166247-63-8

Basic information

• Product Name: 7-DEAZA-7-IODO-2'-DEOXYADENOSINE
• Synonyms: 7-DEAZA-7-IODO-2'-DEOXYADENOSINE;7-Deaza-7-Iodo-2'-deoxyadeonsine;5-Iodo-2'-deoxytubercidin;7-I-7-Deaza-dA;7-(2-Deoxy-beta-D-erythro-pentofuranosyl)-5-iodo-7H-pyrrolo[2,3-d]pyrimidin-4-amine;7-Iodo-7-deaza-2'-deoxyadenosine;(2R,3S,5R)-5-(4-Amino-5-iodo-7H-pyrrolo[2,3-d]pyrimidin-7-yl)-2-(hydroxymethyl)tetrahydrofuran-3-ol;2'-Deoxy-7-iodotubercidin
• CAS NO: 166247-63-8
• Molecular Formula: C₁₁H₁₃IN₄O₃
• Molecular Weight: 376.15
• EINECS: 2017-001-1
• Product Categories: Pharmaceuticals;Intermediates & Fine Chemicals;Heterocycles;Aromatics;Amines, Aromatics, Heterocycles, Pharmaceuticals, Intermediates & Fine Chemicals;Amines
• Mol File: 166247-63-8.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 657.4±55.0 °C(Predicted)
• Appearance: /
• Density: 2.35±0.1 g/cm3(Predicted)
• Storage Temp.: 2-8°C(protect from light)
• Solubility: DMSO (Slightly), Methanol (Slightly, Heated)
• PKA: 13.27±0.60(Predicted)
• Stability: Light Sensitive
• CAS DataBase Reference: 7-DEAZA-7-IODO-2'-DEOXYADENOSINE(CAS DataBase Reference)
• NIST Chemistry Reference: 7-DEAZA-7-IODO-2'-DEOXYADENOSINE(166247-63-8)
• EPA Substance Registry System: 7-DEAZA-7-IODO-2'-DEOXYADENOSINE(166247-63-8)

Safety Data

• Hazardous Substances Data: 166247-63-8(Hazardous Substances Data)

Usage

Uses

5-Iodo-2’-deoxytubercidin is a derivative of 7-Iodo-7-deazadenine designed to be incorporated into DNA by primers extension by using Vent(exo-) polymerase. Possesses photophysical properties.

Upstream product

• 4330-21-6 2-deoxy-3,5-di-O-p-toluoyl-α-D-erythro-pentofuranosyl chloride 
• 123148-78-7 4-chloro-5-iodo-7H-pyrrolo[2,3-d]pyrimidine 
• 178420-94-5 (2R,3S,5R)-5-(4-chloro-5-iodo-7H-pyrrolo[2,3-d]pyrimidin-7-yl)-2-(((4-methylbenzoyl)oxy)methyl)tetrahydrofuran-3-yl 4-methylbenzoate 
• 178995-71-6 9-(β-D-2'-deoxyribofuranosyl)-6-chloro-7-iodo-7-deazapurine 

Downstream Products

• 1429057-66-8 C₅₁H₄₅N₅O₅ 
• 1429057-68-0 C₆₀H₆₂N₇O₆P 
• 1810869-43-2 ((2R,3S,5R)-5-(4-amino-5-iodo-7H-pyrrolo[2,3-d]pyrimidin-7-yl)-3-((tert-butyldimethylsilyl)oxy)tetrahydrofuran-2-yl)methanol 

Relevant articles and documents

The DNA-stabilising nucleoside 7-iodo-2′-deoxytubercidin: Its structure in the solid state and in solution

The crystal structure of 7-iodo-2′-deoxytubercidin 2 has been determined and was compared with those of 2′-deoxytubercidin 3 and 2′-deoxyadenosine 4. The bulky 7-iodo substituent lies 13.2 pm below and the nitrogen of the 6-amino group 5.5 pm above the 7-deazapurine plane. The puckering of compound 2 is 3′E while compound 3 shows a 2′T3′ sugar pucker. The conformation in aqueous solution, determined by 1H NMR spectroscopy, is only slightly different, showing a 2′E conformation. The glycosylic bond torsion angle is anti in all cases.

4'-SUBSTITUTED NUCLEOSIDE REVERSE TRANSCRIPTASE INHIBITORS

Provided is 4'-substituted nucleoside derivatives of Formula I and their use in the inhibition of HIV reverse transcriptase, the prophylaxis of infection by HIV, the treatment of infection by HIV, and the prophylaxis, treatment, and delay in the onset or progression of AIDS and/or ARC.

Palladium-catalyzed cross coupling of 7-iodo-2'-deoxytubercidin with terminal alkynes

The 7-alkynyl-2'-deoxytubercidins (7-deaza-2'-deoxyadenosines) 7-17 have been prepared by the Pd(0)/Cu(I)-catalyzed cross coupling of 7-iodo-2'-deoxytubercidin (2d) with terminal alkynes. The coupling products include 17α-ethynyltestosterone and 17α-ethynylestradiol derivatives (16, 17).