BS-181 HCl - ≥98% , CAS No.1397219-81-6

CAS: 1397219-81-6 Cat. No.: B412709 Summenformel: C₂₂H₃₂N₆·HCl Molekulargewicht: 416.99

GRADE & PURITY ≥98%

Synonyms

BS-181 hydrochloride | N5-(6-aminohexyl)-N7-benzyl-3-isopropylpyrazolo[1,5-a]pyrimidine-5,7-diamine hydrochloride

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

Übersicht

Information

BS-181 HCl is a highly selectiveCDK7inhibitor withIC50of 21 nM. It is more than 40-fold selective for CDK7 than CDK1, 2, 4, 5, 6, or 9.

Targets

CDK7 (Cell-free assay) 21 nM

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.

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.

Cell Research(from reference)

Cell lines：MCF-7 cells 

Concentrations：Dissolved in DMSO, final concentration ~50 μM 

Incubation Time：24 hours 

Specifications

Synonyme

BS-181 hydrochloride | N5-(6-aminohexyl)-N7-benzyl-3-isopropylpyrazolo[1,5-a]pyrimidine-5,7-diamine hydrochloride

Spezifikationen & Reinheit

≥98%

Biochemische und physiologische Mechanismen

BS-181 HCl is a highly selective CDK7 inhibitor with IC50 of 21 nM. It is more than 40-fold selective for CDK7 than CDK1, 2, 4, 5, 6, or 9.

Storage

Store at -20°C

Verschickt in

Ice chest + Ice pads

Dieses Produkt erfordert Kühlkettenversand. Grundversand und andere Economy-Optionen sind nicht verfügbar.

Aktionsart

INHIBITOR

Reinheit

≥98%

Produkteigenschaften

• ALogP: 4.684
• hba_count: 2
• HBD-Zahl: 3
• Rotationsfähige Bindung: 11

Namen und Kennungen

• Pubchem Sid: 488201443
• Pubchem Sid Url: https://pubchem.ncbi.nlm.nih.gov/substance/488201443
• Kanonisches Lächeln: CC(C)C1=C2N=C(C=C(N2N=C1)NCC3=CC=CC=C3)NCCCCCCN.Cl
• IUPAC Name: 5-N-(6-aminohexyl)-7-N-benzyl-3-propan-2-ylpyrazolo[1,5-a]pyrimidine-5,7-diamine;hydrochloride
• InChIKey: NVIJWMOQODWNFN-UHFFFAOYSA-N
• 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
• Isomere SMILES: CC(C)C1=C2N=C(C=C(N2N=C1)NCC3=CC=CC=C3)NCCCCCCN.Cl
• Alternative CAS-Nummer: 1092443-52-1(free base)
• Molekulargewicht: 416.99
• Reaxy-Rn: 26177980
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=26177980&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organoheterocyclic compounds
    • Klasse Pyrazolopyrimidines
      • Subclass Pyrazolo[1,5-a]pyrimidines

• Kingdom: Organic compounds
• Superclass: Organoheterocyclic compounds
• Klasse: Pyrazolopyrimidines
• Subclass: Pyrazolo[1,5-a]pyrimidines
• Intermediate Tree Nodes: Not available
• Direct Parent: Pyrazolo[1,5-a]pyrimidines
• Alternative Parents: Benzylamines Secondary alkylarylamines Aminopyrimidines and derivatives Imidolactams Pyrazoles Heteroaromatic compounds Azacyclic compounds Monoalkylamines Hydrochlorides Hydrocarbon derivatives
• Molecular Framework: Aromatic heteropolycyclic compounds
• Substituents: Pyrazolo[1,5-a]pyrimidine - Benzylamine - Aminopyrimidine - Secondary aliphatic/aromatic amine - Monocyclic benzene moiety - Pyrimidine - Benzenoid - Imidolactam - Heteroaromatic compound - Pyrazole - Azole - Secondary amine - Azacycle - Organic nitrogen compound - Primary amine - Organonitrogen compound - Primary aliphatic amine - Hydrocarbon derivative - Amine - Hydrochloride - Aromatic heteropolycyclic compound
• Beschreibung: This compound belongs to the class of organic compounds known as pyrazolo[1,5-a]pyrimidines. These are aromatic heterocyclic compounds containing a pyrazolo[3,4-d]pyrimidine ring system, which consists of a pyrazole ring fused to and sharing exactly one nitrogen atom with a pyrimidine ring.
• External Descriptors: Not available

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Chemische und physikalische Eigenschaften

• Löslichkeit: Solubility (25°C) In vitro DMSO: 83 mg/mL (199.04 mM); Water: 83 mg/mL (199.04 mM); Ethanol: 22 mg/mL warmed with 50ºC Water: bath (52.75 mM)
• DMSO (mg/ml) Maximale Löslichkeit: 83
• DMSO (mM) Maximale Löslichkeit: 199.0455407
• Wasser (mg/ml) Maximale Löslichkeit: 3
• Wasser (mM) Maximale Löslichkeit: 7.194417132
• Molekulargewicht: 417.000 g/mol
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 11
• Exact Mass: 416.246 Da
• Monoisotopic Mass: 416.246 Da
• Topological Polar Surface Area: 80.300 Ų
• Heavy Atom Count: 29
• Formal Charge: 0
• Complexity: 425.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 0
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 2

XLogP3