## 1-Benzyl-1H-indazol-3-ol: A Versatile Building Block in Research
1-Benzyl-1H-indazol-3-ol is a heterocyclic compound with a unique structure combining an indazole ring system and a benzyl substituent. Its significance in research stems from its versatile applications and potential therapeutic value.
**Structure and Properties:**
* **Indazole Ring:** The indazole ring system, with its nitrogen and carbon atoms, contributes to the compound's unique reactivity and ability to form various derivatives.
* **Benzyl Substituent:** The benzyl group adds bulk and modifies the compound's physical and pharmacological properties.
**Importance in Research:**
1. **Pharmacological Activity:**
* **Anti-Cancer Properties:** Studies have shown that 1-benzyl-1H-indazol-3-ol and its derivatives exhibit potential anti-cancer activity against various cancer cell lines, including leukemia, melanoma, and breast cancer.
* **Anti-Inflammatory Effects:** Some derivatives show anti-inflammatory activity, potentially useful for treating inflammatory conditions like arthritis.
* **Anti-microbial Properties:** The compound's structure offers potential for development as an anti-microbial agent.
* **Other Therapeutic Applications:** Derivatives of this compound have been explored for their potential in treating neurodegenerative disorders, metabolic diseases, and cardiovascular diseases.
2. **Chemical Reactivity:**
* **Versatile Synthetic Intermediate:** The indazole ring allows for various chemical modifications, creating a platform for synthesizing a wide range of derivatives with diverse properties.
* **Ligand for Metal Complexes:** The nitrogen and oxygen atoms in the molecule can coordinate with metal ions, leading to the development of new metal complexes with potential applications in catalysis and materials science.
3. **Biological Research:**
* **Probing Protein Interactions:** The compound can be used as a probe to study protein interactions, providing insights into the mechanisms of various biological processes.
* **Developing New Diagnostic Tools:** Derivatives of this compound have potential as fluorescent probes for imaging biological systems, aiding in diagnosis and drug development.
**Future Research Directions:**
* Further exploration of the compound's therapeutic potential through pre-clinical and clinical studies.
* Development of more potent and selective derivatives with improved pharmacological properties.
* Investigating the compound's use in novel drug delivery systems.
**Conclusion:**
1-Benzyl-1H-indazol-3-ol holds great promise for research due to its versatile applications in various fields. Its potential as a therapeutic agent, a synthetic intermediate, and a biological probe makes it an exciting area of ongoing scientific exploration.
1-benzyl-1H-indazol-3-ol: structure given in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]
| ID Source | ID |
|---|---|
| PubMed CID | 75181 |
| CHEMBL ID | 8612 |
| SCHEMBL ID | 376005 |
| MeSH ID | M0265663 |
| Synonym |
|---|
| CBMICRO_007258 , |
| unii-yl5zxn63q6 |
| yl5zxn63q6 , |
| einecs 218-680-4 |
| nsc 247064 |
| nsc-247064 |
| 2215-63-6 |
| nsc247064 |
| OPREA1_591436 |
| 1-benzyl-1,2-dihydro-indazol-3-one |
| MLS001211149 |
| smr000516810 |
| OPREA1_122894 |
| CHEMDIV2_000492 |
| BIM-0007142.P001 |
| B2411 , |
| 1-benzyl-3-hydroxy-1h-indazole |
| 1-benzyl-2,3-dihydroindazol-3-one |
| 1-benzyl-1h-indazol-3-ol |
| HMS1370G08 |
| CHEMBL8612 , |
| 1-benzyl-2h-indazol-3-one |
| AKOS000675880 |
| inchi=1/c14h12n2o/c17-14-12-8-4-5-9-13(12)16(15-14)10-11-6-2-1-3-7-11/h1-9h,10h2,(h,15,17) |
| sxpjfdsmkwloab-uhfffaoysa- |
| 1-(phenylmethyl)-2h-indazol-3-one |
| bdbm50008993 |
| NCGC00245299-01 |
| CCG-16489 |
| 1-benzyl-1,2-dihydro-3h-indazol-3-one |
| AKOS005174587 |
| CB09677 |
| smsf0011763 |
| HMS2818C04 |
| 1,2-dihydro-1-(phenylmethyl)-3h-indazol-3-one |
| 1-benzyl-3-hydroxyindazole |
| FT-0634136 |
| AB09333 |
| STL363284 |
| SCHEMBL376005 |
| benzopyrazole, 2,3-dihydro-1-benzyl-3-oxo- |
| 1-benzyl-1,2-dihydro-3h-indazol-3-one # |
| 3h-indazol-3-one, 1,2-dihydro-1-(phenylmethyl)- |
| 1h-indazol-3-ol, 1-benzyl- |
| AC-29278 |
| DTXSID30176681 |
| STL450978 |
| mfcd01631173 |
| 1-benzyl-3-hydroxy-1h-indazole, 97% |
| AS-60200 |
| J-014556 |
| benzyl-3-hydroxy-1h-indazole |
| AMY25613 |
| D78420 |
| CS-W013064 |
| PD179505 |
| benzydamine hydrochloride impurity c [ep impurity] |
| EN300-6977209 |
| Protein | Taxonomy | Measurement | Average (µ) | Min (ref.) | Avg (ref.) | Max (ref.) | Bioassay(s) |
|---|---|---|---|---|---|---|---|
| thioredoxin reductase | Rattus norvegicus (Norway rat) | Potency | 56.2341 | 0.1000 | 20.8793 | 79.4328 | AID588456 |
| euchromatic histone-lysine N-methyltransferase 2 | Homo sapiens (human) | Potency | 89.1251 | 0.0355 | 20.9770 | 89.1251 | AID504332 |
| importin subunit beta-1 isoform 1 | Homo sapiens (human) | Potency | 23.1093 | 5.8048 | 36.1306 | 65.1308 | AID540253 |
| snurportin-1 | Homo sapiens (human) | Potency | 23.1093 | 5.8048 | 36.1306 | 65.1308 | AID540253 |
| GTP-binding nuclear protein Ran isoform 1 | Homo sapiens (human) | Potency | 23.1093 | 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) |
|---|---|---|---|---|---|---|---|
| Polyunsaturated fatty acid 5-lipoxygenase | Rattus norvegicus (Norway rat) | IC50 (µMol) | 3.4000 | 0.0046 | 2.0182 | 10.0000 | AID179757 |
| Cytochrome P450 11B1, mitochondrial | Rattus norvegicus (Norway rat) | IC50 (µMol) | 31.0000 | 0.4950 | 3.5289 | 5.0000 | AID179759 |
| Sodium- and chloride-dependent GABA transporter 1 | Rattus norvegicus (Norway rat) | IC50 (µMol) | 31.0000 | 0.0013 | 2.2206 | 8.3000 | AID179759 |
| Sodium- and chloride-dependent GABA transporter 2 | Rattus norvegicus (Norway rat) | IC50 (µMol) | 31.0000 | 0.0032 | 1.7900 | 8.3000 | AID179759 |
| Sodium- and chloride-dependent GABA transporter 3 | Rattus norvegicus (Norway rat) | IC50 (µMol) | 31.0000 | 0.0032 | 1.5431 | 8.3000 | AID179759 |
| Prostaglandin G/H synthase 2 | Rattus norvegicus (Norway rat) | IC50 (µMol) | 31.0000 | 0.0029 | 1.7868 | 10.0000 | AID179759 |
| Sodium- and chloride-dependent betaine transporter | Rattus norvegicus (Norway rat) | IC50 (µMol) | 31.0000 | 0.0032 | 1.5431 | 8.3000 | AID179759 |
| Prostaglandin G/H synthase 1 | Rattus norvegicus (Norway rat) | IC50 (µMol) | 31.0000 | 0.0029 | 1.8232 | 10.0000 | AID179759 |
| [prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023] | |||||||
| Assay ID | Title | Year | Journal | Article |
|---|---|---|---|---|
| AID179759 | In vitro inhibition of PGE-2 production was measured in rat blood | 1991 | Journal of medicinal chemistry, Mar, Volume: 34, Issue:3 | Indazolinones, a new series of redox-active 5-lipoxygenase inhibitors with built-in selectivity and oral activity. |
| AID101295 | Ex vivo inhibition of LTB4 production was measured in dog blood | 1991 | Journal of medicinal chemistry, Mar, Volume: 34, Issue:3 | Indazolinones, a new series of redox-active 5-lipoxygenase inhibitors with built-in selectivity and oral activity. |
| AID179757 | In vitro inhibition of LTB4 production was measured in rat blood | 1991 | Journal of medicinal chemistry, Mar, Volume: 34, Issue:3 | Indazolinones, a new series of redox-active 5-lipoxygenase inhibitors with built-in selectivity and oral activity. |
| 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. |
| 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. |
| 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. |
| AID1745845 | Primary qHTS for Inhibitors of ATXN expression | |||
| 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. |
| AID651635 | Viability Counterscreen for Primary qHTS for Inhibitors of ATXN expression | |||
| 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 | 2 (28.57) | 18.2507 |
| 2000's | 1 (14.29) | 29.6817 |
| 2010's | 3 (42.86) | 24.3611 |
| 2020's | 1 (14.29) | 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 (20.09) 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 | 7 (100.00%) | 84.16% |
| [information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023] | ||