Synthesis of carbon-14 and deuterium labeled 3-nitro-6-propoxyimidazo [1, 2-b]pyridazine - An antiparasitic agent

Abstract

A potent a n t i p a r a s i t i c agent 3-nitro-6-propoxyimidazo[l,2-b]oxy side chain, from n-propanol-l-"T and 6-chloro-3-nitroimidazo-pyridazine (2) was synthesized, labeled w i t h carbon-14 i n the pro-E 1,2-b]pyridazine (2). The f i n a l product was obtained i n 58% radiochemical y i e l d w i t h s p e c i f i c a c t i v i t y o f 1.13 mCi/mnole and radiochemical p u r i t y o f greater than 99%. The deuterium labeled compound (9 was also synthesized f o r absorption and metabolism studies.

Nitro-sulfinate Reductive Coupling to Access (Hetero)aryl Sulfonamides

“…Proposed Reaction Mechanism The title compound was prepared according to a literature procedure. 21 20 4-Fluoro-N-hydroxy-N-phenylbenzenesulfonamide (7).…”

“…The title compound was prepared according to a literature procedure. 21 6-Chloro-imidazo[1,2- b ]pyridazine (2.48 g, 15.8 mmol) was dissolved in 98% H 2 SO 4 (30 mL) and cooled (0 °C). Concentrated HNO 3 (5 mL) was added dropwise over 10 min with vigorous stirring.…”

Product Class 5: Azaindolizines with Two Nitrogen Atoms in the Five-Membered Ring

“…[73,75±77] Investigations of their UV [72] and photoelectron spectra, [78] as well as MO calculations of their electronic density, [78] have been carried out. [17,82±85] Scheme 20 Deuterium Exchange Reactions of Some Imidazodiazines [4,81] Several derivatives of this product subclass have shown valuable biological properties (e.g., á-adrenergic receptor selectivity, [86] positive inotropic, [87,88] antibronchospastic, [89] cytoprotective, [10] antiparasitic, [90] antiviral, [91] benzodiazepine receptor, [92] anxiolytic, [93] antimicrobial, [16] local anesthetic, [19] central nervous system, [94] and antiallergic [95] activity). The latter reactivity order has been rationalized by calculation of molecular electrostatic potential isodensity surfaces.…”