24723-77-1

Basic information

• Product Name: Spongosine
• Synonyms: 2-Methoxyadenosine;Spongosine;Adenosine, 2-methoxy-
• CAS NO: 24723-77-1
• Molecular Formula: C11H15 N5 O5
• Molecular Weight: 297.2673
• Mol File: 24723-77-1.mol

Chemical Properties

• Melting Point: 193 °C
• Boiling Point: 705°Cat760mmHg
• Flash Point: 380.2°C
• Appearance: /
• Density: 1.98g/cm³
• Vapor Pressure: 7.3E-21mmHg at 25°C
• Refractive Index: 1.829
• PKA: 13.07±0.70(Predicted)
• CAS DataBase Reference: Spongosine(CAS DataBase Reference)
• NIST Chemistry Reference: Spongosine(24723-77-1)
• EPA Substance Registry System: Spongosine(24723-77-1)

Safety Data

• Hazardous Substances Data: 24723-77-1(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
Spongosine is used as a potential antiviral agent for its noted antiviral activities, which could be harnessed in the development of new antiviral medications.
Used in Cancer Research:
Spongosine is used as a cytotoxic agent for its potential to exhibit cytotoxic effects, making it a candidate for further research in cancer treatment and drug development.
Used in Drug Discovery:
Spongosine is used as a compound of interest for its unique chemical structure and potential applications in medicinal chemistry, which could lead to the discovery of new drugs with novel mechanisms of action.

InChI:InChI=1/C11H15N5O5/c1-20-11-14-8(12)5-9(15-11)16(3-13-5)10-7(19)6(18)4(2-17)21-10/h3-4,6-7,10,17-19H,2H2,1H3,(H2,12,14,15)

Upstream product

• 28128-30-5 2-methoxy-7⁽⁹⁾H-purin-6-ylamine 
• 124-41-4 sodium methylate 
• 146-77-0 2-Chloroadenosine 
• 266360-70-7 2-nitroadenosine pentaacetate 
• 67-56-1 methanol 
• 266360-74-1 6-amino-2-nitro-9-(2',3',5'-tri-O-acetyl-β-D-ribofuranosyl)-purine 
• 62420-34-2 6,6-diacetylamino-9-[(2,3,5-tri-O-acetyl)-β-D-ribofuranosyl]purine 
• 7387-57-7 triacetyladenosine 
• 31528-52-6 2-(Ethylthio)adenosine 
• 14215-97-5 1-O-acetyl-2,3,5-tri-O-benzoyl-D-ribofuranose 
• 56720-43-5 2-chloro-2',3'-O-(ethoxymethylidene) adenosine 
• 88508-72-9 2,6-dimethoxy-9-(β-D-ribofuranosyl)-9H-purine 
• 854158-99-9 2-nitro-pentabenzoyl adenosine 
• 869477-34-9 2’,3’,5’-O-tri(t-butyldimethylsilyl)-O⁶-methylguanosine 

Downstream Products

• 756818-82-3 C₁₇H₁₈N₆O₅ 

Relevant articles and documents

A new method for synthesis of 2-alkoxyadenosine analogs

O6-Methylguanosine and 2-amino-6-chloropurine riboside derivative were treated with isoamylnitrite in the presence of an appropriate alcohol to give the corresponding 2-alkoxy-6-methoxy (or chloro) purine riboside derivatives.

Regioselective nitration of purine nucleosides: Synthesis of 2- nitroadenosine and 2-nitroinosine

Nitration reactions of 6-substituted purine nucleosides with tetrabutylammonium nitrate/trifluoroacetic anhydride (TBAN/TFAA) have been studied. This nitrating mixture selectively nitrates C-6 substituted purines at the 2-position, but the method is limited to substrates without NH or OH substituents. Acetylated 6-chloropurine riboside was cleanly nitrated (DCM, 0°C, 71%) and converted to nitro substituted adenosine and inosine in a few simple steps. (C) 2000 Elsevier Science Ltd.

SYNTHESIS OF SPONGOSINE

Reaction of 1-O-acetyl-2,3,5-tri-O-benzoyl-β-D-ribofuranose with 2-methoxyadenine to form 9-(2’,3’,5’-tri-O-benzoyl-β-D-ribofuranosyl)-2-methoxyadenine, then deprotection of the 9-(2’,3’,5’-tri-O-benzoyl-β-D-ribofuranosyl)-2-methoxyadenine to form spongosine is described. Synthesis of intermediates for use in the synthesis of spongosine is also described.

IMPROVED SYNTHESIS OF 2-SUBSTITUTED ADENOSINES

Synthesis of 2-substituted adenosines of formula (I) using 2-nitro pentabenzoyl adenosine, or 2-nitro pentaacetyl adenosine, as intermediate is described: Formula (I) wherein R = C1-6 alkoxy (straight or branched), a phenoxy group (unsubstitute

IMPROVED SYNTHESIS OF 2-SUBSTITUTED ADENOSINES

A method of synthesis of a 2-substituted adenosine of formula I which comprises converting a compound of formula II to a compound of formula (I), wherein: R is C 1-6 alkoxy (straight or branched), a phenoxy group (unsubstituted, or mono-, or di-substituted by halo, amino, CF3-, cyano, nitro, C 1-6 alkyl, or C 1-6 alkoxy), a benzyloxy group (unsubstituted, or mono-, or di-substituted by halo, amino, CF3-, cyano, nitro, Cl_6 alkyl, or Cl_6 alkoxy), or a benzoyl group (unsubstituted, or mono-, or di-substituted by halo, amino, CF3-, cyano, nitro, C 1-6 alkyl, or C 1-6 alkoxy); R' = H, or a protecting group.

Anti-HCV nucleoside derivatives

The present invention comprises novel and known purine and pyrimidine nucleoside derivatives which have been discovered to be active against hepatitis C virus (HCV). The use of these derivatives for the treatment of HCV infection is claimed as are the novel nucleoside derivatives disclosed herein.

Formation of 2'-deoxy-2-nitroadenosines by reaction of 2'-deoxyadenosines with copper(II) nitrate/acetic anhydride.

Nitration of 9-substituted [ethyl, (Ac)2-2'-deoxyribosyl, (Ac)3-ribosyl] N6-acetyladenine derivatives with Cu(NO3)2.3H2O/Ac2O was examined. Nitration proceeded at the 2-position, although the yield was low. Removal of the acetyl groups gave 2'-deoxy-2-nitroadenosine derivatives.

2-Nitro analogues of adenosine and 1-deazaadenosine: Synthesis and binding studies at the adenosine A1, A(2A) and A3 receptor subtypes

The influence of nitro substituents on the properties of adenosine and 1-deazaadenosine was studied. Combination of a nitro group at the 2-position with several N6 substituents such as cyclopentyl and m-iodobenzyl gave a series of analogues with good adenosine receptor affinity, showing directable selectivity for the A1, A(2A) and A3 adenosine receptor subtypes. (C) 2000 Elsevier Science Ltd.

A simple method for synthesis of spongosine, azaspongosine, and their antiplatelet effects

Reaction of 2-ethylthioadenine (1) with protected ribose (2) in the presence of stannic chloride gave 2-ethylthioadenosine (4). Oxidation of 5 with potassium permanganate yielded the corresponding sulfone (6) which furnished spongosine (7) after treatment with sodium methoxide. Similarly, reactions of 7-amino-5-ethylthio-1,2,3 triazolo[4,5-d]pyrimidine (8) with the ribose (2) gave 8-azaspongosine (13). The compounds (4) and 7 demonstrated potent antiaggregatory effects both in human platelet-rich plasma and whole blood, whereas, the aza analog (13) showed no inhibitory activity on platelet aggregation. Both (4) and (7) inhibit platelet aggregation in the presence of adenosine deaminase, whereas, adenosine is non-inhibitory, suggesting that analogs (4) and (7) are poor substrates for adenosine deaminase.

2-Alkoxyadenosines: Potent and selective agonists at the coronary artery A2 adenosine receptor

A Langendorff guinea pig heart preparation served for the assay of agonist activity of a series of 24 2-alkoxyadenosines at the A1 and A2 adenosine receptors of, respectively, the atrioventricular node (conduction block) and coronary