4303-00-8

Basic information

• Product Name: 9-(4-thiopentofuranosyl)-9H-purin-6-amine
• CAS NO: 4303-00-8
• Molecular Formula: C₁₀H₁₃N₅O₃S
• Molecular Weight: 283.3069
• Mol File: 4303-00-8.mol
• Article Data: 9

Chemical Properties

• Boiling Point: 657.8°C at 760 mmHg
• Flash Point: 351.6°C
• Density: 2.08g/cm³
• Vapor Pressure: 3.38E-18mmHg at 25°C
• Refractive Index: 1.962
• CAS DataBase Reference: 9-(4-thiopentofuranosyl)-9H-purin-6-amine(CAS DataBase Reference)
• NIST Chemistry Reference: 9-(4-thiopentofuranosyl)-9H-purin-6-amine(4303-00-8)
• EPA Substance Registry System: 9-(4-thiopentofuranosyl)-9H-purin-6-amine(4303-00-8)

Safety Data

• Hazardous Substances Data: 4303-00-8(Hazardous Substances Data)

Upstream product

• 187590-77-8 1,4-anhydro-2,3,5-tri-O-benzyl-4-thio-D-arabinitol 
• 2495-74-1 1,2,3,5-tetra-O-acetyl-4-thio-D-ribofuranose 
• 187590-79-0 (2R,3S,4S)-3,4-Bis-benzyloxy-2-benzyloxymethyl-tetrahydro-thiophene 1-oxide 
• 169736-20-3 1-O-acetyl-2,3,5-tri-O-benzyl-4-thio-D-arabinofuranose 
• 160882-25-7 3-O-benzyl-1-deoxy-4-thio-D-arabino-furanose 
• 191794-50-0 9-((3S,4S,5R)-3,4-Bis-benzyloxy-5-benzyloxymethyl-tetrahydro-thiophen-2-yl)-9H-purin-6-ylamine 
• 161424-49-3 2,3,5-tri-O-benzyl-4-O-p-nitrobenzoyl-L-lyxose dithiobenzylacetal 
• 161512-40-9 1-O-acetyl-2,3,5-tri-O-benzyl-4-thio-α,β-D-ribofuranose 
• 144950-26-5 2,3,5-tri-O-benzyl-L-lyxose dibenzyldithioacetal 
• 153439-75-9 2,3,5-tri-O-benzyl-D-ribose dibenzyldithioacetal 
• 158852-11-0 benzyl 2,3,5-tri-O-benzyl-1,4-dithio-D-ribofuranoside 
• 66224-66-6 adenine 
• 64363-77-5 methyl 2,3,5-tri-O-benzyl-D-ribofuranoside 
• 161424-52-8 9-(2,3,5-tri-O-benzyl-4-thio-α-D-ribofuranosyl)-adenine 

Relevant articles and documents

Inhibitory effects of 9-(4-Thio-β-D-ribo-pentofuranosyl)guanine on tumor growth and angiogenesis

Background: To find a nucleoside with anti-angiogenic activity, we tried to screen an active compound from our nucleoside library. Materials and Methods: The compound inhibiting the growth of human umbilical vein endothelial cell (HUVEC) induced by the conditioned medium of lung carcinoma cell line PC-9 was screened. The antitumor activity of the compound was evaluated against murine sarcoma S-180 implanted onto chick embryo chorioallantoic membrane (CAM). Results: 9-(4-Thio-β-D-ribo-pentofuranosyl)guanine (4′-thioguanosine) was found to be a potent inhibitor of the growth of HUVEC. The growth of S-180 implanted onto CAM was also inhibited by 4′-thioguanosine whereas the in vitro growth of S-180 was not inhibited. The administration of 4′-thioguanosine in mice caused unexpected side effect which suggested neurotoxicity. Conclusions: Antitumor effect of 4′-thioguanosine on S-180 was suggested to be due to inhibition of tumor angiogenesis. Because of toxicity of 4′-thioguanosine in mice, further development of the derivatives which have lower toxicity is required.

Design, synthesis, and biological activity of N6-substituted-4′-thioadenosines at the human A3 adenosine receptor

A large series of N6-substituted-4′-thioadenosines were synthesized starting from d-gulonic-γ-lactone, and structure-activity relationships were studied at the human A3 and other subtypes of adenosine receptors (ARs). 2-Chloro-substi

Thiosugars. X. Novel nucleoside analogues derived from 4-thio-L-lyxofuranose

1-O-Acetyl-2,3,5-tri-O-benzyl-4-thio-L-lyxofuranose 1 was transformed into O-benzyl- and O-acetyl-protected 1-(4-thio-L-lyxofuranosyl) nucleoside derivatives by use of the TMSOTf method. Debenzylation with boron tribromide or deacetylation with sodium methoxide yielded the corresponding pyrimidine (7-11, 17, 18, 26 and 27) and purine (29 and 34) nucleoside analogues. The anomeric configurations were determined by NMR spectroscopy and, in the case of the 5-halo- (7-9) and nitrouridine derivative 11 and the 6-methylcytidine derivative 27, by X-ray structural analyses. - The unprotected nucleosides were not anti-virically inhibitory at 250 μM.