86392-75-8

Basic information

• Product Name: 7-DEAZA-2'-DEOXYGUANOSINE
• Synonyms: 7-DEAZA-2'-DEOXYGUANOSINE;7-Deaza-2'-deoxy-D-guanosine;7-DEAZA-2''-DEOXYGUANOSINE, HPLC PURIFIED, 98% PURE WITH HPLC UV CHROMATOGRAM;7-deaza-2´7-Deaza-2'-dG;7-DEAZE-2'-Deoxyguanosine;4H-Pyrrolo[2,3-d]pyrimidin-4-one,2-amino-7-(2-deoxy-b-D-erythro-pentofuranosyl)-1,7-dihydro-;2-Amino-7-(2-deoxy-beta-D-erythro-pentofuranosyl)-1,7-dihydro-4H-pyrrolo[2,3-d]pyrimidin-4-one
• CAS NO: 86392-75-8
• Molecular Formula: C₁₁H₁₄N₄O₄
• Molecular Weight: 266.25
• EINECS: 500-100-4
• Mol File: 86392-75-8.mol

Chemical Properties

• Melting Point: 262-265 °C
• Boiling Point: 621.4 ºC at 760 mmHg
• Flash Point: 329.6 ºC
• Appearance: /
• Density: 1.9 g/cm³
• Vapor Pressure: 2.64E-16mmHg at 25°C
• Refractive Index: 1.834
• Storage Temp.: Keep in dark place,Sealed in dry,Store in freezer, under -20°C
• PKA: 11.29±0.20(Predicted)
• CAS DataBase Reference: 7-DEAZA-2'-DEOXYGUANOSINE(CAS DataBase Reference)
• NIST Chemistry Reference: 7-DEAZA-2'-DEOXYGUANOSINE(86392-75-8)
• EPA Substance Registry System: 7-DEAZA-2'-DEOXYGUANOSINE(86392-75-8)

Safety Data

• Hazardous Substances Data: 86392-75-8(Hazardous Substances Data)

Usage

Uses

Used in Antiviral Applications:
7-DEAZA-2'-DEOXYGUANOSINE is used as an antiviral agent for its significant activity against hepatitis B and C viruses. It targets the viral replication process, inhibiting the synthesis of viral nucleic acids and proteins, thereby reducing viral load and preventing the progression of viral infections.
Used in Anticancer Applications:
In the field of oncology, 7-DEAZA-2'-DEOXYGUANOSINE is being researched as a potential anticancer agent. Its ability to interfere with nucleic acid synthesis and disrupt cellular processes in cancer cells makes it a promising candidate for the development of novel cancer therapies. It may be used in combination with existing chemotherapeutic drugs to enhance their efficacy and overcome drug resistance in cancer treatment.
Used in Neurological Disorder Applications:
7-DEAZA-2'-DEOXYGUANOSINE is also being explored for its potential in the treatment of neurological disorders. Its ability to modulate cellular processes and interact with specific receptors in the nervous system suggests that it may have therapeutic benefits in conditions such as neurodegenerative diseases and neurological disorders.
Used in HIV Treatment:
7-DEAZA-2'-DEOXYGUANOSINE has demonstrated significant anti-HIV activity, making it a promising candidate for the development of novel antiviral therapies. It targets the HIV replication process, inhibiting the synthesis of viral nucleic acids and proteins, and preventing the progression of the infection. 7-DEAZA-2'-DEOXYGUANOSINE may be used in combination with existing antiretroviral drugs to enhance their efficacy and overcome drug resistance in HIV treatment.

InChI:InChI=1/C11H14N4O4/c12-11-13-9-5(10(18)14-11)1-2-15(9)8-3-6(17)7(4-16)19-8/h1-2,6-8,16-17H,3-4H2,(H3,12,13,14,18)/t6-,7+,8+/m0/s1

Upstream product

• 104291-17-0 2-amino-4-chloro-7-(2-deoxy-β-D-erythro-pentofuranosyl)-7H-pyrrolo[2,3-d]pyrimidine 
• 104291-18-1 2-Amino-7-<2-desoxy-β-D-erythro-pentofuranosyl>-7H-pyrrolo<2,3-d>pyrimidin-4(3H)-thion 
• 115945-80-7 2-amino-7-<2-deoxy-β-D-erythro-pentofuranosyl>-4-isobutoxy-7H-pyrrolo<2,3-d>pyrimidine 
• 115945-79-4 2-amino-4-butoxy-7-(2-deoxy-β-D-erythro-pentofuranosyl)-7H-pyrrolo<2,3-d>pyrimidine 
• 111902-68-2 7-(2-Desoxy-β-D-erythro-pentofuranosyl)-2-<(dimethylamino)methylenamino>-3,7-dihydro-4H-pyrrolo<2,3-d>pyrimidin-4-on 
• 84955-31-7 4-chloro-7H-pyrrolo[2,3-d]pyrimidin-2-amine 
• 104291-20-5 (2R,3S,5R)-5-(2-amino-4-chloro-7H-pyrrolo[2,3-d]pyrimidin-7-yl)-2-(((4-methylbenzoyl)oxy)methyl)tetrahydrofuran-3-yl 4-methylbenzoate 
• 115945-77-2 2-amino-7-<2-deoxy-3,5-di-O-(p-toluoyl)-β-D-erythro-pentofuranosyl>-4-isobutoxy-7H-pyrrolo<2,3-d>pyrimidine 
• 115945-75-0 2-amino-4-butoxy-7-<2-deoxy-3,5-di-O-(p-toluoyl)-β-D-erythro-pentofuranosyl>-7H-pyrrolo<2,3-d>pyrimidine 
• 115945-74-9 2-amino-4-isobutoxy-7H-pyrrolo<2,3-d>pyrimidine 
• 84955-32-8 2-amino-4-methoxy-7H-pyrrolo[2,3-d]-pyrimidine 
• 4330-21-6 2-deoxy-3,5-di-O-p-toluoyl-α-D-erythro-pentofuranosyl chloride 
• 86392-74-7 2-amino-9-(2'-deoxy-β-D-erythro-pentofuranosyl)-6-methoxyl-7H-pyrrolo[2,3-d]pyrimidine 

Downstream Products

• 111869-46-6 7-(2-Desoxy-5-O-(4,4'-dimethoxytriphenylmethyl)-β-D-erythro-pentofuranosyl)-2-<(4,4'-dimethoxytriphenylmethyl)amino>-3,7-dihydro-4H-pyrrolo<2,3-d>pyrimidin-4-on 
• 111869-49-9 2-amino-7-(2,3-dideoxy-β-D-glycero-pentofuranosyl)-7H-pyrrolo<2,3-d>pyrimidin-4(3H)-one 
• 111869-44-4 7-(2,3-Didesoxy-5-O-(4,4'-dimethoxytriphenylmethyl)-β-D-glycero-pentofuranosyl)-2-<(dimethylamino)methylenamino>-3,7-dihydro-4H-pyrrolo<2,3-d>pyrimidin-4-on 
• 111869-42-2 7-<2-Desoxy-5-O-(4,4'-dimethoxytriphenylmethyl)-β-D-erythro-pentofuranosyl>-2-<(dimethylamino)methylenamino>-3,7-dihydro-4H-pyrrolo<2,3-d>pyrimidin-4-on 
• 111869-43-3 7-<2-Desoxy-5-O-(4,4'-dimethoxytriphenylmethyl)-3-O-(phenoxythiocarbonyl)-β-D-erythro-pentofuranosyl>-2-<(dimethylamino)methylenamino>-3,7-dihydro-4H-pyrrolo<2,3-d>pyrimidin-4-on 
• 111869-48-8 7-(2,3-Didesoxy-5-O-(4,4'-dimethoxytriphenylmethyl)-β-D-glycero-pentofuranosyl)-2-<(4,4'-dimethoxytriphenylmethyl)amino>-3,7-dihydro-4H-pyrrolo<2,3-d>pyrimidin-4-on 
• 111869-47-7 7-(2-Desoxy-5-O-(4,4'-dimethoxytriphenylmethyl)-3-O-(phenoxythiocarbonyl)-β-D-erythro-pentofuranosyl)-2-<(4,4'-dimethoxytriphenylmethyl)amino>-3,7-dihydro-4H-pyrrolo<2,3-d>pyrimidin-4-on 
• 1564207-35-7 2-N-(phenoxyacetyl)-8-chloro-7-deaza-2'-deoxyguanosine 
• 1564207-67-5 2-N-(phenoxyacetyl)-8-bromo-7-deaza-2'-deoxyguanosine 
• 1564207-88-0 2-N-(phenoxyacetyl)-8-iodo-7-deaza-2'-deoxyguanosine 
• 1564208-29-2 C₄₉H₅₄ClN₆O₉P 
• 1564208-93-0 C₄₉H₅₄BrN₆O₉P 
• 1564209-77-3 C₄₉H₅₄IN₆O₉P 

Relevant articles and documents

Enhanced triple-helix and double-helix formation with oligomers containing modified purines

Novel oligomers are disclosed which have enhanced ability with respect to forming duplexes or triplexes compared with oligomers containing only conventional bases. The oligomers contain 7-deaza-7-substituted purines or related analogs. The oligomers of the invention are capable of (i) forming triplexes with various target sequences such as virus or oncogene sequences by coupling into the major groove of a target DNA duplex at physiological pH or (ii) forming duplexes by binding to single-stranded DNA or to RNA encoded by target genes. The oligomers of the invention can be constructed to have any desired sequence, provided the sequence normally includes one or more bases that is replaced with the analogs of the invention. Compositions of the invention can be used for diagnostic purposes in order to detect viruses or disease conditions.

Synthesis of 7-Deaza-2',3'-dideoxyguanosine by Deoxygenation of Its 2'-Deoxy-β-D-ribofuranoside

7-Deaza-2',3'-dideoxyguanosine (4) was prepared by Barton deoxygenation from 7-deaza-2'-deoxyguanosine (1).Protection of the 5'-hydroxy group was accomplished by the 4,4'-dimethoxytriphenylmethyl residue.The 2-amino function was protected either with the same group or the dimethylaminomethylene residue.Assignment of 1H- and 13C-NMR signals of the 2',3'-dideoxy-β-D-glycero-pentofuranosyl moiety of 4 was made on the basis of 2D-NMR spectra.In contrast to 2',3'-dideoxyguanosine compound 4 has an extremely stable N-glycosylic bond towards proton-catalyzed hydrolysis.

A facile and improved synthesis of tubercidin and certain related pyrrolo[2,3-d]pyrimidine nucleosides by the stereospecific sodium salt glycosylation procedure [1]

A simple synthesis of tubercidin, 7-deazaguanosine and 2'-deoxy-7-deazaguanosine has been accomplished using the sodium salt glycosylation procedure. Reaction of the sodium salt of 4-chloro- and 2-amino-4-chloro-pyrrolo[2,3-d]pyrimidine, 3 and 4, respectively, with 1-chloro-2,3-O-isopropylidene,5-O-(t-butyl)dimethylsilyl-α-D-ribofur nose gave the corresponding protected nucleosides 6 and 7 with β-anomeric configuration. Deprotection of 6 provided 8, which on heating with methanolic ammonia gave tubercidin in excellent yield. Functional group transformation of 7, followed by deisopropylidenation gave 2-aminotubercidin and 2-amino-7-β-ribofuranosylpyrrolo[2,3-d]pyrimidine-4(3H)-thione. Treatment of 7 with 1N sodium methoxide followed by exposure to aqueous trifluoroacetic acid, and ether cleavage furnished 7-deazaguanosine. 2'-Deoxy-7-deazaguanosine and 2'-deoxy-7-deaza-6-thioguanosine were also prepared by using similar sequence of reactions employing 4 and 1-chloro-2-deoxy-3,5-di-O-p-toluoyl-α-D-erythro-pentofuranose.

LIQUID-LIQUID AND SOLID-LIQUID PHASE-TRANSFER GLYCOSYLATION OF PYRROLOPYRIMIDINES : STEREOSPECIFIC SYNTHESIS OF 2-DEOXY-β-D-RIBOFURANOSIDES RELATED TO 2'-DEOXY-7-CARBAGUANOSINE

The yield of phase-transfer glycosylation of 2-amino-4-methoxy-7H-pyrrolopyrimidine (3b) with 2-deoxy-3,5-di-O-(p-toluoyl)-α-D-erythro-pentofuranosyl chloride (4) is limited under liquid-liquid conditions (50percent aq.NaOH, CH2Cl2, Bu4NHSO4) due t