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17318-31-9

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17318-31-9 Usage

Description

SQ 22,536 is an inhibitor of adenylyl cyclase with an IC50 value of 13 μM for inhibition of prostaglandin E1-stimulated increase in cAMP in intact platelets. It has been used to evaluate adenylyl cyclase activity during iloprost-induced vasorelaxation of isolated pulmonary veins or aorta in several research paradigms, inhibiting cAMP elevation at concentrations of 100-300 μM without effecting relaxation.

Uses

SQ 22,536 was used to study the role of adenylate cyclase in differentiation of PC12 cells and in gap junctional intercellular communication in breast cancer cells.

Definition

ChEBI: A nucleoside analogue that is adenine in which the nitrogen at position 9 has been substituted by a tetrahydrofuran-2-yl group. It is an adenylate cyclase inhibitor.

Biological Activity

Inhibitor of adenylyl cyclase (IC 50 = 1.4 μ M). Inhibits PGE 1 -stimulated increases in cAMP levels in intact human platelets.

Biochem/physiol Actions

SQ 22,536 is an effective inhibitor of not only basal but also prosptaglandin E1-activated adenylate cyclase activities in platelets.1 It reverses hyperalgesia contralaterally and ipsilaterally when injected intramuscularly in rats.2

Check Digit Verification of cas no

The CAS Registry Mumber 17318-31-9 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 1,7,3,1 and 8 respectively; the second part has 2 digits, 3 and 1 respectively.
Calculate Digit Verification of CAS Registry Number 17318-31:
(7*1)+(6*7)+(5*3)+(4*1)+(3*8)+(2*3)+(1*1)=99
99 % 10 = 9
So 17318-31-9 is a valid CAS Registry Number.
InChI:InChI=1/C9H11N5O/c10-8-7-9(12-4-11-8)14(5-13-7)6-2-1-3-15-6/h4-6H,1-3H2,(H2,10,11,12)

17318-31-9 Well-known Company Product Price

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  • Sigma

  • (S153)  SQ 22,536  ≥97% (HPLC), powder

  • 17318-31-9

  • S153-5MG

  • 1,817.01CNY

  • Detail
  • Sigma

  • (S153)  SQ 22,536  ≥97% (HPLC), powder

  • 17318-31-9

  • S153-25MG

  • 7,207.20CNY

  • Detail

17318-31-9SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 17, 2017

Revision Date: Aug 17, 2017

1.Identification

1.1 GHS Product identifier

Product name 9-(Tetrahydrofuran-2-yl)-9H-purin-6-amine

1.2 Other means of identification

Product number -
Other names 9-(oxolan-2-yl)purin-6-amine

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:17318-31-9 SDS

17318-31-9Downstream Products

17318-31-9Relevant articles and documents

Simple and convenient synthesis method of N9-alkylate nucleoside analogs on purine framework

-

Paragraph 0063; 0064; 0065; 0066; 0067; 0068, (2018/03/26)

The invention discloses a simple and convenient synthesis method of N9-alkylate nucleoside analogs on a purine framework. The method comprises the following steps that 2,6-site substituted purine derivatives and excessive alkyl ether are added into a reactor; next, non-metallic catalysts and oxidizing agents are added; oxidization coupling reaction is performed under the heating and stirring conditions; thin layer chromatography is used for tracking the reaction; after the reaction is completed, the materials are cooled to the room temperature; vacuum concentration is performed to remove solvents; column chromatography purification is performed; the N9-alkylate nucleoside analogs on the purine framework are obtained. The synthesis method provided by the invention has the advantages that the raw materials are cheap and can be easily obtained; the reaction conditions are mild; the reaction steps are few; the operation is simple; the problems of easy poisoning by metal catalysts, compatibility difficulty of active groups and many reaction sites in the purine derivatization reaction in the prior art are solved; the N9-alkylate nucleoside analogs on the purine framework can be efficiently synthesized.

N6,9-Disubstituted Adenines: Potent, Selective Antagonists at the A1 Adenosine Receptor

Thompson, Robert D.,Secunda, Sherrie,Daly, John W.,Olsson, Ray A.

, p. 2877 - 2882 (2007/10/02)

N6-Substituted 9-methyladenines are potent antagonists of the activation of A1 adenosine receptors.The present study assessed the effect of N6 and N-9-substituents on the binding of adenines to the A1 and A2 receptors, respectively, of rat brain cortex and striatum and also on the antagonism of the A2 receptor mediated stimulation of the adenylate cyclase of PC12 cells by N-ethyladenosine-5'-uronamide.The potency ranking of 9-substituted adenines varied directly with the hydrophobicity of the substituent: cyclopentyl > phenyl > tetrahydrofuryl > ethyl > methyl > 2-hydroxyethyl.The 9-substituted adenines showed little selectivity for either receptor and the R enantiomer of N6-(1-phenyl-2-propyl)-9-methyladenine was only 4-fold more potent than the S enantiomer at the A1 receptor.An N6-cyclopentyl substituent increased potency at the A1 receptor and decreased potency at the A2 receptor, resulting in selectivity for the A1 receptor of up to 39-fold.The N6-cyclopentyl group completely overshadowed the effect of the hydrophobicity of the 9-substituent.A 2-chloro substituent did not alter the potency of an N6-substituted 9-methyladenine.

Nucleic Acid Derived Allenols: Unusual Analogues of Nucleosides with Antiretroviral Activity

Phadtare, Shashikant,Zemlicka, Jiri

, p. 5925 - 5931 (2007/10/02)

Racemic 1,2-butadien-4-ols substituted with a nucleic acid base were prepared by a base-catalyzed isomerization of the corresponding 2-butynols.With basic heterocycles such as adenine, cytosine, 5-methylcytosine, or N-guanine, the respective allenes were obtained without difficulty, but with guanine, side reactions were observed.Reaction of 2-butynols in stronger base (1 M NaOH) gave cyclized products-oxacyclopentenes 8a-c. (+/-)-Adenallene (3a) and (+/-)-cytallene (3c) are strong inhibitors of replication of human immunodeficiency virus(HIV) in vitro. (+/-)-Adenallene (3a) and butyne 6a are substrates for adenosine deaminase.Racemic 3a was deaminated quantitatively to (+/-)-hypoxallene (3h), indicating a low stereoselectivity as contrasted with the natural substrate-adenosine.When the deamination was stopped ad ca. 50percent conversion, (-)-adenallene (3a) and (+)-hypoxallene (3h) were obtained.Antiretroviral and adenosine deaminase substrate activities are discussed in terms of the similarity of several steric and stereoelectronic features of allenic derivatives of nucleic bases with those of the corresponding nucleosides or 2',3'-dideoxyribonuclesides.

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