System: sulmazole sulfone(77414-24-5)

Safety Data

• Hazardous Substances Data: 77414-24-5(Hazardous Substances Data)

Usage

InChI:InChI=1/C14H13N3O3S/c1-20-12-8-9(21(2,18)19)5-6-10(12)13-16-11-4-3-7-15-14(11)17-13/h3-8H,1-2H3,(H,15,16,17)

Upstream product

• 73384-60-8 sulmazole 
• 77414-25-6 2-(2-Methoxy-4-methylsulfanyl-phenyl)-3H-imidazo[4,5-b]pyridine 

Relevant articles and documents

Structure-activity relationships of arylimidazopyridine cardiotonics: Discovery and inotropic activity of 2-[2-methoxy-4-(methylsulfinyl)phenyl]-1H-imidazo[4,5-c]pyridine

Recently several noncatecholamine, nonglycoside cardiotonic drugs have been discovered that possess both inotropic and vasodilator activities in experimental animals and man. Prototypical compounds include amrinone, sulmazole, and fenoximone. We investigated the structural requirements necessary for optimal inotropic activity in a series of molecules containing a heterocyclic ring fused to 2-phenylimidazole and discovered that 2-phenylimidazo[4,5-c]pyridines were generally 5-10-fold more potent than analogous 2-phenylimidazo[4,5-b]pyridines (e.g., sulmazole) or 8-phenylpurines. Furthermore, all imidazo[4,5-c]pyridine analogues we tested were orally active; in contrast, only one of the imidazo[4,5-b]pyridine derivatives, sulmazole, was significantly active. One of several highly active compounds in the [4,5-c] series was 50 (LY175326, 2-[2-methoxy-4-(methylsulfinyl)phenyl]-1H- imidazo[4,5-c]pyridine hydrochloride). The structure-activity relationship of this series is presented and compared to that of the imidazo[4,5-b]pyridine and purine series.

AR-L 115 BS, comparison of human metabolite pattern and biotransformation with those of other species

Following oral administration of 14C labelled 2-[(2-methoxy-4-methylsulfinyl)phenyl]-1H-imidazo[4,5-b]pyridine (AR-L 115 BS) to the rat, rabbit, dogs, rhesus monkey, baboon and man the metabolic pattern in plasma and urine was compared and human urinary metabolites were isolated. None of the animal species investigated shows a metabolic pattern identical to that of man. The plasma of rat, dog and rabbit shows wide variation with high amounts of two unpolar metabolites of AR-L 115 BS (sulfoxide), namely M0/1 identical with AR-L 113 BS (sulfide). In comparison to man the urines of the animals show higher amounts of the sulfone (AR-L 114 BS) and the sulfide (AR-L 113 BS). A main pathway of the metabolism of the pyrido-imidazole of the AR-L 115 BS-type is the oxidative pyridine-ring cleavage leading to N-acetylated 5-amino-imidazoles. Further metabolites are characterised by a hydroxyl group in the 6-position of the pyrido-imidazole moiety. Besides the oxidation of the sulfoxide function to the sulfone we could also observe the thioether (sulfide) not only of the parent compound itself but also of some of the metabolites in the series of the AR-L 115 BS-biotransformation. The identification of the human urinary metabolites, was carried out by means of TLC, HPLC, UV-, MS- and NMR- spectroscopy.