Bromo‐Substituted Diazenyl‐pyrazolo[1,5‐a]pyrimidin‐2‐amines: Sonogashira Cross‐Coupling Reaction, Photophysical Properties, Bio‐interaction and HSA Light‐Up Sensor

Abstract

A convenient synthesis of a broad series of thirteen examples of alkyne-spacer derivatives 2 from the well-known Sonogashira cross-coupling reaction on diazenyl-pyrazolo[1,5-a]pyrimidin-2amine compounds 1 is reported. The reactivity of heterocycles 1 due the presence of selected electron-donor (EDG) and electron-withdrawing (EWG) groups attached to different alkynes was evaluated. Also, the reactional versatility due the position variation of the bromo atom at the scaffolds 1 was also investigated. In general, derivatives presented strong absorption bands at the 250-500 nm optical window and UV to cyan emission properties. Also, the redox analysis was recorded by electrochemical cyclic voltammetry technique. For HSA biomacromolecule assays, spectroscopic studies by UV-Vis, steadystate and time-resolved emission fluorescence, and molecular docking calculations evidenced the ability of each compound to establish interactions with human serum albumin (HSA). Finally, the behavior presented for this new class of heterocycles makes them a promising tool as optical sensors for albumins.

Recent Expedition inPd‐CatalyzedSonogashira Coupling and Related Processes†

“…[22] The Pd(OAc) 2 /CuI/XPhos catalyst system was applied in the Sonogashira cross-coupling reaction on diazenyl-pyrazolo [1,5-a]pyrimidin-2-amine to synthesize a broad series of alkyne-spacer derivatives which are potentially used as optical sensors for albumins. [23] The synthetic access to functionalized dipolarophiles of Lewis basic complexant scaffolds was reported by Carrick and Chaudhuri in 2018 (Scheme 2a).…”

“…[ 22 ] The Pd(OAc) 2 /CuI/ XPhos catalyst system was applied in the Sonogashira cross‐coupling reaction on diazenyl‐pyrazolo[1,5‐ a ]pyrimidin‐2‐amine to synthesize a broad series of alkyne‐spacer derivatives which are potentially used as optical sensors for albumins. [ 23 ]…”