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Green chemistry oriented synthesis of biologically active natural products and structure-activity relationships

绿色化学导向的生物活性天然产物合成及构效关系

基本信息

批准号：
17590014
负责人：
AOYAGI Yutaka
金额：
$ 2.11万
依托单位：
Tokyo University of Pharmacy and Life Sciences
依托单位国家：
日本
项目类别：
Grant-in-Aid for Scientific Research (C)
财政年份：
2005
资助国家：
日本
起止时间：
2005 至 2006
项目状态：
已结题

项目摘要

The results in this project aimed at 'Green Chemistry' are as follows :1. To discover new biologically active natural products, we explored chemical constituents from higher plants (Labiatae, Coriaceae, Rubiaceae, and Podocarpaceae) using HPLC attached with reversed phase column and aqueous solvent systems. As a results, Some new sesqui-and diterpenes were isolated.2. Some cytotoxic analogues were synthesized from natural products, isolated from Rabdosia excisa, Perovskia abrotanoides, Coriaria japonica, Tricalysia dubia, and Tripterygium wilfordii. The structure-activity relationships (SAR) between the structures of ent-kaurene type, isetexane type, and abietane type natural products and their semisynthetic analogues and cytotoxic activity were discussed. The microwave oven was used for preparation of semisynthetic analogues aimed at 'Green Chemistry'.3. The kinetic resolution of secondary alcohols with lipase TL were carried out to produce optically pure secondary alcohols. One of the secondary alcohols was converted to piperazic acids in semi-large scale. Now we are trying to synthesize a natural hexadepsipeptide GE3, which includes both enatiomers of piperazic acids.4. The facile palladium-catalyzed synthesis of pyrroles and indoles, which are important medicinal molecule skeletons, was developed.5. The nonproteogenic amino acids were synthesized from Garner aldehydes as a chiral pool.

1.为了发现新的生物活性天然产物，我们采用反相色谱柱和水相溶剂系统相结合的高效液相色谱联用技术，对高等植物(唇形科、椰科、茜草科和罗汉果科)的化学成分进行了研究。结果分离得到一些新的倍半萜和二萜类化合物。从香茶菜、香茶菜、马桑、毛滴虫、雷公藤中分离得到的天然产物合成了一些细胞毒类似物。讨论了对位高岭烯型、异己烷型和松香烷型天然产物及其半合成类似物结构与细胞毒活性之间的构效关系。利用微波炉制备了以“绿色化学”为目标的半合成类似物。利用脂肪酶TL对仲醇进行动力学拆分，得到光学纯的仲醇。其中一种仲醇被半大规模转化为哌嗪酸。现在，我们正在尝试合成一种天然的六肽GE3，它包括两种哌嗪酸的对映体。开发了钯催化合成重要的药物分子骨架--吡咯和吲哚的简便方法。以加纳醛为手性池合成了非蛋白生成氨基酸。

项目成果

期刊论文数量（25）

专著数量（0）

科研奖励数量（0）

会议论文数量（0）

专利数量（0）

Semisynthesis and SAR study of C-ring modified cytotoxic triptolide analogues

C环修饰细胞毒雷公藤甲素类似物的半合成及SAR研究

DOI：
发表时间：
2006
期刊：
Bioorg.Med.Chem.Lett. 16
影响因子：
0
作者：
Y.Higuchi;T.Miura;T.Kajimoto;Y.Ohta;Yutaka Aoyagi et al.
通讯作者：
Yutaka Aoyagi et al.

Cytotoxicity of abietane diterpenoids from Perovskia abrotanoides and of their semisynthetic analogues

DOI：
10.1016/j.bmc.2006.03.047
发表时间：
2006-08-01
期刊：
BIOORGANIC & MEDICINAL CHEMISTRY
影响因子：
3.5
作者：
Aoyagi, Yutaka;Takahashi, Yoshinao;Kurihara, Teruo
通讯作者：
Kurihara, Teruo

Efficient synthesis of pyrroles and 4,5,6,7-tetrahydroindoles via palladium-catalyzed oxidation of hydroxy-enamines

DOI：
10.1016/j.tet.2006.06.070
发表时间：
2006-09-04
期刊：
TETRAHEDRON
影响因子：
2.1
作者：
Aoyagi, Yutaka;Mizusaki, Toshihiko;Takeya, Koichi
通讯作者：
Takeya, Koichi

Synthesis of 1-0-monoacyl or 12-0-monoacyl, 1-,12-0-diacyl- and 11,12-dehydrated excisanin A 7,14-acetonides and their cytotoxic activity

1-0-单酰基或12-0-单酰基、1-,12-0-二酰基-和11,12-脱水excisinin A 7,14-丙酮化合物的合成及其细胞毒活性

DOI：
发表时间：
2006
期刊：
Bioorganic ＆ Medicinal Chemistry 14・15
影响因子：
0
作者：
J.Hasegawa;M.Hamada;T.Miyamoto;K.Nishide;T.Kajimoto;J.Uenishi;M.Node;Takashi Iida;Yutaka Aoyagi et al.
通讯作者：
Yutaka Aoyagi et al.

Semisynthesis of icetexane diterpenoid analogues and their cytotoxic activity

icetexane二萜类似物的半合成及其细胞毒活性

DOI：
发表时间：
2006
期刊：
Chemical ＆ Pharmaceutical Bulletin 54・11
影响因子：
0
作者：
Nozomi Saito;Toshihiro Matsunaga;Hiroshi Saito;Miyuki Anzai;Kazuya Takenouchi;Daishiro Miura;Seiichi Ishizuka;Hiroaki Takayama;Atsushi Kittaka;Yutaka Aoyagi et al.
通讯作者：
Yutaka Aoyagi et al.