Synthesis, Structure and H⁺/K⁺‐ATPase Inhibitory Activity of Novel Triazolyl Substituted Tetrahydrobenzofuran Derivatives via One‐pot Three‐component Click Reaction

Abstract

Eleven triazolyl substituted tetrahydrobenzofuran derivatives were synthesized in high yields as novel H+/K+‐ATPase inhibitor via one‐pot CuI‐catalyzed three‐component click reaction of azide, secondary amine and 3‐bromopropyne under mild conditions in water. Their structures were characterized by NMR, IR, ESI‐MS, elemental analysis and single‐crystal X‐ray diffraction analysis. Most of the target compounds exhibited better H+/K+‐ATPase inhibitory activity than commercial omeprazole with IC50 values less than 15 µmol·L−1. The initial structure‐activity analysis suggested that the triazole substituted by cycloalkyl, aromatic ring or O‐containing side‐chain seemed to be beneficial for enhancing the activity.

Synthesis and Characterization of Triazole-Linked Bistetrahydrobenzofuran Derivatives as Anti-Ulcer Agents

“…The solvents were distilled before use following the standard procedure. (E)-2-Phenyl-6,7-dihydrobenzofuran-4(5H)-one O-prop-2-yn-1-yl oxime (I) [9], (Z)-2-phenyl-6,7-dihydrobenzofuran-4(5H)-one O-prop-2-yn-1-yl oxime (II) [9] and 4-azido-2-phenyl-4,5,6,7-tetrahydrobenzofuran (III) [7] were prepared according to the procedures described in our previous literatures.…”

“…Tetrahydrobenzofurans are heterocyclic nucleus with various important pharmacological activities in natural products, pharmaceuticals and diverse synthetic intermediates [5,6]. In our recent work [7,8], the triazole-linked tetrahydrobenzofuran derivatives were also found to possess potent anti-ulcer activities. In continuation of our interest in acquisition of new H + /K + -ATPase inhibitors, herein we report a practical method for the synthesis of triazole-linked bistetrahydrobenzofuran derivatives with aim of obtaining more effective anti-ulcer agents.…”

“…4H) 13. C NMR (100 MHz, CDCl 3 ) δ (ppm): 158 7,. 153.5, 153.4, 152.4, 149.5, 144.5, 130.4, 130.5, 128.6, 127.5, 127.4, 123.6, 123.5, 122.0, 116.6, 114.7, 106.8, 104.0, 67.4, 54.5, 31.2, 28.9, 23.8, 22.8, 22.5, 19.3.…”

Synthesis, crystal structure and in vitro anticancer studies of two bis(8-quinolinolato-N,O)-platinum(II) complexes

“…carboplatin, oxaliplatin, nedaplatin, lobaplatin, and heptaplatin ( Figure 1), and about 10 other complexes are currently under clinical trials [17]. Inspired by the predecessor's excellent work [18][19][20][21][22][23][24][25], our laboratory is engaged in the search of discovering new types of platinum-based compounds and other organic anticancer compounds, not only for providing better anticancer drugs but also for mitigating the drawbacks [26][27][28]. In this paper, we report in detail the synthesis, crystal structure and antitumor activity in vitro of two bis (8-quinolinolato-N,O)-platinum(II) complexes.…”

One‐pot Two‐Step Cycloaddition Reaction for Convenient Synthesis of Polycyclic Spirooxindole‐fused [1,3]Oxazines

“…[1][2][3] Thus, spirooxindole has attracted much interests in synthetic and medical chemistry. [4][5][6][7][8][9] In many elegant synthetic methods for various spirooxindole systems, the multicomponent reactions or domino reactions have emerged as one of the efficient strategies, [10][11][12] which can provide diverse spirooxindoles in an operationally simple one-pot procedure from readily available chemical reagents. [13][14][15][16][17][18][19][20][21][22][23][24][25][26][27] In the past few years, we have also developed several practical procedures for the synthesis of diverse spirooxindoles via multicomponent reactions by using isatins and its 3-methylene, 3-imino derivatives as the substrates.…”