53-85-0

Usage

Uses

Used in Research Applications:
5,6-Dichloro-1-beta-D-ribofuranosylbenzimidazole is used as an inhibitor of RNA polymerase II in various research applications. It helps in studying the mechanisms of cellular regulation and the role of RNA polymerase II in transcription.
Used in Cancer Research:
In cancer research, 5,6-Dichloro-1-beta-D-ribofuranosylbenzimidazole is used as an inhibitor of RNA synthesis, causing premature termination of transcription. This property makes it useful in investigating the effects of RNA synthesis inhibition on cancer cells and their growth.
Used in Mouse Melanoma Cells:
5,6-Dichloro-1-beta-D-ribofuranosylbenzimidazole is used as an inhibitor of RNA polymerase II in mouse melanoma cells, aiding in the study of melanoma cell behavior and the development of potential therapeutic strategies.
Used in Human Prostate Epithelial Cell Lines:
In human prostate epithelial cell lines, 5,6-Dichloro-1-beta-D-ribofuranosylbenzimidazole is used for the inhibition of cyclin D1 mRNA synthesis. This application helps researchers understand the role of cyclin D1 in prostate cancer progression and the potential of DRB as a therapeutic agent.
Used in Jurkat Cells:
5,6-Dichloro-1-beta-D-ribofuranosylbenzimidazole is used in Jurkat cells for the inhibition of interleukin-2 gene transcription. This application is valuable for studying the regulation of immune response genes and the potential impact of DRB on immune cell function.

Biochem/physiol Actions

5,6-Dichlorobenzimidazole 1-β-D-ribofuranoside (DRB), a nucleoside analog that halts mRNA synthesis by phosphorylation of the C-terminal domain of RNA polymerase II, making it inactive. It also interferes with the DNA topoisomerase II, may modulate response to cytokines and blocks the human immunodeficiency virus (HIV) via RNA modification. It also inhibits cyclin-dependent kinases (CDKs) 7 and 9 and favors apoptosis in leukemic cells. It may serve as a therapeutic agent in treating cancer.

References

1) Baumli?et al.?(2010),?Halogen bonds form the basis for selective P-TEFb inhibition by DRB; Chem. Biol.,?17?931 2) Yamaguchi?et al.?(1998),?Interplay between positive and negative elongation factors: drawing a new view of DRB; Genes Cells,?3?9 3) Zandomeni (1989), Kinetics of inhibition by 5,6-dichloro-1-beta-D-ribofuranosylbenzimidazole; Biochem.J., 262 469 4) Wang?et al.?(2014),?Inhibition of P-TEFb by DRB suppresses SIRT1/CK2α pathway and enhances radiosensitivity of human cancer cells; Anticancer Res.,?34?6981 5) Zhu?et al.?(2014),?A kinase-independent activity of Cdk9 modulates glucocorticoid receptor-mediated gene induction; Biochemistry,?53?1753

InChI:InChI=1/C12H12Cl2N2O4/c13-5-1-7-8(2-6(5)14)16(4-15-7)12-11(19)10(18)9(3-17)20-12/h1-2,4,9-12,17-19H,3H2/t9-,10+,11?,12-/m1/s1

Upstream product

• 5348-42-5 4,5-Dichloro-1,2-phenylenediamine 
• 142356-78-3 5,6-dichloro-1-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)benzimidazole-2-thione 
• 142356-77-2 C₁₂H₁₂Cl₂N₂O₄S 
• 13035-61-5 1,2,3,5-tetraacetylribose 
• 6974-32-9 1-O-acetyl-2,3,5-tri-O-benzoyl-β-D-ribofuranose 
• 142356-77-2 5,6-dichloro-2-mercapto-1-(β-D-ribofuranosyl)-benzimidazole 
• 19462-98-7 5,6-dichloro-2,3-dihydro-1H-1,3-benzodiazole-2-thione 
• 6478-73-5 5,6-dichlorobenzimidazole 
• 105499-44-3 2,3,5-tri-O-acetyl-α-D-ribofuranosyl chloride 
• 118-00-3 G 
• 155520-55-1 5,6-dichloro-2-(methylthio)-1-β-D-ribofuranosylbenzimidazole 
• 137016-56-9 5,6-dichloro-1-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)benzimidazole 
• 108126-17-6 (2R,3R,4R,5R)-2-(acetoxymethyl)-5-(5,6-dichloro-1H-benzo[d]imidazol-1-yl)tetrahydrofuran-3,4-diyl diacetate 
• 5991-01-5 2,3,5-(tri-O-benzoyl)-D-ribofuranosyl chloride 

Downstream Products

• 137016-65-0 1-(3-O-tert-butyldimethylsilyl-5-O-p-methoxytrityl-β-D-ribofuranosyl)-5,6-dichlorobenzimidazole 2'-<2-(4-nitrophenyl)ethyl triethylammonium phosphate> 
• 137016-70-7 1-(2-O-tert-butyldimethylsilyl-5-O-p-methoxytrityl-β-D-ribofuranosyl)-5,6-dichlorobenzimidazole 3'-<2-(4-nitrophenyl)ethyl triethylammonium phosphate> 
• 137016-55-8 1-(2-O-tert-butyldimethylsilyl-5-O-p-methoxytrityl-β-D-ribofuranosyl)-5,6-dichlorobenzimidazole 3'-<2,5-dichlorophenyl pyridinium phosphate> 
• 137016-67-2 1-(3-O-tert-butyldimethylsilyl-5-O-p-methoxytrityl-β-D-ribofuranosyl)-5,6-dichlorobenzimidazole 2'-<2,5-dichlorophenyl pyridinium phosphate> 
• 137016-82-1 1-(2-O-tert-butyldimethylsilyl-β-D-ribofuranosyl)-5,6-dichlorobenzimidazolyl-(2'-P-<2-(4-nitrophenyl)ethyl>>->5')-5,6-dichloro 1-(2,3-di-O-tert-butyldimethylsilyl-β-D-ribofuranosyl)benzimidazole 
• 137016-76-3 1-(3-O-tert-butyldimethylsilyl-β-D-ribofuranosyl)-5,6-dichlorobenzimidazolyl-(2'-P-<2-(4-nitrophenyl)ethyl>>->5')-5,6-dichloro 1-(2,3-di-O-tert-butyldimethylsilyl-β-D-ribofuranosyl)benzimidazole 
• 137016-77-4 1-(3-O-tert-butyldimethylsilyl-β-D-ribofuranosyl)-5,6-dichlorobenzimidazolyl-(2'-P-(2,5-dichlorophenyl)>->5')-5,6-dichloro 1-(2,3-di-O-tert-butyldimethylsilyl-β-D-ribofuranosyl)benzimidazole 
• 137016-83-2 1-(2-O-tert-butyldimethylsilyl-β-D-ribofuranosyl)-5,6-dichlorobenzimidazolyl-<2'-P-(2,5-dichlorophenyl)>->5'>-5,6-dichloro 1-(2,3-di-O-tert-butyldimethylsilyl-β-D-ribofuranosyl)benzimidazole 
• 137016-68-3 1-(2-O-tert-butyldimethylsilyl-5-O-p-methoxytrityl-β-D-ribofuranosyl)-5,6-dichlorobenzimidazole 3'-<2,5-dichlorophenyl 2-(4-nitrophenyl)ethyl phosphate> 
• 137016-62-7 1-(3-O-tert-butyldimethylsilyl-5-O-p-methoxytrityl-β-D-ribofuranosyl)-5,6-dichlorobenzimidazole 2'-<2,5-dichlorophenyl 2-(4-nitrophenyl)ethyl phosphate> 
• 137016-63-8 1-(3-O-tert-butyldimethylsilyl-β-D-ribofuranosyl)-5,6-dichlorobenzimidazole 2'-<2,5-dichlorophenyl 2-(4-nitrophenyl)ethyl phosphate> 
• 137016-60-5 5,6-dichloro-1-(2,3-di-O-tert-butyldimethylsilyl-5-O-p-methoxytrityl-β-D-ribofuranosyl)benzimidazole 
• 137016-58-1 1-(2-O-tert-butyldimethylsilyl-5-O-p-methoxytrityl-β-D-ribofuranosyl)-5,6-dichlorobenzimidazole 
• 137016-59-2 1-(3-O-tert-butyldimethylsilyl-5-O-p-methoxytrityl-β-D-ribofuranosyl)-5,6-dichlorobenzimidazole 

Relevant academic research and scientific papers

Visible-light-induced aerobic oxidative desulfurization of 2-mercaptobenzimidazolesviaa sulfinyl radical

A mild transition-metal-free non-toxic aerobic photoredox system was found to enable highly efficient desulfurization of 2-mercaptobenzimidazoles. This viable catalytic system includes Rose Bengal in a low catalyst loading as a photosensitizer and cheap, non-toxic NaCl in a catalytic amount as an additive, combined with an oxygen atmosphere. This protocol provides an important alternative access to a broad range of benzimidazole and deuterated benzimidazole products in generally high yields with good tolerance of various synthetically and pharmaceutically useful functionalities. The mechanistic studies reveal that both single electron transfer and energy transfer probably occur in the initial step and a sulfinyl radical intermediate is involved in the key desulfurization process.

ADENOSINE ANALOG AND ITS USE IN REGULATING THE CIRCADIAN CLOCK

Provided are a kind of nucleoside analogue compounds, and compositions comprising these compounds and pentostatin, their use for modulating circadian rhythm, preferably, for shifting circadian phase, and methods for modulating circadian rhythm, preferably, for shifting circadian phase via these compounds or the compositions.

High-throughput five minute microwave accelerated glycosylation approach to the synthesis of nucleoside libraries

The Vorbrueggen glycosylation reaction was adapted into a one-step 5 min/130 °C microwave assisted reaction. Triethanolamine in acetontrile containing 2% water was determined to be optimal for the neutralization of trimethylsilyl inflate allowing for direct MPLC purification of the reaction mixture. When coupled with a NH3/methanol deprotection reaction, a high-throughput method of nucleoside library synthesis was enabled. The method was demonstrated by examining the ribosylation of 48 nitrogen containing heteroaromatic bases that included 25 purines, four pyrazolopyrimidines, two 8-azapurines, one 2-azapurine, two imidazopyridines, two benzimidazoles, three imidazoles, three 1,2,4-triazoles, two pyrimidines, two 3-deazapyrimidines, one quinazolinedione, and one alloxazine. Of these, 32 yielded single regioisomer products, and six resulted in separable mixtures. Seven examples provided inseparable regioisomer mixtures of -two to three compounds (16 nucleosides), and three examples failed to yield isolable products. For the 45 single isomers isolated, the average two-step overall yield ± SD was 26 ± 16%, and the average purity ± SD was 95 ± 6%. A total of 58 different nucleosides were prepared of which 15 had not previously been accessed directly from glycosylation/deprotection of a readily available base.

Benzimidazoles in the reaction of enzymatic transglycosylation

Substrate activity of a broad spectrum of derivatives of benzimidazole in the reaction of enzymatic ribo- and 2-deoxyribosylation catalyzed by purine nucleoside phosphorylase of whole cells of E. coli BMT-1D/1A has been studied Guanosine or 2'-deoxyguanosine were used as glycosyl donors.

Benzimidazole Ribonucleosides: Design, Synthesis, and Antiviral Activity of Certain 2-(Alkylthio)- and 2-(Benzylthio)-5,6-dichloro-1-(β-D-ribofuranosyl)benzimidazoles

Several 2-alkylthio and 2-benzylthio derivatives of 5,6-dichloro-1-(β-D-ribofuranosyl)benzimidazole (DRB) have been designed and synthesized from 5,6-dichloro-1-(β-D-ribofuranosyl)benzimidazole-2-thione.All compounds were evaluated for activity against hu

Synthesis and properties of 5,6-dichlorobenzimidazole 2'->5'- and 3'->5'-nucleotide dimers and trimers

5,6-Dichloro-1-β-D-ribofuranosylbenzimidazole (2), synthesised by the fusion method, was used for the synthesis of 2'->5'- and 3'->5'-linked di- and tri-meric oligonucleotides.The protecting groups used were p-methoxytrityl for HO-5', tert-butyldimethylsi