Page last updated: 2024-12-06

1h-imidazo(4,5-b)pyridine

Description Research Excerpts Clinical Trials Roles Classes Pathways Study Profile Bioassays Related Drugs Related Conditions Protein Interactions Research Growth Market Indicators

Description

## 1H-Imidazo[4,5-b]pyridine: A Versatile Scaffold in Research

1H-Imidazo[4,5-b]pyridine is a **fused heterocyclic system** that consists of a pyridine ring and an imidazole ring connected at positions 4 and 5 of the pyridine. It's a core structure found in various biologically active compounds and has attracted significant attention in medicinal chemistry and pharmaceutical research.

**Why is it important for research?**

**1. Diverse Biological Activities:** 1H-Imidazo[4,5-b]pyridine derivatives exhibit a broad spectrum of pharmacological properties, including:

* **Anti-cancer activity:** Compounds with this scaffold have shown promising activity against various cancer cell lines, including leukemia, lung, breast, and colon cancer.
* **Anti-inflammatory activity:** Several derivatives demonstrate anti-inflammatory effects by inhibiting enzymes like cyclooxygenase (COX) and lipoxygenase (LOX).
* **Antimicrobial activity:** Some compounds exhibit antibacterial and antifungal activity, targeting specific microbial pathways.
* **CNS activity:** Derivatives have been investigated for their potential in treating neurological conditions like Alzheimer's disease and epilepsy.
* **Cardiovascular activity:** Some compounds display vasodilator properties and can potentially be used to treat cardiovascular diseases.

**2. Structural Versatility:** The scaffold allows for various modifications at different positions, enabling the design and synthesis of a wide range of derivatives with tailored biological properties. This versatility opens up numerous possibilities for optimizing the therapeutic potential of existing drugs and developing novel therapeutic agents.

**3. Synthetic Accessibility:** Efficient and reliable synthetic routes are available for preparing 1H-imidazo[4,5-b]pyridine derivatives, making it a readily accessible scaffold for medicinal chemists.

**Current Research Focus:**

* **Development of novel anticancer agents:** Ongoing research focuses on identifying new 1H-imidazo[4,5-b]pyridine derivatives with improved efficacy and selectivity against specific cancer cell lines.
* **Exploring anti-inflammatory properties:** Studies are exploring the potential of these compounds as anti-inflammatory agents for treating chronic inflammatory diseases like rheumatoid arthritis and inflammatory bowel disease.
* **Investigating CNS activity:** Research aims to develop derivatives with improved CNS penetration and efficacy for treating neurodegenerative diseases and epilepsy.

**Conclusion:**

1H-Imidazo[4,5-b]pyridine stands as a valuable scaffold in medicinal chemistry and pharmaceutical research, offering a promising platform for developing novel therapeutic agents with diverse biological activities. Its versatility, synthetic accessibility, and wide range of pharmacological properties make it a subject of ongoing investigation and a potentially valuable asset for future drug discovery efforts.

1H-imidazo(4,5-b)pyridine: structure given in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

4-azabenzimidazole : The [4,5-b]-fused isomer of imidazopyridine. [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]

Cross-References

ID SourceID
PubMed CID67504
CHEMBL ID4476663
CHEBI ID59952
SCHEMBL ID10759
MeSH IDM0176908

Synonyms (58)

Synonym
7-azabenzimidazole
1h-imidazo(4,5-b)pyridine
3,4-diazaindole
imidazo(4,5-b)pyridine
4-azabenzimidazole
pyrido(2,3-d)imidazole
1-deazapurine
nsc 403091
einecs 205-987-3
273-21-2
nsc403091
nsc-403091
4-azabenzimidazole, 99%
3h-imidazo[4,5-b]pyridine
170245-18-8
CHEBI:59952 ,
azabenzimidazole
1h-imidazo[4,5-b]pyridine
imidazopyridine
170245-19-9
4h-imidazo[4,5-b]pyridine
FT-0617625
FT-0617624
AM20051028
imidazo[4,5-b]pyridine
EPITOPE ID:140094
AKOS009144606
AKOS015900948
32106-04-0
4-aza-1h-benzimidazole
SCHEMBL10759
3Y-0826
imidazo[4,5 b]pyridine
HMS3538H12
4-azabenzodiazole
1,3,4-triaza-1h-indene
7-aza-1h-benzimidazole
1-deaza-9h-purine
AC-23435
3h-imidazo(4,5-b)pyridine
FT-0699482
DTXSID9075375
mfcd01646138
mfcd00005579
Z276130126
CHEMBL4476663 ,
J-010609
J-016732
3h-imidazo[4,5-b]pyridin
Q27126982
SY027512
imidazo[4
A852399
4h-imidazo[4,5-b]pyridine(9ci)
CS-0356773
bdbm50524492
CS-0018962
EN300-197174

Research Excerpts

Dosage Studied

ExcerptRelevanceReference
" Unfortunately these molecules cause a gastric enteropathy after chronic dosing in rats."( Imidazopyridine and Pyrazolopiperidine Derivatives as Novel Inhibitors of Serine Palmitoyl Transferase.
Adams, LA; Brozinick, JT; Estridge, T; Genin, MJ; Gonzalez Valcarcel, IC; Hawkins, E; Holloway, WG; Lamar, J; Mosior, M; Reynolds, VL; Seng, T; Weidner, J; Weller, J; Yurek, D, 2016
)
0.43
" The observation of atypical dose-response curves when some compounds were tested against multidrug resistant malaria parasite strains guided the optimization process to define a chemical space that led to typical sigmoidal dose-response and complete kill of multidrug resistant parasites."( Antimalarial Lead-Optimization Studies on a 2,6-Imidazopyridine Series within a Constrained Chemical Space To Circumvent Atypical Dose-Response Curves against Multidrug Resistant Parasite Strains.
Basarab, GS; Brunschwig, C; Chibale, K; Duffy, J; Eyermann, CJ; Fish, PV; Gibhard, L; Lawrence, N; Le Manach, C; Nchinda, AT; Njoroge, M; Paquet, T; Street, LJ; Taylor, D; Wicht, K; Wittlin, S, 2018
)
0.48
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (1)

ClassDescription
imidazopyridine
[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 (1)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
7,8-dihydro-8-oxoguanine triphosphataseHomo sapiens (human)IC50 (µMol)123.00000.05201.20935.6000AID1596624
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (6)

Processvia Protein(s)Taxonomy
purine nucleoside catabolic process7,8-dihydro-8-oxoguanine triphosphataseHomo sapiens (human)
DNA repair7,8-dihydro-8-oxoguanine triphosphataseHomo sapiens (human)
response to oxidative stress7,8-dihydro-8-oxoguanine triphosphataseHomo sapiens (human)
male gonad development7,8-dihydro-8-oxoguanine triphosphataseHomo sapiens (human)
DNA protection7,8-dihydro-8-oxoguanine triphosphataseHomo sapiens (human)
response to cadmium ion7,8-dihydro-8-oxoguanine triphosphataseHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (13)

Processvia Protein(s)Taxonomy
5'-(N(7)-methylguanosine 5'-triphospho)-[mRNA] hydrolase activity7,8-dihydro-8-oxoguanine triphosphataseHomo sapiens (human)
protein binding7,8-dihydro-8-oxoguanine triphosphataseHomo sapiens (human)
8-oxo-7,8-dihydroguanosine triphosphate pyrophosphatase activity7,8-dihydro-8-oxoguanine triphosphataseHomo sapiens (human)
dATP diphosphatase activity7,8-dihydro-8-oxoguanine triphosphataseHomo sapiens (human)
hydrolase activity, acting on acid anhydrides, in phosphorus-containing anhydrides7,8-dihydro-8-oxoguanine triphosphataseHomo sapiens (human)
snoRNA binding7,8-dihydro-8-oxoguanine triphosphataseHomo sapiens (human)
8-oxo-7,8-dihydrodeoxyguanosine triphosphate pyrophosphatase activity7,8-dihydro-8-oxoguanine triphosphataseHomo sapiens (human)
metal ion binding7,8-dihydro-8-oxoguanine triphosphataseHomo sapiens (human)
ATP diphosphatase activity7,8-dihydro-8-oxoguanine triphosphataseHomo sapiens (human)
2-hydroxy-ATP hydrolase activity7,8-dihydro-8-oxoguanine triphosphataseHomo sapiens (human)
2-hydroxy-dATP hydrolase activity7,8-dihydro-8-oxoguanine triphosphataseHomo sapiens (human)
N6-methyl-(d)ATP hydrolase activity7,8-dihydro-8-oxoguanine triphosphataseHomo sapiens (human)
O6-methyl-dGTP hydrolase activity7,8-dihydro-8-oxoguanine triphosphataseHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (8)

Processvia Protein(s)Taxonomy
acrosomal vesicle7,8-dihydro-8-oxoguanine triphosphataseHomo sapiens (human)
extracellular space7,8-dihydro-8-oxoguanine triphosphataseHomo sapiens (human)
nucleus7,8-dihydro-8-oxoguanine triphosphataseHomo sapiens (human)
cytoplasm7,8-dihydro-8-oxoguanine triphosphataseHomo sapiens (human)
mitochondrion7,8-dihydro-8-oxoguanine triphosphataseHomo sapiens (human)
mitochondrial matrix7,8-dihydro-8-oxoguanine triphosphataseHomo sapiens (human)
cytosol7,8-dihydro-8-oxoguanine triphosphataseHomo sapiens (human)
nuclear membrane7,8-dihydro-8-oxoguanine triphosphataseHomo sapiens (human)
cytoplasm7,8-dihydro-8-oxoguanine triphosphataseHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (3)

Assay IDTitleYearJournalArticle
AID1615596Lipophilicity, log D of the compound2019European journal of medicinal chemistry, Nov-01, Volume: 181Imidazopyridine-based selective and multifunctional ligands of biological targets associated with psychiatric and neurodegenerative diseases.
AID1615597Partition coefficient, log P of the compound2019European journal of medicinal chemistry, Nov-01, Volume: 181Imidazopyridine-based selective and multifunctional ligands of biological targets associated with psychiatric and neurodegenerative diseases.
AID1596624Inhibition of recombinant His-tagged MTH1 (unknown origin) expressed in Escherichia coli BL21(DE3) cells using dGTP as substrate incubated for 15 mins by malachite green dye based pyrophosphatase coupled colorimetric assay2019European journal of medicinal chemistry, Aug-01, Volume: 175Ligand retargeting by binding site analogy.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (99)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's5 (5.05)18.2507
2000's5 (5.05)29.6817
2010's45 (45.45)24.3611
2020's44 (44.44)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 11.01

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 Index11.01 (24.57)
Research Supply Index4.62 (2.92)
Research Growth Index5.63 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (11.01)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews7 (7.00%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other93 (93.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]