120964-45-6

Basic information

• Product Name: 3-Cyclopentene-1,2-diol, 5-(4-aMino-1H-iMidazo[4,5-c]pyridin-1-yl)-3-(hydroxyMethyl)-, (Hydrochloride) (1:1), (1S,2R,5R)-
• Synonyms: 3-Cyclopentene-1,2-diol, 5-(4-aMino-1H-iMidazo[4,5-c]pyridin-1-yl)-3-(hydroxyMethyl)-, (Hydrochloride) (1:1), (1S,2R,5R)-;3-Deazaneplanocin A (hydrochloride);3-Deazaneplanocin hydrochloride;DZNep hydrochloride;NSC 617989 hydrochloride;(-)-1-[(1R,4R,5S)-3-(HydroxyMethyl)-4,5-dihydroxy-2-cyclopenten-1-yl]4-aMinoiMidazo[4,5-c]pyridine hydrochloride DZNep hydrochloride;(1S,2R,5R)-5-(4-Amino-1H-imidazo[4,5-c]pyridin-1-yl)-3-(hydroxymethyl)-3-cyclopentene-1,2-diol hydrochloride (1:1);1H-Imidazo[4,5-c]pyridine, 3-cyclopentene-1,2-diol deriv.
• CAS NO: 120964-45-6
• Molecular Formula: C12H15ClN4O3
• Molecular Weight: 298.7255
• Product Categories: Inhibitors
• Mol File: 120964-45-6.mol
• Article Data: 1

Chemical Properties

• Melting Point: 168-169℃
• Appearance: white to beige/
• Storage Temp.: ?20°C
• Solubility: H2O: ≥5mg/mL
• CAS DataBase Reference: 3-Cyclopentene-1,2-diol, 5-(4-aMino-1H-iMidazo[4,5-c]pyridin-1-yl)-3-(hydroxyMethyl)-, (Hydrochloride) (1:1), (1S,2R,5R)-(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Cyclopentene-1,2-diol, 5-(4-aMino-1H-iMidazo[4,5-c]pyridin-1-yl)-3-(hydroxyMethyl)-, (Hydrochloride) (1:1), (1S,2R,5R)-(120964-45-6)
• EPA Substance Registry System: 3-Cyclopentene-1,2-diol, 5-(4-aMino-1H-iMidazo[4,5-c]pyridin-1-yl)-3-(hydroxyMethyl)-, (Hydrochloride) (1:1), (1S,2R,5R)-(120964-45-6)

Safety Data

• Hazard Codes: Xn
• Statements: 22
• WGK Germany: 3
• Hazardous Substances Data: 120964-45-6(Hazardous Substances Data)

Usage

Uses

Different sources of media describe the Uses of 120964-45-6 differently. You can refer to the following data:
1. 3-Deazaneplanocin A is a a powerful inhibitor of S-adenosylhomocysteine hydrolase that has shown potent and selective in vitro and in vivo antiviral activities.
2. 3-Deazaneplanocin A hydrochloride has been used to test its effect on ovarian tumor progression. It has also been used as a S-adenosyl homocysteine hydrolase (SAH) inhibitor in c33A2 cells.

General Description

3-Deazaneplanocin A hydrochloride is a carbocyclic analog of adenosine. It has antimetastatic?property. It is used to treat Ebola virus disease, gastric cancer, myeloma and lymphoma.

Biochem/physiol Actions

3-Deazaneplanocin A (DZNep) is an S-Adenosylhomocysteine Hydrolase inhibitor and histone methyltransferase EZH2 inhibitor. It switches on repressed tumor suppressor genes and induces apoptosis by inhibiting the expression of EZH2.

Upstream product

• 105522-07-4 (-)-1-<(1R,4R,5S)-3-(Benzyloxymethyl)-4,5-O-isopropylidene-2-cyclopenten-1-yl>-4-chloroimidazo<4,5-c>pyridine 
• 105522-08-5 (-)-1-<(1R,4R,5S)-3-(Hydroxymethyl)-4,5-dihydroxy-2-cyclopenten-1-yl>-4-chloroimidazo<4,5-c>pyridine 
• 2770-01-6 4-chloro-1H-imidazo[4,5-c]pyridine 
• 89291-77-0 (1S,4R,5S)-(-)-3-<(benzyloxy)methyl>-4,5-O-isopropylidene-2-cyclopenten-1-ol methanesulfonate 

Relevant articles and documents

Synthesis of 3-Deazaneplanocin A, a Powerful Inhibitor of S-Adenosylhomocysteine Hydrolase with Potent and Selective in Vitro and in Vivo Antiviral Activities

The neplanocin A analogue 3-deazaneplanocin A (2b) has been synthesized.A direct SN2 displacement on the cyclopentenyl mesylate 3 by the sodium salt of 6-chloro-3-deazapurine afforded the desired regioisomer 4 as the major product.After deprotection, this material was converted to 3-deazaneplanocin A in two steps.X-ray crystallographic analysis confirmed the assigned structure.Consistent with its potent inhibition of S-adenosylhomocysteine hydrolase, 3-deazaneplanocin A displayed excellent antiviral activity in cell culture against vesicular stomatitis, parainfluenza type 3, yellow fever, and vaccinia viruses.Antiviral activitiy was also displayed in vivo against vaccinia virus by using a mouse tailpox assay.The significantly lower cytotoxicity of 3-deazaneplanocin A, relative to its parent compound neplanocin A, may be due to its lack of conversion to 5'-triphosphate and S-adenosylmethionine metabolites.