101622-51-9 Usage
Description
OLOMOUCINE is a purine derivative that exhibits potent inhibitory effects on cyclin-dependent kinases, leading to G1 cell cycle arrest. It is a white to off-white solid with significant potential in various applications across different industries.
Uses
Used in Pharmaceutical Industry:
OLOMOUCINE is used as an anticancer agent for its ability to inhibit cyclin-dependent kinases and induce G1 arrest, playing a crucial role in the development of targeted cancer therapies.
Used in Drug Development:
OLOMOUCINE is utilized as a lead compound in drug development for its potential to modulate cell cycle progression, offering a promising avenue for the creation of novel therapeutic agents.
Used in Research Applications:
As a purine derivative with specific biochemical properties, OLOMOUCINE is used in research settings to study the mechanisms of cell cycle regulation and the development of new strategies for cancer treatment.
Used in Chemical Synthesis:
Due to its unique chemical structure, OLOMOUCINE serves as a key intermediate in the synthesis of other bioactive compounds, contributing to the advancement of medicinal chemistry.
Biological Activity
Cyclin-dependent kinase inhibitor that competes for the ATP binding site of the kinase. Selectively inhibits cdc2/cyclin B (IC 50 = 7 μ M), cdk2/cyclin A (IC 50 = 7 μ M), cdk2/cyclin E (IC 50 = 7 μ M), cdk/p35 kinase (IC 50 = 3 μ M)? and ERK1/MAP kinase (IC 50 = 25 μ M). Arrests human fibroblasts in the G1 phase.
Biochem/physiol Actions
Olomoucine is a purine derivative which inhibits cyclin-dependent kinases and induces G arrest.
Enzyme inhibitor
This ATP site-competitive purine derivative (FW = 298.35 g/mol; CAS 101622-51-9), systematically named 6-benzylamino-2-[2-hydroxyethylamino]- 9-methylpurine, is a potent inhibitor of cyclin-dependent kinases, with an IC50 value of 7 μM for both cdk1 and cdk2 and an IC50 value of 3 μM for cdk5, arresting cells in G1. Olomoucine also inhibits cytokinin 7b-glucosyltransferase.
references
[1]. vesel j, havlicek l, strnad m, et al. inhibition of cyclin-dependent kinases by purine analogues. eur j biochem. 1994 sep 1;224(2):771-86.[2]. abraham rt, acquarone m, andersen a, et al. cellular effects of olomoucine, an inhibitor of cyclin-dependent kinases. biol cell. 1995;83(2-3):105-20.[3]. tian ds, xie mj, yu zy, et al. cell cycle inhibition attenuates microglia induced inflammatory response and alleviates neuronal cell death after spinal cord injury in rats. brain res. 2007 mar 2;1135(1):177-85.
Check Digit Verification of cas no
The CAS Registry Mumber 101622-51-9 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 1,0,1,6,2 and 2 respectively; the second part has 2 digits, 5 and 1 respectively.
Calculate Digit Verification of CAS Registry Number 101622-51:
(8*1)+(7*0)+(6*1)+(5*6)+(4*2)+(3*2)+(2*5)+(1*1)=69
69 % 10 = 9
So 101622-51-9 is a valid CAS Registry Number.
InChI:InChI=1/C15H18N6O/c1-21-10-18-12-13(17-9-11-5-3-2-4-6-11)19-15(16-7-8-22)20-14(12)21/h2-6,10,22H,7-9H2,1H3,(H2,16,17,19,20)
101622-51-9Relevant articles and documents
Novel solid-phase preparation of 2,6,9-trisubstituted purines for combinatorial library generation
Dorff, Peter H.,Garigipati, Ravi S.
, p. 2771 - 2773 (2001)
A novel procedure for the preparation of 2,6,9-trisubstituted purine libraries has been developed.
An efficient direct amination of cyclic amides and cyclic ureas
Wan, Zhao-Kui,Wacharasindhu, Sumrit,Binnun, Eva,Mansour, Tarek
, p. 2425 - 2428 (2006)
An efficient one-step amination of cyclic amides and ureas has been developed. Treatment of cyclic amides and cyclic ureas with BOP in the presence of DBU in various solvents led to the formation of cyclic amidines and cyclic guanidines in good to excellent yields. Concise syntheses of biologically intriguing kinetin and potent kinase inhibitor olomoucin were thus achieved in just one and two steps, respectively.
The scope and mechanism of phosphonium-mediated SNAr reactions in heterocyclic amides and ureas
Wan, Zhao-Kui,Wacharasindhu, Sumrit,Levins, Christopher G.,Lin, Melissa,Tabei, Keiko,Mansour, Tarek S.
, p. 10194 - 10210 (2008/04/12)
(Chemical Equation Presented) An efficient "one-step" synthesis of cyclic amidines and guanidines has been developed. Treatment of cyclic amides and ureas with benzotriazol-l-yloxytris(dimethylamino)phosphonium hexafluorophosphate (BOP), base, and nitrogen nucleophiles leads to the formation of the corresponding cyclic amidines and guanidines, typically in good to excellent yields. This method has also been used to prepare heteroaryl ethers and thioethers using phenol and thiophenol nucleophiles. Time course NMR and HPLC-MS studies have facilitated explicit characterization of the proposed intermediates (the phosphonium salt and HOBt adduct); the data reveal a stepwise reaction pathway.