52377-68-1Relevant articles and documents
Expedient discovery for novel antifungal leads: 1,3,4-Oxadiazole derivatives bearing a quinazolin-4(3H)-one fragment
Chai, Jianqi,Chen, Min,Jin, Fei,Kong, Xiangyi,Wang, Xiaobin,Xue, Wei,Yang, Chunlong
, (2021/08/03)
Developing novel fungicide candidates are intensively promoted by the rapid emergences of resistant fungi that outbreak on agricultural production. Aiming to discovery novel antifungal leads, a series of 1,3,4-oxadiazole derivatives bearing a quinazolin-4(3H)-one fragment were constructed for evaluating their inhibition effects against phytopathogenic fungi in vitro and in vivo. Systematically structural optimizations generated the bioactive molecule I32 that was identified as a promising inhibitor against Rhizoctonia solani with the in vivo preventative effect of 58.63% at 200 μg/mL. The observations that were captured by scanning electron microscopy and transmission electron microscopy demonstrated that the bioactive molecule I32 could induce the sprawling growth of hyphae, the local shrinkage and rupture on hyphal surfaces, the extreme swelling of vacuoles, the striking distortions on cell walls, and the reduction of mitochondria numbers. The above results provided an indispensable complement for the discovery of antifungal lead bearing a quinazolin-4(3H)-one and 1,3,4-oxadiazole fragment.
Rhodium-catalyzed Sommelet-Hauser type rearrangement of α-diazoimines: Synthesis of functionalized enamides
Anbarasan, Pazhamalai,Ramachandran, Kuppan,Reddy, Angula Chandra Shekar,Reddy, Palagulla Maheswar
supporting information, p. 5649 - 5652 (2020/06/09)
An efficient rhodium catalyzed Sommelet-Hauser type rearrangement of sulfur ylides derived from α-thioesters and N-sulfonyl-1,2,3-triazoles has been successfully accomplished for the synthesis of various functionalized enamides. The developed reaction involves the unprecedented [2,3]-sigmatropic rearrangement of sulfur ylides with the imine motif. Importantly, the method works well with various substituted α-thioesters/-amides/-ketones and substituted N-sulfonyl-1,2,3-triazoles and allows the synthesis of diverse enamide derivatives in good to excellent yields. The reaction was also successfully extended to the one-pot synthesis of enamides from terminal alkynes.
Modular Synthesis of Carbon-Substituted Furoxans via Radical Addition Pathway. Useful Tool for Transformation of Aliphatic Carboxylic Acids Based on "build-and-Scrap" Strategy
Matsubara, Ryosuke,Kim, Hojin,Sakaguchi, Takaya,Xie, Weibin,Zhao, Xufeng,Nagoshi, Yuto,Wang, Chaoyu,Tateiwa, Masahiro,Ando, Akihiro,Hayashi, Masahiko,Yamanaka, Masahiro,Tsuneda, Takao
supporting information, p. 1182 - 1187 (2020/02/15)
Utilizing radical chemistry, a new general C-C bond formation on the furoxan ring was developed. By taking advantage of the lability of furoxans, a wide variety of transformation of the synthesized furoxans have been demonstrated. Thus, this developed methodology enabled not only the modular synthesis of furoxans but also short-step transformations of carboxylic acids to a broad range of functional groups.
Design, synthesis and bioactivity evaluation of novel thioether derivatives containing a sulfonohydrazide moiety
Li, Pei,Zhou, Junliang,Liu, Yan,Wang, Xiang
, p. 976 - 980 (2020/07/03)
A series of novel thioether derivatives containing a sulfonohydrazide moiety were synthesized and determined using 1H NMR, 13C NMR, HRMS, and elemental analysis. Their in vitro antibacterial activities against Xanthomonas oryzae pv.
Synthesis and biological evaluation of 2-(4-substituted benzene-1-sulfonyl)-N'-(substituted-1-sulfonyl)acetohydrazide as antibacterial agents
Li, Pei,Zhou, Junliang,Liu, Yan,Wang, Xiang
, p. 4559 - 4565 (2020/07/10)
In this study, a series of new sulfone derivatives containing a sulfonohydrazide moiety were synthesized and their structures were determined using 1H NMR, 13C NMR, and HRMS. Then, the in vitro antibacterial activities against Xanthomonas oryzae pv. oryzae (Xoo) and Xanthomonas axonopodis pv. citri (Xac) were evaluated by performing turbidimeter test. Bioactivity results showed that compound 2-(4-fluorobenzene-1-sulfonyl)-N′-(4-fluorobenzene-1-sulfonyl)acetohydrazide (5g) revealed the best antibacterial activities against Xoo and Xac, with the 50percent effective concentration (EC50) values of 25 and 36?μg/mL, respectively, which were superior to those of thiodiazole copper (110 and 230?μg/mL, respectively) and bismerthiazol (84 and 146?μg/mL, respectively).
Air-stable binuclear Titanium(IV) salophen perfluorobutanesulfonate with zinc power catalytic system and its application to C–S and C–Se bond formation
Wang, Lingxiao,Qiao, Jie,Wei, Jiancong,Liang, Zhiwu,Xu, Xinhua,Li, Ningbo
, (2020/01/08)
An air-stable μ-oxo-bridged binuclear Lewis acid of titanium(IV) salophen perfluorobutanesulfonate [{Ti(salophen)H2O}2O][OSO2C4F9]2 (1) was successfully synthesized by the reaction of TiIV(salophen)Cl2 with AgOSO2C4F9 and characterized by techniques such as IR, NMR and HRMS. This complex was stable open to air over a year, and exhibited good thermal stability and high solubility in polar organic solvents. The complex also had relatively strong acidity with a strength of 0.8 Ho ≤ 3.3, and showed high catalytic efficiency towards various C–S and C–Se bond formations in the presence of zinc power. This catalytic system affords a mild and efficient approach to synthesis of thio- and selenoesters, α-arylthio- and seleno-carbonyl compounds, and thio- and selenoethers.
Rhodium-Catalyzed Rearrangement of S/Se-Ylides for the Synthesis of Substituted Vinylogous Carbonates
Reddy, Angula Chandra Shekar,Anbarasan, Pazhamalai
supporting information, p. 9965 - 9969 (2019/12/24)
An efficient rhodium-catalyzed unprecedented oxa-[2,3]-sigmatropic rearrangement of sulfur ylide derived from α-thioesters/ketones and diazo carbonyl compounds has been accomplished for the synthesis of various sulfur-tethered vinylogous carbonates in good to excellent yields. Important features of the developed reaction include wide functional group tolerance, excellent chemo- and regioselectivity, and efficient rearrangement involving the carbonyl motif. The present reaction also equally works well with α-selenoesters for the synthesis of seleno-containing vinylogous carbonates.
Sulfonium ylide formation and subsequent C[sbnd]S bond cleavage of aromatic isopropyl sulfide catalyzed by hemin in aqueous solvent
Yan, Xiaojing,Li, Chang,Xu, Xiaofei,He, Quan,Zhao, Xiaoyong,Pan, Yuanjiang
supporting information, p. 3081 - 3087 (2019/05/08)
Heme is an abundant and widely existed cofactor for a variety of metalloenzymes, whose broader use is generally impeded by its high instability and poor solubility. Here we report an environment-benign and efficient strategy for the sulfonium ylide formation and subsequent C[sbnd]S bond cleavage of aromatic isopropyl sulfides, which was catalyzed by hemin in assistance of Triton X-100. This aqueous catalytic system exhibited good functional group tolerance to a variety of sulfides and diazo esters. And the reaction mechanism was preliminarily proposed on the basis of designed reactions. Furthermore, the cleavage of C[sbnd]S bond followed by introducing a functional ester group to aromatic sulfides, may potentially be employed for the late stage functionalization (LSF) of organosulfur drug in the future.
Design, Synthesis, and Evaluation of New Sulfone Derivatives Containing a 1,3,4-Oxadiazole Moiety as Active Antibacterial Agents
Li, Pei,Hu, Deyu,Xie, Dandan,Chen, Jixiang,Jin, Linhong,Song, Baoan
, p. 3093 - 3100 (2018/04/05)
This study aimed to synthesize some new sulfone derivatives containing a 1,3,4-oxadiazole moiety and investigate their in vitro antibacterial activities against Xanthomonas oryzae pv. oryzae (Xoo) and Xanthomonas axonopodis pv. citri (Xac), the pathogens
2,5-substituent-1,3,4-oxadiazole sulfone derivative as well as preparation method and application thereof
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Paragraph 0093; 0094; 0105; 0106; 0117; 0118; 0129; 0130, (2018/06/16)
The invention discloses a 2,5-substituent-1,3,4-oxadiazole sulfone derivative as well as a preparation method and application thereof. The 2,5-substituent-1,3,4-oxadiazole sulfone derivative has a general formula shown in a formula (I), wherein R1 is 4-chlorine or 4-fluorine; and R2 is methyl, ethyl, propyl, n-butyl, n-pentyl, benzyl, 4-chlorobenzyl or 4-fluorobenzyl. The 2,5-substituent-1,3,4-oxadiazole sulfone derivative disclosed by the invention has good activity on rice bacterial leaf blight and xanthomonas citri and is simple in structure, simple in preparation technology and low in production cost. (The formula (I) is described in the specification).
