889110-18-3

Basic information

• Product Name: C₁₆H₁₀F₆S₂
• Synonyms: C₁₆H₁₀F₆S₂
• CAS NO: 889110-18-3
• Molecular Weight: 380.378
• Mol File: 889110-18-3.mol

Chemical Properties

• CAS DataBase Reference: C₁₆H₁₀F₆S₂(CAS DataBase Reference)
• NIST Chemistry Reference: C₁₆H₁₀F₆S₂(889110-18-3)
• EPA Substance Registry System: C₁₆H₁₀F₆S₂(889110-18-3)

Safety Data

• Hazardous Substances Data: 889110-18-3(Hazardous Substances Data)

Upstream product

• 375-21-3 2,2,3,3,4,4,4-heptafluoro-butane-1,1-diol 
• 108-98-5 thiophenol 
• 375-02-0 2,2,3,3,4,4,4-heptafluorobutanal 

Downstream Products

• 889110-21-8 3-(Bis-phenylsulfanyl-methylene)-4,4,5,5,5-pentafluoro-1-phenyl-pentan-1-one 
• 889110-20-7 4-(Bis-phenylsulfanyl-methylene)-5,5,6,6,6-pentafluoro-hexan-2-one 
• 889110-22-9 5-(Bis-phenylsulfanyl-methylene)-6,6,7,7,7-pentafluoro-4-methyl-heptan-3-one 
• 889110-25-2 3,3,4,4,4-pentafluoro-2-(2-oxo-2-phenyl-ethyl)-thiobutyric acid S-phenyl ester 
• 889110-26-3 3-methyl-4-oxo-2-pentafluoroethyl-hexanethioic acid S-phenyl ester 

Relevant articles and documents

New route to the 5-((arylthio- and heteroarylthio)methylene)-3-(2,2,2- trifluoroethyl)-furan-2(5H)-ones - Key intermediates in the synthesis of 4-aminoquinoline γ-lactams as potent antimalarial compounds

In this Letter we report on a multi-step synthesis of 5-((arylthio- and heteroarylthio)-methylene)-3-(2,2,2-trifluoroethyl)furan-2(5H)-ones starting from γ-keto thiolester or γ-keto carboxylic acid. The key intermediate γ-lactones were then reacted with 4-aminoquinoline-derived amines via ring opening - ring closure (RORC) process affording the corresponding γ-hydroxy-γ-lactams in moderate to good yields. In vitro antimalarial activity of the resulting new 4-aminoquinoline γ-lactams were evaluated against Plasmodium falciparum clones of variable sensitivity (3D7 and W2) and were found to be active in the range of 89-1600 nM with good resistance index and did not show cytotoxicity in vitro when tested against human umbilical vein endothelial cells (HUVEC) up to concentration of 50 μM.

Incorporation of a 3-(2,2,2-Trifluoroethyl)-γ-hydroxy-γ-lactam motif in the side chain of 4-aminoquinolines. Syntheses and antimalarial activities

In this paper we report the synthesis and antimalarial properties of two series of fluoroalkylated γ-lactams derived from 4-aminoquinoline as potent chemotherapeutic agents for malaria treatment. These molecules obtained in several steps resulted in the identification of very potent structures with in vitro activity against Plasmodium falciparum clones of variable sensitivity (3D7 and W2) in the range of 19-50 nM with resistance indices in the range of 1.0-2.5. In addition, selected molecules (50, 51, 58, 60, 63, 70, 72, 74, 78, 81, 84, and 87) that are representative of the two series of compounds did not show cytotoxicity in vitro when tested against human umbilical vein endothelial cells up to a concentration of 100 μM. The most promising compounds (82 and 84) showed significant IC50 values close to 26 and 19 nM against the chloroquino-sensitive strain 3D7 and 49 and 42 nM against the multi-drug-resistant strain W2. Furthermore, two model compounds (50 and 70) were found to be quite stable over 48 h at pH 7.4 and 5.2. Overall, our preliminary data indicate that this class of structures contains promising candidates for further study.

Synthesis of new trifluoromethylated furans, dihydrofurans and butenolides starting from γ-ketothioesters and diisopropylamine

γ-Ketothioesters were easily transformed into furans, dihydrofurans or butenolides by simple treatment with diisopropylamine in diethyl ether. The substitution pattern of the starting material has a great influence on the outcome of the reaction. Possible