329187-80-6

Basic information

• Product Name: 2,6-Dichloropurine -9-beta-D-(2'-deoxy-3',5'-di-O-benzoyl-2'-fluoro)arabinoriboside
• Synonyms: 2,6-Dichloropurine -9-beta-D-(2'-deoxy-3',5'-di-O-benzoyl-2'-fluoro)arabinoriboside;2,6-Dichloro-9-(2-deoxy- 2-fluoro-β-D-arabinofuranosyl)-9H-purine;2,6-Dichloro-9-(3,5-di-O-benzoyl-2-deoxy-2-fluoro-D-arabinofuranosyl)-9H-purine
• CAS NO: 329187-80-6
• Molecular Formula: C₂₄H₁₇Cl₂FN₄O₅
• Molecular Weight: 531.3199832
• Mol File: 329187-80-6.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 2,6-Dichloropurine -9-beta-D-(2'-deoxy-3',5'-di-O-benzoyl-2'-fluoro)arabinoriboside(CAS DataBase Reference)
• NIST Chemistry Reference: 2,6-Dichloropurine -9-beta-D-(2'-deoxy-3',5'-di-O-benzoyl-2'-fluoro)arabinoriboside(329187-80-6)
• EPA Substance Registry System: 2,6-Dichloropurine -9-beta-D-(2'-deoxy-3',5'-di-O-benzoyl-2'-fluoro)arabinoriboside(329187-80-6)

Safety Data

• Hazardous Substances Data: 329187-80-6(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
2,6-Dichloropurine -9-beta-D-(2'-deoxy-3',5'-di-O-benzoyl-2'-fluoro)arabinoriboside is used as a potential therapeutic agent for the treatment of cancer. Its anticancer properties have been studied, and it may contribute to the development of novel drugs for various types of cancer.
Used in Antiviral Applications:
In the field of virology, 2,6-Dichloropurine -9-beta-D-(2'-deoxy-3',5'-di-O-benzoyl-2'-fluoro)arabinoriboside is used as a potential antiviral agent. Its antiviral properties have been explored, and it may lead to the creation of new treatments for viral infections.
Used in Preclinical Research:
2,6-Dichloropurine -9-beta-D-(2'-deoxy-3',5'-di-O-benzoyl-2'-fluoro)arabinoriboside is utilized in preclinical research to further investigate its potential as a therapeutic agent. This research is crucial for understanding the compound's mechanisms of action, efficacy, and safety before it can be considered for clinical trials and eventual use in medical treatments.

Upstream product

• 97614-44-3 2-deoxy-2-fluoro-3,5-di-O-benzoyl-α-D-arabinofuranosyl bromide 
• 5451-40-1 2,6-dichloro-7H-purine 
• 5451-40-1 2,6 dichloropurine 
• 97614-43-2 1,3,5-tri-O-benzoyl-2-deoxy-2-fluoro-α-D-arabinofuranose 
• 1067137-03-4 3,5-di-O-benzoyl-2-deoxy-2-fluoro-α-D-arabinofuranosyl bromide 
• 98855-71-1 ((2R,3R,4S)-3-(benzoyloxy)-5-bromo-4-fluorotetrahydrofuran-2-yl)methyl benzoate 

Downstream Products

• 758705-70-3 2-Chloro-9-(2-deoxy-2-fluoro-β-D-arabinofuranosyl)-6-methoxy-9H-purine 

Relevant articles and documents

Discovery of AB680: A Potent and Selective Inhibitor of CD73

Extracellular adenosine (ADO), present in high concentrations in the tumor microenvironment (TME), suppresses immune function via inhibition of T cell and NK cell activation. Intratumoral generation of ADO depends on the sequential catabolism of ATP by two ecto-nucleotidases, CD39 (ATP → AMP) and CD73 (AMP → ADO). Inhibition of CD73 eliminates a major pathway of ADO production in the TME and can reverse ADO-mediated immune suppression. Extensive interrogation of structure-activity relationships (SARs), structure-based drug design, and optimization of pharmacokinetic properties culminated in the discovery of AB680, a highly potent (Ki = 5 pM), reversible, and selective inhibitor of CD73. AB680 is further characterized by very low clearance and long half-lives across preclinical species, resulting in a PK profile suitable for long-acting parenteral administration. AB680 is currently being evaluated in phase 1 clinical trials. Initial data show AB680 is well tolerated and exhibits a pharmacokinetic profile suitable for biweekly (Q2W) iv-administration in human.

INHIBITORS OF ADENOSINE 5'-NUCLEOTIDASE

Compounds that modulate the conversion of AMP to adenosine by 5'- nucleotidase, ecto, and compositions containing the compounds and methods for synthesizing the compounds, are described herein. The use of such compounds and compositions for the treatment

INHIBITORS OF CD73-MEDIATED IMMUNOSUPPRESSION

Compounds that modulate the conversion of AMP to adenosine by 5'- nucleotidase, ecto, and compositions containing the compounds and methods for synthesizing the compounds, are described herein. The use of such compounds and compositions for the treatment and/or prevention of a diverse array of diseases, disorders and conditions, including cancer- and immune-related disorders, that are mediated by 5'- nucleotidase, ecto is also provided.

MODULATORS OF 5'-NUCLEOTIDASE, ECTO AND THE USE THEREOF

Compounds that modulate the conversion of AMP to adenosine by 5'- nucleotidase, ecto, and compositions containing the compounds and methods for synthesizing the compounds, are described herein. The use of such compounds and compositions for the treatment and/or prevention of a diverse array of diseases, disorders and conditions, including cancer- and immune-related disorders, that are mediated by 5'-nucleotidase, ecto is also provided.

Method for synthesizing clofarabine

The invention discloses a method for synthesizing clofarabine; the method comprises the following synthetic routes described in the specification, wherein in the formula III and the formula IV, R1 and R2 are the same or different acyl groups. The method comprises the following steps: 1) ammoniation: dissolving a compound represented by the formula III in an organic solvent, introducing ammonia gas, and carrying out a closed reaction, to obtain a compound represented by the formula IV after the reaction is completed, wherein the organic solvent is any combination of one or two or more of acetonitrile, ethyl acetate, dichloromethane and tetrahydrofuran, the concentration of ammonia gas dissolved in the organic solvent is 0.1-20 wt%, the closed reaction is carried out for 10-40 hours, and the reaction temperature is 0-100 DEG C; and 2) protecting group removal: dissolving the compound represented by the formula IV and prepared in the step 1) in alcohol, adding an alcohol solution of sodium alkoxide, carrying out a reaction, then adjusting the pH value to 6-7, cooling and crystallizing, and thus obtaining a clofarabine crude product.

Synthesis and anti-HIV activity of 2′-fluorine modified nucleoside phosphonates: Analogs of GS-9148

Modified purine analogs of GS-9148 [5-(6-amino-purin-9-yl)-4-fluoro-2,5-dihydro-furan-2-yloxymethyl]-phosphonic acid (2′-Fd4AP) were synthesized and their anti-HIV potency evaluated. The antiviral activity of guanosine analog (2′-Fd4GP) was comparable that of to 2′-Fd4AP in MT-2 cells, but selectivity was reduced.

Oligonucleotides containing 9-(2-deoxy-2-fluoro-β-D-arabinofuranosyl)-adenine and -guanine: Synthesis, hybridization and antisense properties

Synthesis of 9-(2-deoxy-2-fluoro-β-D-arabinofuranosyl)-adenine (7, ara-A2′F) and -guanine (12, ara-G2′F) was accomplished via the condensation of 2,6-dichloropurine (1) with 2-deoxy-2-fluoro-1,3,5-tri-O-benzoyl-α-D-arabinofuranose (2) as a key chemical step. Condensation of silylated N6-benzoyladenine (6) with 2 gave, after deblocking and chromatographic separation, ara-A2′F (7) (14%), it's α-anomer 8 (14%) and N7-α-isomer 9 (25%). The PSEUROT analysis of N9-β-D-arabinosides 7 and 12 manifested slight preference for the S rotamer (64%) for the former, and an equal population of the N and S rotamers for the latter. The arabinosides 7 and 12 were used for the preparation of the respective phosphoamidite building blocks 13 and 14 for automated oligonucleotide synthesis. Four 15-mer oligonucleotides (ONs) complementary to the initiation codon region of firefly luciferase mRNA were prepared: unmodified 2′-deoxy-ON (AS 1) and containing (i) ara-A2′F instead of the only A (AS2), (ii) ara-G2′F vs. 3-G from the 5′-terminus (AS3), and (iii) both arabinosides at the same positions (AS4). All these ONs display practically the same (i) affinity to both complementary DNA and RNA, and (ii) ability to inhibit a luciferase gene expression in a cell-free transcription-translation system.