Green chemistry oriented synthesis of biologically active natural products and structure-activity relationships
Green chemistry oriented synthesis of biologically active natural products and structure-activity relationships
批准号:
17590014
负责人:
AOYAGI Yutaka
金额:
$2.11万
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
项目状态:
已结题
起止时间:
2005 至 2006
中文摘要
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。
英文摘要
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.
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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:
--
作者:
[Y.Higuchi, T.Miura, T.Kajimoto, Y.Ohta, Yutaka Aoyagi et al.]
通讯作者:
Yutaka Aoyagi et al.
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
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:
--
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:
--
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.
共 16 条
Identification of genes related with malignant transformation of hepatocellular carcinoma using alpha 1-6 fucosyltransferaseconditional knock-out mice
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批准号:23659395
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项目类别:Grant-in-Aid for Challenging Exploratory Research
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资助金额:$2.33万
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财政年份:2011
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负责人:AOYAGI Yutaka
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依托单位:
Synthesis and Structure-Activity Relationship of Biologically ActiveNatural Products and their Analogues Based on Green Chemistry
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批准号:22590019
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项目类别:Grant-in-Aid for Scientific Research (C)
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资助金额:$1.75万
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财政年份:2010
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负责人:AOYAGI Yutaka
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依托单位:
Development of treatment strategy for patients with hepatocellular carcinoma using serum glycosylation modification
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批准号:20390205
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项目类别:Grant-in-Aid for Scientific Research (B)
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资助金额:$11.56万
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财政年份:2008
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负责人:AOYAGI Yutaka
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依托单位:
Chemoenzymatic Synthesis of Biologically Active Natural products via Lipase TL -Mediated Kinetic Resolution as a Key Step and their Structure Activity Relationship
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批准号:14572014
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项目类别:Grant-in-Aid for Scientific Research (C)
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资助金额:$1.02万
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财政年份:2002
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负责人:AOYAGI Yutaka
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依托单位:
TREATMENT OF HEPATOCELLULAR CARCINOMA BY THE REGULATION OF GLYCOSYLTRANSFERASE
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批准号:13670500
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项目类别:Grant-in-Aid for Scientific Research (C)
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资助金额:$2.3万
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财政年份:2001
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负责人:AOYAGI Yutaka
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依托单位:
ALPHA-1-6 FUCOSYLTRANSFERASE ANTISENSE-OLIGONUCLEOTIDE THERAPY FOR HEPATOCELLULAR CARCINOMA.
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批准号:09670520
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项目类别:Grant-in-Aid for Scientific Research (C)
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资助金额:$1.98万
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财政年份:1997
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负责人:AOYAGI Yutaka
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依托单位:
cDNA CLONING OF HUMAN ALPHA-1-6 FUCOSYLTRANSFERASE AND ITS APPLICATION IN THE EARLY DIAGNOSIS OF HEPATOCELLULAR CARCINOMA.
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批准号:07457132
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项目类别:Grant-in-Aid for Scientific Research (B)
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资助金额:$3.78万
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财政年份:1995
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负责人:AOYAGI Yutaka
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依托单位:
海外基金