65069-55-8

Basic information

• Product Name: 1-(3,4-METHYLENEDIOXYPHENYL)-2-THIOUREA
• Synonyms: N-(1,3-BENZODIOXOL-5-YL)THIOUREA;1-(3,4-METHYLENEDIOXYPHENYL)-2-THIOUREA;IFLAB-BB F1906-0002;1-(Benzo[d][1,3]dioxol-5-yl)thiourea
• CAS NO: 65069-55-8
• Molecular Formula: C₈H₈N₂O₂S
• Molecular Weight: 196.23
• Mol File: 65069-55-8.mol
• Article Data: 8

Chemical Properties

• Melting Point: 198 °C
• Boiling Point: 329.6 °C at 760 mmHg
• Flash Point: 153.2 °C
• Appearance: /
• Density: 1.524 g/cm³
• Vapor Pressure: 0.000175mmHg at 25°C
• Refractive Index: 1.757
• CAS DataBase Reference: 1-(3,4-METHYLENEDIOXYPHENYL)-2-THIOUREA(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(3,4-METHYLENEDIOXYPHENYL)-2-THIOUREA(65069-55-8)
• EPA Substance Registry System: 1-(3,4-METHYLENEDIOXYPHENYL)-2-THIOUREA(65069-55-8)

Safety Data

• HazardClass: IRRITANT
• Hazardous Substances Data: 65069-55-8(Hazardous Substances Data)

Usage

Description

1-(3,4-Methylenedioxyphenyl)-2-thiourea, a chemical compound with the molecular formula C9H9N3O2S, is a derivative of phenylthiourea. It is recognized for its ability to form stable complexes with various metal ions and has been studied for its potential pharmaceutical applications, particularly in the treatment of cancer and other diseases. As a common building block in organic chemistry, it is utilized in the synthesis of various heterocyclic compounds. Its stable and non-toxic nature makes it a popular choice for research and laboratory applications.

Uses

Used in Pharmaceutical Applications:
1-(3,4-Methylenedioxyphenyl)-2-thiourea is used as a precursor in the synthesis of pharmaceutical compounds for the treatment of cancer and other diseases. Its potential medicinal properties are being explored due to its ability to interact with metal ions, which may contribute to its therapeutic effects.
Used in Chemical Reactions:
As a reagent, 1-(3,4-Methylenedioxyphenyl)-2-thiourea is used in various chemical reactions, facilitating the synthesis of other compounds. Its versatility in forming stable complexes with metal ions makes it a valuable component in these processes.
Used in Organic Chemistry:
1-(3,4-Methylenedioxyphenyl)-2-thiourea is used as a building block in the synthesis of heterocyclic compounds, contributing to the development of new organic molecules with potential applications in various fields.
Used in Research and Laboratory Applications:
Due to its stable and non-toxic nature, 1-(3,4-Methylenedioxyphenyl)-2-thiourea is a popular choice for research and laboratory applications, where it is used in experiments and as a component in the development of new chemical processes and compounds.

InChI:InChI=1/C8H8N2O2S/c9-8(13)10-5-1-2-6-7(3-5)12-4-11-6/h1-3H,4H2,(H3,9,10,13)

Upstream product

• 113504-93-1 5-isothiocyanato-benzo[1,3]dioxole 
• 14268-66-7 benzo[1,3]dioxolo-5-ylamine 
• 1147550-11-5 ammonium thiocyanate 
• 2620-45-3 benzo[1,3]dioxol-5-ylamine; hydrochloride 
• 67618-23-9 N-(benzo[d][1,3]dioxol-5-ylcarbamothioyl)benzamide 
• 532-55-8 Benzoyl isothiocyanate 

Downstream Products

• 469891-25-6 N-(benzo[d][1,3]dioxol-5-yl)-4-(4-chlorophenyl)thiazol-2-amine hydrobromide 
• 398471-16-4 C₁₆H₁₂N₂O₂S 
• 1375644-25-9 C₁₇H₁₄N₂O₃S 
• 398471-13-1 C₁₆H₁₁ClN₂O₂S 
• 1375644-22-6 C₁₇H₁₄N₂O₃S 
• 1375644-19-1 C₁₇H₁₄N₂O₃S 
• 1375644-16-8 C₁₆H₁₁ClN₂O₂S 
• 65070-22-6 N'-Benzo[1,3]dioxol-5-yl-N-cyclohexyl-N-methyl-guanidine 
• 139331-59-2 6-[3-[4-(4-fluorophenyl)-1-piperazinyl]propyl]-6H-1,3-dioxolo[4,5-g][1,4]benzothiazin-7(8H)-one.dihydrochloride 
• 50850-94-7 [1,3]dioxolo[4’,5’:4,5]benzo[1,2-d]thiazol-6-amine 

Relevant articles and documents

Design, synthesis, X-ray crystallographic analysis, and biological evaluation of thiazole derivatives as potent and selective inhibitors of human dihydroorotate dehydrogenase

Human dihydroorotate dehydrogenase (HsDHODH) is a flavin-dependent mitochondrial enzyme that has been certified as a potential therapeutic target for the treatment of rheumatoid arthritis and other autoimmune diseases. On the basis of lead compound 4, which was previously identified as potential HsDHODH inhibitor, a novel series of thiazole derivatives were designed and synthesized. The X-ray complex structures of the promising analogues 12 and 33 confirmed that these inhibitors bind at the putative ubiquinone binding tunnel and guided us to explore more potent inhibitors, such as compounds 44, 46, and 47 which showed double digit nanomolar activities of 26, 18, and 29 nM, respectively. Moreover, 44 presented considerable anti-inflammation effect in vivo and significantly alleviated foot swelling in a dose-dependent manner, which disclosed that thiazole-scaffold analogues can be developed into the drug candidates for the treatment of rheumatoid arthritis by suppressing the bioactivity of HsDHODH.

Design, synthesis and evaluation of 2-aminothiazole derivatives as sphingosine kinase inhibitors

Sphingosine kinases (SphK1, SphK2) are main regulators of sphingosine-1-phosphate (S1P), which is a pleiotropic lipid mediator involved in numerous physiological and pathophysiological functions. SphKs are targets for novel anti-cancer and anti-inflammatory agents that can promote cell apoptosis and modulate autoimmune diseases. Herein, we describe the design, synthesis and evaluation of an aminothiazole class of SphK inhibitors. Potent inhibitors have been discovered through a series of modifications using the known SKI-II scaffold to define structure-activity relationships. We identified N-(4-methylthiazol-2-yl)-(2,4′-bithiazol)-2′-amine (24, ST-1803; IC50values: 7.3 μM (SphK1), 6.5 μM (SphK2)) as a promising candidate for further in vivo investigations and structural development.

Synthesis of thiophene-2-carboxamidines containing 2-aminothiazoles and their biological evaluation as urokinase inhibitors

The serine protease urokinase (uPa) has been implicated in the progression of both breast and prostate cancer. Utilizing structure based design, the synthesis of a series of substituted 4-[2-amino-1,3-thiazolyl]-thiophene-2-carboxamidines is described. Further optimization of this series by substitution of the terminal amine yielded urokinase inhibitors with excellent activities.