Synthesis, determination of stereochemistry, and evaluation of new bisindole alkaloida from the myxomycete Arcyria ferruginea:: An approach for Wnt signal inhibitor

被引:50
作者
Kaniwa, Kouken [1 ]
Arai, Midori A. [1 ]
Li, Xiaofan [1 ]
Ishibashi, Masami [1 ]
机构
[1] Chiba Univ, Grad Sch Pharmaceut Sci, Chiba 2638522, Japan
关键词
D O I
10.1016/j.bmcl.2007.05.033
中图分类号
R914 [药物化学];
学科分类号
100701 ;
摘要
To determine the stereochemistry of dihydroarcyriarubin C (1), new bisindole alkaloid isolated from the myxomycete Arcyriajerruginea, cis- (2) and trans-dihydroarcyriarubin C (3) were synthesized. Comparison of their NMR characteristics allowed the trans stereochemistry of the natural product to be confirmed. Moreover, the Writ signal inhibitory activities of 2 and 3 were compared with that of arcyriaflavin C (4), which is a natural product containing a bond between C-2 and C-T. The cis-dihydroar-cyriarubin C (2) showed moderate inhibition of Wnt signal transcription, which suggests that bisindole frameworks might be useful as small-molecule Writ signal inhibitors. (c) 2007 Elsevier Ltd. All rights reserved.
引用
收藏
页码:4254 / 4257
页数:4
相关论文
共 19 条
[1]   Mining the Wnt pathway for cancer therapeutics [J].
Barker, Nick ;
Clevers, Hans .
NATURE REVIEWS DRUG DISCOVERY, 2006, 5 (12) :997-1014
[2]   Regiocontrolled synthesis of the antitumor antibiotic AT2433-A1 [J].
Chisholm, JD ;
Van Vraken, DL .
JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (22) :7541-7553
[3]   INHIBITORS OF PROTEIN-KINASE-C .1. 2,3-BISARYLMALEIMIDES [J].
DAVIS, PD ;
HILL, CH ;
LAWTON, G ;
NIXON, JS ;
WILKINSON, SE ;
HURST, SA ;
KEECH, E ;
TURNER, SE .
JOURNAL OF MEDICINAL CHEMISTRY, 1992, 35 (01) :177-184
[4]   A small molecule inhibitor of β-catenin/cyclic AMP response element-binding protein transcription [J].
Emami, KH ;
Nguyen, C ;
Ma, H ;
Kim, DH ;
Jeong, KW ;
Eguchi, M ;
Moon, RT ;
Teo, JL ;
Oh, SW ;
Kim, HY ;
Moon, SH ;
Ha, JR ;
Kahn, M .
PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 2004, 101 (34) :12682-12687
[5]   Synthetic approaches to indolo[6,7-a]pyrrolo[3,4-c]carbazoles:: Potent cyclin D1/CDK4 inhibitors [J].
Faul, MM ;
Engler, TA ;
Sullivan, KA ;
Grutsch, JL ;
Clayton, MT ;
Martinelli, MJ ;
Pawlak, JM ;
LeTourneau, M ;
Coffey, DS ;
Pedersen, SW ;
Kolis, SP ;
Furness, K ;
Malhotra, S ;
Al-awar, RS ;
Ray, JE .
JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (09) :2967-2975
[6]   New cytotoxic bisindole alkaloids with protein tyrosine kinase inhibitory activity from a myxomycete Lycogala epidendrum [J].
Hosoya, T ;
Yamamoto, Y ;
Uehara, Y ;
Hayashi, M ;
Komiyama, K ;
Ishibashi, M .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2005, 15 (11) :2776-2780
[7]   Bisindole alkaloids from myxomycetes Arcyria denudata and Arcyria obvelata [J].
Kamata, Kazuaki ;
Suetsugu, Tomoko ;
Yamamoto, Yukinori ;
Hayashi, Masahiko ;
Komiyama, Kanki ;
Ishibashi, Masami .
JOURNAL OF NATURAL PRODUCTS, 2006, 69 (08) :1252-1254
[8]   Structure-activity relationship of N-methyl-bisindolylmaleimide derivatives as cell death inhibitors [J].
Katoh, M ;
Dodo, K ;
Fujita, M ;
Sodeoka, M .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2005, 15 (12) :3109-3113
[9]   Lessons from hereditary colorectal cancer [J].
Kinzler, KW ;
Vogelstein, B .
CELL, 1996, 87 (02) :159-170
[10]   Constitutive transcriptional activation by a beta-catenin-Tcf complex in APC(-/-) colon carcinoma [J].
Korinek, V ;
Barker, N ;
Morin, PJ ;
vanWichen, D ;
deWeger, R ;
Kinzler, KW ;
Vogelstein, B ;
Clevers, H .
SCIENCE, 1997, 275 (5307) :1784-1787