17318-31-9

Basic information

• Product Name: SQ 22,536
• Synonyms: 9-(2-tetrahydrofuryl)adenine;SQ 22,536 ADENYLATE CYCLASE INH;9-(Tetrahydro-2-furynal)-9H-purin-6-amine;SQ22,536/Inhibitor;9-(Tetrahydro-2-furanyl)-9H-purin-6-amine, 9-THF-Ade;6-Amino-9-[(tetrahydrofuran)-2-yl]-9H-purine;9-(Tetrahydrofuran-2-yl)-9H-purine-6-amine;6-Amino-9-(tetrahydro-2-furyl)-9H-purine
• CAS NO: 17318-31-9
• Molecular Formula: C9H11N5O
• Molecular Weight: 205.22
• EINECS: 1592732-453-0
• Mol File: 17318-31-9.mol
• Article Data: 5

Chemical Properties

• Melting Point: 160-161℃
• Boiling Point: 474.8 °C at 760 mmHg
• Flash Point: 241 °C
• Appearance: white to off-white/solid
• Density: 1.7 g/cm³
• Vapor Pressure: 3.49E-09mmHg at 25°C
• Refractive Index: 1.83
• Storage Temp.: 0-6°C
• Solubility: H2O: 21 mg/mL
• PKA: 3.82±0.10(Predicted)
• CAS DataBase Reference: SQ 22,536(CAS DataBase Reference)
• NIST Chemistry Reference: SQ 22,536(17318-31-9)
• EPA Substance Registry System: SQ 22,536(17318-31-9)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• Hazardous Substances Data: 17318-31-9(Hazardous Substances Data)

Usage

Description

SQ 22,536 is a nucleoside analogue that functions as an adenylate cyclase inhibitor. It is characterized by an adenine molecule with the nitrogen at position 9 substituted by a tetrahydrofuran-2-yl group. SQ 22,536 has an IC50 value of 13 μM for inhibiting the prostaglandin E1-stimulated increase in cAMP in intact platelets. SQ 22,536 is utilized in various research applications to study the role of adenylate cyclase in cellular processes.

Uses

Used in Cellular Research:
SQ 22,536 is used as a research tool for studying the role of adenylate cyclase in cellular differentiation and communication. It has been particularly useful in examining the differentiation of PC12 cells and gap junctional intercellular communication in breast cancer cells.
Used in Vasorelaxation Studies:
In the field of vascular biology, SQ 22,536 is used as an inhibitor to evaluate adenylyl cyclase activity during iloprost-induced vasorelaxation of isolated pulmonary veins or aorta. It effectively inhibits cAMP elevation at concentrations of 100-300 μM without affecting the relaxation process.
Used in Pharmaceutical Research:
SQ 22,536 serves as a valuable compound in the development of drugs targeting adenylate cyclase. Its ability to inhibit cAMP production makes it a potential candidate for therapeutic applications in conditions where modulation of adenylate cyclase activity is desired.
Used in Analytical Chemistry:
As an adenylate cyclase inhibitor, SQ 22,536 is employed in analytical chemistry to assess the activity of this enzyme in various biological samples. This helps in understanding the role of adenylate cyclase in different physiological and pathological processes.

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

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)

Upstream product

• 1191-99-7 2,3-dihydro-2H-furan 
• 66224-66-6 adenine 
• 1608-67-9 2-acetoxytetrahydrofuran 
• 114987-20-1 (+/-)-N⁹-(1-Oxa-3-cyclopenten-2-yl)adenine 
• 114987-15-4 N⁹-(4-Chloro-2-butyn-1-yl)adenine 
• 114978-79-9 4-(6-Amino-purin-9-yl)-but-2-yn-1-ol 
• 109-99-9 tetrahydrofuran 

Relevant articles and documents

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

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

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

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.