41657-72-1

Usage

General Description

1-{4-[(E)-phenyldiazenyl]phenyl}triaza-1,2-dien-2-ium, also known as phenylazo-phenyl-triaza-dien-ium, is a chemical compound with the molecular formula C15H13N4. It is a positively charged organic molecule that contains a triaza-dien-ium group, a diazenyl group, and a phenyl group. It is commonly used in organic synthesis and as a reagent in chemical reactions. The compound has a yellow-orange color and is often used as a dye or pigment in various industries. Additionally, it exhibits unique optical properties and has potential applications in photochromic materials and optoelectronic devices.

Upstream product

• 60-09-3 aniline yellow 
• 62-53-3 aniline 
• 6004-88-2 N'-(4-phenylazo-phenyl)-hydrazine-sulfonic acid 
• 7782-77-6 cis-nitrous acid 

Downstream Products

• 101285-67-0 4,5-bis-hydroxymethyl-1-(4-phenylazo-phenyl)-1H-[1,2,3]triazole 
• 56031-39-1 (4-methyl-2,6,7-trioxa-1λ⁵-phospha-bicyclo[2.2.2]oct-1-ylidene)-(4-phenylazo-phenyl)-amine 
• 65484-59-5 C₁₉H₁₇N₇ 
• 106-50-3 1,4-phenylenediamine 

Relevant academic research and scientific papers

Alkyne-azide cycloaddition analogues of dehydrozingerone as potential anti-prostate cancer inhibitors: Via the PI3K/Akt/NF-kB pathway

Herein, we report the isolation and synthetic modification of dehydrozingerone (DHZ, 1), a secondary metabolite present in the rhizome of Zingiber officinale. We synthesized O-propargylated dehydrozingerone, which was subsequently coupled by alkyne-azide cycloaddition (3-20) using click chemistry. The compounds (1-20) were evaluated for their in vitro cytotoxic activity in a panel of three cancer cell lines. Among all the DHZ derivatives, 3, 6, 7, 8, 9 and 15 displayed potent cytotoxic potential with an IC50 value ranging from 1.8-3.0 μM in MCF-7, PC-3 and HCT-116 cell lines. Furthermore, compound 7 has proven to be the most potent cytotoxic compound in all the three distinct cancer cell lines and also demonstrated significant anti-invasive potential in prostate cancer. The mechanistic study of compound 7 showed that it not only suppressed the AKT/mTOR signalling which regulates nuclear transcription factor-NF-kB but also augmented the expression of anti-invasive markers E-cadherin and TIMP. Compound 7 significantly decreased the expression of pro-invasive markers vimentin, MMP-2 and MMP-9, respectively. This study underscores an efficient synthetic approach employed to evaluate the structure-activity relationship of dehydrozingerone (1) in search of potential new anticancer agents.