247085-49-0

Upstream product

• 452-58-4 2,3-Diaminopyridine 
• 193979-87-2 3-bromo-4-(4-chlorophenyl)-4-oxo-N,N-dipropylbutanamide 
• 4214-75-9 2-amino-3-nitropyridine 
• 247085-43-4 2-[2-(4-chloro-phenyl)-8-nitro-imidazo[1,2-a]pyridin-3-yl]-N,N-dipropyl-acetamide 

Downstream Products

• 1257411-83-8 N₁-(2-(4-chlorophenyl)-3-(2-(dipropylamino)-2-oxoethyl)imidazo[1,2-a]pyridin-8-yl)-N₆-(1-((2R,3S,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-2-oxo-1,2-dihydropyrimidin-4-yl)adipamide 
• 1257411-82-7 N-(2-(4-chlorophenyl)-3-(2-(dipropylamino)-2-oxoethyl)imidazo[1,2-a]pyridin-8-yl)-6-oxo-6-(2-thioxothiazolidin-3-yl)hexanamide 
• 1257411-80-5 methyl 6-(2-(4-chlorophenyl)-3-(2-(dipropylamino)-2-oxo-ethyl)imidazo[1,2-a]pyridin-8-ylamino)-6-oxohexanoate 
• 1073119-26-2 3-(2-(4-chlorophenyl)-3-(2-(dipropylamino)-2-oxoethyl)imidazo[1,2-a]pyridin-8-ylamino)-3-oxopropanoic acid 
• 1073119-33-1 tert-butyl-2-(2-(4-chlorophenyl)-3-(2-(dipropylamino)-2-oxoethyl)imidazo[1,2-a]pyridin-8-ylamino)-2-oxoethylcarbamate 
• 1073119-28-4 5-(2-(4-chlorophenyl)-3-(2-(dipropylamino)-2-oxoethyl)imidazo[1,2-a]pyridin-8-ylamino)-5-oxopentanoic acid 

Relevant academic research and scientific papers

Platinum(II) complexes with bioactive carrier ligands having high affinity for the translocator protein

Peripheral benzodiazepine receptors (PBRs, also named TSPO) are overexpressed in many tumor types, with the grade of TSPO overexpression correlating with the malignancy of the tumor. For this reason, TSPO-binding ligands have been widely explored as carriers for receptor-mediated drug delivery. In this paper we have selected a ligand with nanomolar affinity for TSPO, [2-(4-chlorophenyl)-8-aminoimidazo[1,2-a]pyridin-3-yl]-N,N-di-n- propylacetamide (3), for preparing platinum adducts that are structural analogues to picoplatin, cis-[PtCl2(NH3)(2-picoline)] (AMD0473, 6), a platinum analogue currently in advanced clinical investigation. In vitro studies assessing receptor binding and cytotoxicity against human and rat glioma cells have shown that the new compounds cis-[PtX2(NH 3){[2-(4-chlorophenyl)-8-aminoimidazo[1,2-a]pyridin-3-yl]-N, N-di-n-propylacetamide}] (X = I, 4; X = Cl, 5) keep high affinity and selectivity for TSPO (nanomolar concentration) and are as cytotoxic as cisplatin. Moreover, they appear to be equally active against sensitive and cisplatin-resistant A2780 cells. Similar to cisplatin, these compounds induce apoptosis but show a favorable 10- to 100-fold enhanced accumulation in the glioma cells.

Novel 2-phenylimidazo[1,2-a]pyridine derivatives as potent and selective ligands for peripheral benzodiazepine receptors: Synthesis, binding affinity, and in vivo studies

The substituent effects at positions 6 and 8 (compounds 17-31) as well as at the amide nitrogen (compounds 32-40) of a series of 2- phenylimidazo[1,2-a]pyridineacetamides were evaluated at both central (CBR) and peripheral (PBR) benzodiazepine receptors. The structure-activity relationship studies detailed herein indicate the key structural features required for high affinity and selectivity for PBR. Substitution on the imidazopyridine nucleus at position 8 with lipophilic substituents and the presence of one chlorine atom at the para position of the phenyl ring at C(2) are crucial features for high binding affinity and selectivity toward PBR. A small subset of active ligands (i.e., 17, 20, 26, 34, and 35) were evaluated in vitro in Xenopus oocytes expressing cloned human GABA(A) receptors for their effects at CBR and in vivo for their ability to stimulate the synthesis of neurosteroids such as pregnenolone, progesterone, allopregnanolone, and allotetrahydrodeoxycorticosterone (THDOC). Compounds 17, 20, 26, and 34 markedly increased the levels of neuroactive steroids in plasma and cerebral cortex, unlike compound 35.