102146-07-6 Usage
Chemical Properties
White Solid
Uses
Different sources of media describe the Uses of 102146-07-6 differently. You can refer to the following data:
1. DPCPX is a potent and very selective A1-adenosine receptor antagonist, with a Ki of 0.46 nM for A1 receptors in rat whole-brain membranes. Its 740-fold A1-selectivity is the highest reported for an adenosine antagonist
2. 8-Cyclopentyl-1,3-dipropylxanthine has been used as an adenosine receptor (A1AR) antagonist in macrophages and human umbilical vein endothelial cells (HUVECs). It has also been used as A1AR antagonist in MCF-7 breast cancer cell line to test its anti-cancer effect.
Definition
ChEBI: An oxopurine that is 7H-xanthine substituted at positions 1 and 3 by propyl groups and at position 8 by a cyclohexyl group.
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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