161407-67-6

Basic information

• Product Name: 1,4:5,8-dianhydro-2-carbamoyl-2,3-dideoxy-1-thionona-1,3-dienitol
• CAS NO: 161407-67-6
• Molecular Formula: C₁₀H₁₃NO₅S
• Molecular Weight: 259.2789
• Mol File: 161407-67-6.mol
• Article Data: 2

Chemical Properties

• Boiling Point: 566.7°C at 760 mmHg
• Flash Point: 296.6°C
• Density: 1.574g/cm³
• Vapor Pressure: 1.11E-13mmHg at 25°C
• Refractive Index: 1.665
• CAS DataBase Reference: 1,4:5,8-dianhydro-2-carbamoyl-2,3-dideoxy-1-thionona-1,3-dienitol(CAS DataBase Reference)
• NIST Chemistry Reference: 1,4:5,8-dianhydro-2-carbamoyl-2,3-dideoxy-1-thionona-1,3-dienitol(161407-67-6)
• EPA Substance Registry System: 1,4:5,8-dianhydro-2-carbamoyl-2,3-dideoxy-1-thionona-1,3-dienitol(161407-67-6)

Safety Data

• Hazardous Substances Data: 161407-67-6(Hazardous Substances Data)

Usage

General Description

1,4:5,8-dianhydro-2-carbamoyl-2,3-dideoxy-1-thionona-1,3-dienitol is a complex chemical compound with a long and precise molecular structure. It contains carbamoyl and dideoxy groups, as well as a unique combination of anhydro and thionona moieties. The compound is a non-nucleoside inhibitor of HIV reverse transcriptase and has potential antiviral properties. Its unique structure and potential medicinal applications make it an interesting subject for further research and development in the field of pharmaceutical chemistry.

Upstream product

• 13035-61-5 1,2,3,5-tetraacetylribose 
• 5751-80-4 thiophene-3-carboxylic acid ethyl ester 

Relevant articles and documents

Furanfurin and Thiophenfurin: Two Novel Thiazofurin Analogues. Synthesis, Structure, Antitumor Activity, and Interactions with Inosine Monophosphate Dehydrogenase

The syntheses of furan and thiophene analogues of tiazofurin (furanfurin and thiophenfurin), respectively) are described.Direct stannic chloride-catalyzed C-glycosylation of ethyl 3-furancarboxylate (6) or ethyl 3-thiophencarboxylate (18) with 1,2,3,5-tetra-O-acetyl-D-ribofuranose gave 2- and 5-glycosylated regioisomers, as a mixture of α- and β-anomers, and the β-2,5-diglycosylated derivatives.Deprotection of ethyl 5-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)furan-3-carboxylate (9β) and ethyl 5-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)thiophene-3-carboxylate (20β) with sodium ethoxide afforded ethyl 5-β-D-ribofuranosylfuran-3-carboxylate (12β) and ethyl 5-β-D-ribofuranosylthiophene-3-carboxylate (23β) which were converted into 5-β-D-ribofuranosylfuran-3-carboxamide (furanfurin, 4) and 5-β-D-ribofuranosylthiophene-3-carboxamide (thiophenfurin, 5) by reaction with ammonium hydroxide.The anomeric configuration and the site of glycosylation were established by 1H-NMR and proton-proton nuclear Overhauser effect difference spectroscopy.The structure of compound 23β was confirmed by X-ray crystallography.Thiophenfurin was found to be cytotoxic in vitro toward murine lymphocytic leukemia P388 and L1210, human myelogenous leukemia K562, human promyelocytic leukemia HL-60, human colon adenocarcinoma LoVo, and B16 melanoma at concentrations similar to that of tiazofurin.In the same test furanfurin proved to be inactive.Thiophenfurin was found active in vivo in BD2F1 mice inoculated with L1210 cells with a percent T/C of 168 at 25 mg/kg.K562 cells incubation with thiophenfurin resulted in inhibition of inosine monophosphate (IMP) dehydrogenase (63percent) and increase in IMP pools (6-fold) with a concurrent decrease in GTP levels (42percent).Incubation of adenosine-labeled K562 cells with thiazofurin, thiophenfurin, and furanfurin resulted in a 2-fold higher NAD analogue formulation by thiophenfurin, and furanfurin resulted in a 2-fold higher NAD analogue formulation by thiophenfurin than by tiazofurin.Furanfurin was converted to the NAD analogue with only 10percent efficiency.The results obtained support the hypothesis that the presence of S in the heterocycle in position 2 with respect to the glycosidic bond is essential for the cytotoxicity and IMP dehydrogenase activity of tiazofurin, while the N atom is not.