5,6-Dichlorobenzimidazole riboside

Modify Date: 2025-08-25 16:19:07

5,6-Dichlorobenzimidazole riboside structure	Common Name	5,6-Dichlorobenzimidazole riboside
	CAS Number	53-85-0	Molecular Weight	319.141
	Density	1.8±0.1 g/cm3	Boiling Point	606.2±65.0 °C at 760 mmHg
	Molecular Formula	C₁₂H₁₂Cl₂N₂O₄	Melting Point	222-224ºC
	MSDS	Chinese USA	Flash Point	320.4±34.3 °C

Use of 5,6-Dichlorobenzimidazole riboside

5,6-Dichlorobenzimidazole riboside is a nucleoside analog that inhibits several carboxyl-terminal domain (CTD) kinases including casein kinase II and CDKs[1][2][3][4]. 5,6-Dichlorobenzimidazole riboside trigger p53-dependent apoptosis of human colon adenocarcinoma cells without inducing genotoxic stress to healthy cells[5].

Name	5,6-Dichloropurine-1-β-D-ribofuanosyl-H-benzimidazole
Synonym	More Synonyms

Description	5,6-Dichlorobenzimidazole riboside is a nucleoside analog that inhibits several carboxyl-terminal domain (CTD) kinases including casein kinase II and CDKs[1][2][3][4]. 5,6-Dichlorobenzimidazole riboside trigger p53-dependent apoptosis of human colon adenocarcinoma cells without inducing genotoxic stress to healthy cells[5].
Related Catalog	Research Areas >> Cancer Signaling Pathways >> Cell Cycle/DNA Damage >> CDK
References	[1]. Zandomeni RO. Kinetics of inhibition by 5,6-dichloro-1-beta-D-ribofuranosylbenzimidazole on calf thymus casein kinase II. Biochem J. 1989 Sep 1;262(2):469-73. [2]. Yankulov K, et al. The transcriptional elongation inhibitor 5,6-dichloro-1-beta-D-ribofuranosylbenzimidazole inhibits transcription factor IIH-associated protein kinase. J Biol Chem. 1995 Oct 13;270(41):23922-5. [3]. Rickert P, et al. Cyclin C/CDK8 and cyclin H/CDK7/p36 are biochemically distinct CTD kinases. Oncogene. 1999 Jan 28;18(4):1093-102. [4]. Schang LM. Cyclin-dependent kinases as cellular targets for antiviral drugs. J Antimicrob Chemother. 2002 Dec;50(6):779-92. [5]. te Poele RH, et al. RNA synthesis block by 5, 6-dichloro-1-beta-D-ribofuranosylbenzimidazole (DRB) triggers p53-dependent apoptosis in human colon carcinoma cells. Oncogene. 1999 Oct 14;18(42):5765-72.

Description

Related Catalog

Research Areas >> Cancer

Signaling Pathways >> Cell Cycle/DNA Damage >> CDK

References

[1]. Zandomeni RO. Kinetics of inhibition by 5,6-dichloro-1-beta-D-ribofuranosylbenzimidazole on calf thymus casein kinase II. Biochem J. 1989 Sep 1;262(2):469-73.

[2]. Yankulov K, et al. The transcriptional elongation inhibitor 5,6-dichloro-1-beta-D-ribofuranosylbenzimidazole inhibits transcription factor IIH-associated protein kinase. J Biol Chem. 1995 Oct 13;270(41):23922-5.

[3]. Rickert P, et al. Cyclin C/CDK8 and cyclin H/CDK7/p36 are biochemically distinct CTD kinases. Oncogene. 1999 Jan 28;18(4):1093-102.

[4]. Schang LM. Cyclin-dependent kinases as cellular targets for antiviral drugs. J Antimicrob Chemother. 2002 Dec;50(6):779-92.

[5]. te Poele RH, et al. RNA synthesis block by 5, 6-dichloro-1-beta-D-ribofuranosylbenzimidazole (DRB) triggers p53-dependent apoptosis in human colon carcinoma cells. Oncogene. 1999 Oct 14;18(42):5765-72.

Density	1.8±0.1 g/cm3
Boiling Point	606.2±65.0 °C at 760 mmHg
Melting Point	222-224ºC
Molecular Formula	C₁₂H₁₂Cl₂N₂O₄
Molecular Weight	319.141
Flash Point	320.4±34.3 °C
Exact Mass	318.017426
PSA	87.74000
LogP	2.05
Vapour Pressure	0.0±1.8 mmHg at 25°C
Index of Refraction	1.750
InChIKey	XHSQDZXAVJRBMX-DDHJBXDOSA-N
SMILES	OCC1OC(n2cnc3cc(Cl)c(Cl)cc32)C(O)C1O
Storage condition	−20°C
Water Solubility	Soluble in DMSO to 75mMSoluble in dimethyl sulfoxide, hot ethanol, dimethyl formamide, (1:2) dimethyl formamide:Phosphate buffer saline, water, methanol and pyridine. Slightly soluble in aqueous buffers.

5,6-Dichlorobenzimidazole riboside MSDS(Chinese)

CHEMICAL IDENTIFICATION

RTECS NUMBER :: DD7310000

CHEMICAL NAME :: Benzimidazole, 5,6-dichloro-1-beta-D-ribofuranosyl-

CAS REGISTRY NUMBER :: 53-85-0

BEILSTEIN REFERENCE NO. :: 0039123

LAST UPDATED :: 199806

DATA ITEMS CITED :: 2

MOLECULAR FORMULA :: C12-H12-Cl2-N2-O4

MOLECULAR WEIGHT :: 319.16

WISWESSER LINE NOTATION :: T56 BN DNJ GG HG B- BT5OTJ CQ DQ E1Q

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

MUTATION DATA

TYPE OF TEST :: Mutation test systems - not otherwise specified

TEST SYSTEM :: Human HeLa cell

DOSE/DURATION :: 40 umol/L

REFERENCE :: PNASA6 Proceedings of the National Academy of Sciences of the United States of America. (National Academy of Sciences, Printing & Pub. Office, 2101 Constitution Ave., Washington, DC 20418) V.1- 1915- Volume(issue)/page/year: 79,2569,1982

Safety Phrases	24/25
RIDADR	NONH for all modes of transport
WGK Germany	3
RTECS	DD7310000
HS Code	29349990

Precursor 5
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DownStream 0

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Name: Inhibition of RNA polymerase II in mouse B16-F1 migrating cells assessed as fold chan...
Source: ChEMBL
Target: DNA-directed RNA polymerase II subunit RPB3
External Id: CHEMBL5677507

Name: Inhibition of RNA polymerase II in mouse B16-F1 migrating cells assessed as fold chan...
Source: ChEMBL
Target: DNA-directed RNA polymerase II subunit RPB3
External Id: CHEMBL5677506

Name: Inhibition of RNA polymerase II in mouse B16-F1 migrating cells assessed as fold chan...
Source: ChEMBL
Target: DNA-directed RNA polymerase II subunit RPB3
External Id: CHEMBL5677509

Name: Inhibition of RNA polymerase II in mouse B16-F1 migrating cells assessed as fold chan...
Source: ChEMBL
Target: DNA-directed RNA polymerase II subunit RPB3
External Id: CHEMBL5677508

Name: Inhibition of RNA polymerase II in mouse B16-F1 migrating cells assessed as fold chan...
Source: ChEMBL
Target: DNA-directed RNA polymerase II subunit RPB3
External Id: CHEMBL5677511

Name: Inhibition of RNA polymerase II in mouse B16-F1 migrating cells assessed as fold chan...
Source: ChEMBL
Target: DNA-directed RNA polymerase II subunit RPB3
External Id: CHEMBL5677510

Name: Inhibition of RNA polymerase II in mouse B16-F1 migrating cells assessed as fold chan...
Source: ChEMBL
Target: DNA-directed RNA polymerase II subunit RPB3
External Id: CHEMBL5677513

Name: Inhibition of RNA polymerase II in mouse B16-F1 migrating cells assessed as fold chan...
Source: ChEMBL
Target: DNA-directed RNA polymerase II subunit RPB3
External Id: CHEMBL5677512

Name: Inhibition of RNA polymerase II in mouse B16-F1 migrating cells assessed as fold chan...
Source: ChEMBL
Target: DNA-directed RNA polymerase II subunit RPB3
External Id: CHEMBL5677515

Name: Compound was evaluated for the visual cytotoxicity scored on HFF cells at time of HCM...
Source: ChEMBL
Target: HFF
External Id: CHEMBL694723

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1H-Benzimidazole, 5,6-dichloro-1-β-D-ribofuranosyl- (9CI)

5,6-Dichloro-1-(β-D-ribofuranosyl)benzimidazole

5,6-Dichloro-1-(β-D-ribofuranosyl)-1H-benzimidazole

DRB

5,6-Dichlorobenzimidazole riboside

5,6-Dichloro-1-β-D-ribofuranosylbenzimidazole

MFCD00036785

5,6-Dichlorobenzimidazole 1-β-D-Ribofuranoside

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Product Name: 1H-Benzimidazole,5,6-dichloro-1-b-D-ribofuranosyl-
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