Novel Spiroannulated 3-Benzofuranones. Synthesis and Inhibition of the Human Peptidyl Prolyl cis/trans Isomerase Pin1

Abstract

The novel 3H-spiro[1-benzofuran-2-cyclopentan]-3-one skeleton has been made accessible by different routes. One- and two-step protocols lead to tricyclic and tetracyclic benzofuranones 2 and 3, respectively. A four-step synthesis to spirocompound 4 is described. The novel spirocyclic benzofuranones display modest to no inhibition of the human peptidyl prolyl cis/trans isomerase Pin1.

NHC-Catalyzed Organocatalytic Asymmetric Approach to 2,2-Disubstituted Benzofuran-3(2H)-ones Containing Fully Substituted Quaternary Stereogenic Center

“…Similar results were obtained using fenchone-derived NHCs (F, G, H) (Table 1, entries 6-8). We next evaluated triazolium NHC catalysts derived from camphor J-L, which displayed significantly better outcomes (Table 1, entries [10][11][12]. Gratifyingly, the desired product 2a was obtained in 98% yield with 84% ee when the precatalyst L, bearing a 2,4,6-trichlorophenyl Nsubstituent, was employed (entry 12).…”

“…3-Coumaranones (benzofuran-3(2H)-one) and naphthofuranone derivatives constitute an interesting class of heterocycles because of their presence in many naturally occurring and biologically interesting compounds and they are regarded as having a "privileged" structure in medicinal chemistry [3][4][5][6][7][8][9]. They have also been found to be important building blocks in the synthesis of valuable biologically active heterocycles and possess interesting cytotoxic and pharmacological properties such as antifungal, anticancer, and antipsychotic [10][11][12][13][14][15]. In one particularly valuable context, 2,2-disubstituted coumaranones bearing a fully substituted quaternary stereogenic center act as synthetic intermediates, since the core skeleton is present in several natural products, including pterocarpans, lignans, and other biologically active agents such as Geodin [16], griseofulvin (an antifungal agent) [17], linobiflavonoid (an anticancer agent) [18], and Sch 202,596 (which combats Alzheimer's disease) [19] (Figure 1).…”

Regioselectivity of nitrilimines 1,3‐dipolar cycloaddition: Novel synthesis of spiro[4,4]nona‐2,8‐dien‐6‐one derivatives

“…Also, pyrazoline derivatives have been found to possess antifungal 7,8, antidepressant 9–12, anticonvulsant 11,12, anti‐inflammatory 13, antibacterial 8,14, and antitumor 15 activities. Furthermore, many spirocompounds were found to possess antimicrobial 16, antitumor 17 activities and display modest inhibition of human peptidyl prolyl cis/trans isomerase Pin1 18. Moreover, spirocompounds were found to exhibit vasodilation activities 19.…”

A novel bioassay for the monitoring of carcinoembryonic antigen in human biofluid using polymeric interface and immunosensing method

“…[30][31][32][33][34][35][36][37][38][39][40] But, electrochemical fabrication is so interesting method for the sensor fabrication. 29,[41][42][43][44][45] In this study, application of AuNPs as a new matrix for provid-…”