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

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

Used in Pharmaceutical Industry:
7-DEAZA-7-IODO-2'-DEOXYADENOSINE is used as a therapeutic agent for the treatment of certain types of cancer. Its unique chemical structure allows it to be incorporated into DNA during replication, leading to the inhibition of DNA synthesis and ultimately causing cell death in cancerous cells. The compound's photophysical properties also enable it to be used in photodynamic therapy, where it can generate reactive oxygen species upon light activation, causing damage to cancer cells.
Used in Research and Development:
7-DEAZA-7-IODO-2'-DEOXYADENOSINE is utilized as a research tool in the study of nucleic acid biochemistry, molecular biology, and drug discovery. Its ability to be incorporated into DNA by primer extension using specific polymerases makes it a valuable probe for investigating DNA replication, repair, and mutagenesis. Additionally, its photophysical properties can be exploited in the development of novel imaging techniques and sensors for monitoring cellular processes and detecting specific molecular targets.
Used in Diagnostic Applications:
The unique properties of 7-DEAZA-7-IODO-2'-DEOXYADENOSINE also make it a potential candidate for use in diagnostic applications. Its ability to be incorporated into DNA and its photophysical properties can be harnessed to develop assays for detecting specific genetic mutations, monitoring disease progression, or assessing the efficacy of therapeutic interventions.

Upstream product

• 178995-71-6 9-(β-D-2'-deoxyribofuranosyl)-6-chloro-7-iodo-7-deazapurine 
• 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 
• 123148-78-7 4-chloro-5-iodo-7H-pyrrolo[2,3-d]pyrimidine 
• 4330-21-6 2-deoxy-3,5-di-O-p-toluoyl-α-D-erythro-pentofuranosyl chloride 

Downstream Products

• 178995-74-9 7-(2-deoxy-β-D-erythro-pentofuranosyl)-5-(phenylethynyl)-7H-pyrrolo[2,3-d]pyrimidin-4-amine 
• 178420-75-2 7-(2-deoxy-β-D-erythro-pentofuranosyl)-5-[3-(3-trifluoroacetamido)prop-1-ynyl]-7H-pyrrolo[2,3-d]pyrimidin-4-amine 
• 15676-19-4 4-amino-5-cyano-7-(2-deoxy-β-D-erythro-pentofuranosyl)-7H-pyrrolo[2,3-d]pyrimidine 
• 60129-59-1 2'-deoxy-7-deazaadenosine 
• 375346-80-8 N-(7-{5-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-hydroxy-tetrahydro-furan-2-yl}-5-iodo-7H-pyrrolo[2,3-d]pyrimidin-4-yl)-acetamide 
• 375346-76-2 N-{7-{5-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-hydroxy-tetrahydro-furan-2-yl}-5-[3-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-prop-1-ynyl]-7H-pyrrolo[2,3-d]pyrimidin-4-yl}-acetamide 
• 83379-28-6 4-amino-5-carboxamido-7-(2-deoxy-β-D-erythro-pentofuranosyl)-7H-pyrrolo[2,3-d]pyrimidine 
• 259244-23-0 5-cyano-7-[2-deoxy-5-O-(4,4'-dimethoxytriphenylmethyl)-β-D-erythro-pentofuranosyl]-4-{[(dimethylamino)-methylene]amino}-7H-pyrrolo[2,3-d]pyrimidine 
• 200066-17-7 7-[2-deoxy-5-O-(4,4'-dimethoxytriphenylmethyl)-β-D-erythro-pentofuranosyl]-N⁴-[(dimethylamino)methylidene]-5-[(3-trifluoroacetamido)prop-1-ynyl]-7H-pyrrolo[2,3-d]pyrimidin-4-amine 
• 259097-15-9 7-[2-deoxy-5-O-(4,4'-dimethoxytriphenylmethyl)-β-D-erythro-pentofuranosyl]-N⁴-[(dimethylamino)methylidene]-5-(dodec-1-ynyl)-7H-pyrrolo[2,3-d]pyrimidin-4-amine 

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.

Synthesis and photophysical evaluation of new fluorescent 7-arylethynyl-7-deazaadenosine analogs

Three new fluorescent 7-deaza-2′-deoxyadenosine analogs were synthesized via the Sonogashira cross-coupling reaction of 7-iodo-7-deaza-2′-deoxyadenosine with 1-ethynylpyrene, 2-ethynyl-6-methoxynaphthalene, and 9-ethynylphenanthrene. The spectral properties of these analogs were evaluated in dioxane, EtOH, and H2O to determine their potential for use as environmentally sensitive fluorescent probes. All three analogs displayed large solvatofluorochromicity in H2O, relative to their emission wavelengths in dioxane or EtOH. Moreover, all three analogs exhibited microenvironmental sensitivity of their fluorescence emission intensity, being moderate to high quantum yields in dioxane and EtOH and significantly lower in H2O. Various attempts to perform domino cross-coupling and annuation reactions on 7-deaza-7-alkynyladenine derivatives to form a new fused tricyclic adenine analog were unsuccessful.

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.

Method and reagent for gene sequence analysis

Provided is a nucleic acid substrate which has nucleic acid substrate characteristics equivalent to those of dATP, has a low substrate specificity for luciferase, exerts no negative effect on enzymatic reactions such as a complementary-strand synthesis, and therefore is particularly suitable for the pyrosequencing method. As a nucleic acid substrate complementary to nucleotide T, a 7-substituted deoxyribonucleotide triphosphate whose 7-position of a purine group is modified by a substituent is used as a substitute for a nucleotide α-thiotriphosphate analog.

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).