104291-17-0

Basic information

• Product Name: 2-AMINO-4-CHLORO-7-(BETA-D-2-DEOXYRIBOFURANOSYL)PYRROLO-[2,3-D]PYRIMIDINE
• Synonyms: 2-AMINO-4-CHLORO-7-(BETA-D-2-DEOXYRIBOFURANOSYL)PYRROLO-[2,3-D]PYRIMIDINE;7-Deaza-4-Cl-2'-dG;4-Chloro-7-(2-deoxy-beta-D-erythro-pentofuranosyl)-7H-pyrrolo[2,3-d]pyrimidin-2-amine;7-Deaza-4-Cl-2'-deoxyguanosine;2-Amino-4-chloro-7-(β-D-2-deoxyribofuranosyl)pyrrolo[2,3-d]pyrimidine
• CAS NO: 104291-17-0
• Molecular Formula: C₁₁H₁₃ClN₄O₃
• Molecular Weight: 284.7
• EINECS: 1592732-453-0
• Mol File: 104291-17-0.mol
• Article Data: 4

Chemical Properties

• Melting Point: 169-172 °C
• Boiling Point: 655.5±65.0 °C(Predicted)
• Appearance: /
• Density: 1.87±0.1 g/cm3(Predicted)
• PKA: 13.30±0.60(Predicted)
• CAS DataBase Reference: 2-AMINO-4-CHLORO-7-(BETA-D-2-DEOXYRIBOFURANOSYL)PYRROLO-[2,3-D]PYRIMIDINE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-AMINO-4-CHLORO-7-(BETA-D-2-DEOXYRIBOFURANOSYL)PYRROLO-[2,3-D]PYRIMIDINE(104291-17-0)
• EPA Substance Registry System: 2-AMINO-4-CHLORO-7-(BETA-D-2-DEOXYRIBOFURANOSYL)PYRROLO-[2,3-D]PYRIMIDINE(104291-17-0)

Safety Data

• Hazardous Substances Data: 104291-17-0(Hazardous Substances Data)

Usage

General Description

2-AMINO-4-CHLORO-7-(BETA-D-2-DEOXYRIBOFURANOSYL)PYRROLO-[2,3-D]PYRIMIDINE is a chemical compound that belongs to the family of pyrrolopyrimidine nucleosides. It is a synthetic purine analog that has been studied for its potential antiviral and anticancer properties. The compound contains a chloro group and a deoxyribofuranosyl moiety, which are essential for its biological activity. It has been investigated for its ability to inhibit viral replication and to induce apoptosis in cancer cells. The chemical structure and properties of 2-AMINO-4-CHLORO-7-(BETA-D-2-DEOXYRIBOFURANOSYL)PYRROLO-[2,3-D]PYRIMIDINE make it a potential candidate for drug development in the fields of virology and oncology.

Upstream product

• 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 
• 91713-42-7 2,4-Dichlor-7-<2-desoxy-3,5-di-O-(p-toluoyl)-β-D-erythro-pentofuranosyl>-7H-pyrrolo-<2,3-d>pyrimidin 
• 90213-66-4 2,4-dichloro-7H-pyrrolo[2,3-d]pyrimidine 
• 52162-55-7 2-deoxy-3,5-di-O-(p-toluoyl)-α-D-erythro-pentofuranosyl chloride 
• 4330-21-6 2-deoxy-3,5-di-O-p-toluoyl-α-D-erythro-pentofuranosyl chloride 
• 84955-31-7 4-chloro-7H-pyrrolo[2,3-d]pyrimidin-2-amine 
• 104291-21-6 4-Amino-2-chlor-7-<2-desoxy-3,5-di-O-(p-toluoyl)-β-D-erythro-pentofuranosyl>-7H-pyrrolo-<2,3-d>pyrimidin 

Downstream Products

• 123439-71-4 Imidazole-1-carbothioic acid O-[(2R,3S,5R)-5-(2-amino-4-chloro-pyrrolo[2,3-d]pyrimidin-7-yl)-2-(tert-butyl-diphenyl-silanyloxymethyl)-tetrahydro-furan-3-yl] ester 
• 123439-72-5 2-amino-4-chloro-7-<2-deoxy-5-O-<(1,1-dimethylethyl)diphenylsilyl>-3-O-(methoxythiocarbonyl)-β-D-erythro-pentofuranosyl>-7H-pyrrolo<2,3-d>pyrimidine 
• 123439-73-6 2-amino-4-chloro-7-<2,3-dideoxy-5-O-<(1,1-dimethylethyl)diphenylsilyl>-β-D-glycero-pentofuranosyl>-7H-pyrrolo<2,3-d>pyrimidine 
• 111869-49-9 2-amino-7-(2,3-dideoxy-β-D-glycero-pentofuranosyl)-7H-pyrrolo<2,3-d>pyrimidin-4(3H)-one 
• 123439-64-5 2-amino-4-chloro-7-<2-deoxy-5-O-(p-toluoyl)-β-D-erythro-pentofuranosyl>-7H-pyrrolo<2,3-d>pyrimidine 
• 123439-63-4 4-chloro-7-<2-deoxy-5-O-(p-toluoyl)-β-D-erythro-pentofuranosyl>-2-(p-toluoylamino)-7H-pyrrolo<2,3-d>pyrimidine 
• 123439-62-3 4-chloro-7-<2-deoxy-3,5-bis-O-(p-toluoyl)-β-D-erythro-pentofuranosyl>-2-(p-toluoylamino)-7H-pyrrolo<2,3-d>pyrimidine 
• 86392-75-8 7-deaza-2'-deoxyguanosine 
• 123439-69-0 2-amino-4-chloro-7-<2-deoxy-3,5-O-bis<(1,1-dimethylethyl)diphenylsilyl>-β-D-erythro-pentofuranosyl>-7H-pyrrolo<2,3-d>pyrimidine 

Relevant articles and documents

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.

7-Deazaisoguanine quartets: Self-assembled oligonucleotides lacking the Hoogsteen motif

Oligonucleotides containing consecutive 7-deazaisoguanine residues form self-assembled quartets, indicating that the purine nitrogen-7 of isoguanine is not participating in the hydrogen bonding pattern.