Synthesis, Structure Elucidation and H⁺/K⁺‐ATPase Inhibitory Activity of Bisabolangelone Reduction Derivatives

Abstract

Nine bisabolangelone reduction derivatives were synthesized and separated as potential anti-ulcer agent. Their structures were characterized by 2D NMR, IR, ESI-MS, elemental analysis and single-crystal X-ray diffraction analysis. Preliminarily H ＋ /K ＋ -ATPase activity evaluation indicated that all the target compounds had a certain inhibitory effect, and compounds II and IV exhibited the better inhibitory activity against H ＋ /K ＋ -ATPase than bisabolangelone and the commercial omeprazole with the IC 50 of 23.21 and 65.32 µmol/L, respectively. The initial structure-activity analysis suggested that the presence of carbonyl group in six-membered ring and double bond in side-chain seemed to be necessary to the activity.

Crystal structure of poly[bis(μ2-5-hydroxynicotinato-κ2N:O3)zinc]

“…For transition metal complexes with 5-hydroxynicotinate ligands, see: Jiang & Feng (2008); Zhang et al (2011); Yang et al (2010). For corresponding rare earth metal complexes, see: Zhang et al (2012); Mi et al (2012); Xu et al (2013).…”

(2S*,3S*,3aS*,6S*,7aR*)-3-Hydroxy-2-[(2R*,3S*)-3-isopropyloxiran-2-yl]-3,6-dimethyl-3,3a,5,6,7,7a-hexahydro-1-benzofuran-4(2H)-one

“…For pharmacological uses of bisabolangelone, a sesquiterpene isolated from the roots of Angelica polymorpha Maxim, see: Fang & Liao (2006); Muckensturm et al (1981). Huang et al (2012); Wang et al (2009). For the crystal structure of bisabolangelone, see: Wang et al (2007).…”

“…Data collection: CrystalClear (Rigaku, 2011); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL. and H + /K + -ATPase inhibition activity, the catalytic hydrogenated reduction (Huang et al, 2012) and epoxidation of bisabolangelone were undertaken, and the structure determination of the target compound was conducted by X-ray singlecrystal analysis for the first time.…”

Synthesis, crystal structure and in vitro anticancer studies of two bis(8-quinolinolato-N,O)-platinum(II) complexes

“…carboplatin, oxaliplatin, nedaplatin, lobaplatin, and heptaplatin ( Figure 1), and about 10 other complexes are currently under clinical trials [17]. Inspired by the predecessor's excellent work [18][19][20][21][22][23][24][25], our laboratory is engaged in the search of discovering new types of platinum-based compounds and other organic anticancer compounds, not only for providing better anticancer drugs but also for mitigating the drawbacks [26][27][28]. In this paper, we report in detail the synthesis, crystal structure and antitumor activity in vitro of two bis (8-quinolinolato-N,O)-platinum(II) complexes.…”