17791-62-7Relevant academic research and scientific papers
Antimalarial Benzimidazole Derivatives Incorporating Phenolic Mannich Base Side Chains Inhibit Microtubule and Hemozoin Formation: Structure-Activity Relationship and in Vivo Oral Efficacy Studies
Dziwornu, Godwin Akpeko,Coertzen, Dina,Leshabane, Meta,Korkor, Constance M.,Cloete, Cleavon K.,Njoroge, Mathew,Gibhard, Liezl,Lawrence, Nina,Reader, Janette,Van Der Watt, Mari?tte,Wittlin, Sergio,Birkholtz, Lyn-Marie,Chibale, Kelly
, p. 5198 - 5215 (2021)
A novel series of antimalarial benzimidazole derivatives incorporating phenolic Mannich base side chains at the C2 position, which possess dual asexual blood and sexual stage activities, is presented. Structure-activity relationship studies revealed that the 1-benzylbenzimidazole analogues possessed submicromolar asexual blood and sexual stage activities in contrast to the 1H-benzimidazole analogues, which were only active against asexual blood stage (ABS) parasites. Further, the former demonstrated microtubule inhibitory activity in ABS parasites but more significantly in stage II/III gametocytes. In addition to being bona fide inhibitors of hemozoin formation, the 1H-benzimidazole analogues also showed inhibitory effects on microtubules. In vivo efficacy studies in Plasmodium berghei-infected mice revealed that the frontrunner compound 41 exhibited high efficacy (98% reduction in parasitemia) when dosed orally at 4 × 50 mg/kg. Generally, the compounds were noncytotoxic to mammalian cells.
Regioselective syntheses of 2- and 4-formylpyrido[2,1-b]benzoxazoles
Li, Ke-Lai,Du, Zong-Bo,Guo, Can-Cheng,Chen, Qing-Yun
supporting information; experimental part, p. 3286 - 3292 (2009/09/08)
o-Acetaminophenols (2) reacted with Vilsmeier reagent under Meth-Cohn conditions to yield 2-formylpy-rido[2,l-6]benzoxazoles (5) unexpectedly besides the known compounds 2-(benzoxazol-2′-yl)-3-dimethylaminoacroleins (4). Refluxing 4 in acetic anhydride gave 4-formylpyrido[2,l-6]benzoxazoles (6), an isomer of 5. Both 5a and 6a were structurally characterized by X-ray crystallography. A mechanism for the formation of 5 involving sequential chlorination, dimerization, intramolecular elimination of HC1 to form the oxazole ring, formylation twice, and regioselective intramolecular nucleophilic cyclization to construct the pyridone ring is proposed.
Neutral Anion Receptors: Synthesis and Evaluation as Sensing Molecules in Chemically Modified Field Effect Transistors
Antonisse, Martijn M. G.,Snellink-Ruel, Bianca H. M.,Yigit, Isteyfo,Engbersen, Johan F. J.,Reinhoudt, David N.
, p. 9034 - 9038 (2007/10/03)
A new class of anion selective receptors is based on the neutral uranylsalophene building block as Lewis acidic binding site. Additional hydrogen bond accepting or donating moieties near the anion binding site offer the possibility of varying the binding
Reactions of Phenols with Thianthrene Cation Radical
Shin, Seung-Rim,Shine, Henry J.
, p. 2706 - 2710 (2007/10/02)
The phenols 2-R1-6-R2-phenol 1a-g in which R1 = R2 = tert-butyl, methyl, isopropyl, Cl, Br, F, and H reacted with thianthrene cation radical perchlorate (TH+ClO4-) to give 5-(4-hydroxyaryl)thianthreniumyl perchlorates 2a-g in good yield. o-Allylphenol (1i) behaved similarly. o-tert-Butylphenol (1h) gave both 5-(3-tert-butyl-4-hydroxyphenyl)thianthreniumyl perchlorate (2h) and a quinonoidal perchlorate (3), namely, 5-(3-thianthreniumyl-5-tert-butyl-6-oxo-2,4-cyclohexadien-1-ylidene)-5,5-dihydrothianthrene perchlorate.The 2,6-di-tert-butyl-4-R3-phenols 4a-c, R3 = tert-butyl, methoxy, and methyl, reacted with Th+ClO4- in nitrile solvents (RCN) to give 2-R-5-R3-7-tert-butylbenzoxazoles 5a-e.The tert-butyl group that was displaced by RCN in forming 5 was converted into t-BuNHCOR (8), tert-butyl alcohol, and isobutene.In contrast, 2-tert-butyl-4,6-dimethylphenol (9) gave, in CH3CN, 4-tert-butyl-2,5,7-trimethylbenzoxazole (11), that is, with migration of the displaced tert-butyl group.The reactions of 4-tert-butylphenol (14) and 2,4-di-tert-butylphenol (17) are also described.
