79428-77-6Relevant articles and documents
Discovery of Highly Potent Pinanamine-Based Inhibitors against Amantadine- and Oseltamivir-Resistant Influenza A Viruses
Zhao, Xin,Li, Runfeng,Zhou, Yang,Xiao, Mengjie,Ma, Chunlong,Yang, Zhongjin,Zeng, Shaogao,Du, Qiuling,Yang, Chunguang,Jiang, Haiming,Hu, Yanmei,Wang, Kefeng,Mok, Chris Ka Pun,Sun, Ping,Dong, Jianghong,Cui, Wei,Wang, Jun,Tu, Yaoquan,Yang, Zifeng,Hu, Wenhui
supporting information, p. 5187 - 5198 (2018/06/04)
Influenza pandemic is a constant major threat to public health caused by influenza A viruses (IAVs). IAVs are subcategorized by the surface proteins hemagglutinin (HA) and neuraminidase (NA), in which they are both essential targets for drug discovery. While it is of great concern that NA inhibitor oseltamivir resistant strains are frequently identified from human or avian influenza virus, structural and functional characterization of influenza HA has raised hopes for new antiviral therapies. In this study, we explored a structure-activity relationship (SAR) of pinanamine-based antivirals and discovered a potent inhibitor M090 against amantadine-resistant viruses, including the 2009 H1N1 pandemic strains, and oseltamivir-resistant viruses. Mechanism of action studies, particularly hemolysis inhibition, indicated that M090 targets influenza HA and it occupied a highly conserved pocket of the HA2 domain and inhibited virus-mediated membrane fusion by locking the bending state of HA2 during the conformational rearrangement process. This work provides new binding sites within the HA protein and indicates that this pocket may be a promising target for broad-spectrum anti-influenza A drug design and development.
The Discovery of Citral-Like Thiophenes in Fried Chicken
Cannon, Robert J.,Curto, Nicole L.,Esposito, Cynthia M.,Payne, Richard K.,Janczuk, Adam J.,Agyemang, David O.,Cai, Tingwei,Tang, Xiao-Qing,Chen, Michael Z.
, p. 5690 - 5699 (2017/07/24)
The isomers of 3,7-dimethyl-2,6-octadienal, more commonly known together as citral, are two of the most notable natural compounds in the flavor and fragrance industry. However, both isomers are inherently unstable, limiting their potential use in various applications. To identify molecules in nature that can impart the fresh lemon character of citral while demonstrating stability under acidic and thermal conditions has been a major challenge and goal for the flavor and fragrance industry. In the study of fried chicken, several alkyl thiophenecarbaldehydes were identified by gas chromatography-mass spectrometry and gas chromatography-olfactometry that provided a similar citral-like aroma. The potential mechanism of formation in fried chicken is discussed. Furthermore, in order to explore the organoleptic properties of this structural backbone, a total of 35 thiophenecarbaldehyde derivatives were synthesized or purchased for evaluation by odor and taste. Certain organoleptic trends were observed as the length of the alkyl or alkenyl chain increased or when the chain was moved to different positions on the thiophene backbone. The 3-substituted alkyl thiophenecarbaldehydes, specifically 3-butyl-2-thiophenecarbaldehyde and 3-(3-methylbut-2-en-1-yl)-2-thiophenecarbaldehyde, exhibited strong citrus and citral-like notes. Several alkyl thiophenecarbaldehydes were tested in high acid stability trials (4 °C vs 38 °C) and outperformed citral both in terms of maintaining freshness over time and minimizing off-notes. Additional measurements were completed to calculate the odor thresholds for a select group of thiophenecarbaldehydes, which were found to be between 4.7-215.0 ng/L in air.
Chromium-thiophene-salen-based polymers for heterogeneous asymmetric hetero-Diels-Alder reactions
Zulauf, Anais,Mellah, Mohamed,Guillot, Regis,Schulz, Emmanuelle
experimental part, p. 2118 - 2129 (2009/04/11)
New chiral thiophene-salen ligands have been synthesized and the corresponding chromium complexes proved to be efficient catalysts for promoting asymmetric hetero-Diels-Alder reactions with good activities and high enantio-selectivities (up to 88% ee). Th
A CONVENIENT SYNTHESIS OF 3-ALKYLTHIOPHENES
Pham, Chiem Van,Mark, Harry B.,Zimmer, Hans
, p. 689 - 696 (2007/10/02)
The known procedures for the synthesis of 3-alkylthiophenes are rather lengthy or involved.By using the NiDPPP++ catalyzed cross-coupling method between 3-bromothiophene and Grignard reagents derived from alkyl halides a number of 3-alkylthiophenes have been prepared in a one-step reaction in good to excellent yields.
Regiospecific Synthesis of 3-Alkylfuranes and 3-Alkylthiophenes via Organoboranes
Akimoto, Itaru,Sano, Masahiro,Suzuki, Akira
, p. 1587 - 1588 (2007/10/02)
The reaction of bromide or iodide with ate-complexes obtained from trialkylboranes and 3-lithiofuran or 3-lithiothiophene gives the corresponding 3-alkylfurans or 3-alkylthiophenes in good yields, respectively.
