65069-55-8

Usage

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

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

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 academic research and scientific papers

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.

Multi-dimensional target profiling of N,4-diaryl-1,3-thiazole-2-amines as potent inhibitors of eicosanoid metabolism

Eicosanoids like leukotrienes and prostaglandins play a considerable role in inflammation. Produced within the arachidonic acid (AA) cascade, these lipid mediators are involved in the pathogenesis of pain as well as acute and chronic inflammatory diseases like rheumatoid arthritis and asthma. With regard to the lipid cross-talk within the AA pathway, a promising approach for an effective anti-inflammatory therapy is the development of inhibitors targeting more than one enzyme of this cascade. Within this study, thirty N-4-diaryl-1,3-thiazole-2- amine based compounds with different substitution patterns were synthesized and tested in various cell-based assays to investigate their activity and selectivity profile concerning five key enzymes involved in eicosanoid metabolism (5-, 12-, 15-lipoxygenase (LO), cyclooxygenase-1 and -2 (COX-1/-2)). With compound 7, 2-(4-phenyl)thiazol-2-ylamino)phenol (ST-1355), a multi-target ligand targeting all tested enzymes is presented, whereas compound 9, 2-(4-(4-chlorophenyl)thiazol-2-ylamino)phenol (ST-1705), represents a potent and selective 5-LO and COX-2 inhibitor with an IC50 value of 0.9 ± 0.2 μM (5-LO) and a residual activity of 9.1 ± 1.1% at 10 μM (COX-2 product formation). The promising characteristics and the additional non-cytotoxic profile of both compounds reveal new lead structures for the treatment of eicosanoid-mediated diseases.

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.

HETEROARYL COMPOUNDS, COMPOSITIONS, AND METHODS OF USE IN CANCER TREATMENT

Provided herein are novel heteroaryl compounds, compositions comprising the compounds, and methods of treatment or prevention comprising administration of the compounds. The compounds are effective in the targeting of cells defective in the von Hippel-Lindau gene and in inducing autophagic cell death. The methods are directed to treating or preventing diseases such as cancer, and in particular cancers resulting from von Hippel-Lindau disease. The compounds of the invention may be administered in combination with another therapeutic agent.

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.

Synthesis and biological activities of new 1,4-benzothiazine derivatives

New 2H-1,4-benzothiazin-3(4H)-one derivatives possessing (4-phenyl-1-piperazinyl)alkyl moieties at the 2-position were synthesized and tested for calcium antagonistic and calmodulin antagonistic activities. Antihypertensive effects in spontaneously hypertensive rats were also evaluated. In general, these compounds were rather weak calcium channel blockers, although, in contrast, many of them had moderate to potent calmodulin antagonistic activity, and 2-[3-(4-(4-fluorophenyl)-1-piperazinyl]propyl]-2H-1,4-benzothiazin-3(4H )-one derivatives 45, 74 and 75 showed potent antihypertensive effects.

Improved Procedures for the Preparation of Cycloalkyl-, Arylalkyl-, and Arylthioureas

An improved procedure for the preparation of arylthioureas consists of the reaction of benzoyl isothiocyanate with anilines in acetone and debenzoylation of the resultant N-aryl-N'-benzoylthioureas with 5percent aqueous sodium hydroxide.Bicycloalkylthioureas and N-(arylalkyl)thioureas (e.g. 9H-9-fluorenylthiourea) are directly prepared from the corresponding isothiocyanates and ammonia.

Nitrogen heterocyclic carboximidamide compounds

5-, 6- or 7-Membered fully saturated 1-azacarbocyclic-2-ylidene derivatives of guanidine having anti-secretory and hypoglycemic activities, and further useful for treatment of cardiovascular disease states.