61448-81-5

Upstream product

• 61448-77-9 3,5-bis-((Ξ)-4-methoxy-benzylidene)-tetrahydro-thiopyran-4-one 
• 61448-77-9 tetrahydro-3,5-bis-[(4-methoxyphenyl)methylene]-4H-thiopyran-4-one 
• 1072-72-6 Tetrahydrothiopyran-4-one 
• 123-11-5 4-methoxy-benzaldehyde 
• 17396-35-9 1,1-dioxotetrahydrothiopyran-4-one 

Downstream Products

• 69559-30-4 4-[(4,5-Dihydro-2-thiazolyl)amino]tetrahydro-3,5-bis[(4-methoxyphenyl)methylene]thiopyran-4-ol-1,1-dioxide 
• 69700-69-2 2,3,8,9-Tetrahydro-5-(4-methoxyphenyl)-9-[(4-methoxyphenyl)-methylene]-5H,6H-thiazolo[3,2-a]thiopyrano[4,3-d]pyrimidine-7,7-dioxide 
• 61448-66-6 3-(4-Methoxy-phenyl)-7-[1-(4-methoxy-phenyl)-meth-(Z)-ylidene]-2-propyl-2,3,3a,4,6,7-hexahydro-thiopyrano[4,3-c]pyrazole 5,5-dioxide 
• 62121-51-1 3-(4-Methoxy-phenyl)-7-[1-(4-methoxy-phenyl)-meth-(Z)-ylidene]-2-[3-(4-methyl-piperazin-1-yl)-propyl]-2,3,3a,4,6,7-hexahydro-thiopyrano[4,3-c]pyrazole 5,5-dioxide 

Relevant academic research and scientific papers

Synthesis, characterization, and optimization for in vivo delivery of a nonselective isopeptidase inhibitor as new antineoplastic agent

Bis-arylidenecycloalkanones structurally related to the nonselective isopeptidase inhibitor G5 were synthesized and tested for cytotoxic activity against glioblastoma cells. Cytotoxicities correlate well with Hammett σ constants for substituted arylidene groups, confirming the proposed inhibition mechanism. A new inhibitor (2c) based on the 4-hydroxycyclohexanone scaffold, which favors apoptosis over necrosis, was selected for further development. 2c inhibited representative deubiquitinases with micromolar IC50, and its proapoptotic activity was studied on several cancer cell lines. Inhibitor 2c was conjugated to PEG via dicarbamate and diester linkers. While the dicarbamate was inactive, the diester (2cPE) behaves like a prodrug and is converted into the active species 2c by secreted esterase activities. Finally, 2cPE was also tested in vivo on A549 lung carcinoma xenografts generated in mice. Intravenous treatment with 2cPE led to a significant reduction in primary tumor growth, without appreciable toxicity to mice.

Synthesis and antiinflammatory activity of hexahydrothiopyrano[4,3-c]pyrazoles and related analogues

A series of novel hexahydrothiopyrano[4,3-c]pyrazoles and related analogues were prepared and tested for antiinflammatory activity by using the mouse active Arthus reaction and the delayed hypersensitivity skin reaction in guinea pigs as primary screens.