135733-30-1

Basic information

• Product Name: (2-Oxido-4-phenyl-1,2,5-oxadiazol-2-ium-3-yl)methanol
• Synonyms: NSC688494;(2-oxido-4-phenyl-1,2,5-oxadiazol-2-ium-3-yl)methanol;135733-30-1;CHEMBL567641;3-(hydroxymethyl)-4-phenyl-1,2,5-oxadiazole 2-oxide;SCHEMBL20167031;4-phenyl-3-hydroxymethyl-furoxan;DTXSID10327811;BDBM50300757;NSC-688494;NCGC00168370-01;NCI60_031935;3-(Hydroxymethyl)-4-phenylfurazan 2-oxide;3-(Hydroxymethyl)-4-phenyl-1,2.lambda.~5~,5-oxadiazol-2-ol
• CAS NO: 135733-30-1
• Molecular Weight: 192.174
• Mol File: 135733-30-1.mol
• Article Data: 36

Chemical Properties

• CAS DataBase Reference: (2-Oxido-4-phenyl-1,2,5-oxadiazol-2-ium-3-yl)methanol(CAS DataBase Reference)
• NIST Chemistry Reference: (2-Oxido-4-phenyl-1,2,5-oxadiazol-2-ium-3-yl)methanol(135733-30-1)
• EPA Substance Registry System: (2-Oxido-4-phenyl-1,2,5-oxadiazol-2-ium-3-yl)methanol(135733-30-1)

Safety Data

• Hazardous Substances Data: 135733-30-1(Hazardous Substances Data)

Usage

Description

(2-Oxido-4-phenyl-1,2,5-oxadiazol-2-ium-3-yl)methanol, also known as benzyl oxadiazolone, is a heterocyclic chemical compound with the formula C8H7N2O2. It features an oxadiazole ring and a phenyl group, making it a versatile building block in pharmaceutical research for the synthesis of biologically active compounds.

Uses

Used in Pharmaceutical Research:
(2-Oxido-4-phenyl-1,2,5-oxadiazol-2-ium-3-yl)methanol is used as a building block for the synthesis of various biologically active compounds, contributing to the development of new drugs and therapeutic agents.
Used in Bioimaging:
As a fluorescent probe, (2-Oxido-4-phenyl-1,2,5-oxadiazol-2-ium-3-yl)methanol is utilized in bioimaging to visualize and study biological processes at the molecular level, aiding in research and diagnostics.
Used in Light-Emitting Diodes (LEDs):
(2-Oxido-4-phenyl-1,2,5-oxadiazol-2-ium-3-yl)methanol serves as a stabilizer for light-emitting diodes, enhancing their performance and longevity.
Used in Materials Science:
(2-Oxido-4-phenyl-1,2,5-oxadiazol-2-ium-3-yl)methanol has potential applications in materials science, where its unique properties can be harnessed to develop new materials with specific characteristics.
Used in Organic Synthesis:
(2-Oxido-4-phenyl-1,2,5-oxadiazol-2-ium-3-yl)methanol is also used in organic synthesis for the creation of various organic compounds, expanding the scope of chemical research and applications.
It is important to handle (2-Oxido-4-phenyl-1,2,5-oxadiazol-2-ium-3-yl)methanol with care, as it may possess hazardous properties. It should only be used by trained professionals in a controlled laboratory setting to ensure safety and proper utilization.

Upstream product

• 621-82-9 Cinnamic acid 
• 140-10-3 (E)-3-phenylacrylic acid 
• 4407-36-7 (2E)-3-phenyl-2-propen-1-ol 
• 103-36-6 ethyl 3-phenyl-2-propenoate 
• 100-52-7 benzaldehyde 
• 793724-13-7 ethyl 4-phenylfuroxan-3-carboxylate 
• 104-54-1 3-Phenylpropenol 
• 6898-86-8 3-methyl-4-phenylfuroxan 
• 169614-78-2 3-(bromomethyl)-2-oxido-4-phenyl-1,2,5-oxadiazole 
• 135733-31-2 4-(hydroxymethyl)-3-phenylfuroxan 

Downstream Products

• 135733-32-3 4-phenyl-3-furazanmethanol 
• 151733-56-1 4-phenyl-3-furoxanylcarbaldehyde oxime 
• 125520-62-9 4-phenyl-3-furoxancarbonitrile 

Relevant articles and documents

Design, synthesis and biological study of hybrid drug candidates of nitric oxide releasing cucurbitacin-inspired estrone analogs for treatment of hepatocellular carcinoma

Development of hybrid drug candidates is well known strategy for designing antitumor agents. Herein, a novel class of nitric oxide donating cucurbitacin inspired estrone analogs (NO-CIEAs) were designed and synthesized as multitarget agents. Synthesized analogs were initially evaluated for their anti-hepatocellular carcinoma activities. Among the tested analogs, NO-CIEAs 17 and 20a exhibited more potent activity against HepG2 cells (IC50 = 4.69 and 12.5 μM, respectively) than the reference drug Erlotinib (IC50 = 25 μM). Interestingly, NO-CIEA 17 exerted also a high potent activity against Erlotinib-resistant HepG2 cell line (HepG2-R) (IC50 = 8.21 μM) giving insight about its importance in drug resistance therapy. Intracellular measurements of NO revealed that NO-CIEAs 17 and 20a showed a significant increase in NO production in tumor cells after 1 h of incubation comparable to the reference prodrug JS-K. Flow cytometric analysis showed that both NO-CIEAs 17 and 20a mainly arrested the HepG2 cells in the G0/G1 phase. Also, In-Cell Based ELISA screening showed that NO-CIEA 17 resulted in a potential inhibitory activity towards the EGFR and MAPK (25% and 29% inhibition compared to untreated control cells, respectively). This data suggests the binding ability of NO-CIEA 17 to the EGFR and ERK to be well correlated along with the docking and cellular studies. Also, treatment of HepG2-R cells with NO-CIEA 17 showed a potential reduction of MRP2 expression in a dose dependent manner providing a significant impact on the chemotherapeutic resistance. Overall, the current study provides a potential new approach for the discovery of a novel antitumor agent against HCC.

A surprising new route to 4-nitro-3-phenylisoxazole

A one-pot synthesis of 4-nitro-3-phenylisoxazole has been carried out by treatment of cinnamyl alcohol dissolved in acetic acid with sodium nitrite; in addition, 4-phenyl-3-furoxanmethanol was obtained in 40% yield.

Synthesis of lathyrane diterpenoid nitrogen-containing heterocyclic derivatives and evaluation of their anti-inflammatory activities

As our ongoing work on lathyrane diterpenoid derivatization, three series of lathyrane diterpenoid derivatives were designed and synthesized based combination principles, including pyrazole, thiazole and furoxan moieties. Biological evaluation indicated t

Multi-target anti-tumor retinoic acid derivative and synthesis method and application thereof

The invention provides a multi-target anti-tumor retinoic acid derivative and a synthesis method and application thereof. Based on the guidance of a multi-target drug theory, a furazan nitrogen (Furoxans) NO donor is selected as an NO source by taking Am5

Aurovertin B derivative and preparation method and application thereof

The invention relates to an aurovertin B derivative and a preparation method of the aurovertin B derivative, and application of the aurovertin B derivative in preparation of a medicine for treating triple-negative breast cancer. Compared with aurovertin B, the aurovertin B derivative disclosed by the invention has the advantages that the water solubility of the compound is improved, the bioavailability can be improved, and the preparation is convenient to prepare. Meanwhile, compared with aurovertin B, the aurovertin B derivative disclosed by the invention has the advantages that the derivative has obvious dose dependence, the toxicity of the compound to normal cells is reduced, and the druggability of the compound is improved. The aurovertin B derivative disclosed by the invention has a very strong inhibition effect on proliferation of triple-negative breast cancer cells, and the activity of the aurovertin B derivative is stronger than that of paclitaxel serving as a clinical drug.