123002-38-0

Basic information

• Product Name: sulfenosine
• Synonyms: sulfenosine;2-Amino-9-β-D-ribofuranosyl-9H-purine-6-sulfenamide
• CAS NO: 123002-38-0
• Molecular Formula: C10H14 N6 O4 S
• Molecular Weight: 314.321
• Mol File: 123002-38-0.mol
• Article Data: 2

Chemical Properties

• Boiling Point: 820.3°Cat760mmHg
• Flash Point: 449.9°C
• Appearance: /
• Density: 2.25g/cm³
• Vapor Pressure: 1.79E-28mmHg at 25°C
• Refractive Index: 1.999
• CAS DataBase Reference: sulfenosine(CAS DataBase Reference)
• NIST Chemistry Reference: sulfenosine(123002-38-0)
• EPA Substance Registry System: sulfenosine(123002-38-0)

Safety Data

• Hazardous Substances Data: 123002-38-0(Hazardous Substances Data)

Usage

InChI:InChI=1/C10H14N6O4S/c11-10-14-7-4(8(15-10)21-12)13-2-16(7)9-6(19)5(18)3(1-17)20-9/h2-3,5-6,9,17-19H,1,12H2,(H2,11,14,15)/t3-,5-,6-,9-/m1/s1

Upstream product

• 85-31-4 6-thioguanosine 

Downstream Products

• 124508-99-2 3-deazasulfinosine 
• 123002-39-1 2-amino-9-β-D-ribofuranosylpurine-6-sulfonamide 

Relevant articles and documents

Synthesis and Antitumor Evaluation in Mice of Certain 7-Deazapurine (Pyrrolopyrimidine) and 3-Deazapurine (Imidazopyridine) Nucleosides Structurally Related to Sulfenosine, Sulfinosine, and Sulfonosine

7-Deaza (pyrrolopyrimidine) and 3-deaza (imidazopyridine congeners of sulfenosine (5a and 9), sulfinosine (6a and 10), and sulfonosine (7a) have been prepared and evaluated for their antileukemic activity in mice.Amination of 2-amino-7-β-D-ribofuranosylpyrrolopyrimidine-4(3H)-thione (4a) and its 2'-deoxy analogue (4c) with a chloramine solution gave the corresponding 4-sulfenamides (5a and 5c, respectively), which on selective oxidation with m-chloroperoxybenzoic acid (MCPBA) gave the respective diastereomeric 2-amino-7-β-D-ribofuranosylpyrrolopyrimidine-4-sulfinamide (7-deazasulfinosine, 6a) and its 2'-deoxy derivative (6c).A similar amination of 7-(2-deoxy-β-D-erythro-pentofuranosyl)pyrrolopyrimidine-4(3H)-thione (4b) gave the corresponding 4-sulfenamide derivative (5b).Oxidation of 5b with 1 molar equiv of MCPBA furnished (R,S)-7-(2-deoxy-β-D-erythro-pentofuranosyl)pyrrolopyrimidine-4-sulfinamide (6b), whereas use of excess of MCPBA afforded the corresponding sulfonamide derivative (7b).Treatment of 3-deaza-6-thioguanosine (8) with a chloramine solution gave 3-deazasulfenosine (6-amino-1-β-D-ribofuranosylimidazopyridine-4-sulfenamide, 9).Controlled oxidation of 9 with MCPBA afforded 3-deazasulfinosine (10).As gauged by increases in the mean postinoculation life spans of L1210 inoculated mice, none of these nucleosides exhibited biologically significant activity (T/C 125).Even so, antileukemic activity appeared to be influenced, albeit not uniformly, by structural modifications in the base and carbohydrate moieties of sulfenosine and sulfinosine.Thus, while several of the compounds were lacking in cytotoxic activity, eight others (4c, 5a, 5c, 6a, 6b, 7b, 9, and 10) were estimated to have reduced body burdens of viable L1210 cells by 16-77percent.