Zhongwen Wang

Utilizing a readily available and highly efficient organic photocatalyst (QXPT-NPy, 0.5 mol %) and inexpensive CBr₄ (0.5 mol %) as a bromine radical precursor, the [3 + 2] cycloadditions of vinylcyclopropanes with alkenes/alkynes were successfully achieved under irradiation of 420 nm blue LEDs. A broad scope of alkenes and alkynes participated efficiently in the reaction, and structurally diverse cyclopentane and cyclopentene derivatives were afforded in up to 97% yield and 95:5 dr.

Angular tricyclic and polycyclic skeletons feature typical cores in an intriguing type of natural products. We herein report the Lewis acids-catalyzed dearomative (3 + 2) cycloadditions of donor-acceptor cyclopropanes with benzene ring, by which structurally complex and diverse angular tricyclic and polycyclic carbocycles were efficiently constructed from cheap and easily available feedstock and with convenient operation. This is also the example of (3 + 2) cycloaddition of a C3-synthon with the C = C of benzene. We believe this will demonstrate its potential in the total syntheses of natural products and drug discovery.

Concise total syntheses of (–)-quinocarcinol methyl ester and (–)-oxa-quinocarcinol methyl ester have been achieved. The features of the synthetic strategy include a stereoselective [3 + 2]IMCC and a stereoselective Krapcho decarboxylation.

Concise and scalable formal syntheses of (-)-quinocarcinamide and (-)-quinocarcin have been achieved in 9 steps with 9% overall yield from simple commercially available chemicals. The synthetic strategy features an ortho-regioselective Pictet-Spengler cyclization for the construction of the tetrahydroisoquinoline skeleton, a stereoselective formal intramolecular [3 + 2] cross cycloaddition of cyclopropane 1,1-diester with an imine for the construction of the 3,8-diazabicyclo[3.2.1]octane skeleton.

Diamide insecticides have gained popularity due to their high efficacy and low toxicity to nontarget organisms. However, diamide-associated resistance has emerged recently, causing a significant reduction in their potency, thereby hindering sustainable agricultural development. Here, we explored novel diamide insecticide analogs and, using a structure-based approach, rationally designed and synthesized 28 nitrophenyl substituted anthranilic diamides. Most of the compounds showed moderate to good activity against Mythimna separata, Plutella xylostella, and Spodoptera frugiperda. Among them, compounds Ia and Im showed extraordinarily high activity and their mode of action was verified on isolated neurons. Additionally, Im exhibited over 10-fold greater potency than chlorantraniliprole in a HEK293 cell line stably expressing S. frugiperda ryanodine receptors (SfRyRs) containing the resistance mutations, G4891E and I4734M. The binding modes of Im in the SfRyRs were predicted using in silico molecular docking analysis. Our novel nitrophenyl substituted anthranilic diamide derivatives provide valuable insights for the design of insecticidal RyR-targeting compounds to effectively control both wild type and diamide insecticide-resistant lepidopteran pests.

Research of thermally activated delayed fluorescence (TADF) and room‐temperature phosphorescence (RTP) materials is attractive owing to their extensive applications in various fields. However, achieving organic TADF and RTP materials, particularly those with stimulus‐responsiveness and tunability, is highly desirable but challenging and rarely reported. Herein, two easily synthesized organic molecules are reported with abnormal stimulus‐responsive switchable TADF and RTP effects, in which phenothiazine (PTZ) and benzo[b]phenothiazine (BPTZ) based donor−acceptor molecules PTZ‐DBQ and BPTZ‐DBQ show mechanical‐induced TADF in crystalline phase and photo‐responsive RTP in doping poly(methyl methacrylate) (PMMA) films. This is the first time tetracyclic BPTZ has been used as a donor in achieving TADF and RTP materials, and it is found that BPTZ‐DBQ exhibits remarkably better photophysical properties than PTZ‐DBQ. Systematic studies of experimental results and theoretical calculations indicate that the conformational heterogeneity plays an essential role in achieving mechanical‐induced TADF with mechanochromic luminescence (MCL) property. Embedding the organic phosphors into rigid polymer matrices effectively suppresses the molecular motion, thus turning on the RTP emission channel. The conversion of ³O₂ to ¹O₂ under UV irradiation is mainly responsible for the photo‐induced process. These multifunctional luminescent materials have great potential applications in chemical sensors, information encryption, and anti‐counterfeiting.

We have developed a visible-light-mediated formal [4 + 2] cycloaddition of arylcyclobutylamines with olefins, using QXPT-NPhCN as an organic photocatalyst. The corresponding cycloadducts could be obtained from electron-deficient olefins, aryl olefins and exocyclic olefins. We found that the addition of K₃PO₄ could significantly promote the cycloadditions. Using this method, 2-functionalized cyclohexylamines including the ones with spiro-skeletons can be expediently obtained. Based on the “3D-bioisostere” principle, we designed and synthesized three cyclohexylamine 2-sulfonylurea compounds.

Methicillin-resistant Staphylococcus aureus (MRSA) is a worldwide health threat and has already tormented humanity during its long history, creating an urgent need for the development of new classes of antibacterial agents. In this study, twenty-one novel sulfonylurea derivatives containing phenyl-5-vinyl and pyrimidinyl-4-aryl moieties were designed and synthesized, among which, nine compounds exhibited inhibitory potencies against Gram-positive bacterial strains: MRSA (Chaoyang clinical isolates), S. aureus ATCC6538, vancomycin-resistant Enterococci-309 (VRE-309), and Bacillus subtilis ATCC 6633. Especially, 9i and 9q demonstrated inhibitory activities against the four bacterial strains with minimum inhibitory concentrations (MICs) of 0.78–1.56 μg/mL, and quite a few of other MRSA clinical strains with MICs of 0.78 μg/mL, superior to those of the positive controls vancomycin (MIC of 1 μg/mL) and methicillin (MIC of >200 μg/mL). This is the very first time that sulfonylurea derivatives have been identified as promising inhibitors against different MRSA clinical isolates. In addition, all the MIC values of the synthesized compounds against Candida albicans were greater than 100 μg/mL. Since the reported anti-Candida activities of sulfonylureas were due to acetohydroxyacid synthase (AHAS) inhibition, the molecular target against MRSA for the target sulfonylureas was thought to be a different mode of action. Density functional theory (DFT) calculations were finally performed to understand the structure–activity relationships, based on which, significant differences were observed between their HOMO maps for compounds with strong antibacterial activities and weak anti-MRSA effects. The present results hence provide valuable guidance for the discovery of novel agents to treat bacterial infections, especially against MRSA.

We developed a visible-light-mediated [3 + 2] cycloaddition of arylcyclopropylamine with structurally diverse olefins using QXPT-NPh as a highly efficient organic photoredox catalyst. We first achieved the use of various alkyl-substituted alkenes in intermolecular [3 + 2] cycloadditions with cyclopropylamine. We also developed a general and efficient strategy for the construction of structurally diverse cyclopentane-based spiro[4.n] skeletons with 1,3-difunctional groups, which broadly exist in natural products and synthetic molecules. Furthermore, we proposed a hydrogen-bond mode between the arylcyclopropylamine and the photocatalyst QXPT-NPh.