Synthesis and evaluation of the cytotoxicities of neoflavenes

被引：6

作者：

Li, Sie-Rong ^{[2
]}

Chen, Hsing-Ming ^{[3
]}

Chen, Po-Yuan

Tsai, Jui-Chi ^{[2
]}

Chen, Liang-Yeu ^{[2
]}

Wang, Eng-Chi ^{[1
]}

Huang, Yi-Ting ^{[4
]}

Wei, Yun-Chen ^{[4
]}

Lu, Pei-Jung ^{[4
]}

机构：

[1] Kaohsiung Med Univ, Fac Med & Appl Chem, Kaohsiung 807, Taiwan

[2] Kaohsiung Med Univ, Inst Pharmaceut Sci, Kaohsiung 807, Taiwan

[3] Fooyin Univ, Sch Med & Hlth Sci, Kaohsiung 831, Taiwan

[4] Natl Cheng Kung Univ, Inst Clin Med, Tainan 70101, Taiwan

来源：

JOURNAL OF THE CHINESE CHEMICAL SOCIETY | 2008年 / 55卷 / 04期

关键词：

neoflavenes; ring-closing metathesis; cytotoxicities;

D O I：

10.1002/jccs.200800137

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The synthesis of neoflavene and neoflavenes with methoxy substituents at different positions are described. As starting materials, various salicylaidehydes were run through sequential reactions such as O-allylation, Grignard reaction, oxidation, Wittig reaction, and ring-closing metathesis to yield the target neoflavenes in good yield. Among the prepared neoflavenes, 7-methoxy-4'-methoxyneoflavene (6e) and 8-methoxy-4'-methoxyneoflavene (6f) exhibiting potential cell toxicities against various cells were disclosed. In particular, 6f which exhibited an IC50 value of 6.5 +/- 2.0 and 5.1 +/- 1.1 mu M against gastric carcinoma and lung carcinoma cells in vitro was found, respectively. Meanwhile, the structure and activity relationship of our synthesized neoflavenes is further discussed briefly.

引用

页码：923 / 932

页数：10

共 26 条

[1] THE STEREOCHEMISTRY OF ORGANOMETALLIC COMPOUNDS .35. HYDROFORMYLATION OF ORTHO-PROPENYLANILINES AND ORTHO-PROPENYLPHENOLS - A NEW ROUTE TO 4,5-DIHYDRO-3H-1-BENZAZEPINES [J].

ANASTASIOU, D ;

JACKSON, WR .

AUSTRALIAN JOURNAL OF CHEMISTRY, 1992, 45 (01) :21-37

[2] THERMAL CLAISEN REARRANGEMENT OF ARYL ALLENYLMETHYL ETHERS - SYNTHESIS OF 2-(O-HYDROXYARYL)BUTA-1,3-DIENES AND 4-METHYL-2H-1-BENZOPYRANS [J].

BALASUBRAMANIAN, T ;

BALASUBRAMANIAN, KK .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1992, (24) :1760-1761

[3]

BLACK M, 1998, J CHEM SOC P1, V11, P1825

[4] Studies toward the synthesis of natural and unnatural dienediynes. Part 2: A practical approach to functionalised cyclopentenones [J].

Caddick, S ;

Khan, S ;

Frost, LM ;

Smith, NJ ;

Cheung, S ;

Pairaudeau, G .

TETRAHEDRON, 2000, 56 (45) :8953-8958

[5] Synthesis of trisubstituted alkenes via olefin cross-metathesis [J].

Chatterjee, AK ;

Grubbs, RH .

ORGANIC LETTERS, 1999, 1 (11) :1751-1753

[6] Synthesis of neoflavenes by ligand coupling reactions with aryllead triacetates [J].

Donnelly, DMX ;

Finet, JP ;

Guiry, PJ ;

Nesbitt, K .

TETRAHEDRON, 2001, 57 (02) :413-423

[7] Synthesis of neoflavenes by a palladium-catalyzed cross-coupling reaction of 4-trifluoromethylsulfonyloxy-2H-chromenes with arylboronic acids [J].

Eguchi, T ;

Hoshino, Y ;

Ayame, A .

BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 2002, 75 (03) :581-585

[8] PtCl2-catalyzed rearrangement of methylenecyclopropanes [J].

Furstner, Alois ;

Aissa, Christophe .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (19) :6306-6307

[9] A novel synthesis of substituted naphthalenes via Claisen rearrangement and RCM reaction [J].

Huang, KS ;

Wang, EC .

TETRAHEDRON LETTERS, 2001, 42 (35) :6155-6157

[10]

IWAI I, 1963, CHEM PHARM BULL, V11, P1042

← 1 2 3 →