Article
Biochemistry & Molecular Biology
Agata Jaskulska, Katarzyna Gach-Janczak, Joanna Drogosz-Stachowicz, Tomasz Janecki, Anna Ewa Janecka
Summary: Quinolinones have long been recognized as broad-spectrum synthetic antibiotics, but recent research has revealed their potential as anticancer agents. Specific synthetic analogs were found to exhibit high cytotoxic activity against HL-60 cancer cells while showing lower toxicity to normal cells.
Article
Chemistry, Organic
Christian P. Bold, Kay Yeung, Felix Pape, Daniel Kaiser, Varinder K. Aggarwal
Summary: The stereochemistry of the lipophilic side chain of (+)-rakicidin F has been determined recently through the efficient synthesis of all-syn isomers and comparison with the natural product. The completion of the total synthesis further confirmed the stereochemical findings of Wang and Chen for the structure of (+)-rakicidin F.
Article
Chemistry, Organic
Katsuya Saito, Kazuki Kurasawa, Chiaki Takino, Shigefumi Kuwahara, Masaru Enomoto
Summary: The asymmetric total synthesis of (-)-rossinone A, a meroterpene with pharmacologically important biological activities, has been achieved for the first time from geraniol in a concise eight step sequence involving the Horner-Wadsworth-Emmons reaction of an aldehyde derived from a geranylated hydroquinone intermediate with a chiral phosphonate prepared via the highly diastereoselective Davis oxidation of a known oxazolidinone derivative.
TETRAHEDRON LETTERS
(2021)
Article
Chemistry, Medicinal
Yumiko Yamano, Mari Tanabe, Atsushi Shimada, Akimori Wada
Summary: The first total synthesis of loroxanthin (1) was achieved using a series of reactions, and the detailed operation methods of each reaction step were described. This synthesis method provides a basis for further research and application of loroxanthin.
Article
Biochemistry & Molecular Biology
Monika Bilska-Markowska, Marcin Kazmierczak
Summary: New fluorinated and nonfluorinated sugar alkenylphosphonates were successfully synthesized using 1,2;5,6-di-O-iso-propylidene-alpha-D-glucofuranose as the starting material and Horner-Wadsworth-Emmons olefination as the key synthetic method. The resulting products exhibited exclusive or predominant E-stereochemistry.
CARBOHYDRATE RESEARCH
(2023)
Article
Chemistry, Organic
Satapanawat Sittihan, Somsak Ruchirawat
Summary: This paper reports the first total synthesis of microansamycin I via a five-step chemical sequence, with an early-stage Heck reaction and Horner-Wadsworth-Emmons olefination as key steps.
TETRAHEDRON LETTERS
(2021)
Article
Chemistry, Organic
Paul R. Mears, Eric J. Thomas
Summary: The stereoselective synthesis of a carboxylic acid ester corresponding to the C1 -C16 fragment of bryostatin was successfully achieved through key steps including reactions and oxidation.
Article
Chemistry, Multidisciplinary
Thilo Kratz, Pit Steinbach, Stefan Breitenlechner, Golo Storch, Christoph Bannwarth, Thorsten Bach
Summary: This study describes a visible-light-mediated, enantioselective approach for the synthesis of axially chiral alkenes. By selectively transferring triplet energy from a racemic mixture, a major alkene enantiomer is formed. A small catalyst loading ensures consistently high selectivities and yields.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2022)
Article
Chemistry, Organic
Akira Nakamura, Kouhei Yamamoto, Ryo Murakami, Norihito Kawashita, Kouichi Matsumoto, Tomohiro Maegawa
Summary: A method for synthesizing six-membered heterocyclic compounds was developed using O,P-acetals, involving intramolecular cyclization and Horner-Wadsworth-Emmons olefination to yield isochroman-4-one and benzoxazin-3-one derivatives with an alkylidene moiety.
SYNTHESIS-STUTTGART
(2021)
Article
Chemistry, Medicinal
Ainhoa Garcia, Laura Vila, Paloma Marin, Alvaro Bernabeu, Carlos Villarroel-Vicente, Nathalie Hennuyer, Bart Staels, Xavier Franck, Bruno Figadere, Nuria Cabedo, Diego Cortes
Summary: A series of 2-prenylated benzopyrans were synthesized as analogues of the natural dual PPAR alpha/gamma agonist polycerasoidol, showing high efficacy in activating both hPPAR alpha and hPPAR gamma. These compounds have the potential to be lead compounds for preventing cardiometabolic diseases.
ACS MEDICINAL CHEMISTRY LETTERS
(2021)
Article
Chemistry, Physical
Tomasz Bartosik, Joanna Drogosz-Stachowicz, Anna Janecka, Jacek Kedzia, Barbara Pacholczyk-Sienicka, Jacek Szymanski, Katarzyna Gach-Janczak, Tomasz Janecki
Summary: This report presents efficient and stereoselective syntheses of various methylidenetetrahydropyran-4-one compounds with different substitution patterns. The cytotoxic activity of these compounds against cancer cell lines was evaluated, and two of the most cytotoxic compounds were further investigated for their effects on cancer cells. Both compounds induced apoptosis, inhibited proliferation, and generated DNA damage in cancer cells. Additionally, one of the compounds arrested the cell cycle in the G2/M phase and both compounds inhibited the activity of topoisomerase II alpha. These findings suggest that the investigated compounds may have potential as new and effective topoisomerase II inhibitors.
Article
Chemistry, Applied
Toshiro Noshita, Tatsuya Sato, Takahito Iwayama, Yohei Yamada, Hidekazu Ouchi
Summary: The syntheses of two phenolic compounds isolated from Piper betle, 4-[(1E, 3E, 5E)-6-(4-octyloxyphenyl)hexa-1,3,5-trien-1-yl]benzene-1,2-diol and 3-(n-dodecyloxy) phenol, were described. The triene moiety of 4-[(1E, 3E, 5E)-6-(4-octyloxyphenyl)hexa-1,3,5-trien-1-yl]benzene-1,2-diol was formed using two different methods, resulting in spectral data differences compared to naturally occurring compounds.
NATURAL PRODUCT RESEARCH
(2021)
Article
Biochemistry & Molecular Biology
Monika Bilska-Markowska, Wojciech Jankowski, Marcin Hoffmann, Marcin Kazmierczak
Summary: In this study, we applied fluorinated carbohydrate-derived building blocks for the synthesis of alpha-hydroxy beta-fluoro/beta-trifluoromethyl and unsaturated phosphonates. Pudovik and Horner-Wadsworth-Emmons reactions were used to achieve this goal. The proposed pathway of the key reactions was supported by experimental results and quantum chemical calculations. The structures of the products were determined by spectroscopic and spectrometric techniques. Based on our findings, we conclude that the progress of the Pudovik and HWE reactions is influenced by acidic protons present in the molecules.
Article
Chemistry, Medicinal
M. A. Gromova, Yu. V. Kharitonov, S. A. Borisov, T. V. Rybalova, T. G. Tolstikova, E. E. Shul'ts
Summary: A synthetic method was developed for isopimaric acid derivatives, and their anti-inflammatory activity was studied. Significant anti-inflammatory activity was found in the new C4-modified isopimaric acid derivatives.
CHEMISTRY OF NATURAL COMPOUNDS
(2022)
Article
Polymer Science
Hiroki Fukumoto, Kazuki Shiitsuka, Keisuke Yamada, Shigeyuki Yamada, Tsutomu Konno, Toshio Kubota, Tomohiro Agou
Summary: The intramolecular oxidative photocyclization of 1,2-diarylhexafluorocyclopentene under light irradiation provided a hexafluorocyclopentene-fused phenanthrene in moderate yield, which was subsequently copolymerized to produce a fluorine-containing polyphenylene vinylene with high thermal stability. Polymer-2 showed different photophysical properties compared to Polymer-1, and exhibited a very low photoluminescence intensity in the solid state due to the partial aggregation of polymer molecules.
POLYMER INTERNATIONAL
(2022)
