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

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

Uses

Used in Pharmaceutical Industry:
2-AMINO-4-CHLORO-7-(BETA-D-2-DEOXYRIBOFURANOSYL)PYRROLO-[2,3-D]PYRIMIDINE is used as an antiviral agent for its ability to inhibit viral replication. Its unique structure allows it to target specific viral enzymes or pathways, thereby reducing the spread of viruses in the body.
Used in Oncology Research:
In the field of oncology, 2-AMINO-4-CHLORO-7-(BETA-D-2-DEOXYRIBOFURANOSYL)PYRROLO-[2,3-D]PYRIMIDINE is used as an anticancer agent due to its potential to induce apoptosis in cancer cells. Its mechanism of action may involve the disruption of cellular processes that promote tumor growth and survival, leading to the elimination of cancerous cells.
Used in Drug Development:
2-AMINO-4-CHLORO-7-(BETA-D-2-DEOXYRIBOFURANOSYL)PYRROLO-[2,3-D]PYRIMIDINE serves as a lead compound in drug development for the creation of novel therapeutics targeting viral infections and cancer. Its chemical structure and properties can be further optimized and modified to enhance its efficacy, selectivity, and safety profile, making it a valuable asset in the development of new antiviral and anticancer drugs.

Upstream product

• 52162-55-7 2-deoxy-3,5-di-O-(p-toluoyl)-α-D-erythro-pentofuranosyl chloride 
• 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 
• 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 
• 104291-20-5 (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 
• 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

• 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 
• 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 

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.

The base-pairing properties of 7-deaza-2'-deoxyisoguanosine and 2'- deoxyisoguanosine in oligonucleotide duplexes with parallel and antiparallel chain orientation

Oligonucleotides with parallel (ps) or antiparallel (aps) chain orientation containing 7-deaza-2'-deoxyisoguanosine (1) or 2'- deoxyisoguanosine (2) were prepared. The phosphoramidite and phosphonate building blocks 3-6 were synthesized and used in solid-phase synthesis. The diphenylcarbamoyl (dpc) residue was used for the 2-oxo group protection and the isobutyryl (iBu=ib) residue for the amino function. Hybridization experiments were performed with oligonucleotides containing 7-deazaisoguanine or isoguanine. Regarding 7-deazapurine-containing oligonucleotides, the 7- deazaisoguanine cytosine base pair was the strongest in ps-duplexes, while that of 7-deazaisoguanine. 5-methylisocytosine was the most stable one in apsDNA. Ambiguous base pairing of 7-deazaisoguanine with cytosine, 5- methylisocytosine, thymine, and guanine was observed in the case of aps- duplexes, whereas in ps-duplexes, the ambiguity was extended to adenine. The 7-deazaisoguanine-containing duplexes showed almost identical base-pair stabilities as those containing isoguanine. According to this, various base- pair motifs are proposed. The 7-deaza-2'-deoxyisoguanosine was found to be an effective substitute of 2'-deoxyisoguanosine.

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.

2-Amino-2'-deoxytubercidin and Related Pyrrolopyrimidinyl 2'-Deoxyribofuranosides

Phase-transfer glycosylation of 2-amino-4-chloro-7H-pyrrolopyrimidine (4a) with 1-chloro-3,5-di-O-(p-toluoyl)-α-D-erythro-pentofuranose (7) yields in a regio- and diastereoselective reaction the crystalline condensation product 5a.Nucleophilic disp