212844-53-6 Usage
Uses
Used in Anti-cancer Applications:
Purvalanol A is used as a potent CDK inhibitor for the treatment of cell proliferative disorders, particularly in the context of cancer therapy. It targets various cyclin-dependent kinases, which play a crucial role in regulating cell cycle progression, and its inhibition can lead to the suppression of tumor growth and the induction of apoptosis in cancer cells.
Used in Pharmaceutical Industry:
Purvalanol A is used as a research tool and potential therapeutic agent in the pharmaceutical industry. Its ability to modulate cell cycle progression and induce apoptosis makes it a valuable compound for the development of drugs targeting cancer and other cell proliferative disorders. Additionally, its cell permeability allows for better drug delivery and bioavailability, enhancing its potential as a therapeutic agent.
Biological Activity
Cyclin-dependent kinase inhibitor. IC 50 values are 4, 70, 35, 850 and 75 nM for cdc2/cyclin B, cdk2/cyclin A, cdk2/cyclin E, cdk4/cyclin D1 and cdk5-p35 respectively. Reversibly arrests synchronised cells in G1 and G2, and inhibits cell proliferation and cell death.
References
1) Gray?et al.?(1998),?Exploiting chemical libraries, structure, and genomics in the search for kinase inhibitors; Science,?281?533
2) Villerbu?et al.?(2002),?Cellular effects of purvalanol A: a specific inhibitor of cyclin-dependent kinase activities; Int. J. Cancer,?97?761
3) Coker-Gurkan?et al.?(2015),?Purvalanol induces endoplasmic reticulum stress-mediated apoptosis and autophagy in a time dependent manner in HCT116 colon cancer cells; Oncol. Rep.,?33?2761
4) Hikita?et al.?(2010),?Purvalanol A, a CDK inhibitor, effectively suppresses Src-mediated transformation by inhibiting both CDKs and c-Src; Genes Cells,?15?1051
5) Goga?et al.?(2007),?Inhibition of CDK1 as a potential therapy for tumors over-expressing MYC; Nat. Med.,?13?820
Check Digit Verification of cas no
The CAS Registry Mumber 212844-53-6 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 2,1,2,8,4 and 4 respectively; the second part has 2 digits, 5 and 3 respectively.
Calculate Digit Verification of CAS Registry Number 212844-53:
(8*2)+(7*1)+(6*2)+(5*8)+(4*4)+(3*4)+(2*5)+(1*3)=116
116 % 10 = 6
So 212844-53-6 is a valid CAS Registry Number.
InChI:InChI=1/C19H25ClN6O/c1-11(2)15(9-27)23-19-24-17(22-14-7-5-6-13(20)8-14)16-18(25-19)26(10-21-16)12(3)4/h5-8,10-12,15,27H,9H2,1-4H3,(H2,22,23,24,25)/t15-/m0/s1
212844-53-6Relevant academic research and scientific papers
Oxidative amination of cuprated pyrimidine and purine derivatives
Boudet, Nadege,Dubbaka, Srinivas Reddy,Knochel, Paul
supporting information; experimental part, p. 1715 - 1718 (2009/04/10)
Using regioselective cuprations (via magnesiations), various primary, secondary and tertiary aminated pyrimidine and purine derivatives were prepared by the oxidative coupling of lithium amidocuprates using chloranil. DNA and RNA units such as aminated uracil or thymine, and adenine, as well as a CDK inhibitor, purvalanol A, were all obtained under mild conditions and satisfactory yields.
2-(Benzylsulfanyl)-6-chloro-9-isopropylpurine, a valuable intermediate in the synthesis of diaminopurine cyclin dependent kinase inhibitors
Taddei, David,Slawin, Alexandra M. Z.,Woollins, J. Derek
, p. 939 - 947 (2007/10/03)
The synthetic potential of a novel precursor of 2,6-diaminopurine CDK inhibitors, 2-(benzylsulfanyl)-6-chloro-9-isopropylpurine, is described. The Traube purine synthesis was chosen to prepare the required 2-(benzylsulfanyl) hypoxanthine intermediate. Attempts to prepare its purin-6-yl methanesulfonic ester analogue failed. Conversion to the 6-chloropurine derivative enabled the introduction of arylamines in the presence of catalytic amounts of acid. Further chemical variety was introduced on the purine through a regioselective Mitsunobu N-9 alkylation. Oxidative cleavage of the 2-(benzylsulfanyl) leaving group with an aliphatic amine was implemented as previously reported. Purvalanol A, a potent CDK inhibitor, was synthesised using this methodology. The template and intermediates were fully characterised by modern spectroscopic techniques and single-crystal X-ray diffraction. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005.
