2128-87-2

Basic information

• Product Name: Pyridinium, 1,1'-[1,4-phenylenebis(methylene)]bis[3-[(diethylamino)carbonyl]-, dibromide
• CAS NO: 2128-87-2
• Molecular Formula: C28H36N4O2.2Br
• Molecular Weight: 620.427
• Mol File: 2128-87-2.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: Pyridinium, 1,1'-[1,4-phenylenebis(methylene)]bis[3-[(diethylamino)carbonyl]-, dibromide(CAS DataBase Reference)
• NIST Chemistry Reference: Pyridinium, 1,1'-[1,4-phenylenebis(methylene)]bis[3-[(diethylamino)carbonyl]-, dibromide(2128-87-2)
• EPA Substance Registry System: Pyridinium, 1,1'-[1,4-phenylenebis(methylene)]bis[3-[(diethylamino)carbonyl]-, dibromide(2128-87-2)

Safety Data

• Hazardous Substances Data: 2128-87-2(Hazardous Substances Data)

Usage

General Description

Pyridinium, 1,1'-[1,4-phenylenebis(methylene)]bis[3-[(diethylamino)carbonyl]-, dibromide is a chemical compound that belongs to the class of quaternary ammonium compounds. It is composed of two benzene rings linked by a methylene bridge, with two nitrogen atoms each carrying diethylamino carbonyl groups attached to the phenylene ring. The compound also contains two bromide ions. This chemical is commonly used as a reactant and reagent in organic synthesis and research laboratories. It is known for its ability to act as a phase transfer catalyst and facilitate various chemical reactions.

Upstream product

• 10400-19-8 3-pyridinecarbonyl chloride 
• 59-67-6 nicotinic acid 
• 623-24-5 1,4-bis(bromomethyl)benzene 
• 59-26-7 N,N-diethylnicotinamide 

Downstream Products

• 2128-88-3 meso-α,α'-bis<3-(N,N-diethylcarbamoyl)piperidino>-p-xylene dibromide 
• 142566-21-0 α,α'-bis<3-<(N,N-diethylamino)methyl>piperidino>-p-xylene 

Relevant articles and documents

Synthesis of phenylene 1,3- and 1,4-bis(methylene)-3-carbamoylpyridinium bromides

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Molecular Determinants of the Platelet Aggregation Inhibitory Activity of Carbamoylpiperidines

A series of α,α'-bis-p-xylenes were synthesized and tested for their inhibitory activity on ADP-induced aggregation of human platelets.A parabolic curve was obtained when log 1/C (activity) was plotted against log P (octanol/water partition coefficient).Using this as a model, a new analogue, α,α'-bis-p-xylene (3g), was synthesized with a predicted IC50 of 25 μM.When this compound was subsequently evaluated, the IC50 was 22.1 +/- 5.5 μM, demonstrating the applicability of this model.The amide oxygen of the carbamoyl substituent appeared necessary for activity.Thus, for example, when the amide carbonyl group of 3a (IC50 = 44.5 μM) was reduced to CH2, the resulting compound 4 had a dramatically reduced activity, IC50 = 1565 μM.Compound 3a was resolved into (+) and (-) enantiomers and a meso (0) diastereomer using fractional crystallization, diastereomeric tartrate formation, and chiral HPLC.Compared to (-)-3a, the (+) isomer was 15 times more potent when ADP was the agonist and 19 times more active when collagen was used as the agonist.Molecullar modeling of R,R and S,S-3a using the SYBYL program was used to examine their interactions with phosphatidylinositol (PI).There was a better fit between PI and the R,R-3a with the energy of interaction being 17.6 kcal/mol less than that of S,S-3a/PI complex.Although the absolute stereochemistry of individual enantiomers is not known, this study shows that R,R-3a interacts more favorably with PI than does S,S-3a and that (+)-3a is a more potent inhibitor of human platelet aggregation than (-)-3a.It is postulated that because of their lipophilicity, these compounds penetrate the platelet membrane and are then protonated at the pH of the cytosol.The protonated N then neutralizes the anionic charge on the membrane phosphoinositides, thereby rendering them less susceptible to hydrolysis by phospholipase C.Thus, the determinant parameters for optimum antiplatelet activity in 3-carbamoylpiperidines are (1) the amide carbonyl, (2) appropriate stereochemistry of the 3-substituent and (3) a log P value of about 4.5.