93-84-5Relevant articles and documents
Oxidative Cyclization-Induced Activation of a Phosphoinositide 3-Kinase Inhibitor for Enhanced Selectivity of Cancer Chemotherapeutics
Zhu, Haizhou,Mishra, Rosalin,Yuan, Long,Abdul Salam, Safnas F.,Liu, Jing,Gray, George,Sterling, Alyssa D.,Wunderlich, Mark,Landero-Figueroa, Julio,Garrett, Joan T.,Merino, Edward J.
supporting information, p. 1933 - 1939 (2019/11/19)
In this work, we designed a prodrug that reacts with cellular oxidative equivalents leading to ether cleavage and cyclization to release an active phosphatidylinositol 3-kinase (PI3K) inhibitor. We show that the compound reduces affinity for PI3KA relative to the PI3K inhibitor, is slow to intercellularly oxidize, and is resistant to liver microsomes. We observed modest activity in untreated acute myeloid leukemia cells and 14-fold selectivity relative to non-cancerous cells. The cellular activity of the compound can be modulated by the addition of antioxidants or oxidants, indicating the compound activity is sensitive to cellular reactive oxygen species (ROS) state. Co-treatment with cytosine arabinoside or doxorubicin was used to activate the compound inside cells. We observed strong synergistic activity specifically in acute myeloid leukemia (AML) cancer cells with an increase in selective anticancer activity of up to 90-fold. Thus, these new self-cyclizing compounds can be used to increase the selectivity of anticancer agents.
Sulfated polyborate-catalyzed efficient and expeditious synthesis of (un)symmetrical ureas and benzimidazolones
Rekunge, Deelip S.,Khatri, Chetan K.,Chaturbhuj, Ganesh U.
supporting information, p. 4304 - 4307 (2017/10/12)
The excellent catalytic potential of sulfated polyborate is utilized in the synthesis of (un)symmetrical ureas and benzimidazolones by heating amines or substituted OPDA and urea or N-phenylureas under a solvent-free condition at 120 °C is described. The key advantages of the present protocol are phosgene-free, and other hazardous reagents or organic solvent free, high reaction rates and yields, simple workup procedure, and recyclability of the catalyst.
Facile Synthesis of Benzo[ d ]azol-2(3 H)-ones Using 2-Phenoxycarbonyl-4,5-dichloropyridazin-3(2 H)-one as Green CO Source
Ryu, Ki Eun,Kim, Bo Ram,Sung, Gi Hyeon,Yoon, Hyo Jae,Yoon, Yong-Jin
supporting information, p. 1985 - 1990 (2015/09/01)
Developing eco-friendly, stable, and easy-to-handle acyl sources is of great importance in synthetic and green chemistry. This study describes the synthesis of benzo[d]azol-2(3H)-ones such as benzo[d]thiazol-2(3H)-ones, benzo[d]oxazol-2(3H)-ones, and benzo[d]imidazol-2(3H)-ones using 2-phenoxycarbonyl-4,5-dichloropyridazin-3(2H)-one in one pot. The reaction reported is carried out under neutral or acidic conditions in the presence of zinc or sodium bicarbonate to give the corresponding heterocycles in good to excellent yields. The reaction uses a solid stable carbonyl source that is a recyclable functional-group carrier, pyridazin-3(2H)-one.
