59587-07-4

Basic information

• Product Name: 2-Azidoadenosine
• Synonyms: NSC 36905
• CAS NO: 59587-07-4
• Molecular Formula: C₁₀H₁₂N₈O₄
• Molecular Weight: 308.25
• Product Categories: Nucleotides and Nucleosides;Bases & Related Reagents;Nucleotides
• Mol File: 59587-07-4.mol
• Article Data: 4

Chemical Properties

• Melting Point: 170-172°C
• Appearance: Off-white to grey solid
• Storage Temp.: -20°C Freezer
• CAS DataBase Reference: 2-Azidoadenosine(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Azidoadenosine(59587-07-4)
• EPA Substance Registry System: 2-Azidoadenosine(59587-07-4)

Safety Data

• Hazardous Substances Data: 59587-07-4(Hazardous Substances Data)

Usage

Description

2-Azidoadenosine is a modified nucleoside that features an azide group at the 2' position of the adenosine molecule. It is a significant compound in the field of medicinal chemistry and has potential applications in various industries due to its unique chemical properties.

Uses

Used in Pharmaceutical Industry:
2-Azidoadenosine is used as a synthetic intermediate for the development of potent and selective coronary vasodilators. These vasodilators are crucial in treating various cardiovascular conditions by improving blood flow and reducing the workload on the heart.
Used in Chemical Research:
As a modified nucleoside, 2-Azidoadenosine can be employed in chemical research to study the effects of structural modifications on the biological activity of adenosine and its derivatives. This can lead to the discovery of new therapeutic agents with improved properties.
Used in Drug Development:
The unique azide functionality in 2-Azidoadenosine allows for further chemical modifications and the development of new drug candidates with potential applications in various therapeutic areas, such as cardiovascular, neurological, and antiviral treatments.

InChI:InChI=1/C10H12N8O4/c11-7-4-8(15-10(14-7)16-17-12)18(2-13-4)9-6(21)5(20)3(1-19)22-9/h2-3,5-6,9,19-21H,1H2,(H2,11,14,15)/t3-,5-,6-,9-/m1/s1

Synthetic route

Acetic acid (2R,3R,4R,5R)-4-acetoxy-5-acetoxymethyl-2-(2-azido-6-chloro-purin-9-yl)-tetrahydro-furan-3-yl ester (174500-37-9) → 2-Azidoadenosine (59587-07-4)

Conditions	Yield
With ammonia In ethanol at 30℃; for 48h;	89%

2-Chloroadenosine (146-77-0) → 2-Azidoadenosine (59587-07-4)

Conditions	Yield
Stage #1: 2-Chloroadenosine With hydrazine hydrate at 20℃; for 16h; Stage #2: With acetic acid; sodium nitrite In water for 1h; cooling;	61%
Multi-step reaction with 2 steps 1: H2NNH2*H2O / 20 °C 2: NaNO2; acetic acid / H2O / 0 °C View Scheme

2-hydrazono-adenosine → 2-Azidoadenosine (59587-07-4)

Conditions	Yield
With acetic acid; sodium nitrite

2-hydrazinoadenosine (15763-11-8) → 2-Azidoadenosine (59587-07-4)

Conditions	Yield
With acetic acid; sodium nitrite In water at 0℃;

1-O-acetyl-2,3,5-tri-O-benzoyl-β-D-ribofuranose (6974-32-9) + thioether-bound (4-hydroxypyrimidine-2-yl)-Merrifield resin → 2-Azidoadenosine (59587-07-4)

Conditions	Yield
Multi-step reaction with 3 steps 1.1: SnCl4 / acetonitrile / 20 °C 2.1: NH3 / methanol / 20 °C 3.1: hydrazine monohydrate / 16 h / 20 °C 3.2: 61 percent / sodium nitrite; acetic acid / H2O / 1 h / cooling View Scheme

(2R,3R,4R,5R)-2-((benzoyloxy)methyl)-5-(2,6-dichloro-9H-purin-9-yl)tetrahydrofuran-3,4-diyl dibenzoate (15373-23-6) → 2-Azidoadenosine (59587-07-4)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: NH3 / methanol / 20 °C 2.1: hydrazine monohydrate / 16 h / 20 °C 2.2: 61 percent / sodium nitrite; acetic acid / H2O / 1 h / cooling View Scheme

2,6 dichloropurine (5451-40-1) → 2-Azidoadenosine (59587-07-4)

Conditions	Yield
Multi-step reaction with 3 steps 1.1: SnCl4 / acetonitrile / 20 °C 2.1: NH3 / methanol / 20 °C 3.1: hydrazine monohydrate / 16 h / 20 °C 3.2: 61 percent / sodium nitrite; acetic acid / H2O / 1 h / cooling View Scheme

2-amino-6-chloro-9-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)purine (16321-99-6) → 2-Azidoadenosine (59587-07-4)

Conditions	Yield
Multi-step reaction with 2 steps 1: 75 percent / isoamyl nitrite, trimethylsilyl azide / acetonitrile / 1) -20 deg C, 12 h; 2) 0 deg C, 2 d 2: 89 percent / NH3 / ethanol / 48 h / 30 °C View Scheme

G (118-00-3) → 2-Azidoadenosine (59587-07-4)

Conditions	Yield
Multi-step reaction with 4 steps 1: pyridine / dimethylformamide 2: POCl, Et4NCl, N,N-dimethylaniline / acetonitrile 3: 75 percent / isoamyl nitrite, trimethylsilyl azide / acetonitrile / 1) -20 deg C, 12 h; 2) 0 deg C, 2 d 4: 89 percent / NH3 / ethanol / 48 h / 30 °C View Scheme

2',3',5'-tri-O-acetyl-guanosine (6979-94-8) → 2-Azidoadenosine (59587-07-4)

Conditions	Yield
Multi-step reaction with 3 steps 1: POCl, Et4NCl, N,N-dimethylaniline / acetonitrile 2: 75 percent / isoamyl nitrite, trimethylsilyl azide / acetonitrile / 1) -20 deg C, 12 h; 2) 0 deg C, 2 d 3: 89 percent / NH3 / ethanol / 48 h / 30 °C View Scheme

2-azido-9-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)-9H-purin-6-amine → 2-Azidoadenosine (59587-07-4)

Conditions	Yield
With methanol; ammonia at 50℃; for 15h; Inert atmosphere;

2-Azidoadenosine (59587-07-4) → 2-azidoadenosine 5'-triphosphate

Conditions	Yield
With trimethyl phosphite; tri(n-butyl)ammonium pyrophosphate; trichlorophosphate	58%

2-Azidoadenosine (59587-07-4) → C10H13N9O12P3(3-)

Conditions	Yield
With trimethyl phosphite; (Bu3NH)4*(PO3)2NH; trichlorophosphate	58%

2-Azidoadenosine (59587-07-4) → (2R,3R,4S,5R)-2-(8-Amino-tetrazolo[1,5-a]purin-5-yl)-5-hydroxymethyl-tetrahydro-furan-3,4-diol

Conditions	Yield
In dimethylsulfoxide-d6 at 24.85℃; Equilibrium constant; Thermodynamic data; Further Variations:; Solvents; Temperatures;

2-Azidoadenosine (59587-07-4) + 2,2-dimethoxy-propane (77-76-9) → 2-azido-2',3'-O-isopropylideneadenosine (160150-06-1)

Conditions	Yield
With toluene-4-sulfonic acid In acetone at 20℃; for 16h; Inert atmosphere;	1.57 g

(3-(5H,6H-11,12-didehydrodibenzo[b,f]azocin-5-yl)-3-oxopropyl)amine (1255942-06-3) + 2-Azidoadenosine (59587-07-4) → C28H28N10O5 + C28H28N10O5

Conditions	Yield
In methanol at 20℃; for 16h;

(1R,8S)-9-hydroxymethyl-bicyclo[6.1.0]nonyne + 2-Azidoadenosine (59587-07-4) → C20H26N8O5 + C20H26N8O5

Conditions	Yield
In water; acetonitrile at 20℃; for 2h; Overall yield = 100 %; Overall yield = 9.3 mg;

triethylamine carbonate (15715-58-9) + 2-Azidoadenosine (59587-07-4) → 2-azidoadenosine monophosphate triethylammonium salt + (x)C6H15N*C10H13N8O7P

Conditions	Yield
Stage #1: 2-Azidoadenosine With trimethyl phosphite; N,N,N',N'-tetramethyl-1,8-diaminonaphthalene; trichlorophosphate In acetonitrile at 0℃; Stage #2: triethylamine carbonate In acetonitrile at 0℃; for 0.5h;	A 60 %Spectr. B 40 %Chromat.

triethylamine carbonate (15715-58-9) + 2-Azidoadenosine (59587-07-4) → 2-azidonicotinamide adenosine diphosphate triethylammonium salt + (x)C6H15N*C21H27N10O14P2(1+)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: trichlorophosphate; trimethyl phosphite; N,N,N',N'-tetramethyl-1,8-diaminonaphthalene / acetonitrile / 0 °C 1.2: 0.5 h / 0 °C 2.1: triethylamine; 1,1'-carbonyldiimidazole / N,N-dimethyl-formamide / 4 h / 20 °C 2.2: 96 h / 20 °C View Scheme

Upstream product

• 174500-37-9 Acetic acid (2R,3R,4R,5R)-4-acetoxy-5-acetoxymethyl-2-(2-azido-6-chloro-purin-9-yl)-tetrahydro-furan-3-yl ester 
• 146-77-0 2-Chloroadenosine 
• 15763-11-8 2-hydrazinoadenosine 
• 6974-32-9 1-O-acetyl-2,3,5-tri-O-benzoyl-β-D-ribofuranose 
• 15373-23-6 (2R,3R,4R,5R)-2-((benzoyloxy)methyl)-5-(2,6-dichloro-9H-purin-9-yl)tetrahydrofuran-3,4-diyl dibenzoate 
• 5451-40-1 2,6 dichloropurine 
• 16321-99-6 2-amino-6-chloro-9-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)purine 
• 118-00-3 G 
• 6979-94-8 2',3',5'-tri-O-acetyl-guanosine 

Relevant articles and documents

Inhibition of siderophore biosynthesis by 2-triazole substituted analogues of 5′-O-[N-(salicyl)sulfamoyl]adenosine: Antibacterial nucleosides effective against Mycobacterium tuberculosis

The synthesis, biochemical, and biological evaluation of a systematic series of 2-triazole derivatives of 5′-O-[N-(salicyl)sulfamoyl]adenosine (Sal-AMS) are described as inhibitors of aryl acid adenylating enzymes (AAAE) involved in siderophore biosynthesis by Mycobacterium tuberculosis. Structure-activity relationships revealed a remarkable ability to tolerate a wide range of substituents at the 4-position of the triazole moiety, and a majority of the compounds possessed subnanomolar apparent inhibition constants. However, the in vitro potency did not always translate into whole cell biological activity against M. tuberculosis, suggesting that intrinsic resistance plays an important role in the observed activities. Additionally, the well-known valence tautomerism between 2-azidopurines and their fused tetrazole counterparts led to an unexpected facile acylation of the purine N-6 amino group.

Synthesis and biological evaluation of β-D-pentofuranonucleoside derivatives of 2-azidoadenine and 6-azidopurines

β-D-pentofuranonucleoside derivatives of 2-azidoadenine and 6-azidopurines have been synthesized. The azido-tetrazolo tautomerism observed on such nucleoside analogues has been studied. The compounds were tested for their activity against HIV and HBV but they did not show significant antiviral effect.