397333-51-6Relevant academic research and scientific papers
Design, synthesis, and discovery of novel trans-stilbene analogues as potent and selective human cytochrome P450 1B1 inhibitors
Kim,Ko,Jae Eun Park,Jung,Sang Kwang Lee,Chun
, p. 160 - 164 (2002)
A series of trans-stilbene derivatives containing a 3,5-dimethoxyphenyl moiety were prepared through a new efficient solution phase synthetic pathway, and their inhibitory activities were evaluated on human cytochrome P450s (CYP) 1A1, 1A2, and 1B1 to find a potent and selective CYP1B1 inhibitor. We found that a substituent at the 2-position of the stilbene skeleton plays a very important role in discriminating between CYP1As and CYP1B1. Among the compounds tested, the most selective and potent CYP1B1 inhibitor was 2,3',4,5'-tetramethoxystilbene. Compound 7j, 2-[2-(3,5-dimethoxy-phenyl)vinyl]thiophene, showed greater inhibitory activities but had a lower selectivity toward all of the CYPls tested.
Transition-Metal-Free C(sp2)–C(sp2) Cross-Coupling of Diazo Quinones with Catechol Boronic Esters
Che, Chi-Ming,Wu, Kai,Wu, Liang-Liang,Zhou, Cong-Ying
, p. 16202 - 16208 (2020/07/17)
A transition-metal-free C(sp2)?C(sp2) bond formation reaction by the cross-coupling of diazo quinones with catechol boronic esters was developed. With this protocol, a variety of biaryls and alkenyl phenols were obtained in good to high yields under mild conditions. The reaction tolerates various functionalities and is applicable to the derivatization of pharmaceuticals and natural products. The synthetic utility of the method was demonstrated by the short synthesis of multi-substituted triphenylenes and three bioactive natural products, honokiol, moracin M, and stemofuran A. Mechanistic studies and density functional theory (DFT) calculations revealed that the reaction involves attack of the boronic ester by a singlet quinone carbene followed by a 1,2-rearrangement through a stepwise mechanism.
Trans-O-hydroxy-diphenyl ethylene derivatives and its preparation method and application
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Paragraph 0045; 0053; 0056, (2016/12/01)
The invention discloses a trans-o-hydroxy stilbene derivative as well as a preparation method and application thereof. The preparation method comprises the following steps: in the presence of a rhodium catalyst and acetate, reacting an o-hydroxy styrene compound with arylboronic acid in a solvent, and after the reaction is completed, treating, thereby obtaining the trans-o-hydroxy stilbene derivative. The preparation method is mild in reaction conditions, procedures are simple and can be rapidly performed, and the yield is relatively high. The cell experiment shows that compared with resveratrol, a product prepared from the trans-o-hydroxy stilbene derivative is generally better in anti-tumor activity.
Synthesis and antiproliferative evaluation of 2-hydroxylated (E)-stilbenes
Zhang, Yan,Shen, Mingyun,Cui, Sunliang,Hou, Tingjun
supporting information, p. 5470 - 5472 (2015/02/19)
A simple synthesis of 2-hydroxylated (E)-stilbenes was accomplished in good yields via oxidative coupling of 2-hydroxystyrenes and arylboronic acids, with Rh(III)-catalyst and Cu(OAc)2 as oxidant. The antiproliferative evaluation of all the synthesized compounds were assessed on four different human cancer cell lines (Colo-205, MDA-468, HT29, and MGC80-3), and the results showed that several compounds exhibit strong antiproliferative activities (up to IC50 = 35 nM for MGC80-3).
[11C]METHOXY-RADIOLABELLED 2,3',4,5'-TETRAMETHYLSTILBENE (TMS) AND ITS PREPARATION AND USE
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Page/Page column 32, (2009/03/07)
This invention pertains generally to the field of radiochemical synthesis, and more specifically to methods of preparing [11C]methoxy-radiolabelled 2,3',4,5' -tetramethoxystilbene (TMS) from an unlabelled hydroxy precursor of 2,3',4,5' -tetramethoxystilbe
Synthesis of (E)-2,3′,4,5′-tetramethoxy[2-11C] stilbene
Schweiger, Lutz,Craib, Stuart,Welch, Andrew,Smith, Tim A. D.
, p. 1206 - 1210 (2008/04/05)
In this paper, we describe the radiosynthesis of the compound (E)-2,3′,4,5′-tetramethoxy[2-11C]stilbene, a potential, universal tumour positron emission tomography imaging agent. The production of (E)-2,3′,4,5′-tetramethoxy[2-11C]sti
Styrylheterocycles as a novel class inhibitor of cyclooxygenase-2-mediated prostaglandin E2 production
Lee, Sang Kook,Park, Eun-Jung,Lee, Eunjung,Min, Hye-Young,Kim, Eun-Young,Lee, Taeho,Kim, Sanghee
, p. 2105 - 2108 (2007/10/03)
The inhibitory effects of a series of styrylheterocycles on the production of cyclooxygenase-2-mediated prostaglandin E2 (PGE2) were evaluated in lipopolysaccharide-stimulated RAW264.7 murine macrophages. A new series of potential inhibitors, including 3-[2-(4-methoxy-phenyl)-vinyl]- thiophene, have been identified, thus providing novel chemical leads for the further development of potential inhibitors in this capacity. The suppression of COX-2 mRNA expression by the active styrylheterocycles, in part, was involved in the inhibitory activity against the overproduction of PGE2.
