Page last updated: 2024-12-09

1H-indazole-3-carboxylic acid methyl ester

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

## 1H-Indazole-3-carboxylic acid methyl ester: Structure, Importance & Research Applications

**1H-indazole-3-carboxylic acid methyl ester** is an organic compound with the chemical formula C10H8N2O2. It's a heterocyclic compound containing an indazole ring system, a five-membered ring with two nitrogen atoms, and a methyl ester group attached to the third carbon atom.

**Why is it important for research?**

This compound has emerged as a valuable scaffold in medicinal chemistry research due to its diverse pharmacological activities and potential applications in various therapeutic areas. Here are some key reasons for its importance:

* **Anti-cancer activity:** 1H-indazole-3-carboxylic acid methyl ester derivatives have demonstrated promising anti-cancer activities against various cancer cell lines, including leukemia, lung, breast, and colon cancer. They work through various mechanisms, including inhibition of cell proliferation, induction of apoptosis, and suppression of angiogenesis.
* **Anti-inflammatory activity:** Some derivatives have shown anti-inflammatory activity, inhibiting the production of inflammatory mediators like TNF-α and IL-6. This opens possibilities for treating inflammatory conditions like rheumatoid arthritis, inflammatory bowel disease, and asthma.
* **Antimicrobial activity:** 1H-indazole-3-carboxylic acid methyl ester derivatives have exhibited antibacterial and antifungal activity against a range of pathogens, including bacteria and fungi responsible for infections.
* **Anti-viral activity:** Some derivatives have shown potential antiviral activity against viruses like HIV and influenza, suggesting potential use in treating viral infections.
* **Other biological activities:** The compound has also been investigated for its potential in treating neurological disorders like Alzheimer's disease, cardiovascular diseases, and diabetes.

**Research Applications:**

1H-indazole-3-carboxylic acid methyl ester and its derivatives are extensively used in various research areas:

* **Drug discovery and development:** Researchers are continuously exploring new derivatives of this compound with enhanced biological activities, improved pharmacological properties, and reduced side effects.
* **Structure-activity relationship (SAR) studies:** Studying the relationship between the chemical structure of the compound and its biological activity allows for optimizing its efficacy and selectivity.
* **Mechanistic studies:** Investigating how this compound interacts with biological targets helps understand its mode of action and potential pathways for therapeutic intervention.
* **Pre-clinical studies:** Testing the safety and efficacy of promising derivatives in animal models provides crucial information for future clinical trials.

**Overall, 1H-indazole-3-carboxylic acid methyl ester represents a valuable starting point for the development of novel therapeutic agents with potential applications in diverse disease areas. Ongoing research continues to explore its therapeutic potential and develop safer and more effective derivatives for treating various conditions.**

Cross-References

ID SourceID
PubMed CID657476
CHEMBL ID1558246
CHEBI ID119835
SCHEMBL ID498053

Synonyms (47)

Synonym
MLS000037996 ,
smr000038274
NCGC00020846-01
CHEBI:119835
methyl 1h-indazole-3-carboxylate
STK895597
AKOS003239708
A6978
NCGC00020846-02
43120-28-1
HMS2281G14
1h-indazole-3-carboxylic acid methyl ester
FT-0604106
AM20040465
PB14207
AKOS017259738
BBL022387
methyl1h-indazole-3-carboxylate
SS-4639
methyl-1h-indazole-3-carboxylate
KWTCVAHCQGKXAZ-UHFFFAOYSA-N
methyl 1h-indazol-3-yl carboxylate
3-indazolecarboxylic acid methyl ester
indazole-3-carboxylic acid methyl ester
methyl indazole-3-carboxylate
methyl 3-indazolylcarboxylate
methyl 3-indazolecarboxylate
SCHEMBL498053
CHEMBL1558246
cid_657476
bdbm43550
J-650197
1h-indazole-3-carboxylic acid, methyl ester
CS-W020527
AC-29514
Q27207315
J-522648
methyl 1h-indazole-3-carboxylate, 97%
DTXSID20349685
mfcd01138133
SY032788
863637-26-7
2h-indazole-3-carboxylic acid methyl ester
BCP11314
methyl 2h-indazolecarboxylate
indazole-3-carboxylic methyl ester
EN300-98794
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (1)

ClassDescription
indazoles
[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 (9)

Potency Measurements

ProteinTaxonomyMeasurementAverage (µ)Min (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Chain A, 2-oxoglutarate OxygenaseHomo sapiens (human)Potency28.18380.177814.390939.8107AID2147
LuciferasePhotinus pyralis (common eastern firefly)Potency30.13130.007215.758889.3584AID588342
hypoxia-inducible factor 1, alpha subunit (basic helix-loop-helix transcription factor)Homo sapiens (human)Potency10.00000.00137.762544.6684AID914; AID915
importin subunit beta-1 isoform 1Homo sapiens (human)Potency27.10595.804836.130665.1308AID540253; AID540263
snurportin-1Homo sapiens (human)Potency27.10595.804836.130665.1308AID540253; AID540263
GTP-binding nuclear protein Ran isoform 1Homo sapiens (human)Potency29.09295.804816.996225.9290AID540253
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
STAT3, partialHomo sapiens (human)IC50 (µMol)3.32600.07604.07588.6430AID1398
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Activation Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
karyopherin alpha 2 (RAG cohort 1, importin alpha 1), isoform CRA_bHomo sapiens (human)EC50 (µMol)53.16000.918141.9368121.5000AID435026
signal transducer and activator of transcription 1-alpha/beta isoform alphaHomo sapiens (human)EC50 (µMol)55.70000.41801.36182.9980AID1406
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Bioassays (13)

Assay IDTitleYearJournalArticle
AID1745845Primary qHTS for Inhibitors of ATXN expression
AID588499High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain A protease, MLPCN compound set2010Current protocols in cytometry, Oct, Volume: Chapter 13Microsphere-based flow cytometry protease assays for use in protease activity detection and high-throughput screening.
AID588499High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain A protease, MLPCN compound set2006Cytometry. Part A : the journal of the International Society for Analytical Cytology, May, Volume: 69, Issue:5
Microsphere-based protease assays and screening application for lethal factor and factor Xa.
AID588499High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain A protease, MLPCN compound set2010Assay and drug development technologies, Feb, Volume: 8, Issue:1
High-throughput multiplex flow cytometry screening for botulinum neurotoxin type a light chain protease inhibitors.
AID504812Inverse Agonists of the Thyroid Stimulating Hormone Receptor: HTS campaign2010Endocrinology, Jul, Volume: 151, Issue:7
A small molecule inverse agonist for the human thyroid-stimulating hormone receptor.
AID588501High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Lethal Factor Protease, MLPCN compound set2010Current protocols in cytometry, Oct, Volume: Chapter 13Microsphere-based flow cytometry protease assays for use in protease activity detection and high-throughput screening.
AID588501High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Lethal Factor Protease, MLPCN compound set2006Cytometry. Part A : the journal of the International Society for Analytical Cytology, May, Volume: 69, Issue:5
Microsphere-based protease assays and screening application for lethal factor and factor Xa.
AID588501High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Lethal Factor Protease, MLPCN compound set2010Assay and drug development technologies, Feb, Volume: 8, Issue:1
High-throughput multiplex flow cytometry screening for botulinum neurotoxin type a light chain protease inhibitors.
AID651635Viability Counterscreen for Primary qHTS for Inhibitors of ATXN expression
AID588497High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain F protease, MLPCN compound set2010Current protocols in cytometry, Oct, Volume: Chapter 13Microsphere-based flow cytometry protease assays for use in protease activity detection and high-throughput screening.
AID588497High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain F protease, MLPCN compound set2006Cytometry. Part A : the journal of the International Society for Analytical Cytology, May, Volume: 69, Issue:5
Microsphere-based protease assays and screening application for lethal factor and factor Xa.
AID588497High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain F protease, MLPCN compound set2010Assay and drug development technologies, Feb, Volume: 8, Issue:1
High-throughput multiplex flow cytometry screening for botulinum neurotoxin type a light chain protease inhibitors.
AID504810Antagonists of the Thyroid Stimulating Hormone Receptor: HTS campaign2010Endocrinology, Jul, Volume: 151, Issue:7
A small molecule inverse agonist for the human thyroid-stimulating hormone receptor.
[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-19900 (0.00)18.7374
1990's0 (0.00)18.2507
2000's1 (20.00)29.6817
2010's3 (60.00)24.3611
2020's1 (20.00)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 23.15

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 moderate demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index23.15 (24.57)
Research Supply Index1.79 (2.92)
Research Growth Index4.36 (4.65)
Search Engine Demand Index21.17 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (23.15)

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]