Article
Chemistry, Organic
Wei Guo, Zhen Xie, Liuhuan Cai, Gongping Liu, Ling Deng, Weijie Mei, Xiaoying Zou, Yumei Zhong, Xiaoya Zhuo, Lvyin Zheng, Xiaolin Fan
Summary: A new photocatalyst-free visible-light-enhanced strategy for the synthesis of pyrazolo[1,5-a][1,3,5]triazine-2,4-diamines via the formation of electron donor-acceptor (EDA) complexes has been reported. The reaction involves three C-N bond formations in a one-pot protocol without the need for external transition metals, oxidants, bases, or ligands. This efficient methodology provides potential synthetic applications in drug research and development.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Physical
M. S. Raghu, K. Yogesh Kumar, M. K. Prashanth, V. S. Anusuya Devi, Fahd Alharethy, Byong-Hun Jeon
Summary: We developed a series of pyrazolo[1,5-a][1,3,5]triazine derivatives (5a-l) through condensation, intramolecular ring annulation, and acylation processes. These compounds exhibited moderate to substantial antioxidant activity and were effective in inhibiting LOX and XO enzyme activity. Particularly, compound 5f showed excellent antioxidant and enzyme inhibition abilities. Molecular docking studies further confirmed the correlation between docking scores and experimental antioxidant and enzyme inhibition activity.
JOURNAL OF MOLECULAR STRUCTURE
(2023)
Article
Biochemistry & Molecular Biology
Jonathan Elie, Corinne Fruit, Thierry Besson
Summary: This paper describes a convenient sequential one-pot approach for the synthesis of a series of 14 pyrazolo[1,5-a][1,3,5]triazines, with advantages in terms of yields, reaction times, and convenient gram scale synthesis compared to traditional methods. The combination of efficient heating using dielectric microwave heating and sequential one-pot reactions eliminates the need for laborious work-up and purification of intermediate compounds, allowing for sustainable synthesis processes.
Article
Biochemistry & Molecular Biology
Mateusz Kciuk, Somdutt Mujwar, Anna Szymanowska, Beata Marciniak, Karol Bukowski, Mariusz Mojzych, Renata Kontek
Summary: In this study, MM compounds exhibited anticancer activity at low concentrations without cytotoxicity in normal cells. The mechanism of action may involve the inhibition of BTK kinase, the AKT-mTOR pathway, and PD1-PD-L1 interaction. These sulfonamide derivatives could be a potential source of new anticancer drugs after optimization.
INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES
(2022)
Article
Biochemistry & Molecular Biology
Mateusz Kciuk, Somdutt Mujwar, Beata Marciniak, Adrianna Gielecinska, Karol Bukowski, Mariusz Mojzych, Renata Kontek
Summary: Pyrazolo[4,3-e]tetrazolo[1,5-b][1,2,4]triazine sulfonamides are a new group of heterocyclic compounds with broad biological activities, including anticancer properties. In this study, the investigated compounds showed antiproliferative activity against BxPC-3 and PC-3 cancer cells at micromolar concentrations. The compounds induced significant DNA damage in cancer cells but not in normal human lung fibroblasts. The study also evaluated the impact of MM compounds on DNA damage response factors using molecular docking and molecular dynamics simulation.
INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES
(2023)
Article
Chemistry, Organic
Pengzhen Zhong, Cheng Zhang, Yue Li, Chengwu Su, Chen Zhang, Dong-Mei Cui
Summary: An efficient method for the synthesis of alpha-(1,3,5-triazinylthio)-ketones from 1,3-dicarbonyl compounds with 1,3,5-triazine-2-thiols has been developed. The reaction involves C-C bond cleavage and C-S bond reconstruction of 1,3-dicarbonyl compounds, and can tolerate beta-keto esters, beta-keto amides, and 1,3-diones. In addition, the annulation of 1,3,5-triazine-2-thiols with chalcones has been achieved for the synthesis of thiazolo-[3,2-a]-[1,3,5]-triazines in moderate to good yields, and with a broad functional group tolerance.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Evgenia S. Velihina, Nataliya V. Obernikhina, Stepan G. Pilyo, Oleksiy D. Kachkovsky, Volodymyr S. Brovarets
Summary: The study examines the effects of extended phenyl substituents on the electron structure and anticancer activity of pyrazolo[1,5-a][1,3,5]triazines, suggesting that the introduction of phenyl substituents may increase the likelihood of interaction with protein molecules.
CURRENT ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Thanh V. Q. Nguyen
Summary: We report a general and straightforward synthesis of C7-arylated pyrazolo[1,5-a]azines via palladium-catalyzed direct C-H arylation using low-cost and abundant aryl chlorides as the aryl source. The catalytic system is robust and covers a wide range of heteroarenes and aryl chlorides, with possible extension to [1,2,4]triazolo[1,5-a]pyrimidines. This study also demonstrates the rare use of aryl chlorides for the direct C-H arylation of six-membered heteroarenes.
CHEMISTRY-A EUROPEAN JOURNAL
(2023)
Article
Biochemistry & Molecular Biology
Karol Bukowski, Beata Marciniak, Mateusz Kciuk, Somdutt Mujwar, Mariusz Mojzych, Renata Kontek
Summary: The study evaluates the anticancer potential of three synthesized pyrazolo[4,3-e]tetrazolo[1,5-b][1,2,4]triazine sulfonamides against human cancer cells. The sulfonamides showed pro-apoptotic activity by affecting mitochondrial function, cell membrane structure, and cell cycle progression. Computational studies suggested that one of the sulfonamides had the strongest binding affinity to CDK enzymes. The compounds exhibited strong pro-apoptotic and pro-oxidative properties, suggesting their potential as anticancer agents.
INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES
(2023)
Article
Chemistry, Organic
Pu-Yen Hsiao, Rong Chang, Andrew C. -H. Sue, Jean -Ho Chu, Guan-Wei Liao, Yi-Hsin Lee, Jui-Yang Huang
Summary: This paper presents the synthesis of a range of 3,3'-bipyrazolo[1,5-a]pyridine derivatives through direct cross-dehydrogenative coupling of pyrazolo[1,5-a]pyridine precursors. The method, which involves palladium(II)-catalyzed C-H bond activation, is simple and efficient with good functional group tolerance and high product yield (up to 94.6%). Through experimental studies and theoretical calculations, a plausible reaction mechanism is outlined. The subsequent derivatizations of the resulting compounds further extend their pi-conjugation and enhance their twisted conformations, providing new opportunities for tailor-made organic luminescent materials.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Biochemistry & Molecular Biology
Nazarii Sabat, Abdelhakim Ouarti, Evelyne Migianu-Griffoni, Marc Lecouvey, Olivier Ferraris, Florian Gallier, Christophe Peyrefitte, Nadege Lubin-Germain, Jacques Uziel
Summary: Phosphoramidates obtained using the ProTide strategy have been known to enhance the biological activity of nucleosides. In this study, a series of prodrugs of SRO-91 were synthesized and investigated for their antitumor and antiviral activities. Two compounds showed inhibitory effects on cell proliferation, while another compound exhibited antiviral activity against Crimean-Congo Hemorrhagic Fever virus.
BIOORGANIC CHEMISTRY
(2022)
Article
Biochemistry & Molecular Biology
Karol Bukowski, Beata Marciniak, Mateusz Kciuk, Mariusz Mojzych, Renata Kontek
Summary: This study evaluated for the first time the cytotoxicity and genotoxicity of newly synthesized pyrazolo[4,3-e]tetrazolo[1,5-b][1,2,4]triazine sulfonamides in human tumor cell lines. The tested compounds exhibited strong anticancer properties and induced significant DNA damage in exposed cells at low concentrations.
Article
Chemistry, Organic
Yasufumi Fuchi, Miho Kawaguchi, Yuta Ito, Yoshiyuki Hari
Summary: In this study, two adenosine-like C-nucleosides bearing thieno[3,2-d]pyrimidine rings were synthesized and investigated as monomer nucleosides. The synthesized C-nucleosides were not recognized by adenosine deaminase (ADA) and exhibited fluorescence emissions. Furthermore, when incorporated into oligonucleotides, these modified C-nucleosides formed stable duplexes with DNA and RNA and showed fluorescence emission.
Article
Engineering, Environmental
Yuteng Cao, Ziwu Cai, Honglei Xia, Kangcai Wang, Yu Liu, Qinghua Zhang, Wenquan Zhang
Summary: In this study, a novel 5,6-fused energetic molecule NTTD was designed and easily obtained. By introducing oxidants and high energy groups, derivatives of NTTD were prepared with good comprehensive properties. NTTD exhibited excellent thermostability and low mechanical sensitivities. The whole preparation process had advantages of simple operation, short time, cheap and simple reagents, good repeatability, and high yield, indicating its potential as a heat-resistant and insensitive explosive candidate.
CHEMICAL ENGINEERING JOURNAL
(2022)
Article
Chemistry, Organic
Tathagata Choudhuri, Suvam Paul, Sourav Das, Devendra Deo Pathak, Avik Kumar Bagdi
Summary: An efficient visible-light-induced methodology using erythrosine B as the photocatalyst has been developed for the regioselective selenylation of pyrazolo[1,5-a]pyrimidine derivatives. The methodology has also been demonstrated to be efficient for selenylation of different electron-rich heterocycles. The use of erythrosine B as the photocatalyst, along with the simplicity of the procedure and the eco-friendly energy, oxidant, and solvent employed, are attractive characteristics of this methodology.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
