Page last updated: 2024-12-08
1,4-diphenyl-1,2,3-triazole
## 1,4-Diphenyl-1,2,3-triazole: A Versatile Building Block for Research
1,4-Diphenyl-1,2,3-triazole, also known as **1,4-diphenyl-1H-1,2,3-triazole**, is a heterocyclic compound that plays a significant role in various research fields.
**Structure and Properties:**
* **Structure:** It consists of a five-membered ring containing three nitrogen atoms and two phenyl groups attached at positions 1 and 4.
* **Properties:** 1,4-diphenyl-1,2,3-triazole is a white crystalline solid with a high melting point (110-112°C). It is stable, inert to air and moisture, and exhibits excellent solubility in common organic solvents.
**Importance in Research:**
1,4-Diphenyl-1,2,3-triazole holds considerable importance in research due to its versatility and applications in various fields. Here are some key reasons:
**1. Click Chemistry:** 1,4-Diphenyl-1,2,3-triazole is a key component in the **copper(I)-catalyzed azide-alkyne cycloaddition (CuAAC) reaction**, a powerful and versatile tool in **click chemistry**. This reaction allows for the efficient and reliable formation of 1,4-disubstituted 1,2,3-triazoles from azides and alkynes.
**2. Materials Science:**
* **Polymer Synthesis:** 1,4-Diphenyl-1,2,3-triazole is used as a **monomer** for the synthesis of **polytriazoles**, which possess unique properties like thermal stability, high refractive index, and conductivity.
* **Metal-Organic Frameworks (MOFs):** The triazole ring can act as a **ligand** in the synthesis of MOFs, leading to materials with high porosity, surface area, and potential applications in gas storage, catalysis, and separation.
**3. Biomedicine:**
* **Drug Discovery:** 1,4-Diphenyl-1,2,3-triazole is incorporated into various drug candidates due to its **biocompatibility, metabolic stability, and ease of synthesis**. It finds use in developing antibacterial, antifungal, antiviral, and anticancer agents.
* **Bioconjugation:** The CuAAC reaction is employed for **bioconjugation**, attaching triazole-containing molecules to biomolecules (proteins, peptides, nucleic acids) for studying their interactions and developing targeted therapies.
**4. Organic Synthesis:**
* **Catalyst:** Triazoles can act as **catalysts** in various organic transformations.
* **Synthetic Intermediates:** They serve as versatile **building blocks** for the synthesis of various complex organic molecules.
**Conclusion:**
1,4-Diphenyl-1,2,3-triazole is a valuable compound with a wide range of applications in diverse research areas. Its versatility stems from its ease of synthesis, stability, and unique properties. The compound is crucial for advancing research in click chemistry, materials science, biomedicine, and organic synthesis, contributing to the development of new materials, drugs, and technologies.
Cross-References
ID Source | ID |
PubMed CID | 281057 |
CHEMBL ID | 1269718 |
SCHEMBL ID | 1119554 |
MeSH ID | M0577278 |
Synonyms (15)
Synonym |
1h-1,3-triazole, 1,4-diphenyl- |
nsc133541 |
13148-78-2 |
nsc-133541 |
1,4-diphenyltriazole |
CHEMBL1269718 |
1,4-diphenyl-1h-[1,2,3]triazole |
SCHEMBL1119554 |
UIXYUQXWIFEYBN-UHFFFAOYSA-N |
1,4-diphenyl-1h-1,2,3-triazole |
1h-1,2,3-triazole, 1,4-diphenyl- |
1,4-diphenyl-1,2,3-triazole |
1,4-diphenyl-1h-1,2,3-triazole # |
DTXSID80299894 |
CCG-247247 |
Bioassays (6)
Assay ID | Title | Year | Journal | Article |
AID526103 | Inhibition of MAOA by spectrofluorimetry | 2010 | Bioorganic & medicinal chemistry letters, Nov-01, Volume: 20, Issue:21
| 'Click' assembly of selective inhibitors for MAO-A. |
AID690964 | Inhibition of rat NaV1.6-mediated current expressed in human HEK293 cells at 10 uM by patch clamp assay | 2012 | Bioorganic & medicinal chemistry letters, Oct-15, Volume: 22, Issue:20
| Inhibition of NaV1.6 sodium channel currents by a novel series of 1,4-disubstituted-triazole derivatives obtained via copper-catalyzed click chemistry. |
AID1140402 | Antagonist activity at androgen receptor in human LNCAP cells assessed as inhibition of androgen-stimulated cell growth at 40 uM measured every 3 days relative to dihydrotestosterone | 2014 | Bioorganic & medicinal chemistry, May-01, Volume: 22, Issue:9
| Preliminary investigations into triazole derived androgen receptor antagonists. |
AID526104 | Inhibition of MAOB by spectrofluorimetry | 2010 | Bioorganic & medicinal chemistry letters, Nov-01, Volume: 20, Issue:21
| 'Click' assembly of selective inhibitors for MAO-A. |
AID690965 | Inhibition of rat NaV1.6-mediated current expressed in human HEK293 cells by patch clamp assay | 2012 | Bioorganic & medicinal chemistry letters, Oct-15, Volume: 22, Issue:20
| Inhibition of NaV1.6 sodium channel currents by a novel series of 1,4-disubstituted-triazole derivatives obtained via copper-catalyzed click chemistry. |
AID1140401 | Antagonist activity at androgen receptor in human LNCAP cells assessed as inhibition of androgen-stimulated cell growth at 20 uM measured every 3 days relative to dihydrotestosterone | 2014 | Bioorganic & medicinal chemistry, May-01, Volume: 22, Issue:9
| Preliminary investigations into triazole derived androgen receptor antagonists. |
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023] |
Research
Studies (5)
Timeframe | Studies, This Drug (%) | All Drugs % |
pre-1990 | 0 (0.00) | 18.7374 |
1990's | 0 (0.00) | 18.2507 |
2000's | 0 (0.00) | 29.6817 |
2010's | 5 (100.00) | 24.3611 |
2020's | 0 (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: 13.28
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.
Metric | This Compound (vs All) |
---|
Research Demand Index | 13.28 (24.57) | Research Supply Index | 1.79 (2.92) | Research Growth Index | 5.08 (4.65) | Search Engine Demand Index | 0.00 (26.88) | Search Engine Supply Index | 0.00 (0.95) |
| |
Study Types
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] |