Page last updated: 2024-11-06

2-(2-methoxy-4-(methylsulfinyl)phenyl)-1h-imidazo(4,5-c)pyridine

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Description

2-(2-methoxy-4-(methylsulfinyl)phenyl)-1H-imidazo(4,5-c)pyridine: RN & structure given in first source; RN given refers to parent cpd; closely related to sulmazole [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID55690
CHEMBL ID2110680
CHEBI ID91691
SCHEMBL ID145963
MeSH IDM0132482

Synonyms (33)

Synonym
2-(4-methanesulfinyl-2-methoxy-phenyl)-3h-imidazo[4,5-c]pyridine
2-(4-methanesulfinyl-2-methoxy-phenyl)-1h-imidazo[4,5-c]pyridine(isomazole)
2-(4-methanesulfinyl-2-methoxy-phenyl)-1h-imidazo[4,5-c]pyridine
bdbm50045010
BRD-A41722204-003-01-5
isomazole
86315-52-8
2-[2-(methyloxy)-4-(methylsulfinyl)phenyl]-3h-imidazo[4,5-c]pyridine
1h-imidazo(4,5-c)pyridine, 2-(2-methoxy-4-(methylsulfinyl)phenyl)-
isomazole [inn]
isomazol [spanish]
isomazolum [latin]
2-(2-methoxy-4-(methylsulfinyl)phenyl)-1h-imidazo(4,5-c)pyridine
isosulmazole
HSCI1_000150
2-(2-methoxy-4-methylsulfinylphenyl)-3h-imidazo[4,5-c]pyridine
2-(2-methoxy-4-methylsulfinylphenyl)-3h-imidazo[5,4-c]pyridine
l8o2gv23dc ,
isomazol
isomazolum
unii-l8o2gv23dc
AKOS015906082
SCHEMBL145963
CHEMBL2110680
JQUKCPUPFALELS-UHFFFAOYSA-N
2-(2-methoxy-4-methylsulfinylphenyl)imidazo[4,5-c]pyridine
DTXSID3020754
CHEBI:91691
Q27163512
tert-butyl ((3r,4r)-1-benzyl-3-methylpiperidin-4-yl)(propyl)carbamate
323mhb;isosulmazole
86315-52-8 (free base)
AKOS040748596
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (1)

ClassDescription
imidazolesA five-membered organic heterocycle containing two nitrogen atoms at positions 1 and 3, or any of its derivatives; compounds containing an imidazole skeleton.
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Protein Targets (3)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
cGMP-specific 3',5'-cyclic phosphodiesteraseHomo sapiens (human)IC50 (µMol)58.00000.00001.18439.6140AID157161
cGMP-inhibited 3',5'-cyclic phosphodiesterase BHomo sapiens (human)IC50 (µMol)42.00000.00002.072410.0000AID157152
cGMP-inhibited 3',5'-cyclic phosphodiesterase AHomo sapiens (human)IC50 (µMol)42.00000.00031.990110.0000AID157152
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (32)

Processvia Protein(s)Taxonomy
positive regulation of cardiac muscle hypertrophycGMP-specific 3',5'-cyclic phosphodiesteraseHomo sapiens (human)
regulation of nitric oxide mediated signal transductioncGMP-specific 3',5'-cyclic phosphodiesteraseHomo sapiens (human)
T cell proliferationcGMP-specific 3',5'-cyclic phosphodiesteraseHomo sapiens (human)
negative regulation of T cell proliferationcGMP-specific 3',5'-cyclic phosphodiesteraseHomo sapiens (human)
cGMP catabolic processcGMP-specific 3',5'-cyclic phosphodiesteraseHomo sapiens (human)
oocyte developmentcGMP-specific 3',5'-cyclic phosphodiesteraseHomo sapiens (human)
negative regulation of cardiac muscle contractioncGMP-specific 3',5'-cyclic phosphodiesteraseHomo sapiens (human)
relaxation of cardiac musclecGMP-specific 3',5'-cyclic phosphodiesteraseHomo sapiens (human)
positive regulation of oocyte developmentcGMP-specific 3',5'-cyclic phosphodiesteraseHomo sapiens (human)
cAMP-mediated signalingcGMP-specific 3',5'-cyclic phosphodiesteraseHomo sapiens (human)
angiogenesiscGMP-inhibited 3',5'-cyclic phosphodiesterase BHomo sapiens (human)
negative regulation of cell adhesioncGMP-inhibited 3',5'-cyclic phosphodiesterase BHomo sapiens (human)
G protein-coupled receptor signaling pathwaycGMP-inhibited 3',5'-cyclic phosphodiesterase BHomo sapiens (human)
negative regulation of angiogenesiscGMP-inhibited 3',5'-cyclic phosphodiesterase BHomo sapiens (human)
cellular response to insulin stimuluscGMP-inhibited 3',5'-cyclic phosphodiesterase BHomo sapiens (human)
negative regulation of cell adhesion mediated by integrincGMP-inhibited 3',5'-cyclic phosphodiesterase BHomo sapiens (human)
negative regulation of lipid catabolic processcGMP-inhibited 3',5'-cyclic phosphodiesterase BHomo sapiens (human)
negative regulation of adenylate cyclase-activating G protein-coupled receptor signaling pathwaycGMP-inhibited 3',5'-cyclic phosphodiesterase BHomo sapiens (human)
cAMP-mediated signalingcGMP-inhibited 3',5'-cyclic phosphodiesterase BHomo sapiens (human)
oocyte maturationcGMP-inhibited 3',5'-cyclic phosphodiesterase AHomo sapiens (human)
lipid metabolic processcGMP-inhibited 3',5'-cyclic phosphodiesterase AHomo sapiens (human)
G protein-coupled receptor signaling pathwaycGMP-inhibited 3',5'-cyclic phosphodiesterase AHomo sapiens (human)
response to xenobiotic stimuluscGMP-inhibited 3',5'-cyclic phosphodiesterase AHomo sapiens (human)
cAMP-mediated signalingcGMP-inhibited 3',5'-cyclic phosphodiesterase AHomo sapiens (human)
cGMP-mediated signalingcGMP-inhibited 3',5'-cyclic phosphodiesterase AHomo sapiens (human)
regulation of meiotic nuclear divisioncGMP-inhibited 3',5'-cyclic phosphodiesterase AHomo sapiens (human)
negative regulation of apoptotic processcGMP-inhibited 3',5'-cyclic phosphodiesterase AHomo sapiens (human)
negative regulation of vascular permeabilitycGMP-inhibited 3',5'-cyclic phosphodiesterase AHomo sapiens (human)
positive regulation of vascular permeabilitycGMP-inhibited 3',5'-cyclic phosphodiesterase AHomo sapiens (human)
steroid hormone mediated signaling pathwaycGMP-inhibited 3',5'-cyclic phosphodiesterase AHomo sapiens (human)
negative regulation of cAMP-mediated signalingcGMP-inhibited 3',5'-cyclic phosphodiesterase AHomo sapiens (human)
positive regulation of oocyte developmentcGMP-inhibited 3',5'-cyclic phosphodiesterase AHomo sapiens (human)
regulation of ribonuclease activitycGMP-inhibited 3',5'-cyclic phosphodiesterase AHomo sapiens (human)
cellular response to cGMPcGMP-inhibited 3',5'-cyclic phosphodiesterase AHomo sapiens (human)
cellular response to transforming growth factor beta stimuluscGMP-inhibited 3',5'-cyclic phosphodiesterase AHomo sapiens (human)
apoptotic signaling pathwaycGMP-inhibited 3',5'-cyclic phosphodiesterase AHomo sapiens (human)
negative regulation of adenylate cyclase-activating G protein-coupled receptor signaling pathwaycGMP-inhibited 3',5'-cyclic phosphodiesterase AHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (10)

Processvia Protein(s)Taxonomy
3',5'-cyclic-nucleotide phosphodiesterase activitycGMP-specific 3',5'-cyclic phosphodiesteraseHomo sapiens (human)
protein bindingcGMP-specific 3',5'-cyclic phosphodiesteraseHomo sapiens (human)
cGMP bindingcGMP-specific 3',5'-cyclic phosphodiesteraseHomo sapiens (human)
metal ion bindingcGMP-specific 3',5'-cyclic phosphodiesteraseHomo sapiens (human)
3',5'-cyclic-GMP phosphodiesterase activitycGMP-specific 3',5'-cyclic phosphodiesteraseHomo sapiens (human)
3',5'-cyclic-AMP phosphodiesterase activitycGMP-specific 3',5'-cyclic phosphodiesteraseHomo sapiens (human)
3',5'-cyclic-nucleotide phosphodiesterase activitycGMP-inhibited 3',5'-cyclic phosphodiesterase BHomo sapiens (human)
3',5'-cyclic-AMP phosphodiesterase activitycGMP-inhibited 3',5'-cyclic phosphodiesterase BHomo sapiens (human)
cGMP-inhibited cyclic-nucleotide phosphodiesterase activitycGMP-inhibited 3',5'-cyclic phosphodiesterase BHomo sapiens (human)
protein bindingcGMP-inhibited 3',5'-cyclic phosphodiesterase BHomo sapiens (human)
protein kinase B bindingcGMP-inhibited 3',5'-cyclic phosphodiesterase BHomo sapiens (human)
metal ion bindingcGMP-inhibited 3',5'-cyclic phosphodiesterase BHomo sapiens (human)
3',5'-cyclic-GMP phosphodiesterase activitycGMP-inhibited 3',5'-cyclic phosphodiesterase BHomo sapiens (human)
3',5'-cyclic-nucleotide phosphodiesterase activitycGMP-inhibited 3',5'-cyclic phosphodiesterase AHomo sapiens (human)
3',5'-cyclic-AMP phosphodiesterase activitycGMP-inhibited 3',5'-cyclic phosphodiesterase AHomo sapiens (human)
cGMP-inhibited cyclic-nucleotide phosphodiesterase activitycGMP-inhibited 3',5'-cyclic phosphodiesterase AHomo sapiens (human)
protein bindingcGMP-inhibited 3',5'-cyclic phosphodiesterase AHomo sapiens (human)
nuclear estrogen receptor activitycGMP-inhibited 3',5'-cyclic phosphodiesterase AHomo sapiens (human)
metal ion bindingcGMP-inhibited 3',5'-cyclic phosphodiesterase AHomo sapiens (human)
3',5'-cyclic-GMP phosphodiesterase activitycGMP-inhibited 3',5'-cyclic phosphodiesterase AHomo sapiens (human)
estrogen bindingcGMP-inhibited 3',5'-cyclic phosphodiesterase AHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (6)

Processvia Protein(s)Taxonomy
cellular_componentcGMP-specific 3',5'-cyclic phosphodiesteraseHomo sapiens (human)
cytosolcGMP-specific 3',5'-cyclic phosphodiesteraseHomo sapiens (human)
endoplasmic reticulumcGMP-inhibited 3',5'-cyclic phosphodiesterase BHomo sapiens (human)
Golgi apparatuscGMP-inhibited 3',5'-cyclic phosphodiesterase BHomo sapiens (human)
cytosolcGMP-inhibited 3',5'-cyclic phosphodiesterase BHomo sapiens (human)
membranecGMP-inhibited 3',5'-cyclic phosphodiesterase BHomo sapiens (human)
guanyl-nucleotide exchange factor complexcGMP-inhibited 3',5'-cyclic phosphodiesterase BHomo sapiens (human)
cytosolcGMP-inhibited 3',5'-cyclic phosphodiesterase AHomo sapiens (human)
membranecGMP-inhibited 3',5'-cyclic phosphodiesterase AHomo sapiens (human)
cytosolcGMP-inhibited 3',5'-cyclic phosphodiesterase AHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (22)

Assay IDTitleYearJournalArticle
AID60175The effective dose to produce a maximum increase in dP/dt diastolic blood pressure and heart rate1990Journal of medicinal chemistry, Aug, Volume: 33, Issue:8
Inotropic "A" ring substituted sulmazole and isomazole analogues.
AID157161In vitro inhibition of PDE-V isolated from porcine pulmonary artery.1993Journal of medicinal chemistry, May-14, Volume: 36, Issue:10
Cyclic nucleotide phosphodiesterase inhibition by imidazopyridines: analogues of sulmazole and isomazole as inhibitors of the cGMP specific phosphodiesterase.
AID59591Maximum percentage change in dP/dt, diastolic blood pressure and heart rate produced by the compound at a dose 0.3 mg/kg1990Journal of medicinal chemistry, Aug, Volume: 33, Issue:8
Inotropic "A" ring substituted sulmazole and isomazole analogues.
AID59301The effective dose to produce the 30%decrease in diastolic blood pressure.1990Journal of medicinal chemistry, Aug, Volume: 33, Issue:8
Inotropic "A" ring substituted sulmazole and isomazole analogues.
AID157151Effective dose against PDE-III for increase in contractility following administration to anaesthetised dogs1993Journal of medicinal chemistry, May-14, Volume: 36, Issue:10
Cyclic nucleotide phosphodiesterase inhibition by imidazopyridines: analogues of sulmazole and isomazole as inhibitors of the cGMP specific phosphodiesterase.
AID157159In vitro inhibition of PDE-IV isolated from guinea pig ventricle at 100 uM.1993Journal of medicinal chemistry, May-14, Volume: 36, Issue:10
Cyclic nucleotide phosphodiesterase inhibition by imidazopyridines: analogues of sulmazole and isomazole as inhibitors of the cGMP specific phosphodiesterase.
AID49059Response ratio = (percent increase to drug)/(percent increase to 10 E-4 M isoproterenol)1985Journal of medicinal chemistry, Jun, Volume: 28, Issue:6
Structure-activity relationships of arylimidazopyridine cardiotonics: discovery and inotropic activity of 2-[2-methoxy-4-(methylsulfinyl)phenyl]-1H-imidazo[4,5-c]pyridine.
AID59725Maximum percentage increase in heart rate produced by the compound at a dose 0.3 mg/kg1990Journal of medicinal chemistry, Aug, Volume: 33, Issue:8
Inotropic "A" ring substituted sulmazole and isomazole analogues.
AID157152Inhibition of PDE 3 (phosphodiesterase III) from guinea pig ventricle1993Journal of medicinal chemistry, May-14, Volume: 36, Issue:10
Cyclic nucleotide phosphodiesterase inhibition by imidazopyridines: analogues of sulmazole and isomazole as inhibitors of the cGMP specific phosphodiesterase.
AID59485Compound tested for contractility in anesthetized dog when administered intravenously.1985Journal of medicinal chemistry, Jun, Volume: 28, Issue:6
Structure-activity relationships of arylimidazopyridine cardiotonics: discovery and inotropic activity of 2-[2-methoxy-4-(methylsulfinyl)phenyl]-1H-imidazo[4,5-c]pyridine.
AID60173Tested in anesthetized dog for its inotropic activity after intravenous administration1988Journal of medicinal chemistry, Aug, Volume: 31, Issue:8
Imidazo[1,2-a]pyrimidines and imidazo[1,2-a]pyrazines: the role of nitrogen position in inotropic activity.
AID49060Response ratio = (percent increase to drug)/(percent increase to 10 E-5 M isoproterenol)1985Journal of medicinal chemistry, Jun, Volume: 28, Issue:6
Structure-activity relationships of arylimidazopyridine cardiotonics: discovery and inotropic activity of 2-[2-methoxy-4-(methylsulfinyl)phenyl]-1H-imidazo[4,5-c]pyridine.
AID157154Percent inhibition of PDE 3 (phosphodiesterase III) from guinea pig ventricle at 10 uM (or 100 uM)1993Journal of medicinal chemistry, May-14, Volume: 36, Issue:10
Cyclic nucleotide phosphodiesterase inhibition by imidazopyridines: analogues of sulmazole and isomazole as inhibitors of the cGMP specific phosphodiesterase.
AID50434Compound tested for contractility in isolated cat papillary muscle at 10 e-4 M.1985Journal of medicinal chemistry, Jun, Volume: 28, Issue:6
Structure-activity relationships of arylimidazopyridine cardiotonics: discovery and inotropic activity of 2-[2-methoxy-4-(methylsulfinyl)phenyl]-1H-imidazo[4,5-c]pyridine.
AID47761Inotropic activity in cat papillary muscle at 10e-5 M expressed as percent of control1988Journal of medicinal chemistry, Aug, Volume: 31, Issue:8
Imidazo[1,2-a]pyrimidines and imidazo[1,2-a]pyrazines: the role of nitrogen position in inotropic activity.
AID59622Percent change in heart rate in anesthetized dog1985Journal of medicinal chemistry, Jun, Volume: 28, Issue:6
Structure-activity relationships of arylimidazopyridine cardiotonics: discovery and inotropic activity of 2-[2-methoxy-4-(methylsulfinyl)phenyl]-1H-imidazo[4,5-c]pyridine.
AID59124The effective dose was measured to produce the 10%increase in heart rate. 1990Journal of medicinal chemistry, Aug, Volume: 33, Issue:8
Inotropic "A" ring substituted sulmazole and isomazole analogues.
AID79659In vitro concentration required to give a 50% increase in basal contractile force in an isolated paced guinea pig papillary muscle preparation1990Journal of medicinal chemistry, Aug, Volume: 33, Issue:8
Inotropic "A" ring substituted sulmazole and isomazole analogues.
AID59623Percent change in mean arterial blood pressure in anesthetized dog1985Journal of medicinal chemistry, Jun, Volume: 28, Issue:6
Structure-activity relationships of arylimidazopyridine cardiotonics: discovery and inotropic activity of 2-[2-methoxy-4-(methylsulfinyl)phenyl]-1H-imidazo[4,5-c]pyridine.
AID50436Compound tested for contractility in isolated cat papillary muscle at 10 e-5 M.1985Journal of medicinal chemistry, Jun, Volume: 28, Issue:6
Structure-activity relationships of arylimidazopyridine cardiotonics: discovery and inotropic activity of 2-[2-methoxy-4-(methylsulfinyl)phenyl]-1H-imidazo[4,5-c]pyridine.
AID59569Maximum percentage decrease in diastolic blood pressure produced by the compound at a dose 1 mg/kg1990Journal of medicinal chemistry, Aug, Volume: 33, Issue:8
Inotropic "A" ring substituted sulmazole and isomazole analogues.
AID233939Relative positive inotropic activity (ED50) and PDE 3 inhibition (IC50)1993Journal of medicinal chemistry, May-14, Volume: 36, Issue:10
Cyclic nucleotide phosphodiesterase inhibition by imidazopyridines: analogues of sulmazole and isomazole as inhibitors of the cGMP specific phosphodiesterase.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (5)

TimeframeStudies, This Drug (%)All Drugs %
pre-19903 (60.00)18.7374
1990's2 (40.00)18.2507
2000's0 (0.00)29.6817
2010's0 (0.00)24.3611
2020's0 (0.00)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 12.60

According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be weak demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index12.60 (24.57)
Research Supply Index1.79 (2.92)
Research Growth Index4.39 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (12.60)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews0 (0.00%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other5 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]