Total Synthesis and Structure-Activity Relationship Studies of Phelligridins C and D, and Phellifuropyranone A

被引：3

作者：

Ohyoshi, Takayuki ^{[1
]}

Mitsugi, Keisuke ^{[1
]}

Ichimura, Fumitaka ^{[1
]}

Higuma, Tatsuya ^{[1
]}

Yoshida, Masahito ^{[1
]}

Kigoshi, Hideo ^{[1
]}

机构：

[1] Univ Tsukuba, Grad Sch Pure & Appl Sci, Dept Chem, 1-1-1 Tennodai, Tsukuba, Ibaraki 3058571, Japan

来源：

BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN | 2020年 / 93卷 / 12期

关键词：

Phelligridins; Phellifuropyranone A; Structure-activity relationship; PHELLINUS; DERIVATIVES; HISPIDIN; ACCESS; FUNGI;

D O I：

10.1246/bcsj.20200212

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

alpha-Pyrone polyphenols, phelligridins C and D (meshimakobnols B and A), and phellifuropyranone A, isolated from a Japanese mushroom, are growth inhibitors of cancer cells. Herein, we report full details of the total synthesis of phelligridins C and D. The key reactions of the synthetic pathways were Pd catalyzed cross-coupling and aldol-type condensation. This strategy also enabled the total synthesis of phellifuropyranone A and artificial analogs of phelligridins. Subsequent biological evaluation of these compounds clarified that the whole skeleton of phelligridin C and the catechol group of the left hand side are essential for the cytotoxicity.

引用

页码：1540 / 1551

页数：12

共 20 条

[1] ADAM W, 1994, SYNTHESIS-STUTTGART, P1133
[2] Aihara Y, 2017, HETEROCYCLES, V94, P1280, DOI [10.3987/com-17-13733, 10.3987/COM-17-13733]
[3] Access to trifluoromethylated 4-alkoxy-2-pyrones, pyridones and quinolones
Clarke, Sarah L.
McGlacken, Gerard P.
[J]. TETRAHEDRON, 2015, 71 (19) : 2906 - 2913
[4] Et3N-Induced Demethylation-Annulation of 3-Alkynyl-4-methoxy-2-pyridones and Structurally Related Compounds in the Synthesis of Furan-Fused Heterocycles
Conreaux, David
Belot, Sebastien
Desbordes, Philippe
Monteiro, Nuno
Balme, Genevieve
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2008, 73 (21) : 8619 - 8622
[5] CONSTITUENTS OF HIGHER FUNGI .2. SYNTHESIS OF HISPIDIN
EDWARDS, RL
WILSON, DV
[J]. JOURNAL OF THE CHEMICAL SOCIETY, 1961, (NOV): : 5003 - &
[6] Synthesis of N-substituted benzo[c][1,7]- and benzo[c][1,8] phenanthrolin-(5H)-6-ones through a Pd-mediated Suzuki-Miyaura heteroaryl-aryl coupling reaction
Genes, Constance
Michel, Sylvie
Tillequin, Francois
Poree, Francois-Hugues
[J]. TETRAHEDRON, 2009, 65 (48) : 10009 - 10015
[7] Facile syntheses of 2,2-dimethyl-6-(2-oxoalkyl)-1,3-dioxin-4-ones and the corresponding 6-substituted 4-hydroxy-2-pyrones
Katritzky, AR
Wang, ZQ
Wang, MY
Hall, CD
Suzuki, K
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (12) : 4854 - 4856
[8] Aplyronine A, a potent antitumor substance of marine origin, aplyronines B and C, and artificial analogues: Total synthesis and structure-cytotoxicity relationships
Kigoshi, H
Suenaga, K
Mutou, T
Ishigaki, T
Atsumi, T
Ishiwata, H
Sakakura, A
Ogawa, T
Ojika, M
Yamada, K
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (16) : 5326 - 5351
[9] Phellifuropyranone A:: A new furopyranone compound isolated from fruit bodies of wild Phellinus linteus
Kojima, Kazuo
Ohno, Takamasa
Inoue, Makoto
Mizukami, Hajime
Nagatsu, Akito
[J]. CHEMICAL & PHARMACEUTICAL BULLETIN, 2008, 56 (02) : 173 - 175
[10] Styrylpyrone-class compounds from medicinal fungi Phellinus and Inonotus spp., and their medicinal importance
Lee, In-Kyoung
Yun, Bong-Sik
[J]. JOURNAL OF ANTIBIOTICS, 2011, 64 (05) : 349 - 359

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