Methyl 6-(phenylsulfinyl)imidazo[1,2-a]pyridine-2-carbamate, a potent, new anthelmintic

Abstract

A series of methyl imidazo-[11,2-a]pyridine-2-carbamates was synthesized for anthelmintic testing. The preparation of this class of compounds was simplified by utilization of a novel one-step condensation of the appropriately substituted 2-aminopyridine and methyl chloroacetylcarbamate. The most potent compound, methyl 6-(phenylsulfinyl)-imidazo[1,2-a]pyridine-2-carbamate, was orally effective against a broad range of helminths in sheep and cattle, at a dosage of 2.5 mg/kg. Limited trials in swine and dogs demonstrated anthelmintic activity at higher dosages. Limited observations in sheep and cattle indicated that, in both species, a single oral dose of 200 mg/kg was well tolerated.

Synthesis and Binding Affinity of 2-Phenylimidazo[1,2-a]pyridine Derivatives for both Central and Peripheral Benzodiazepine Receptors. A New Series of High-Affinity and Selective Ligands for the Peripheral Type

“…2 - Amino - 5 - iodopyridine. This compound was prepared following a previously published procedure . Full characterization of this compound is reported here: IR (KBr) 3285, 3370 cm -1 ; 1 H NMR (CDCl 3 ) δ 4.57 (s,2H, NH 2 ), 6.37 (d, J = 8 Hz, 1H, C(3)-H), 7.66 (dd, J = 8 and 2 Hz, 1H, C(4)-H), 8.25 (d, J = 2 Hz, 1H, C(6)-H); MS m/z 220 (base M + ).…”

“…This compound was prepared following a previously published procedure. 23 Full characterization of this compound is reported here: IR (KBr) 3285, 3370 cm 2-Amino-5-methoxypyridine. A mixture of 2-amino-5iodopyridine 23 (3 g, 14 mmol), Na (96 mg), and copper powder (1.2 g) in methanol (60 mL) was heated in a sealed tube at 160 °C for 48 h. After cooling, the reaction mixture was filtered, and the filtrate was evaporated under reduced pres-sure.…”

“…23 Full characterization of this compound is reported here: IR (KBr) 3285, 3370 cm 2-Amino-5-methoxypyridine. A mixture of 2-amino-5iodopyridine 23 (3 g, 14 mmol), Na (96 mg), and copper powder (1.2 g) in methanol (60 mL) was heated in a sealed tube at 160 °C for 48 h. After cooling, the reaction mixture was filtered, and the filtrate was evaporated under reduced pres-sure. The residue was purified by silica gel column chromatography [light petroleum ether/ethyl acetate, 2/8 (v/v), as eluent] to give 0.80 g (51% yield) of the title compound: IR (Nujol) 3290, 3332 cm -1 ; 1 H NMR (CDCl3) δ 3.83 (s,3H, OCH3), 6.53 (d, J ) 3 Hz, 1H, C(3)-H), 7.16 (dd, J ) 9 and 3 Hz, 1H, C(4)-H), 7.80 (d, J ) 3 Hz, 1H, C(6)-H); MS m/z 124 (base M + ).…”

Synthesis, biological evaluation and molecular docking studies of 6-(4-nitrophenoxy)-1H-imidazo[4,5-b]pyridine derivatives as novel antitubercular agents: future DprE1 inhibitors

“…Fortunately, 3-deazaneplanocin A was also found to be effective for the treatment against Ebola virus disease [23–26]. In addition, compounds containing the moiety imidazopyridine have significant biological applications such as antimycobacterial, anticoccidial, antimicrobial [27–34].…”

Synthesis, molecular docking and anti-mycobacterial evaluation of new imidazo[1,2-a]pyridine-2-carboxamide derivatives

“…Different compounds containing the moiety imidazo[1,2-a]pyridine have significant biological applications such as anti-mycobacterial [15e21], anticancer [22,23], antiviral [24e27], antimicrobial [28e30], anti-HIV [31], antiulcer [32,33], antihelminthic [34] and anticoccidial activity [35,36]. As a result of our interest in the synthesis of imidazopyridine-containing compounds and their antimicrobial activity [37], we initiated a program directed towards the synthesis of the new imidazopyridine amide derivatives.…”