13980-76-2

Basic information

• Product Name: 5-MERCAPTO-1-(4-METHOXYPHENYL)-1H-TETRAZOLE
• Synonyms: 1,2-dihydro-1-(4-methoxyphenyl)-5H-Tetrazole-5-thione;mercaptomethoxyphenyltetrazole;5-MERCAPTO-1-(4-METHOXYPHENYL)-1H-TETRAZOLE;5-MERCAPTO-1-(P-METHOXYPHENYL)-1H-TETRAZOLE;AKOS BBS-00000462;1-(4-METHOXYPHENYL)-1H-TETRAZOLE-5-THIOL;1-(4-METHOXYPHENYL)-5-MERCAPTOTETRAZOLE;5-MERCAPTO-1-(4-METHOXYPHENYL)-1H-TETRAZOLE 98+%
• CAS NO: 13980-76-2
• Molecular Formula: C₈H₈N₄OS
• Molecular Weight: 208.24
• Mol File: 13980-76-2.mol

Chemical Properties

• Melting Point: 156-160°C
• Appearance: /
• CAS DataBase Reference: 5-MERCAPTO-1-(4-METHOXYPHENYL)-1H-TETRAZOLE(CAS DataBase Reference)
• NIST Chemistry Reference: 5-MERCAPTO-1-(4-METHOXYPHENYL)-1H-TETRAZOLE(13980-76-2)
• EPA Substance Registry System: 5-MERCAPTO-1-(4-METHOXYPHENYL)-1H-TETRAZOLE(13980-76-2)

Safety Data

• Statements: 11
• Safety Statements: 7/9-15-16-33
• RIDADR: 1325
• HazardClass: 4.1
• PackingGroup: II
• Hazardous Substances Data: 13980-76-2(Hazardous Substances Data)

Usage

Uses

Used in Coordination Chemistry:
5-Mercapto-1-(4-methoxyphenyl)-1H-tetrazole is used as a ligand for the formation of coordination compounds. Its ability to bind with metal ions makes it a valuable component in the development of new materials with specific catalytic, optical, or electronic properties.
Used in Medicinal Chemistry:
In the pharmaceutical industry, 5-Mercapto-1-(4-methoxyphenyl)-1H-tetrazole is used as a building block in the synthesis of bioactive molecules. Its unique structure can be incorporated into drug candidates to enhance their pharmacological properties, such as potency, selectivity, and bioavailability.
Used in Material Science:
5-Mercapto-1-(4-methoxyphenyl)-1H-tetrazole is utilized in the development of advanced materials with tailored properties. Its incorporation into polymers, for instance, can lead to materials with improved mechanical strength, thermal stability, or specific chemical reactivity.
Used in Catalysis:
As a component in catalytic systems, 5-Mercapto-1-(4-methoxyphenyl)-1H-tetrazole contributes to the enhancement of reaction rates and selectivity in various chemical transformations. Its presence can facilitate or activate specific reaction pathways, leading to more efficient and environmentally friendly processes.
It is important to handle and store 5-Mercapto-1-(4-methoxyphenyl)-1H-tetrazole with care, as it is sensitive to air, light, and moisture, which can affect its stability and reactivity.

Upstream product

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Downstream Products

• 92044-04-7 1-(4-methoxy-phenyl)-4-morpholin-4-ylmethyl-1,4-dihydro-tetrazole-5-thione 
• 110074-66-3 C₅H₅Ti(CH₃OC₆H₄CN₄S)3 
• 110074-65-2 C₅H₅Ti(CH₃OC₆H₄CN₄S)2Cl 
• 107450-64-6 bis(1-(4-methoxyphenyl)tetrazol-5-yl) disulfide 
• 36951-54-9 5-bromo-1-(4-methoxyphenyl)-1H-tetrazole 
• 1453810-39-3 5-bromo-1-(3-bromo-4-methoxyphenyl)-1H-tetrazole 
• 188717-36-4 Na⁽¹⁺⁾*C₈H₇N₄OS^(1-)=NaC₈H₇N₄OS 
• 1618101-52-2 5-[(3,5-diaminobenzyl)sulfanyl]-1-(4-methoxyphenyl)-1H-tetrazole 
• 1618101-53-3 3-nitro-5-{[(1-(4-methoxyphenyl)-1H-tetrazol-5-yl)thio]methyl}aniline 
• 3206-50-6 1-(4-methoxy-phenyl)-5-methylsulfanyl-1H-tetrazole 
• 78356-18-0 [1-(4-Methoxyphenyl)tetrazol-5-ylthio]acetic acid 

Relevant articles and documents

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Histone lysine-specific demethylase 1 (LSD1) is an important epigenetic modulator, and is implicated in malignant transformation and tumor pathogenesis in different ways. Therefore, the inhibition of LSD1 provides an attractive therapeutic target for cancer therapy. Based on drug repurposing strategy, we screened our in-house chemical library toward LSD1, and found that the EGFR inhibitor erlotinib, an FDA-approved drug for lung cancer, possessed low potency against LSD1 (IC50 = 35.80 μM). Herein, we report our further medicinal chemistry effort to obtain a highly water-soluble erlotinib analog 5k (>100 mg/mL) with significantly enhanced inhibitory activity against LSD1 (IC50 = 0.69 μM) as well as higher specificity. In MGC-803 cells, 5k suppressed the demethylation of LSD1, indicating its cellular activity against the enzyme. In addition, 5k had a remarkable capacity to inhibit colony formation, suppress migration and induce apoptosis of MGC803 cells. Furthermore, in MGC-803 xenograft mouse model, 5k treatment resulted in significant reduction in tumor size by 81.6% and 96.1% at dosages of 40 and 80 mg/kg/d, respectively. Our findings indicate that erlotinib-based analogs provide a novel structural set of LSD1 inhibitors with potential for further investigation, and may serve as novel candidates for the treatment of LSD1-overexpressing cancers.

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