25379-20-8Relevant academic research and scientific papers
Dithiolation indolizine exerts viability suppression effects on A549 cells via triggering intrinsic apoptotic pathways and inducing G2/M phase arrest
Li, Guanting,Wu, Xianwei,Sun, Peng,Zhang, Zhiyang,Shao, Enxian,Mao, Jianping,Cao, Hua,Huang, Hongliang
, (2021)
Indolizine derivatives have been reported for the treatment of numerous diseases. However, few studies were carried out for non-small cell lung cancer (NSCLC). We synthesized series of indolizine compounds. The results of MTT assay showed compound 8 (C8) markedly inhibited the proliferation of A549 cells, however, C8 (15, 30 μg/mL) had little cytotoxicity in other cell lines (SH-SY5Y, HepG2, and BEAS-2B cells), Hoechst staining and JC-1 staining showed that C8 induced changes in the nucleus morphology, increased the loss in mitochondrial membrane potential in A549 cells. The results of flow cytometry manifested that cell cycle of the cells was arrested in the G2 / M phase by C8, ROS levels and the proportion of apoptosis of cells increased. We performed western blotting analysis to detect the expression levels of apoptosis and cycle-related proteins. These results validated that the apoptosis of cells was triggered by endoplasmic reticulum stress (ERS) and the PI3K/Akt-mediated mitochondrial pathway collaboratively. Besides, the utilization of PI3K/Akt inhibitors and p53 inhibitors further proves the above argument and C8-induced cycle arrest of A549 cells is majorly regulated by p53. C8 induced the accumulation of ROS contents involved in mitochondrial damage. The proliferation of A549 cells was inhibited after treatment with the compound, which induced apoptosis and cycle arrest of cells. It is suggested that C8(dithiolation indolizine) is a potential candidate compound against non-small cell lung cancer.
Electrochemical diselenylation of indolizines: Via intermolecular C-Se formation with 2-methylpyridines, α-bromoketones and diselenides
Li, Junxuan,Liu, Xiang,Deng, Jiadi,Huang, Yingshan,Pan, Zihao,Yu, Yue,Cao, Hua
, p. 735 - 738 (2020)
An efficient electrochemical system for the construction of diselenytlated indolizines from available pyridines, ketones and diselenides under undivided electrolytic conditions was developed. No external oxidants and transition-metal catalysts are needed for achieving this three-component tandem reaction realizing C-C, C-N and C-Se bond formations.
Photocatalytic Synthesis of 3-Sulfanyl- and 1,3-Bis(sulfanyl)indolizines Mediated by Visible Light
Gomes, Caroline S.,Lenard?o, Eder J.,Monzon, Loana I.,Penteado, Filipe,Perin, Gelson,Silveira, Claudio C.
, (2020)
A metal-free method for the synthesis of 3-sulfanyl indolizines from thiols and 2-arylindolizines, is reported. The reaction is mediated by eosin Y under blue LED light irradiation and uses atmospheric oxygen as oxidant. By the use of a catalytic amount of I2, the corresponding 1,3-bis-sulfanyl indolizines are obtained, in good yields.
Transition-Metal-Free Regioselective Cross-Coupling: Controlled Synthesis of Mono- or Dithiolation Indolizines
Li, Bin,Chen, Zhiyu,Cao, Hua,Zhao, Hong
, p. 3291 - 3295 (2018)
An efficient transition-metal-free regioselective C-H/S-H cross-coupling of indolizines with thiols has been developed for the first time to describe a workable route to indolizine thioethers. This finding provides a new method and more straightforward pathway for controllable synthesis of mono- or dithiolation indolizines that are otherwise difficult to obtain by the literature methods. The reaction exhibits good functional group tolerance and high efficiency and affords the products in good to excellent yields.
Oxidation Potential-Guided Electrochemical Radical-Radical Cross-Coupling Approaches to 3-Sulfonylated Imidazopyridines and Indolizines
Kim, Wansoo,Kim, Hun Young,Oh, Kyungsoo
, p. 15973 - 15991 (2021/07/26)
Oxidation potential-guided electrochemical radical-radical cross-coupling reactions between N-heteroarenes and sodium sulfinates have been established. Thus, simple cyclic voltammetry measurement of substrates predicts the likelihood of successful radical-radical coupling reactions, allowing the simple and direct synthetic access to 3-sulfonylated imidazopyridines and indolizines. The developed electrochemical radical-radical cross-coupling reactions to sulfonylated N-heteroarenes boast the green synthetic nature of the reactions that are oxidant- and metal-free.
Mechanochemical Synthesis of 1,2-Diketoindolizine Derivatives from Indolizines and Epoxides Using Piezoelectric Materials
Wang, Yumei,Zhang, Ziwu,Deng, Lichan,Lao, Tianfeng,Su, Zhengquan,Yu, Yue,Cao, Hua
supporting information, p. 7171 - 7176 (2021/09/14)
A simple and efficient mechanochemical-induced approach for the synthesis of 1,2-diketoindolizine derivatives has been developed. BaTiO3 was used as the piezoelectric material in this transformation. This method features no usage of solvent, simple experimental operation, scalable potential, and high conversion efficiency, which make it attractive and practical.
Regioselective C-H dithiocarbamation of indolizines with tetraalkylthiuram disulfide under metal-free conditions
Cao, Hua,Lin, Jiatong,Liu, Xiang,Song, Dan,Zhan, Haiying,Zhang, Zemin,Zhuang, Canzhan
supporting information, p. 5284 - 5288 (2021/06/28)
An efficient and straightforward metal-free regioselective C-H dithiocarbamation of indolizines with tetraalkylthiuram disulfide has been described. A series of indolizine-dithiocarbamate derivatives were easily accessed in moderate to good yields with a broad scope. In addition, imidazo[1,2-a]pyridines were also well tolerated to afford diverse imidazoheterocycle-dithiocarbamate products, which are expected to be utilized for drug discovery. Of note, the reaction could be readily scaled up, and shows its practical value in organic synthesis.
Synthesis of 1,2-Dicyano-3-arylcycl[3.2.2]azines – First 1,2-Dicarbonitriles Based on Cyclazine Heterocycle
Chernyak, Alexander V.,Kalashnikov, Valery V.,Kazachenko, Vladimir P.,Pushkarev, Victor E.,Simakov, Anton O.,Simonov, Sergey V.,Starikov, Andrei S.,Tarakanov, Pavel A.,Tkachev, Valery V.,Tomilova, Larisa G.,Yarkov, Alexander V.,Zhurkin, Fedor E.
, p. 5852 - 5856 (2020/09/21)
The first 1,2-dicarbonitriles have been prepared for cyclazine systems. In particular, a synthetic procedure to 1,2-dicyano-3-arylcycl[3.2.2]azines has been developed. Unexpected chlorination of 3-arylcycl[3.2.2]azine-1,2-dicarboxylic acid derivatives by thionyl chloride at 4-position was found, which according to theoretical considerations can proceed by the electrophilic (SEAr) mechanism. The compounds are blue fluorophores in 450–480 nm region with quantum yields in toluene of ca. 30 % for non-chlorinated derivatives, which decrease to 3–4 % for chlorinated ones.
Enantioselective Synthesis of 3-Allylindolizines via Sequential Rh-Catalyzed Asymmetric Allylation and Tschitschibabin Reaction
Li, Ke,Li, Changkun
supporting information, p. 9456 - 9461 (2020/12/21)
The first highly regio- and enantioselective synthesis of 3-allylindolizines has been developed by the sequential Rh-catalyzed asymmetric allylation and Tschitschibabin reaction. Above the 20:1 branch/linear ratio, up to a 96% yield and 99% ee could be obtained with the help of tert-butyl-substituted chiral bisoxazolinephosphine ligand. In situ generated highly nucleophilic 2-alkylpyridinium ylides are utilized to undergo the asymmetric alkylation reaction before cyclization.
NH4I-catalyzed C–S bond formation via an oxidation relay strategy: Efficient access to dithioether decorated indolizines
Zhu, Yu,Yang, Liechao,Fang, Liyun,Du, Xiaofan,Chen, Keda,Yu, Chuanming,Jiang, Xinpeng
supporting information, (2020/09/15)
An efficient NH4I-catalyzed C–H/S–H cross-coupling reaction of indolizines with thiols is reported. Compared to previous methods, this environmentally friendly oxidation relay strategy uses O2 as an oxidant to afford dithioether decorated indolizines in up to 98% yield. Promising results have been obtained, indicating the high applicability and atom economy of this method.
