75843-20-8

Basic information

• Product Name: 3-acetyl-4-hydroxy-6-methyl-2H-pyran-2-one thiosemicarbazone
• Synonyms: 3-acetyl-4-hydroxy-6-methyl-2H-pyran-2-one thiosemicarbazone
• CAS NO: 75843-20-8
• Molecular Weight: 241.271
• Mol File: 75843-20-8.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: 3-acetyl-4-hydroxy-6-methyl-2H-pyran-2-one thiosemicarbazone(CAS DataBase Reference)
• NIST Chemistry Reference: 3-acetyl-4-hydroxy-6-methyl-2H-pyran-2-one thiosemicarbazone(75843-20-8)
• EPA Substance Registry System: 3-acetyl-4-hydroxy-6-methyl-2H-pyran-2-one thiosemicarbazone(75843-20-8)

Safety Data

• Hazardous Substances Data: 75843-20-8(Hazardous Substances Data)

Upstream product

• 771-03-9 3-acetyl-4-hydroxy-6-methyl-2H-pyran-2-one 
• 79-19-6 thiosemicarbazide 
• 520-45-6 Dehydracetic acid 

Downstream Products

• 1351946-49-0 3-methyl-4-(3-methylisoxazol-5-yl)-1-(4-p-tolylthiazol-2-yl)-1H-pyrazol-5-ol 
• 1351946-50-3 1-(4-(4-methoxyphenyl)thiazol-2-yl)-3-methyl-4-(3-methylisoxazol-5-yl)-1H-pyrazol-5-ol 
• 1351946-51-4 1-(4-(4-chlorophenyl)thiazol-2-yl)-3-methyl-4-(3-methylisoxazol-5-yl)-1H-pyrazol-5-ol 
• 129302-15-4 1-<5-hydroxy-3-methyl-1-(4-phenyl-2-thiazolyl)-4-pyrazolyl>-1,3-butanedione 
• 1351946-52-5 1-(5-hydroxy-3-methyl-1-(4-tolylthiazol-2-yl)-1H-pyrazol-4-yl)butane-1,3-dione 
• 1351946-53-6 1-(5-hydroxy-1-(4-(4-methoxyphenyl)thiazol-2-yl)-3-methyl-1H-pyrazol-4-yl)butane-1,3-dione 
• 1351946-54-7 1-(1-(4-(4-chlorophenyl)thiazol-2-yl)-5-hydroxy-3-methyl-1H-pyrazol-4-yl)butane-1,3-dione 
• 1351946-48-9 3-methyl-4-(3-methylisoxazol-5-yl)-1-(4-phenylthiazol-2-yl)-1H-pyrazol-5-ol 
• 151504-48-2 4-hydroxy-6-methyl-3-(1-(2-(4-phenylthiazol-2-yl)hydrazono)ethyl)-2H-pyran-2-one 
• 338978-03-3 4-hydroxy-6-methyl-3-(1-(2-(4-tolylthiazol-2-yl)hydrazono)ethyl)-2H-pyran-2-one 
• 1351946-43-4 4-hydroxy-3-(1-(2-(4-(4-methoxyphenyl)thiazol-2-yl)hydrazono)ethyl-6-methyl)-2H-pyran-2-one 
• 339009-25-5 3-(1-(2-(4-(4-chlorophenyl)thiazol-2-yl)hydrazono)ethy)-4-hydroxy-6-methyl-2H-pyran-2-one 
• 318949-53-0 C₁₇H₁₄ClN₃O₃S 
• 318949-54-1 C₂₃H₁₈ClN₅OS 

Relevant articles and documents

Synthesis and antimicrobial activity evaluation of novel 4-thiazolidinones containing a pyrone moiety

A series of thiosemicarbazones 3a-d and 4-thiazolidinones 5a-d, 7a-d, and 9a-h were synthesized and evaluated for their in vitro antimicrobial activity. Condensation of 3-acetyl-4-hydroxy-6-methyl-2H pyran-2-one1 (dehydroacetic acid) with thiosemicarbazide 2a-d in ethanol at room temperature yielded the thiosemicarbazones 3a-d. These compounds were exploited to synthesize the 4-thiazolidinones 5a-d via their reactions with ethyl 2-bromo propionate4. Derivatives 7a-d were prepared by reaction of the thiosemicarbazones 3a-d with phenyl bromoacetate 6. The 4-thiazolidinones 9a-h were obtained by treatment of compound 3a or 3c with maleimide derivatives 8a-d in refluxing ethanol, under sulfuric acid catalysis. All compounds were screened in vitro for their antibacterial and antifungal activities against five human pathogens microorganisms: Escherichia coli ATCC 25992, Pseudomonas aeruginosa ATCC 27852, Staphylococcus aureus ATCC 43300, Staphylococcus aureus ATCC 25923, and Candida albicans.

Synthesis and antimicrobial evaluation of some 1-(4-arylthiazol--2-yl)-1′-(aryl/heteroaryl)-3,3′-dimethyl-[4,5′-bi-1H-pyrazol]-5-ols

A series of sixteen 1-(4-arylthiazol-2-yl)-1′-(aryl/heteroaryl)-3,3′-dimethyl-[ 4,5′-bi-1H-pyrazol]-5-ols (7a.p) was synthesized starting from dehydroacetic acid (DHA, 1) via the stepwise formation of thiosemicarbazone (2), 3-(1-(2-(4-arylthiazol-2-yl)hydrazono)ethyl)-4-hydroxy-6-methyl-2H-pyran- -2-ones (4a.d) and 1-(1-(4-arylthiazol-2-yl)-5-hydroxy-3-methyl-1H-pyrazol- -4-yl)butane-1,3-diones (5a.d) in high yields. The in vitro antibacterial and antifungal activities of the synthesized bipyrazoles 7a.p were investigated against two Gram-positive bacterial strains, viz. Bacillus subtilis (MTCC 441) and Staphylococcus aureus (MTCC 7443), one Gram-negative bacterial strain, viz. Escherichia coli (MTCC 42), and two fungal strains, viz. Candida albicans (MTCC 183) and Aspergillus Niger (MTCC 282). The compounds 7a and 7e were found to exhibit better inhibitory activity against A. Niger than the reference fluconazole. Moreover, the antifungal activities of the title compounds were more prolific than their antibacterial activities. Furthermore, in order to study binding interactions, docking simulations of compounds 7a, 7m and 7o were performed into the active site of S. aureus 1,4-dihydroxy-2-naphthoyl- -CoA synthase.