82626-74-2

Usage

Chemical Properties

Brown Solid

InChI:InChI=1/C15H10Cl2N2O2/c16-10-3-1-9(2-4-10)15-12(7-14(20)21)19-8-11(17)5-6-13(19)18-15/h1-6,8H,7H2,(H,20,21)

Upstream product

• 1381932-40-6 C₁₄H₁₄ClNO₆ 
• 1072-98-6 5-chloro-2-pyridylamine 
• 706-07-0 1-chloro-4-(2-nitrovinyl)benzene 
• 99-91-2 para-chloroacetophenone 
• 89781-40-8 C₁₂H₁₁ClO₃ 
• 104-88-1 4-chlorobenzaldehyde 
• 35158-46-4 3-bromo-4-(4-chloro-phenyl)-4-oxo-butyric acid ethyl ester 
• 53503-49-4 ethyl 4-(4-chlorophenyl)-4-oxobutanoate 
• 365213-33-8 [6-chloro-2-(4-chlorophenyl)-imidazo[1,2-a]pyridin-3-ylmethyl]-dimethylamine 
• 88964-99-2 6-chloro-2-(4-chlorophenyl)imidazo[1,2-a]pyridine 
• 82626-73-1 2-[6-Chloro-2-(4-chloro-phenyl)-imidazo[1,2-a]pyridin-3-yl]-acetamide 
• 193979-48-5 ethyl 2-(6-chloro-2-(4-chlorophenyl)imidazo[1,2-a]pyridin-3-yl)acetate 

Downstream Products

• 1257411-86-1 2-(6-chloro-2-(4-chlorophenyl)imidazo[1,2-a]pyridin-3-yl)-N-(1-((2R,3S,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-2-oxo-1,2-dihydropyrimidin-4-yl)acetamide 
• 946618-52-6 2-[6-chloro-2-(4-chlorophenyl)imidazo[1,2-a]pyridine-3-yl]-N-[2-(3,4-di-tert-butyldimethylsilyloxyphenyl)ethyl]acetamide 
• 946618-48-0 (S)-ethyl-2-{2-[6-chloro-2-(4-chlorophenyl)imidazo[1,2-a]pyridine-3-yl]acetylamino}-3-[3,4-bis(tert-butyldimethylsilyloxy)phenyl]propanoate 
• 946618-38-8 (S)-ethyl-2-{2-[6-chloro-2-(4-chlorophenyl)imidazo[1,2-a]pyridine-3-yl]acetylamino}-3-(3,4-dihydroxyphenyl)propanoate 
• 82625-99-8 2-(6-chloro-2-(4-chlorophenyl)imidazo[1,2-a]pyridin-3-yl)-N,N-dimethylacetamide 

Relevant academic research and scientific papers

COMPOSITIONS AND METHODS FOR REDUCING TACTILE DYSFUNCTION, ANXIETY, AND SOCIAL IMPAIRMENT

The present invention features novel peripherally-restricted non-benzodiazipene analogs with reduced blood brain barrier permeability and methods of use thereof for reducing tactile dysfunction, social impairment, and anxiety in a subject diagnosed with A

Flow chemistry synthesis of zolpidem, alpidem and other GABAA agonists and their biological evaluation through the use of in-line frontal affinity chromatography

The flow of information between chemical and biological research can present a bottleneck in pharmaceutical research. Tools that bridge these disciplines and aid information exchange have therefore clear value. Over the last few years, both synthetic chemistry and biological screening have benefited from automation, and a seamless chemistry-biology interface is now possible. We report here on the use of flow processes to perform synthesis and biological evaluation in an integrated manner. As proof of concept, a flow synthesis of a series of imidazo[1,2-a]pyridines, including zolpidem and alpidem, was developed and connected to a Frontal Affinity Chromatography screening assay to investigate their interaction with Human Serum Albumin (HSA). The Royal Society of Chemistry 2013.

Synthesis of imidazopyridines from the Morita-Baylis-Hillman acetates of nitroalkenes and convenient access to alpidem and zolpidem

A variety of functionalized imidazo[1,2-a]pyridines have been synthesized through a one-pot, room temperature, and reagent-free reaction between MBH acetates of nitroalkenes and 2-aminopyridines. The reaction involves a cascade inter-intramolecular double aza-Michael addition of 2-aminopyridines to MBH acetates. Our methodology is marked by excellent yield, regioselectivity and, above all, adaptability to synthesize imidazopyridine-based drug molecules such as Alpidem and Zolpidem.

Alpidem analogues containing a GABA or glycine moiety as new anticonvulsant agents

Alpidem analogues containing a GABA (1-3) or glycine (4-6) moiety were synthesized and their interaction with the GABA/benzodiazepine receptor complex at central (CBR) and peripheral (PBR) level was evaluated. In particular, their ability to modulate the specific binding of [3H]-GABA to washed membrane preparations from the rat cerebral cortex, as well as their effects on human recombinant GABAA receptors in Xenopus laevis oocytes, were assessed. Results from these in vitro assays showed that the most active compounds were 1 and 4. Intraperitoneal administration of compound 1 at a dose of 150 mg/kg significantly antagonized pentylenetetrazole-induced seizures in rats and the protective effects were evident for 90 min. However, compound 4 failed to interact with strychnine-sensitive Gly-binding sites. Consistent with these binding results, intraperitoneal administration of compound 4 at 150 mg/kg showed no effect against convulsions induced by strychnine, except for a prolonged time of the latency of convulsions. The results obtained suggest that compound 1 possesses interesting anticonvulsant activity and deserves further investigation as a novel lipophilic GABA derivative.

A structure-activity relationship study of the affinity of selected imidazo[1,2-a]pyridine derivatives, congeners of zolpidem, for the ω1-subtype of the benzodiazepine receptor

A series of 6-substituted 2-aryl-N,N-dimethylimidazol [1,2-a]pyridine-3-acetamides, congeners of zolpidem and alpidem, was synthesized and tested in vitro for binding with the benzodiazepine receptor in the competition with 3H-zolpidem as an ω1-selective radioligand. Molecular electrostatic potential (MEP) and the HOMO and LUMO energies were calculated for the compounds by semi-empirical quantum chemistry methods. The lipophilicity parameter of the compounds, expressed as the logarithm of the octanol-water partition coefficient (log P), was calculated; alternatively, standard values of the Hansch hydrophobic substituent constants π were used. In agreement with earlier investigations on the benzodiazepine receptor ligands with a high preference for the ω1-subtype, a quantitative correlation of the biological data with molecular parameters has revealed a significant dependence (r=0.954) of the binding affinity (IC50) on the deepest MEP minimum, in this case associated with the amide carbonyl oxygen atom. The lipophilicity parameters were found to be of lower significance.

Synthesis and binding affinity of 2-phenylimidazo[1,2-α]pyridine derivatives for both central and peripheral benzodiazepine receptors. A new series of high-affinity and selective ligands for the peripheral type

A number of 6-substituted or 6,8-disubstituted alkyl 2- phenylimidazo[1,2-a]pyridine-3-carboxylates 5a-h,-acetates 5i-s, 6a-g, and - propionates 5t, 6h and of N,N-dialkyl-2-phenylimidazo[1,2-α]pyridlne-3- carboxamides 7a-d, -aceramides 7e-t or -propionamide 7u were prepared following new synthetic methods, and their affinities for both the central (CBR) and the peripheral (PBR) benzodiazepine receptors evaluated. The compounds of the ester series displayed low affinity for both receptor types. Conversely, most of N,N-dialkyl(2-phenylimidazo[1,2-a]pyridin-3-yl)acetamides 7e-t proved to possess high affinity and selectivity for CBR or PBR depending on the nature of substituents at C(6)- and/or C(8) on the heterocyclic ring system. In particular, the 6-substituted compounds 7f-n displayed ratios of IC50 values (IC50(CBR)/IC50(PBR)) ranging from 0.32 (7m) to 232 (7k), while the 6,8-disubstituted compounds 7o-t were more than 1000-fold more selective for PBR versus CBR. Compounds 7f,m were examined in several different benzodiazepine receptor subtypes. Expression of specific GABA(A) receptor subunit assemblies in Xenopus oocytes was utilized to evaluate functionally both the efficacy and potency of the positive modulation of GABA-evoked C1+ currents by 7f and 7m in comparison with Zolpidem. The rank order of potencies of these drugs was 7f (EC50 = 3.2 x 10-8 M) > Zolpidem (EC50 = 3.6 x 10-8 M) > 7m (EC50 = 2.2 x 10-7 M). The actions of these compounds were also tested on α2β2γ2(s) receptors. However, the EC50 of these compounds was increased, compared to α1β2γ2(s) receptors, by 30-, 4-, and 5-fold for 7m, 7f, and Zolpidem, respectively. Finally, these compounds were almost completely devoid of activity at receptors containing the α5 subunit.