SYNTHETIC STUDIES ON BIOLOGICALLY ACTIVE TRYPTOPHAN METABOLITES.

生物活性色氨酸代谢物的综合研究。

• 批准号: 62470134
• 负责人: HINO Tohru
• 金额: $ 4.1万
• 依托单位: Chiba University
• 依托单位国家: 日本
• 项目类别: Grant-in-Aid for General Scientific Research (B)
• 财政年份: 1987
• 资助国家: 日本
• 起止时间: 1987 至 1989
• 项目状态: 已结题
• 来源: https://kaken.nii.ac.jp/en/grant/KAKENHI-PROJECT-62470134/
• 关键词: Tryptophan; Eudistomin; beta-Carboline; Pictet-Spengler reaction; Oxathiazepine; D-Cystein; Marine natural products; Propargyl alcohol Co-complex; ユ-デイストミン; Pictet-Spenglu反応; オキサチアゼピン; D-システイン; プロパルギルアルコ-ルコバルト錯体; トリプトファン代謝産物; ユーデイストミン; ピクテ-

1. Eudistomins. Marine alkaloids, eudistomin H, I, and P (1) have been synthesized from tryptamine and proline. Eudistomine C, F. L and debromoeudistomin L (2) which have a oxathiazepine ring and a tetrahydro-B- carboline ring and display anti-virus activity, have been synthesized as the first time from N-hydroxytryptamine and D-cysteinal.2. Flustramines : 3a-(1,1-dimethylpropargyl)pyrrolo 2,3-b indole (3) has been prepared by the reaction of tryptamine carbamate and propargylalcolhol Co-complex in the presence of a Lewis acid.3. The 4,5,6-tribromo-3-indoleacetamide (4) which is the indole moiety of chartelline, was prepared from the cyclic tautomer of 3-indoleacetamide.4.12alpha- and 12beta-Fumitremorgin C (5) has been prepared from the intermediate to fumitremorgin B.5. Optically active 1-substituted-1 2,3,4-tetrahydro-beta-carbolines (6) have been prepared by the asymmetic reduction of 1-substituted-3,4-dihydro-beta-carbolines with moderate optical purity.

1. Eudistomins。以色胺和脯氨酸为原料合成了海洋生物碱eudistomin H、I和P（1）。Eudistomine C、F.本论文的主要工作如下：1.以N-羟色胺和D-半胱氨酸为原料，首次合成了具有抗病毒活性的含氧硫氮杂卓环和四氢-B-咔啉环的去溴eudistomin L（2）。氟胺：在刘易斯酸存在下，色胺氨基甲酸酯与炔丙醇共络合物反应合成了3 a-（1，1-二甲基炔丙基）吡咯并2，3-B吲哚（3）.从3-吲哚乙酰胺的环状互变异构体中制备了查特林的吲哚部分4，5，6-三溴-3-吲哚乙酰胺（4）。4.12 α-和12 β-烟曲霉素C（5）由烟曲霉素B的中间体制备。通过不对称还原1-取代-3，4-二氢-β-咔啉制备了光学活性的1-取代-1，2，3，4-四氢-β-咔啉（6）。

项目成果

M.Nakagawa: J.Chem.Soc.Chem.Commun.(1988)

M.Nakakawa：J.Chem.Soc.Chem.Commun.（1988）

中川昌子: "New avidence for the presence of a spiroigdolenine intermediate in Pictet-Spengler reaction of Nb-hydroxytryptamine." J.C.S.Chem.Commun.463-464 (1988)

Masako Nakakawa：“Nb-羟色胺的 Pictet-Spengler 反应中存在螺环胺中间体的新证据。”J.C.S.Chem.Commun.463-464 (1988)

J.Kobayashi: "Eudistomin derivative, novel phospho-esterase inhibitors: synthesis and relative activity." J.Pharm.Pharmacol. 40.62-63, 1988.

J.Kobayashi：“Eudistomin 衍生物，新型磷酸酯酶抑制剂：合成和相对活性。”

劉進軍: "Total synthesis of(-)-eudistomin F." Heterocycles. (1990)

刘进军：“(-)-eudistomin F的全合成”(1990)。

中川昌子: "Synthetic approaches fumitremorgins.Synthesis of optically pure pentacyclic ring systems,and their oxidation at ring C" Chem.Pharm.Bull.,. 37. 23-32 (1989)

Masako Nakakawa：“Fumitremorgins 的合成方法。光学纯五环系统的合成及其在环 C 处的氧化”Chem.Pharm.Bull., 37. 23-32 (1989)