Article
Biochemistry & Molecular Biology
Qingfei Meng, Xue Ren, Rui Wang, Yu Han, Xiufen Li, Qin Zhang, Zhenpeng Li, Yuexing Wang, Longjiang Huang, Haibo Yu
Summary: A series of 3(1,2,3,6-tetrahydropyridine)-7-azaindole derivatives were synthesized and evaluated for their anticonvulsant activities and neurotoxicity. Compounds 4i, 4p, and 5k showed significant anticonvulsant activities in the PTZ-induced epilepsy model, but not in the MES model. These compounds also exhibited lower neurotoxicity. The presence of a N-atom at the 7-position of the 7-azaindole and a double-bond in the 1,2,3,6-tetrahydropyridine skeleton were found to be essential for the antiepileptic activities.
BIOORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Robin Jeanneret, Carlo Walz, Maarten van Meerbeek, Sarah Coppock, M. Carmen Galan
Summary: A new practical, catalytic, and highly stereoselective method for directly accessing 1,1-alpha,alpha'-linked 2-deoxy trehalose analogues via AuCl3-catalyzed dehydrative glycosylation using hemiacetal glycosyl donors and acceptors is described. The method relies on the chemoselective Bronsted acid-type activation of tribenzylated 2-deoxy hemiacetals in the presence of other less reactive hemiacetals.
Article
Chemistry, Organic
Valter E. Murie, Paula Nicolino, Thiago dos Santos, Guido Gambacorta, Rodolfo H. Nishimura, Icaro S. Perovani, Luciana C. Furtado, Leticia Costa-Lotufo, Anderson Moraes de Oliveira, Ricardo Vessecchi, Ian R. Baxendale, Giuliano C. Clososki
Summary: A library of functionalized quinolines has been prepared through magnesiation of 7-chloroquinolines under mild conditions. The synthesized 4-carbinol quinolines showed interesting antiproliferative properties, with their hydroxyl group serving as a suitable amino group bioisostere. The study also reported a two-step approach for optically active derivatives.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Philip T. Baily, H. Patricio Del Castillo, Irodiel Vinales, Juan E. M. Urbay, Aurelio Paez, Matthew R. Weaver, Roberto Iturralde, Igor L. Estevao, Sohan R. Jankuru, Igor C. Almeida, Chunqiang Li, Carl W. Dirk, Katja Michael
Summary: The photolytic properties of N-acyl-7-nitroindolines make them attractive for various applications such as photocleavable protecting groups and caged compounds. However, their synthesis is usually complex and direct acylation of 7-nitroindolines is challenging. This study presents a short and efficient synthesis of a new class of photoreactive compounds, 5-bromo-7nitroindoline-S-thiocarbamates, and investigates their photochemical and photophysical properties.
Article
Spectroscopy
Ming-Xing Zhang, Xiaofei Yang, Fen Tan, Hongquan Zhang, Guoping Zeng, Zhiqiang Xu, Sheng Hua Liu
Summary: In this study, two new luminescent molecules with distorted phenothiazine-S-oxide and phenothiazine-S,S dioxide skeletons were synthesized using different oxidation reactions. The compounds were confirmed through various spectroscopic techniques. The different oxidation states of the S-atom resulted in distinct fluorescence emission colors. Furthermore, the molecule with the phenothiazine-S-oxide skeleton exhibited solvent-dependent emission and self-recovery mechanochromism. These findings were further supported by theoretical calculations and X-ray single-crystal diffraction analysis.
SPECTROCHIMICA ACTA PART A-MOLECULAR AND BIOMOLECULAR SPECTROSCOPY
(2023)
Review
Polymer Science
Hao Hu, Binshen Wang, Bihua Chen, Xi Deng, Guohua Gao
Summary: Swellable poly(ionic liquid)s (SPILs) are ionic polymers with unique swelling ability, which depends on the compatibility of polymer chains with solvent molecules and the dissociation of ionic groups in solvents. Compared to non-swellable poly(ionic liquid)s, SPILs have good solvent affinity and distinctive physicochemical properties, making them widely applicable in catalysts, actuators, sensors, absorbents, and separation membranes, among others.
PROGRESS IN POLYMER SCIENCE
(2022)
Article
Chemistry, Medicinal
Rada Bunthawong, Uthaiwan Sirion, Arthit Chairoungdua, Kanoknetr Suksen, Pawinee Piyachaturawat, Apichart Suksamrarn, Rungnapha Saeeng
Summary: Two new series of andrographolide analogues were designed and synthesized from natural andrographolide, showing different cytotoxicity against cancer cells. Compounds with formyl group exhibited selective activity on P-388 cell line. Computational studies revealed the importance of specific functional groups in cytotoxicity.
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS
(2021)
Article
Biochemistry & Molecular Biology
Julia S. P. Mawer, Jennifer Massen, Christina Reichert, Niklas Grabenhorst, Constantine Mylonas, Peter Tessarz
Summary: Ribosome biogenesis is a complex cellular process that involves integration of extracellular cues, such as metabolic state and intracellular signaling, transcriptional regulation, and chromatin accessibility at the ribosomal DNA. The recently identified histone modification, methylation of H2AQ105 (H2AQ105me), plays a key role in this process, dependent on the mTor signaling pathway and acetylation of histone H3. The ribonucleoprotein Nhp2 acts as an epigenetic reader of this modification, bridging rDNA chromatin with components of the small subunit processome to coordinate transcription of rRNA with its post-transcriptional processing.
Article
Chemistry, Organic
Natsuhisa Oka, Mayuka Kanda, Minami Furuzawa, Wakaba Arai, Kaori Ando
Summary: A serendipitous one-step transformation of 5'-deoxy-5'-heteroarylsulfonylnucleosides into cyclopentene derivatives is reported in this study. The transformation likely proceeds via a domino reaction to eventually generate the cyclopentene ring. Additionally, heteroarylthio and acylthio groups can be incorporated into the cyclopentene core under specific conditions.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Organic
Yuttawat Hashmi, Tienthong Thongpanchang
Summary: In this study, novel oxa[7]helicenes with various substituents in the central ring were designed and successfully synthesized using efficient strategies. The research evaluated their photochemical and electrochemical properties, showing that substituents on the central ring can influence electron delocalization and charge transporting ability. Compared to the parent carbo[7]helicene, the oxa[7]helicenes exhibited a bathochromic shift and higher fluorescence quantum yield, indicating promising characteristics for optoelectronic applications.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
So Young Kim, Yu Ri Kim, Hyun Tae Kim, Ashok Kumar Jaladi, Duk Keun An
Summary: In this study, a facile and partial reduction method for carboxylic acid derivatives to aldehydes has been demonstrated using a DIBALH and morpholine system. The system was optimized to achieve almost excellent yields of aldehydes by evaluating various mole ratios of DIBALH and morpholine. The methodology has the advantages of commercial availability of reagents, milder reaction conditions, short reaction time (<1-60 min), and excellent yields. It also shows a broad substrate scope, allowing the reduction of aromatic, heterocyclic, polycyclic, and aliphatic substrates.
Article
Chemistry, Physical
Srishylam Penjarla, Paidi Yella Reddy, Santhosh Penta, Yogesh S. Sanghvi, Ludek Eyer, Michal Stefanik, Daniel Ruzek, Shyamapada Banerjee
Summary: An efficient synthetic approach leading to novel C-nucleosides containing oxadiazole or thiadiazole ring system is reported. This provides an ideal framework for the development of new antiviral and antitumor drugs. Two of the synthesized compounds showed mild anti-SARS-CoV-2 activity, with a decrease in viral titers by <1 log10 PFU/ml compared with controls. Mechanism for the formation of 5-substituted 1,3,4-thiadiazole ring is proposed and a structure-activity relationship is established with these C-nucleosides.
JOURNAL OF MOLECULAR STRUCTURE
(2023)
Article
Chemistry, Organic
Tomas Lasek, Juraj Dobias, Milos Budesinsky, Jaroslav Kozak, Barbora Lapunikova, Ivan Rosenberg, Gabriel Birkus, Ondrej Pav
Summary: This study describes a new synthetic route for fluorinated nucleoside analogs and a universal synthetic route for nucleosides bearing purine nucleobases. The compounds were evaluated for inhibitory potency against viral polymerases and tested in cell cultures against various viruses, including influenza and SARS-CoV-2.
Article
Chemistry, Organic
Yi-Xian Li, Jun-Zhe Wang, Yuna Shimadate, Maki Kise, Atsushi Kato, Yue-Mei Jia, George W. J. Fleet, Chu-Yi Yu
Summary: The C-7 fluorinated derivatives of casuarine and australine, important polyhydroxylated pyrrolizidines, were successfully synthesized using organocatalytic stereoselective alpha-fluorination of aldehydes as a key step. This strategy can also be applied to the synthesis of challenging fluorinated iminosugars and carbohydrates. Docking studies revealed that the potent inhibitions of trehalase and amyloglucosidase by the fluorinated polyhydroxylated pyrrolizidines are mainly due to the interaction of fluorine atoms in these iminosugars with the amino acid residues of the corresponding enzymes. Additionally, unusual anion-pi interactions were established between the C-7 fluoride and a hydrophobic pocket in amyloglucosidase. These unexpected docking modes and structure-activity relationship studies highlight the significance of fluorination in the design of polyhydroxylated pyrrolizidine glycosidase inhibitors.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Medicinal
Chang-Bo Zheng, Wen-Cong Gao, Pan-Pan Pang, Xin Ma, Li-Chun Peng, Liang Yang, Xun Li
Summary: A series of novel 7-methoxyl-2,3-disubstituted quinoxaline derivatives were synthesized and examined for their potential antihypertensive activities, revealing that five compounds showed endothelium-independent relaxation effects in aortic rings precontracted with high extracellular K+ and phenylephrine. These compounds, unlike commonly used vasodilators, exhibited slow but effective inhibitory effects on vasoconstriction.
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS
(2021)