Page last updated: 2024-12-08

1,4-diphenyl-1,2,3-triazole

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

## 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 SourceID
PubMed CID281057
CHEMBL ID1269718
SCHEMBL ID1119554
MeSH IDM0577278

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
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Bioassays (6)

Assay IDTitleYearJournalArticle
AID526103Inhibition of MAOA by spectrofluorimetry2010Bioorganic & medicinal chemistry letters, Nov-01, Volume: 20, Issue:21
'Click' assembly of selective inhibitors for MAO-A.
AID690964Inhibition of rat NaV1.6-mediated current expressed in human HEK293 cells at 10 uM by patch clamp assay2012Bioorganic & 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.
AID1140402Antagonist 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 dihydrotestosterone2014Bioorganic & medicinal chemistry, May-01, Volume: 22, Issue:9
Preliminary investigations into triazole derived androgen receptor antagonists.
AID526104Inhibition of MAOB by spectrofluorimetry2010Bioorganic & medicinal chemistry letters, Nov-01, Volume: 20, Issue:21
'Click' assembly of selective inhibitors for MAO-A.
AID690965Inhibition of rat NaV1.6-mediated current expressed in human HEK293 cells by patch clamp assay2012Bioorganic & 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.
AID1140401Antagonist 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 dihydrotestosterone2014Bioorganic & 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)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's0 (0.00)18.2507
2000's0 (0.00)29.6817
2010's5 (100.00)24.3611
2020's0 (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.

MetricThis Compound (vs All)
Research Demand Index13.28 (24.57)
Research Supply Index1.79 (2.92)
Research Growth Index5.08 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (13.28)

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]