## 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.**
ID Source | ID |
---|---|
PubMed CID | 657476 |
CHEMBL ID | 1558246 |
CHEBI ID | 119835 |
SCHEMBL ID | 498053 |
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 |
Class | Description |
---|---|
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 | Taxonomy | Measurement | Average (µ) | Min (ref.) | Avg (ref.) | Max (ref.) | Bioassay(s) |
---|---|---|---|---|---|---|---|
Chain A, 2-oxoglutarate Oxygenase | Homo sapiens (human) | Potency | 28.1838 | 0.1778 | 14.3909 | 39.8107 | AID2147 |
Luciferase | Photinus pyralis (common eastern firefly) | Potency | 30.1313 | 0.0072 | 15.7588 | 89.3584 | AID588342 |
hypoxia-inducible factor 1, alpha subunit (basic helix-loop-helix transcription factor) | Homo sapiens (human) | Potency | 10.0000 | 0.0013 | 7.7625 | 44.6684 | AID914; AID915 |
importin subunit beta-1 isoform 1 | Homo sapiens (human) | Potency | 27.1059 | 5.8048 | 36.1306 | 65.1308 | AID540253; AID540263 |
snurportin-1 | Homo sapiens (human) | Potency | 27.1059 | 5.8048 | 36.1306 | 65.1308 | AID540253; AID540263 |
GTP-binding nuclear protein Ran isoform 1 | Homo sapiens (human) | Potency | 29.0929 | 5.8048 | 16.9962 | 25.9290 | AID540253 |
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023] |
Protein | Taxonomy | Measurement | Average | Min (ref.) | Avg (ref.) | Max (ref.) | Bioassay(s) |
---|---|---|---|---|---|---|---|
STAT3, partial | Homo sapiens (human) | IC50 (µMol) | 3.3260 | 0.0760 | 4.0758 | 8.6430 | AID1398 |
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023] |
Protein | Taxonomy | Measurement | Average | Min (ref.) | Avg (ref.) | Max (ref.) | Bioassay(s) |
---|---|---|---|---|---|---|---|
karyopherin alpha 2 (RAG cohort 1, importin alpha 1), isoform CRA_b | Homo sapiens (human) | EC50 (µMol) | 53.1600 | 0.9181 | 41.9368 | 121.5000 | AID435026 |
signal transducer and activator of transcription 1-alpha/beta isoform alpha | Homo sapiens (human) | EC50 (µMol) | 55.7000 | 0.4180 | 1.3618 | 2.9980 | AID1406 |
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023] |
Assay ID | Title | Year | Journal | Article |
---|---|---|---|---|
AID1745845 | Primary qHTS for Inhibitors of ATXN expression | |||
AID588499 | High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain A protease, MLPCN compound set | 2010 | Current protocols in cytometry, Oct, Volume: Chapter 13 | Microsphere-based flow cytometry protease assays for use in protease activity detection and high-throughput screening. |
AID588499 | High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain A protease, MLPCN compound set | 2006 | Cytometry. 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. |
AID588499 | High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain A protease, MLPCN compound set | 2010 | Assay and drug development technologies, Feb, Volume: 8, Issue:1 | High-throughput multiplex flow cytometry screening for botulinum neurotoxin type a light chain protease inhibitors. |
AID504812 | Inverse Agonists of the Thyroid Stimulating Hormone Receptor: HTS campaign | 2010 | Endocrinology, Jul, Volume: 151, Issue:7 | A small molecule inverse agonist for the human thyroid-stimulating hormone receptor. |
AID588501 | High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Lethal Factor Protease, MLPCN compound set | 2010 | Current protocols in cytometry, Oct, Volume: Chapter 13 | Microsphere-based flow cytometry protease assays for use in protease activity detection and high-throughput screening. |
AID588501 | High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Lethal Factor Protease, MLPCN compound set | 2006 | Cytometry. 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. |
AID588501 | High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Lethal Factor Protease, MLPCN compound set | 2010 | Assay and drug development technologies, Feb, Volume: 8, Issue:1 | High-throughput multiplex flow cytometry screening for botulinum neurotoxin type a light chain protease inhibitors. |
AID651635 | Viability Counterscreen for Primary qHTS for Inhibitors of ATXN expression | |||
AID588497 | High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain F protease, MLPCN compound set | 2010 | Current protocols in cytometry, Oct, Volume: Chapter 13 | Microsphere-based flow cytometry protease assays for use in protease activity detection and high-throughput screening. |
AID588497 | High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain F protease, MLPCN compound set | 2006 | Cytometry. 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. |
AID588497 | High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain F protease, MLPCN compound set | 2010 | Assay and drug development technologies, Feb, Volume: 8, Issue:1 | High-throughput multiplex flow cytometry screening for botulinum neurotoxin type a light chain protease inhibitors. |
AID504810 | Antagonists of the Thyroid Stimulating Hormone Receptor: HTS campaign | 2010 | Endocrinology, 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] |
Timeframe | Studies, This Drug (%) | All Drugs % |
---|---|---|
pre-1990 | 0 (0.00) | 18.7374 |
1990's | 0 (0.00) | 18.2507 |
2000's | 1 (20.00) | 29.6817 |
2010's | 3 (60.00) | 24.3611 |
2020's | 1 (20.00) | 2.80 |
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023] |
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.
| This Compound (23.15) All Compounds (24.57) |
Publication Type | This drug (%) | All Drugs (%) |
---|---|---|
Trials | 0 (0.00%) | 5.53% |
Reviews | 0 (0.00%) | 6.00% |
Case Studies | 0 (0.00%) | 4.05% |
Observational | 0 (0.00%) | 0.25% |
Other | 5 (100.00%) | 84.16% |
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023] |