Total synthesis of moniliformediquinone and calanquinone A as potent inhibitors for breast cancer
Journal
Tetrahedron
Journal Volume
67
Journal Issue
34
Pages
6166-6172
Date Issued
2011
Author(s)
Thangaraj S.
Tsao W.-S.
Luo Y.-W.
Lee Y.-J.
Chang C.-F.
Lin C.-C.
Uang B.-J.
Yu C.-C.
Teng C.-M.
Abstract
The first synthesis of moniliformediquinone has been achieved in which the longest linear sequence is only nine steps. The synthesis proceeds in 23% overall yield from commercially available 2,4,5-trimethoxybenzaldehyde. The key transformations include a Pd-catalyzed coupling between a phenyl triflate and an acetylene, and a TiCl4-mediated cyclization of a benzoquinone intermediate. In addition, in vitro inhibitory effects of moniliformediquinone, denbinobin, moscatilin, and calanquinone A were determined to have IC 50 values of 0.7, 1.6, 2.5, and 1.5 μM, respectively. ? 2011 Elsevier Ltd. All rights reserved.
Subjects
Calanquinone A; Denbinobin; Moniliformediquinone; Moscatilin; TiCl 4-mediated
SDGs
Other Subjects
1 (2 bromo 3,5 dimethoxyphenyl) 2 (2,4,5 trimethoxyphenyl)ethane; 1 (2 iodo 3,5 dimethoxyphenyl) 2 (2,4,5 trimethoxyphenyl)ethane; 1 (3,5 dimethoxyphenyl) 2 (2,4,5 trimethoxyphenyl)ethane; 1,1 dibromo 2 (2,4,5 trimethoxyphenyl)ethene; 2,4,5 trimethoxyphenylacetylene; 3,5 diacetoxy 1 [2 (2,4,5 trimethoxyphenyl)ethynyl]benzene; 3,5 dimethoxyphenyl triflate; 5 diacetoxy 1 [2 (2,4,5 trimethoxyphenyl)ethyl]benzene; 5 methoxy 2 (2 bromo 3,5 dimethoxyphenethyl) 1,4 benzoquinone; 5 methoxy 2 (2 iodo 3,5 dimethoxyphenethyl) 1,4 benzoquinone; 5 methoxy 2 (3,5 dimethoxyphenethyl) 1,4 benzoquinone; 5',7' dimethoxy spiro(2,5 dimethoxy cyclohexa 2,5 dien 4 one 1,1' indan); 5',7' dimethoxy spiro(4 methoxy 3 cyclohexen 2,5 dione 1,1' indan); 9,10 dihydro 3,5,7 trimethoxy 1,4 phenanthrenedione; calanquinone; cis 1 (3,5 diacetoxy) 2 (2,4,5 trimethoxy)stilbene; cis 1 (3,5 dimethoxy) 2 (2,4,5 trimethoxy)stilbene; denbinobin; moniliformediquinone; moscatilin; quinone derivative; tamoxifen; unclassified drug; antineoplastic activity; article; breast cancer; cancer cell; catalysis; cyclization; drug structure; drug synthesis; herbal medicine; human; IC 50; in vitro study; medicinal plant; priority journal
Type
journal article