Journal of Medicinal Chemistry: Latest Articles (ACS Publications)
Authors: Mariana C. Almeida, Paulo M. da Costa, Emília Sousa, and Diana I. S. P. Resende
dx.doi.org/http://dx.doi.org/10.1021/acs.jmedchem.2c01212
Journal of the American Chemical Society: Latest Articles (ACS Publications)
Authors: Jack W. Jordan, Alexander I. Chernov, Graham A. Rance, E. Stephen Davies, Anabel E. Lanterna, Jesum Alves Fernandes, Alexander Grüneis, Quentin Ramasse, Graham N. Newton, and Andrei N. Khlobystov
dx.doi.org/https://doi.org/10.1021/jacs.2c10961
Formation of new 2-trifluoromethyl-4(3H)-quinazolinone derivatives.
Due to the significant properties and applications of quinazolinones and fluorinated compounds, there is increasing interest in the design and synthesis of new quinazolinone structures and fluorinated compounds. So, new derivatives of 2-trifluoromethyl-4(3H)-quinazolinone were synthesized. Reaction of 2-trifluoromethyl-3,1-benzoxazine-4-one benzoxazine-4-one 1 with some aniline derivatives afforded 3-aryl-2-trifluoromethyl-4(3H)-quinazolinone derivatives 3 in good yields. On the other hand, treatment of 3,1-benzoxazine-4-one 1 with aliphatic binucleophile afforded bis-benzamide derivative 5 rather than bisquinazolines derivative 4. The reaction of benzoxazine-4-one 1 with 1,4-phenylenediamine afforded bisquinazoline derivative 6. Reaction of 3-amino-4(3H)-quinazolinone 7 with aldehydes or isothiocyanates gave the corresponding Schiff’s base 8 and thiourea 9 derivatives, respectively. The structures of newly synthesized 2,3-disubstituted 4(3H)-quinazolinone derivatives were demonstrated through NMR (proton carbon and fluorine) experiment as well as mass spectra and elemental analyses. Most of the synthesized compounds were obtained in excellent yields, so they will share in enrichment the chemical libraries.
Exocyclic tetra-substituted carbon-carbon double bonds in uniform configuration and creation of tertiary or quaternary stereogenic centers in a diastereoselective or enantioselective manner – these are structural motives that are accessible by a cascade consisting of a Heck reaction and subsequent Suzuki-Miyaura coupling with suitable palladium catalysts that guarantee a high degree of stereoselectivity.
Palladium catalysis enables efficient and versatile domino reactions that are initiated by an intramolecular Mizoroki-Heck reaction and then terminated by a Suzuki-Miyaura coupling. The stereochemistry of this cascade is concerned under three aspects: Firstly, as stereoselective formation of carbon-carbon-double bonds, when the initial carbometalation occurs at an alkyne moiety. Secondly as diastereoselective and thirdly enantioselective formation of stereogenic carbon centers when the intramolecular Heck step is directed to an alkene moiety. Valuable protocols lead to – otherwise not easily accomplished – stereo control in the formation of tri- and tetra-substituted double bonds according to the first conception. The diastereoselective versions permit the formation of multiple stereocenters in mono- and polycycles. Enantioselective protocols were developed only recently. The fact that the newly created stereocenters are highly-substituted, tertiary or quaternary ones, makes the methods that are presented in this review useful and versatile tools in synthesis.
Wiley: European Journal of Organic Chemistry: Table of Contents
Authors: Manfred Braun
chemistry-europe.onlinelibrary.wiley.com/doi/10.1002/ejoc.202201282
![Synthesis and Properties of Bis(naphthofuran)-Fused [7]Helicene Derivatives](https://chemistry-europe.onlinelibrary.wiley.com/cms/asset/f4494dba-1ced-416d-b74d-20061edcefdc/ejoc202201373-toc-0001-m.png)
Late-stage cyclization of the McMurry dimerized product furnished oxa[7]helicene with functional group tunability.
Novel benzo[1,2-b:4,3-b′]dinaphthofuran (oxa[7]helicene) with various substituents in the central ring were designed and successfully synthesized based on the late stage central ring formation strategy from naphthofuranoneby using an efficient McMurry coupling or Friedel-Crafts acylation. The photochemical properties of helicenes were evaluated by UV-Visible absorption spectroscopy and fluorescence spectroscopy, while electrochemical behaviour including their energy profile were investigated by cyclic voltammetry and DFT calculations. According to the computational study, substituents on the central ring could influence both electron delocalization and MO distribution of oxa[7]helicenes resulting in the change in charge transporting ability. In comparison to the parent carbo[7]helicene, the furan unit in conjunction with substituents on helical system caused the bathochromic shift with different absorption pattern and exhibited higher fluorescence quantum yield (ϕf up to 0.63). These new materials showed promising characteristics in optoelectronic application.
Wiley: European Journal of Organic Chemistry: Table of Contents
Authors: Yuttawat Hashmi, Tienthong Thongpanchang
chemistry-europe.onlinelibrary.wiley.com/doi/10.1002/ejoc.202201373
An efficient Brønsted acid-promoted sulfonylation of propargylic alcohols with sodium sulfinates as a sulfonyl source was developed for the synthesis of triaryl allenyl sulfones. This transformation proceeds well to give various triaryl-substituted allenyl sulfones in moderate to excellent yields under mild conditions.
An efficient and practical approach for the synthesis of triaryl allenyl sulfones from easily accessible propargylic alcohols was developed, by using sodium sulfinates as a sulfonyl source in the presence of Brønsted acid. The reaction proceeded via allenyl carbocation as the key intermediate and was followed by a nucleophilic attack of sodium sulfinates to produce allenyl sulfones in moderate to excellent yields.
Wiley: European Journal of Organic Chemistry: Table of Contents
Authors: Shimin Jiang, Sha Du, Ruchun Yang, Fengyan Jin, Zhao‐Zhao Zhou, Wan‐Fa Tian, Xian‐Rong Song, Qiang Xiao
chemistry-europe.onlinelibrary.wiley.com/doi/10.1002/ejoc.202201377
“After finishing two weeks of quarantine during a typical Finnish winter … we succeeded to have the setup working and perform a wide range of studies … Overall, the visits of Nina turned out to be challenging due to the special times, but also rewarding from a professional as well as cultural and social point of life.” Find out more about the collaboration of Bert Weckhuysen and his co-workers in their Team Profile.
This invited Team Profile was created by the Inorganic Chemistry and Catalysis group, Department of Chemistry, University of Utrecht, the Netherlands; X-ray Laboratory, Department of Physics, University of Helsinki, Finland; Laboratory of Inorganic Chemistry, Department of Chemistry and Applied Biosciences, ETH Zürich, Switzerland; Center for Materials Science and Nanotechnology, Department of Physics, University of Oslo, Norway; and Catalysis Research Center, Department of Chemistry, University of Oslo, Norway. They recently published an article on their successfully designed laboratory-based setup enabling operando multi-edge X-ray absorption near-edge structure (XANES), which offers possibilities for advanced catalyst characterization, as demonstrated for mono-, bi-, and trimetallic CO2 hydrogenation catalysts consisting of Ni, Cu, and Fe. Synergistic effects during catalyst reduction and their influence on catalytic performance were unravelled, guiding rational design of multielement solid catalysts for various applications. “Operando Laboratory-based Multi-edge X-ray Absorption Near-Edge Spectroscopy of Solid Catalysts”, N. S. Genz, A.-J. Kallio, R. Oord, F. Krumeich, A. Pokle, Ø. Prytz, U. Olsbye, F. Meirer, S. Huotari, B. M. Weckhuysen, Angew. Chem. Int. Ed. 2022, e202209334; Angew. Chem. 2022, e202209334.
Wiley: Angewandte Chemie International Edition: Table of Contents
Authors:
onlinelibrary.wiley.com/doi/10.1002/anie.202216327
“Beyond the subject of the study, there are two lessons: the first lesson is that the question itself is more important than the answer … The most exciting aspect of this project was the correlation found between electrochemical properties and colloidal chemistry.” Find out more about collaborative work in the Laboratory of Electrochemistry, Electroanalytic, and Sensor Development (LEEDS) in their Team Profile.
This invited Team Profile was created by the Laboratory of Electrochemistry, Electroanalytic, and Sensor Development (LEEDS), Department of Analytical Chemistry, Institute of Chemistry, University of Campinas, Brazil. They recently published an article about the origin of the zeta potential on an aqueous graphite dispersion prepared without passivating agents, with a minimal number of functional groups, and using concentrated ammonium hydroxide. Ammonia transfers electrons to graphite and raises the Fermi level of the carbon material above the original value. This electron excess generates the negative zeta potential, therefore it accounts for colloidal stability. “The Electronic Origin of the Zeta Potential is Supported by the Redox Mechanism on an Aqueous Dispersion of Exfoliated Graphite”, J. P. V. Damasceno, L. T. Kubota, Angew. Chem. Int. Ed. 2022, e202214995; Angew. Chem. 2022, e202214995
Wiley: Angewandte Chemie International Edition: Table of Contents
Authors:
onlinelibrary.wiley.com/doi/10.1002/anie.202217518
The design and synthesis as well as biochemical and structural characterization of long-chain maytansinoids and maytansinoid conjugates is reported. The results show the prospects of maytansinoids as probes to study microtubule dynamics and lead towards the design of new maytansine-based derivatives.
Maytansinoids are a successful class of natural and semisynthetic tubulin binders, known for their potent cytotoxic activity. Their wider application as cytotoxins and chemical probes to study tubulin dynamics has been held back by the complexity of natural product chemistry. Here we report the synthesis of long-chain derivatives and maytansinoid conjugates. We confirmed that bulky substituents do not impact their high activity or the scaffold’s binding mode. These encouraging results open new avenues for the design of new maytansine-based probes.
Wiley: Chemistry – A European Journal: Table of Contents
Authors: Zlata Boiarska, Helena Pérez‐Peña, Anne‐Catherine Abel, Paola Marzullo, Beatriz Álvarez‐Bernad, Francesca Bonato, Benedetta Santini, Dragos Horvath, Daniel Lucena‐Agell, Francesca Vasile, Maurizio Sironi, J. Fernando Díaz, Andrea E. Prota, Stefano Pieraccini, Daniele Passarella
chemistry-europe.onlinelibrary.wiley.com/doi/10.1002/chem.202203431
![Palladium-catalyzed synthesis of novel pyrido[3,4-d]pyridazin-1(2H)-ones as promising α-glucosidase, α-amylase and EGFR inhibitors along with molecular docking](https://onlinelibrary.wiley.com/cms/asset/9fb0f558-7ba1-4c73-a368-dc19123dc75b/jhet4615-toc-0001-m.png)
A novel route has been established for the synthesis of novel pyrido[3,4-d]pyridazin-1(2H)-one derivative.
Ten novel derivatives were synthesized, isolated, and characterized by various spectroscopic techniques.
All synthesized molecules were screened for in silico parameters and evaluated for α-glucosidase and α-amylase inhibitory assay.
all synthesized molecules were screened for anticancer activity on A549, A375, and MCF-7 cancer cell lines.
Compound 8g exhibited more potency than positive control doxorubicin on lung, breast, and melanoma cancer cell lines.
A novel route has been established for the synthesis of novel pyrido[3,4-d]pyridazin-1(2H)-one derivative. Synthesis of intermediate 4-methyl-7-(piperazin-1-yl)pyrido[3,4-d]pyridazin-1(2H)-one carried out in the presence of Pd(PPh3)2Cl2 catalyst. Ten novel derivatives were synthesized, isolated, and characterized by various spectroscopic techniques. All synthesized molecules were screened for in silico parameters and evaluated for α-glucosidase and α-amylase inhibitory assay. Furthermore, all synthesized molecules were screened for anticancer activity against human lung cell line (A549), human melanoma cell line (A375) and breast cancer (MCF-7) cell lines and their cytotoxic effects were compared. Among the compounds, 8i showed higher inhibition than standard acarbose in the antidiabetic assay. In addition, 8 g exhibited more potency than positive control doxorubicin on lung, breast, and melanoma cancer cell lines. A molecular docking study was carried out on 1RPK and 4HJO as Epidermal growth factor receptor (EGFR) proteins.
The Journal of Organic Chemistry: Latest Articles (ACS Publications)
Authors: Souad Diana Tork, Emma Zsófia Aletta Nagy, Raluca Bianca Tomoiagă, and László Csaba Bencze
dx.doi.org/https://doi.org/10.1021/acs.joc.2c02106
Journal of Medicinal Chemistry: Latest Articles (ACS Publications)
Authors: Hao Zhang, Chenglong Liu, Di Zhu, Qingwei Zhang, and Jianqi Li
dx.doi.org/http://dx.doi.org/10.1021/acs.jmedchem.2c01016
Accounts of Chemical Research: Latest Articles (ACS Publications)
Authors: Nianjun Yang and Xin Jiang
dx.doi.org/https://doi.org/10.1021/acs.accounts.2c00644
Journal of the American Chemical Society: Latest Articles (ACS Publications)
Authors: Martin Keilwerth, Weiqing Mao, Sergio A. V. Jannuzzi, Liam Grunwald, Frank W. Heinemann, Andreas Scheurer, Jörg Sutter, Serena DeBeer, Dominik Munz, and Karsten Meyer
dx.doi.org/https://doi.org/10.1021/jacs.2c09072
Journal of the American Chemical Society: Latest Articles (ACS Publications)
Authors: Xiaoyi Xu, Shuoqing Zhang, Kai Xu, Hongzheng Chen, Xiulin Fan, and Ning Huang
dx.doi.org/https://doi.org/10.1021/jacs.2c10509
Journal of the American Chemical Society: Latest Articles (ACS Publications)
Authors: Sally B. Morton, L. David Finger, Roxanne van der Sluijs, William D. Mulcrone, Michael Hodskinson, Christopher L. Millington, Christina Vanhinsbergh, Ketan J. Patel, Mark J. Dickman, Puck Knipscheer, Jane A. Grasby, and David M. Williams
dx.doi.org/https://doi.org/10.1021/jacs.2c10070
Organic Letters: Latest Articles (ACS Publications)
Authors: Steven J. Underwood and Christopher J. Douglas
dx.doi.org/https://doi.org/10.1021/acs.orglett.2c03961
Journal of the American Chemical Society: Latest Articles (ACS Publications)
Authors: Graham A. Cooper, Connor J. Clarke, and Jan R. R. Verlet
dx.doi.org/https://doi.org/10.1021/jacs.2c11440
Organic Letters: Latest Articles (ACS Publications)
Authors: Ziqi Zhang, Jianyan Wang, Mengxia Yu, Shengqing Ye, and Jie Wu
dx.doi.org/https://doi.org/10.1021/acs.orglett.2c04291
Journal of the American Chemical Society: Latest Articles (ACS Publications)
Authors: Alexander T. Bakker, Ioli Kotsogianni, Liza Mirenda, Verena M. Straub, Mariana Avalos, Richard J. B. H. N. van den Berg, Bogdan I. Florea, Gilles P. van Wezel, Antonius P. A. Janssen, Nathaniel I. Martin, and Mario van der Stelt
dx.doi.org/https://doi.org/10.1021/jacs.2c10819
Journal of the American Chemical Society: Latest Articles (ACS Publications)
Authors: J. David Schnettler, Oskar James Klein, Tomasz S. Kaminski, Pierre-Yves Colin, and Florian Hollfelder
dx.doi.org/https://doi.org/10.1021/jacs.2c10673
Journal of the American Chemical Society: Latest Articles (ACS Publications)
Authors: J. David Schnettler, Oskar James Klein, Tomasz S. Kaminski, Pierre-Yves Colin, and Florian Hollfelder
dx.doi.org/https://doi.org/10.1021/jacs.2c10673
Organic Letters: Latest Articles (ACS Publications)
Authors: Mingyue Cui, Ke Feng, Rongqiang Tian, and Zheng Duan
dx.doi.org/https://doi.org/10.1021/acs.orglett.2c04052
Journal of the American Chemical Society: Latest Articles (ACS Publications)
Authors: Martin Keilwerth, Weiqing Mao, Sergio A. V. Jannuzzi, Liam Grunwald, Frank W. Heinemann, Andreas Scheurer, Jörg Sutter, Serena DeBeer, Dominik Munz, and Karsten Meyer
dx.doi.org/https://doi.org/10.1021/jacs.2c09072
Organic Letters: Latest Articles (ACS Publications)
Authors: Yibing Liu, Liqun Hu, Yuzhu Zheng, Xiong Fang, and Youwei Xie
dx.doi.org/https://doi.org/10.1021/acs.orglett.2c03846
