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1092443-52-1 molecular structure
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5-N-(6-aminohexyl)-7-N-benzyl-3-(propan-2-yl)pyrazolo[1,5-a]pyrimidine-5,7-diamine hydrochloride

ChemBase ID: 72751
Molecular Formular: C22H33ClN6
Molecular Mass: 416.99062
Monoisotopic Mass: 416.24552277
SMILES and InChIs

SMILES:
c1(cc(nc2n1ncc2C(C)C)NCCCCCCN)NCc1ccccc1.Cl
Canonical SMILES:
NCCCCCCNc1cc(NCc2ccccc2)n2c(n1)c(cn2)C(C)C.Cl
InChI:
InChI=1S/C22H32N6.ClH/c1-17(2)19-16-26-28-21(25-15-18-10-6-5-7-11-18)14-20(27-22(19)28)24-13-9-4-3-8-12-23;/h5-7,10-11,14,16-17,25H,3-4,8-9,12-13,15,23H2,1-2H3,(H,24,27);1H
InChIKey:
NVIJWMOQODWNFN-UHFFFAOYSA-N

Cite this record

CBID:72751 http://www.chembase.cn/molecule-72751.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
5-N-(6-aminohexyl)-7-N-benzyl-3-(propan-2-yl)pyrazolo[1,5-a]pyrimidine-5,7-diamine hydrochloride
IUPAC Traditional name
5-N-(6-aminohexyl)-7-N-benzyl-3-isopropylpyrazolo[1,5-a]pyrimidine-5,7-diamine hydrochloride
Synonyms
BS-181 hydrochloride
CAS Number
1092443-52-1
PubChem SID
162037672
PubChem CID
49867928

DATA SOURCES

DATA SOURCES

All Sources Commercial Sources Non-commercial Sources
Data Source Data ID Price
Selleck Chemicals
S1572 external link Add to cart Please log in.
Data Source Data ID
PubChem 49867928 external link

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem
Polar Surface Area 80.27 Å2 Rotatable Bonds 11 
Lipinski's Rule of Five true  Acid pKa 19.458256 
H Acceptors H Donor
LogD (pH = 5.5) 0.08851656  LogD (pH = 7.4) 1.2835636 
Log P 3.9212356  Molar Refractivity 129.1932 cm3
Polarizability 44.122795 Å3

PROPERTIES

PROPERTIES

Safety Information Pharmacology Properties Product Information Bioassay(PubChem)
Storage Condition
-20°C expand Show data source
Target
CDK expand Show data source
Salt Data
Hydrochloride expand Show data source

DETAILS

DETAILS

Selleck Chemicals Selleck Chemicals
Selleck Chemicals - S1572 external link
Research Area
Description Cancer
Biological Activity
Description BS-181 is a highly selective CDK inhibitor for CDK7 with IC50 of 21 nM.
Targets CDK7
IC50 21 nM [1]
In Vitro BS-181 is a small molecule inhibitor of CDK7 in a cell-free environment, which displays more potential activity than roscovitine with IC 50 of 510 nM. Among the CDKs and other 69 kinases from many different classes, BS-181 shows high inhibitory selectivity for CDK7, inhibits CDK2 at concentrations lower than 1 μM which being inhibited 35-fold less potently (IC50 with 880 nM) than CDK7, shows slight inhibition for CDK1, CDK4, CDK5, CDK6 and CDK9 with IC50 values higher than 3.0 μM, and only shows inhibition for several kinases from other classes at high concentrations (>10 μM). BS-181 promotes cell cycle arrest and inhibits the cancer cell growth of a range of tumor types, including breast, lung, prostate and colorectal cancer with IC50 in the range of 11.5-37 μM. In MCF-7 cells, BS-181 inhibits the phosphorylation of the CDK7 substrate RNA polymerase II COOH-terminal domain (CTD), and promotes cell cycle arrest and apoptosis to inhibit the growth of cancer cell lines. [1]
In Vivo BS-181 is stable in vivo with a plasma elimination half-life in mice of 405 minutes after i.p. administration of 10 mg/kg. BS-181 inhibits the growth of MCF-7 xenografts in the nude mice model in a dose-dependent manner, with 25% and 50% reduction in tumor growth after 2 weeks of treatment at 10 mg/kg/day and 20 mg/kg/day, respectively without apparent toxicity. [1]
Clinical Trials
Features BS-181 shows higher inhibitory selectivity for CDK7 than other CDKs and kinases from many different classes.
Protocol
Kinase Assay [1]
In vitro kinase inhibition. Inhibition of CDK7 activity is measured by incubation of increasing amounts of BS-181 with purified recombinant CDK7/CycH/MAT1 complex, followed by measurement of free ATP remaining in the reaction using a luciferase assay, luciferase activity therefore providing a measure of inhibition of CDK7 activity for the determination of IC50.
Cell Assay [1]
Cell Lines MCF-7 cells
Concentrations Dissolved in DMSO, final concentration ~50 μM
Incubation Time 24 hours
Methods MCF-7 cells are exposed to BS-181 for 24 hours. For the determination of cell cycle and apoptosis, cells are stained with propidium iodide or labeled with Annexin V-FITC, then labeled cells are acquired within 1 hour, by using the RXP cytomics software on a Beckman Coulter Elite ESP, and the data are analyzed using Flow Jo v7.2.5. For the assessment of CDKs, cells are lysed and analyzed by western blotting.
Animal Study [1]
Animal Models MCF-7 cells are established in female nu/nu-BALB/c athymic nude mice
Formulation Prepared in the vehicle of 10% DMSO / 50 mM HCl / 5% Tween 20 / 85% saline.
Doses 10 or 20 mg/kg
Administration Twice daily by i.p. injection
References
[1] Ali S, et al. Cancer Res, 2009, 69(15), 6208-6215.

REFERENCES

REFERENCES

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