102146-07-6 Usage
Description
8-Cyclopentyl-1,3-dipropylxanthine, also known as DPCPX, is an oxopurine derivative with a cyclohexyl group at position 8 and propyl groups at positions 1 and 3. It is a potent and highly selective A1-adenosine receptor antagonist, characterized by its white solid appearance and a Ki of 0.46 nM for A1 receptors in rat whole-brain membranes.
Uses
Used in Pharmaceutical Industry:
8-Cyclopentyl-1,3-dipropylxanthine is used as an adenosine receptor (A1AR) antagonist for various applications, including its high selectivity towards A1 receptors, which makes it a valuable compound in the development of pharmaceuticals targeting adenosine receptors.
Used in Cancer Research:
8-Cyclopentyl-1,3-dipropylxanthine is used as an A1AR antagonist in cancer cell lines, such as MCF-7 breast cancer cells, to test its potential anti-cancer effects. Its ability to modulate adenosine receptor activity may contribute to the development of novel cancer therapies.
Used in Immunology Research:
8-Cyclopentyl-1,3-dipropylxanthine has been utilized as an A1AR antagonist in macrophages and human umbilical vein endothelial cells (HUVECs). This application aids in understanding the role of adenosine receptors in immune cell function and their potential as therapeutic targets in various immunological disorders.
Used in Neuropharmacology Research:
As a potent A1-adenosine receptor antagonist, 8-Cyclopentyl-1,3-dipropylxanthine is used in neuropharmacological studies to investigate the role of adenosine receptors in the central nervous system. This can help in the development of treatments for neurological disorders and conditions related to adenosine receptor dysregulation.
Biological Activity
Potent and selective A 1 adenosine receptor antagonist, both in vitro and in vivo . K i values are 3.9, 130, 50 and 4000 nM for human A 1 , A 2A , A 2B and A 3 receptors respectively.
Biochem/physiol Actions
8-Cyclopentyl-1,3-dipropylxanthine (DPCPX) is a selective A1?adenosine receptor antagonist. DPCPX possesses anti-cancer functionality. It induces apoptosis in breast cancer cells and favors mRNA expression of caspases.
Check Digit Verification of cas no
The CAS Registry Mumber 102146-07-6 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 1,0,2,1,4 and 6 respectively; the second part has 2 digits, 0 and 7 respectively.
Calculate Digit Verification of CAS Registry Number 102146-07:
(8*1)+(7*0)+(6*2)+(5*1)+(4*4)+(3*6)+(2*0)+(1*7)=66
66 % 10 = 6
So 102146-07-6 is a valid CAS Registry Number.
InChI:InChI=1/C16H24N4O2/c1-3-9-19-14-12(15(21)20(10-4-2)16(19)22)17-13(18-14)11-7-5-6-8-11/h11H,3-10H2,1-2H3,(H,17,18)
102146-07-6Relevant articles and documents
Convenient one-pot synthesis of 8-substituted xanthines from 6-amino-5- nitrosouracils
Moore,Schow,Lum,Nelson,Melville
, p. 1123 - 1126 (1999)
C-8 substituted 1,3-dipropylxanthines are typically prepared by reduction of the aminonitrosouracil 2 to the corresponding diamine, which is acylated and then treated with strongly basic or dehydrating reagents to afford the xanthine 1. Working to discover a milder, more efficient, reaction sequence it was found that the C-6 amino group of 2 can be acylated, and that treatment of the resulting compounds with Sn(OAc)2 gave 8-substituted xanthines. Overall, a one-pot conversion of the aminonitrosouracil 2 to dipropylxanthines 1a-i was achieved involving in situ acylation, reduction, and cyclodehydration. These conditions can be used to generate the imidazole substructure in the presence of acid and base sensitive groups on the C-8 position that may be problematic the conventional three-step xanthine syntheses.
Xanthines, optionally incorporated in liposomes, for promoting skin or hair pigmentation
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, (2008/06/13)
A method of treating skin or hair for promoting pigmentation wherein a xanthine component, in an amount effective to promote pigmentation, is incorporated in liposomes or hydrated lipidic lamellar phases.
8-(Dicyclopropylmethyl)-1,3-dipropylxanthine: A Potent and Selective Adenosine A1 Antagonist with Renal Protective and Diuretic Activities
Shimada, Junichi,Suzuki, Fumio,Nonaka, Hiromi,Karasawa, Akira,Mizumoto, Hideaki,et al.
, p. 466 - 469 (2007/10/02)
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