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

HCID 3165
NotesReactions
Basic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
Substructure searchFind similar structures

Basic information

CAS
53-85-0
Standard SMILES
OCC1OC(n2cnc3cc(Cl)c(Cl)cc32)C(O)C1O
InChIKey
XHSQDZXAVJRBMX-UHFFFAOYSA-N
Molecular formula
C12H12Cl2N2O4
Average molar mass
319.14 g/mol
Monoisotopic mass
318.0174123

Overview

5,6-dichloro-1-beta-D-ribofuranosyl-1H-benzimidazole is a 1-ribosylbenzimidazole that is 5,6-dichloro-1H-benzimidazole attached to a beta-D-ribofuranosyl residue at position 1 via a glycosidic (N-glycosyl) linkage. It is an inhibitor for RNA polymerase II transcription. It has a role as an antineoplastic agent, an EC 2.7.7.6 (RNA polymerase) inhibitor and an apoptosis inducer. It is an organochlorine compound and a 1-ribosylbenzimidazole.

Names & identifiers

Preferred name
5,6-Dichloro-1-beta-D-ribofuranosylbenzimidazole
IUPAC
2-(5,6-dichlorobenzimidazol-1-yl)-5-(hydroxymethyl)oxolane-3,4-diol
English name
DRB
Molecular formula
C12H12Cl2N2O4
Molecular weight
319.14

Names & synonyms

(2R,3R,4S,5R)-2-(5,6-dichlorobenzimidazol-1-yl)-5-(hydroxymethyl)oxolane-3,4-diolMLS0031715032-(5,6-dichlorobenzimidazol-1-yl)-5-(hydroxymethyl)oxolane-3,4-diol5,6-Dichloro-1-beta-D-ribofuranosylbenzimidazoleC12H12Cl2N2O4DRBDRB;NSC4015755,6-dichlororibofuranosylbenzimidazoleNSC-401575Kinome_36395,6-Dichlorobenzimidazole 1-beta-D-ribofuranoside
Show more names
DBRDRB1DR betaHLA-DRBHLA-DR1BDR beta 1DR beta 3NSC 401575DRB USP/EP/BP
MRKI-28CHEMBL267071SCHEMBL23982247CHEBI:49852CHEBI:232947HMS3373F12NCGC00096104-01NCGC00096104-02

Database identifiers

CAS
53-85-0
PubChem CID
3165

Properties

Computed structural properties

XLogP
1.1
Topological polar surface area
87.7 Ų
Hydrogen bond donors
3
Hydrogen bond acceptors
5
Rotatable bonds
2
Heavy atoms
20
Formal charge
0
Complexity
364

Physicochemical properties

Melting point
222 · 222-224°C
Boiling point
606.2 · 606.2±65.0 °C(Predicted)
Density
1.5917 · 1.5917 (rough estimate)
refractive index
1.62 · 1.6200 (estimate)
storage temp.
-20 °C · -20°C
solubility
Soluble in DMSO (up to 20 mg/ml)
pka
13.23 · 13.23±0.70(Predicted)
form
White solid
color
White
Water Solubility
75 mMSoluble · 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.
λmax
296 nm · 296nm(lit.)
BRN
39123 · 39123
Stability
1 year · Stable for 1 year from date of purchase as supplied. Solutions in DMSO may be stored at -20°C for up to 3 months.
InChI
1S/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

Safety & regulation

Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.

Safety data

wgk
3
rtecs
DD7310000
hs_code
29349990
Signal word
Warning
Symbol(GHS)
GHS07
safety_code
24/25
Storage Class
11 - Combustible Solids
Hazard statements
H315-H319-H335
Precautionary statements
P261-P305+P351+P338

Chemistry & industry

Applications · 4 items

DescriptionDRB (53-85-0) is a classic inhibitor of transcription by RNA polymerase II.A relatively selective inhibitor of Cdk9 (IC50=3 μM), the kinase of the positive transcription elongation factor b (P-TEF-b) required for processive transcription elongation by RNA polymerase II.1,2Also inhibits casein kinase II, IC50=4-10 μM.3Suppresses the SIRT1/CK2α pathway and enhances the radiosensitivity of human cancer cells.4Kinase-independent activities of Cdk9 such as glucocorticoid receptor modulation are not inhibited by DRB.5

UsesInhibits casein kinase II and blocks RNA synthesis. An adenosine analog.5,6-Dichlorobenzimidazole riboside is used as an inhibitor of RNA Polymerase II. It is nucleoside analogue and used in research to study the mechanisms of cellular regulation. Further, it inhibits some protein kinases.

Uses5,6-Dichlorobenzimidazole 1-β-D-ribofuranoside has been used:as an inhibitor of RNA polymerase II in mouse melanoma cellsfor the inhibition of cyclin D1 mRNA synthesis in human prostate epithelial cell linesin the inhibition of interleukin-2 gene transcription in Jurkat cells

UsesDRB is an inhibitor of RNA synthesis (causes premature termination of transcription).

Suppliers61 total

梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]
湖北永阔科技有限公司027-59223108 15972152991 · [email protected]
湖南韵邦生物科技股份有限公司0731-88532326 13319508186 · [email protected]
成都超九八生物科技有限公司13348960310 13348960310 · [email protected]
武汉敬康恩生物医药科技有限公司13720134139 086-15871494362 13720134139 · [email protected]
上海优宁维生物科技股份有限公司

Related reactions

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Compound notes

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On this pageBasic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
ChEMBL
CHEMBL267071
ChEBI
CHEBI:49852
InChIKey
XHSQDZXAVJRBMX-AYLPWXGPSA-N
SMILES
Clc1cc2[n](cnc2cc1Cl)[C@@H]3O[C@@H]([C@H]([C@H]3O)O)CO
CAS DataBase Reference
53 · 53-85-0
FDA UNII
8153319 T3Q · 8153319T3Q
UNSPSC Code
12352200 · 12352200
NACRES
77 · NA.77
Symbol(GHS)
7 · GHS07
Signal word
Warning
Hazard statements
315 · H315-H319-H335
Precautionary statements
261 · P261-P305+P351+P338
Safety Statements
24 · 24/25
WGK Germany
3 · 3
RTECS
7310000 · DD7310000
HS Code
29349990 · 29349990
Storage Class
11 · 11 - Combustible Solids
15921930842 15921930842 · [email protected]
Aladdin Scientific[email protected]
武汉易泰科技有限公司上海分公司18930552037 · [email protected]
攀纳燊(河南)医药科学技术有限公司0371-65325800 13700860222 · [email protected]
欧利希(湖北)医药科技有限公司17316404525 17316404525 · [email protected]
成都普思生物科技股份有限公司028-85370565-229 18080489829 · [email protected]
MedBio脉铂医药021-69568360 18916172912 · [email protected]
怀化市冰峰化工有限公司0745-2866851 17711757908 · [email protected]
銳迪國際科技有限公司18024082417 · [email protected]
上海梅凯科技有限公司021-68689288 15300790979 · [email protected]
上海三牧化工技术有限公司021-38681880 13817889927 · [email protected]
TCI AMERICA800-4238616 · [email protected]
TOKYO CHEMICAL INDUSTRY CO., LTD.03-36680489 · [email protected]
TCI Europe320-37350700 · [email protected]
郑州安步防护用具有限公司+86-0371-88006763; +86-15988602810 · [email protected]
上海毕得医药科技股份有限公司400-164-7117 18317119277 · [email protected]
北京奥秘佳得医药科技有限公司+86-13522808617 · [email protected]
Wuhan Jingkang en Biomedical Technology Co., Ltd+86-0086-13720134139 · [email protected]
武汉开诺医药科技有限公司18040571231/1402788087
天津普西唐生物医药科技有限公司010-60605840 · [email protected]
上海麦克林生化科技股份有限公司15221275939 15221275939 · [email protected]
陕西缔都医药化工有限公司029-81024372 17792795018 · [email protected]
凯试(上海)科技有限公司021-50135380 · [email protected]
Sigma-Aldrich西格玛奥德里奇(上海)贸易有限公司021-61415566 800-8193336 · [email protected]
上海楼岚生物科技有限公司021-52996696,15000506266 15000506266
杭州六可生物科技有限公司+86-571-86912261 19975279805 · [email protected]
BOC Sciences16314854226 · [email protected]
上海陶术生物科技股份有限公司+1-781-999-5354; +1-00000000000 · [email protected]
北京秦岭医药科技有限公司010-61241352 18901327973 · [email protected]
南通全益生物科技有限公司0513-66337626 18051384581 · [email protected]
嘉兴市浙嘉生物科技有限公司0573-85609002 · [email protected]
上海一飞生物科技有限公司021-65675885 18964387627 · [email protected]
上海源叶生物科技有限公司18916372613 · [email protected]
上海瀚思化工有限公司18916268197 · [email protected]
上海贤鼎生物科技有限公司021-021-52271985 17721149837 · [email protected]
上海立崎生物医学研究中心18014399201 · [email protected]
浙江麦格生物医药有限公司4000-156-528 13355733872 · [email protected]
江苏艾康生物医药研发有限公司025-58859352 19370895928 · [email protected]
河南天孚化工有限公司+86-0371-55170693 +86-19937530512 · [email protected]
范德(北京)生物科技有限责任公司15911056312 · [email protected]
TCI Chemicals (India) Pvt. Ltd.[email protected]
武汉爱默尔特科技有限公司027-888-4366503 13986279625 · [email protected]
湖北摆渡化学有限公司027-59106051 13627137652 · [email protected]
湖北信康医药化工有限公司027-027-59308705 18871579363 · [email protected]
上海皓鸿生物医药科技有限公司400-8210725 4008210725 · [email protected]