89178-21-2

Basic information

• Product Name: 2-bromo-2'-deoxyadenosine
• Synonyms: NSC-341936
• CAS NO: 89178-21-2
• Molecular Formula: C₁₀H₁₂BrN₅O₃
• Molecular Weight: 330.14
• Mol File: 89178-21-2.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 717.2°C at 760 mmHg
• Flash Point: 387.5°C
• Appearance: /
• Density: 2.3g/cm³
• Vapor Pressure: 1.38E-21mmHg at 25°C
• Refractive Index: 1.898
• CAS DataBase Reference: 2-bromo-2'-deoxyadenosine(CAS DataBase Reference)
• NIST Chemistry Reference: 2-bromo-2'-deoxyadenosine(89178-21-2)
• EPA Substance Registry System: 2-bromo-2'-deoxyadenosine(89178-21-2)

Safety Data

• Hazardous Substances Data: 89178-21-2(Hazardous Substances Data)

Usage

General Description

2-bromo-2'-deoxyadenosine is a synthetic chemical compound that belongs to the class of nucleoside analogs. It is a modified form of the natural nucleoside adenosine, where the hydroxyl group on the 2' carbon of the deoxyribose sugar is replaced with a bromine atom. This modification gives 2-bromo-2'-deoxyadenosine unique properties that make it an effective tool for studying DNA synthesis and repair. It is also being investigated for its potential anti-cancer and antiviral properties, as well as its ability to inhibit the activity of certain enzymes involved in nucleic acid metabolism. Overall, 2-bromo-2'-deoxyadenosine is an important compound in the field of biochemical research and drug development.

InChI:InChI=1/C10H12BrN5O3/c11-10-14-8(12)7-9(15-10)16(3-13-7)6-1-4(18)5(2-17)19-6/h3-6,17-18H,1-2H2,(H2,12,14,15)

Upstream product

• 28128-25-8 2-bromo-9H-purin-6-amine 
• 50-89-5 thymidine 
• 1009639-09-1 O⁶-(benzotriazol-1-yl)-3′,5′-di-O-(t-butyldimethylsilyl)-2′-deoxyguanosine 
• 4330-21-6 2-deoxy-3,5-di-O-p-toluoyl-α-D-erythro-pentofuranosyl chloride 
• 1196-41-4 2,6-dibromopurine 
• 5437-25-2 purine-2,6(1H,3H)-dithione 
• 110096-57-6 2,6-dibromo-9-(2-deoxy-3,5-di-p-toluoyl-β-D-ribofuranosyl)purine 

Downstream Products

• 24757-70-8 2'-deoxyspongosine 
• 146331-56-8 2-bromo-9-<2'-deoxy-5'-O-(4,4'-dimethoxytrityl)-β-D-erythro-pentofuranosyl>-6-<<(dimethylamino)methylidene>amino>-9H-purine 3'-triethylammonium phosphonate 
• 146196-22-7 2-bromo-9-<2'-deoxy-5'-O-(4,4'-dimethoxytrityl)-β-D-erythro-pentofuranosyl>-6-<<(dimethylamino)methylidene>amino>-9H-purine 
• 958-09-8 2'-deoxy-D-adenosine 

Relevant articles and documents

Cladribine analogues via O6-(benzotriazolyl) derivatives of guanine nucleosides

Cladribine, 2-chloro-2'-deoxyadenosine, is a highly efficacious, clinically used nucleoside for the treatment of hairy cell leukemia. It is also being evaluated against other lymphoid malignancies and has been a molecule of interest for well over half a century. In continuation of our interest in the amide bond-activation in purine nucleosides via the use of (benzotriazol-1yl-oxy)tris(dimethylamino)phosphonium hexafluorophosphate, we have evaluated the use of O6-(benzotriazol-1-yl)-2'-deoxyguanosine as a potential precursor to cladribine and its analogues. These compounds, after appropriate deprotection, were assessed for their biological activities, and the data are presented herein. Against hairy cell leukemia (HCL), T-cell lymphoma (TCL) and chronic lymphocytic leukemia (CLL), cladribine was the most active against all. The bromo analogue of cladribine showed comparable activity to the ribose analogue of cladribine against HCL, but was more active against TCL and CLL. The bromo ribose analogue of cladribine showed activity, but was the least active among the C6-NH2-containing compounds. Substitution with alkyl groups at the exocyclic amino group appears detrimental to activity, and only the C6 piperidinyl cladribine analogue demonstrated any activity. Against adenocarcinoma MDA-MB-231 cells, cladribine and its ribose analogue were most active.

Convenient Synthesis of 2-Halo-2'-deoxyadenosines

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