1123-99-5Relevant articles and documents
Direct iodination of electron-deficient benzothiazoles: Rapid access to two-photon absorbing fluorophores with quadrupolar D-π-A-π-D architecture and tunable heteroaromatic core
Fakis, Mihalis,Georgiou, Dimitris,Hrobárik, Peter,Nociarová, Jela,Osusky, Patrik,Polyzos, Ioannis,Rakovsky, Erik
, p. 3460 - 3465 (2021)
Direct iodination of benzothiazoles under strong oxidative/acidic conditions leads to a mixture of iodinated heteroarenes with 1-2 major components, which are easily separable and which structures depend on the I2 equivalents used. Among the unexpected bu
Combretastatin A-4 sulfur-containing heterocyclic derivatives: Synthesis, antiproliferative activities and molecular docking studies
Faouzi, Abdelfattah,Arnaud, Alexandre,Bancet, Alexandre,Barette, Caroline,Preto, Jordane,Do, Cong Viet,Jordheim, Lars Petter,Bousfiha, Zineb,Nguyen, Thi Thanh Binh,Verrière, Marion,Farce, Amaury,Fauvarque, Marie-Odile,Barret, Roland,Lomberget, Thierry
, (2021)
Combretastatin A-4 inspired heterocyclic derivatives were synthesized and evaluated for their biological activities on tubulin polymerization and cell proliferation. Among the 19 described sulfur-containing compounds, derivatives (Z)-4h and (Z)-4j exhibited interesting in cellulo tubulin polymerization inhibition and antiproliferative activities with IC50 values for six different cell lines between 8 and 27 nM. Furthermore, in silico docking studies within the colchicine/CA-4 binding site of tubulin were carried out to understand the interactions of our products with the protein target. The effects on the cell cycle of follicular lymphoma cells were also investigated at 1–10 nM concentrations showing that apoptotic processes occurred.
Ionic Reactivity of 2-Isocyanoaryl Thioethers: Access to 2-Halo and 2-Aminobenzothia/Selenazoles
Dong, Jinhuan,Hu, Junlin,Liu, Xiaoli,Sun, Shaoguang,Bao, Lan,Jia, Mengying,Xu, Xianxiu
, p. 2845 - 2852 (2022/02/23)
An ionic cascade insertion/cyclization reaction of thia-/selena-functionalized arylisocyanides has been successfully developed for the efficient and practical synthesis of 2-halobenzothiazole/benzoselenazole derivatives. This synthetic protocol, incorporating a halogen atom when forming the five-membered ring of benzothia/selenazoles, is different from the existing ones, where halogenation of the preformed benzothia/selenazole precursors happens. Additionally, a facile access to 2-aminobenzothiazoles is also achieved by the one-pot cascade reaction of 2-isocyanoaryl thioethers, iodine, and amines.
T -BuONa-mediated direct C-H halogenation of electron-deficient (hetero)arenes
Liu, Xia,Zhao, Xin,Liang, Fushun,Ren, Baoyi
supporting information, p. 886 - 890 (2018/02/19)
An efficient halogenation of electron-deficient (hetero)arenes is described. The reaction utilizes common t-BuONa as a catalyst (for iodination) or a promoter (for bromination and chlorination), and perfluorobutyl iodide, CBr4 or CCl4 as the readily-available halogenating agents, respectively. The protocol features broad scope, high efficiency, mild conditions and gram scalability. An ionic pathway involving halogen bond formation and halophilic attack is proposed. The utility of the resulting iodinated heteroarenes is demonstrated in visible light-mediated Caryl-Caryl cross-coupling reaction.