105522-08-5

Basic information

• Product Name: (1S,2R,5R)-5-(4-chloro-1H-imidazo[4,5-c]pyridin-1-yl)-3-(hydroxymethyl)cyclopent-3-ene-1,2-diol
• Synonyms: (1S,2R,5R)-5-(4-chloro-1H-imidazo[4,5-c]pyridin-1-yl)-3-(hydroxymethyl)cyclopent-3-ene-1,2-diol;(1S,2R,5R)-5-(4-chloro-1H-iMidazo[4,5-c]pyridin-1-yl)-3-(hydroxy;(1S,2R)-5-(4-chloro-1H-iMidazo[4,5-c]pyridin-1-yl)-3-(hydroxyMethyl)cyclopent-3-ene-1,2-diol;(1S,2R,5R)-5-(4-chloroimidazo[4,5-c]pyridin-1-yl)-3-(hydroxymethyl)cyclopent-3-ene-1,2-diol
• CAS NO: 105522-08-5
• Molecular Formula: C12H12ClN3O3
• Molecular Weight: 281.69498
• Mol File: 105522-08-5.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 583.2±60.0 °C(Predicted)
• Appearance: /
• Density: 1.74±0.1 g/cm3(Predicted)
• Storage Temp.: 2-8°C
• PKA: 13.49±0.70(Predicted)
• CAS DataBase Reference: (1S,2R,5R)-5-(4-chloro-1H-imidazo[4,5-c]pyridin-1-yl)-3-(hydroxymethyl)cyclopent-3-ene-1,2-diol(CAS DataBase Reference)
• NIST Chemistry Reference: (1S,2R,5R)-5-(4-chloro-1H-imidazo[4,5-c]pyridin-1-yl)-3-(hydroxymethyl)cyclopent-3-ene-1,2-diol(105522-08-5)
• EPA Substance Registry System: (1S,2R,5R)-5-(4-chloro-1H-imidazo[4,5-c]pyridin-1-yl)-3-(hydroxymethyl)cyclopent-3-ene-1,2-diol(105522-08-5)

Safety Data

• Hazardous Substances Data: 105522-08-5(Hazardous Substances Data)

Usage

General Description

The chemical compound "(1S,2R,5R)-5-(4-chloro-1H-imidazo[4,5-c]pyridin-1-yl)-3-(hydroxymethyl)cyclopent-3-ene-1,2-diol" is a complex molecule with a cyclopentene ring structure that contains a chloro-substituted imidazo[4,5-c]pyridine group. It also contains a hydroxymethyl group attached to the cyclopentene ring. (1S,2R,5R)-5-(4-chloro-1H-imidazo[4,5-c]pyridin-1-yl)-3-(hydroxymethyl)cyclopent-3-ene-1,2-diol is likely to have biological activity due to the presence of the imidazo[4,5-c]pyridine group, which is a common structural motif found in many bioactive molecules. The hydroxymethyl group can participate in various chemical reactions, making this compound potentially useful for medicinal or synthetic chemistry applications. Further research and analysis are needed to fully understand the properties and potential uses of this chemical compound.

Upstream product

• 877651-81-5 1-[(1R,4R,5S)-3-(trityloxymethyl)-4,5-O-iso-propylidinene-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 
• 105522-07-4 (-)-1-<(1R,4R,5S)-3-(Benzyloxymethyl)-4,5-O-isopropylidene-2-cyclopenten-1-yl>-4-chloroimidazo<4,5-c>pyridine 

Downstream Products

• 120964-45-6 3-deazaneplanocin A hydrochloride 

Relevant articles and documents

CYCLOPENTENOL NUCLEOSIDE COMPOUNDS, INTERMEDIATES FOR THEIR SYNTHESIS AND METHODS OF TREATING VIRAL INFECTIONS

The present invention relates to compounds according to the structure (I), Where B is formula (Ia), formula (Ib) or formula (Ic); A is H, OR2 or halogen (F, Cl, Br, I, preferably F or Br, more preferably F); A' is H, OR2 or halogen (F, Cl, Br, I, preferably F or Br, more preferably F); A" is H or OR1, with the proviso that when A' is OR , A is H; and when A is OR2 , A' is H; X is C-R3 or N; Y is C-R3 or N; preferably X or Y is N and X and Y are not both simultaneously N; R3 is H or C1-C3 alkyl; D is H or NHR2; E is absent or H; G is O or NHR2; J is N or C-R4; K is N or C-H; R4 is H, halogen (F, Cl, Br, I), CN, -C(=O)NH2, NH2, NO2, -C=C-H (cis or trans) or -C≡C-H; Ra is H or CH3; Each R1 is independently H, an acyl group, a C1 - C20 alkyl or ether group, a phosphate, diphosphate, triphosphate, phosphodiester group; Each R2 is independently H, an acyl group, a C1 - C20 alkyl or ether group; and Pharmaceutically acceptable salts, solvates or polymorphs thereof.

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.