Design, synthesis, and bioactivity evaluation of novel thiochromanone derivatives containing an oxime or oxime ether moiety

Abstract

In this study, using botanical active component thiochromanone as the lead compound, a series of novel thiochromanone derivatives containing an oxime or oxime ether moiety were designed and synthesized. The half-maximal effective concentration (EC 50 ) values of compound 4a against Xanthomonas oryzae pv. oryzae (Xoo), Xanthomonas oryzae pv. oryzicolaby (Xoc), and Xanthomonas axonopodis pv. citri (Xac) were 6, 10, and 15 μg/ml, respectively, which were superior to those of Bismerthiazol and Thiodiazole-copper. Meanwhile, compound 4a also revealed better antifungal activity against Botrytis cinerea, with the EC 50 value of 18 μg/ml, than that of Carbendazim. To the best of our knowledge, this is the first report on the antibacterial and antifungal activities of this series of novel thiochromanone derivatives containing an oxime or oxime ether moiety.

Oxime Derivatives: A Valid Pharmacophore in Medicinal Chemistry

“…[4] These compounds have been effectively converted into amides [5] and amines, [6] including nitroalkanes, 1,3-oxazoles, [7] -thiazoles and -diazoles, hydroxylamines, [8] and hydroxylamine O-ethers, nitroalkanes. [9] Typically, oxime anions in solution behave amorphously, but they can function as weak bases (pK b = 12) and weak acids (pK a = 11). Therefore, they can be used to prepare other chemicals.…”

“…The order of the target compounds' bioactivities was 18 a > 18 c,18 b > 18 d, and 18 e > 18 f. Thus, it was concluded that to manage plant bacterial and fungal diseases, this study provided a useful tool for directing the design and synthesis of new and more promising active small molecules of thiochromanone derivatives that contain an oxime or oxime ether moiety. [9] was substituted for the C atom. Compound 19 w demonstrated great larvicidal activity against oriental armyworms.…”

“…Oximes are attractive functional frameworks with widespread applications not only in synthesis but also in medicine and materials chemistry [4] . These compounds have been effectively converted into amides [5] and amines, [6] including nitroalkanes, 1,3‐oxazoles, [7] ‐thiazoles and ‐diazoles, hydroxylamines, [8] and hydroxylamine O‐ethers, nitroalkanes [9] . Typically, oxime anions in solution behave amorphously, but they can function as weak bases (pK b =12) and weak acids (pK a =11).…”

Antimicrobial Activity and DFT Studies of a Novel Set of Spiropyrrolidines Tethered with Thiochroman-4-one/Chroman-4-one Scaffolds

“…Thiochromanones, the thio-analogs of chromanones, feature interesting scaffolds, which have been reported to exert a plethora of pronounced biological and pharmacological properties including antimicrobial [39][40][41][42], anticancer [43][44][45][46], human steroid sulfatase inhibition [47,48], α-adrenergic antagonist [49], antiviral [50], and insecticidal activities [51] (Figure 1). In light of the significance of spiropyrrolidine and thiochromanone/chromanone heterocycles in medicinal chemistry, we felt a great potential to combine these two moieties into one single scaffold to design a novel class of hybrid spiroheterocycles, which may exhibit interesting biological profiles.…”

“…Thiochromanones, the thio-analogs of chromanones, feature interesting scaffolds, which have been reported to exert a plethora of pronounced biological and pharmacological properties including antimicrobial [39][40][41][42], anticancer [43][44][45][46], human steroid sulfatase inhibition [47,48], α-adrenergic antagonist [49], antiviral [50], and insecticidal activities [51] (Figure 1).…”