New naphtho/thienobenzo-triazoles with interconnected anti-inflammatory and cholinesterase inhibitory activity

Synthesis, Photochemistry, Computational Study and Potential Application of New Styryl-Thiophene and Naphtho-Thiophene Benzylamines

“…Electrocyclic derivative 15 showed the most promising inhibitory potential, with an IC 50 value of about 32.3 µM for BChE (IC 50 of galantamine is 7.9 µM for BChE). The achieved inhibitory activity of compound 15 toward BChE is in the range of triazolo-stilbenes, triazolo-thienostilbenes, and their photocyclization products that were previously investigated [28]. In that paper, it was found that the triazolo-thienostilbene derivative with trans-configuration and propyl substituent at 1,2,3-triazolo ring inhibited BChE with an IC 50 value of 18.7 µM [28], whereas its photocyclization product was active toward both enzymes (IC 50 48.8 µM for BChE and 607.0 µM for AChE).…”

“…The achieved inhibitory activity of compound 15 toward BChE is in the range of triazolo-stilbenes, triazolo-thienostilbenes, and their photocyclization products that were previously investigated [28]. In that paper, it was found that the triazolo-thienostilbene derivative with trans-configuration and propyl substituent at 1,2,3-triazolo ring inhibited BChE with an IC 50 value of 18.7 µM [28], whereas its photocyclization product was active toward both enzymes (IC 50 48.8 µM for BChE and 607.0 µM for AChE). Among these derivatives, the best result was achieved with allyl-thienobenzotriazole IV (Figure 1), which inhibited BChE with an excellent IC 50 value of 3.8 µM and AChE with a very good IC 50 value of 56.2 µM.…”

“…According to our previous experience in the field of the synthesis and photochemistry of heterostilbene molecules [27][28][29], we herein designed, synthesized, and photochemically transformed the new amino-thienostilbenes (Figure 1I) as interesting structures with potential biological activity and specific chemical and photophysical characteristics. so-called NLO materials (nonlinear optical materials) [12,13].…”

“…According to our previous experience in the field of the synthesis and photochemistry of heterostilbene molecules [27][28][29], we herein designed, synthesized, and photochemically transformed the new amino-thienostilbenes (Figure 1I) as interesting structures with potential biological activity and specific chemical and photophysical characteristics. The basic structure of new and known heterostilbenes and their photocyclization products: new amino-thienostilbenes (I), amino-oxazolostilbenes (II) [27], naphthooxazolo-amines (III) [27], and thienobenzo-triazoles (IV) [29], as proven active compounds, and amino-styryl organic dye (V) [30].…”

“…New amino-thienostilbenes, stable under acidic conditions and with favorable photophysical properties, could be used to prepare their water-soluble ammonium salts as potentially biologically active compounds. On the other hand, their functionalized photocyclization products could be good candidates for cholinesterase inhibition, given that they have the same basic skeleton as some already proven bioactive derivatives [28,29]. New styryl-thiophene benzylamines 2-8 (Scheme 1) are synthesized by the Buchwald-Hartwig amination reactions [27] from the previously prepared chloro derivative 1 [34].…”