50274-58-3Relevant academic research and scientific papers
Novel salicylanilides from 4,5-dihalogenated salicylic acids: Synthesis, antimicrobial activity and cytotoxicity
Paraskevopoulos, Georgios,Monteiro, Sara,Vosátka, Rudolf,Krátky, Martin,Navrátilová, Lucie,Trejtnar, Franti?ek,Stola?íková, Ji?ina,Vin?ová, Jarmila
, p. 1524 - 1532 (2017/02/18)
Salicylanilides have proved their activity against tuberculosis (TB). One weak electron-withdrawing substituent is favored at the salicylic part, specially Cl or Br atoms at positions 4 or 5. On the other hand, the antimycobacterial activity of salicylanilides is negatively affected when a strong electron-withdrawing substituent ([sbnd]NO2) is present at the same positions. Herein we describe the synthesis and characterization of novel salicylanilides possessing two weak electron-withdrawing groups (halogen atoms) at their salicylic part and compare their antitubercular activity with their monohalogenated analogues. All dihalogenated derivatives proved to possess antitubercular activity at a very narrow micromolar range (MIC?=?1–4?μM), similar with their most active monohalogenated analogues. More importantly, the most active final molecules were further screened against multidrug resistant strains and found to inhibit their growth at the range of 0.5–4?μM.
Synthesis and biological activity of novel 1,3-benzoxazine derivatives as K+ channel openers
Yamamoto, Satoshi,Hashiguchi, Shohei,Miki, Shokyo,Igata, Yumiko,Watanabe, Toshifumi,Shiraishi, Mitsuru
, p. 734 - 745 (2007/10/03)
A new series of 1,3-benzoxazine derivatives with a 2-pyridine 1-oxide group at C4 was designed to explore novel K+ channel openers. Synthesis was carried out by using a palladium(0)-catalyzed carbon-carbon bond formation reaction of imino-triflates with organozinc reagents and via a new one-pot 1,3-benzoxazine skeleton formation reaction of benzoylpyridines. The compounds were tested for vasorelaxant activity in tetraethylammonium chloride (TEA) and BaCl2-induced and high KCl-induced contraction of rat aorta to identify potential K+ channel openers, and also for oral hypotensive effects in spontaneously hypertensive rats. An electron- withdrawing group with the proper shape at C6 and a methyl or halogens group at C7 of the 1,3-benzoxazine nucleus were required for the development of optimal vasorelaxant and hypotensive activity. In particular, 2-(6-bromo-7- chloro-2,2-dimethyl-2H-1,3-benzoxazin-4-yl)pyridine 1-oxide (71) showed more potent vasorelaxant activity (EC50=0.14 μM) against TEA and BaCL2- induced contraction and longer-lasting hypotensive effects than cromakalim (1).
Reductive Dechlorination of Chloro-phenols and -benzoic acids by Raney Co-Al Alloy in an Alkaline Deuterium Oxide Solution and Preparation of Deuterated Salicylic Acids
Tashiro, Masashi,Tsuzuki, Hirohisa,Matsumoto, Jun-ichi,Mataka, Shuntaro,Nakayama, Kouji,et al.
, p. 2826 - 2851 (2007/10/02)
Reduction of monochloro-phenols (1a-c) and -benzoic acids (3a-c) by using Raney Co-Al alloy in 10percent NaOD-D2O gave phenols (2a-c) and benzoic acids (4a-c) in 86-93percent isotopic purities.The reduction of di-, tri-, and tetra-chlorinated derivatives, (1) and (3), gave the deuteriated products, (2) and (4), in somewhat low isotopic purities (70-84percent).In the reduction of polychlorinated benzoic acids (3), the use of a mixed solution (1/1 = v/v) of 10percent Na2CO3-D2O and 10percent NaOD-D2O was effective and gave 4 in 80-89percent isotopic purities.The treatment of chlorosalicylic acids (5) with Raney Co-Al alloy in 10percent NaOD-D2O gave 1> (6) - 3> (6) in 91-93percent isotopic purities.
