SYNTHESIS AND DESIGN OF ANTITUMOR NITROGEN CONTAINING NATURAL PRODUCTS-STUDIES BASED ON NATURAL PRODUCTS AS PROBES OF BIOLOGICAL FUNCTION-
抗肿瘤含氮天然产物的合成与设计-以天然产物为生物功能探针的研究-
基本信息
- 批准号:08457579
- 负责人:
- 金额:$ 1.66万
- 依托单位:
- 依托单位国家:日本
- 项目类别:Grant-in-Aid for Scientific Research (B)
- 财政年份:1996
- 资助国家:日本
- 起止时间:1996 至 1998
- 项目状态:已结题
- 来源:
- 关键词:
项目摘要
I.Enantioselective total synthetic approaches to manzamine A and dynemicin AI) Synthesis of the tetracyclic core of manzamine A (1) was achieved via Diels-Alder reaction of the dihydropyridinones. Conversion of the two D-A products to the key tricyclic ketone was conducted through a conventional pathway as well as a new pathway developed.2) The highly stereoselective synthesis of the optically active tetracyclic core of Manzamine A was achieved via the Diels-Alder reaction of dihydropyridinone, derived from L-serine, with siloxydienes, followed by sequential new and conventional pathways.3) Preparation of the 1-methoxycarbonyl-3-phenylthio-2-quinolinone from dihydro-2-quinolinone and its Diels-Alder reaction with 2-trimethylsilyloxy- 1, 3-butadiene and 2-TMSO- 1, 3-pentadiene under Lewis acid catalyst was developed. Conversion of the D-A adduct to 9-phenanthridinone ketal will open a new synthetic route to a dynemicin A core structure.4). We found an efficient synthesis of a, beta-unsaturated ketones by the reaction of acid chlorides with trialkylaluminum (1/3 mole equiv) in the presence of AlC13 (I mol equiv).II.Both L-threo and D-ervthro-1-phenyl-2-palmitoylamino-3-morpholino- 1-propanol (PPMP) and the decanoyl derivative (PDMP) were synthesized stereselectively from L-serine.III.The crystal structure of Vsr endonuclease was determined by X-ray analysis.IV.The first example of a reagent-controlled enantioselective Pictet-Spengler reaction was achieved. Using diisopinocampheylchloroborane as a chiral Lewis acid catalyst, the Pictet-Spengler reaction of Nb-hydroxytryptamine with aldehydes gave the corresponding 2-hydroxytetrahydro-beta-carbolines in up to 90% ee. The enantioselective Pictet-Spengler reaction catalyzed by chiral binaphthol-derived Brphindted acid-assisted Lewis acids, with up to 91% ee, was also achieved.
I.曼扎胺A和动力霉素的对映选择性全合成方法AI)通过二氢吡啶酮的Diels-Alder反应合成曼扎胺A的四环核(1)。2)以L-丝氨酸为原料,通过二氢吡啶酮与二氢萘二烯的Diels-Alder反应,高立体选择性地合成了Manzamine A的光学活性四环核,3)由二氢-2-喹啉酮制备1-甲氧羰基-3-苯硫基-2-喹啉酮及其与2-三甲基甲硅烷氧基-1,3,以3-丁二烯和2-TMSO- 1,3-戊二烯为原料,在刘易斯酸催化下,合成了3-丁二烯和2-TMSO- 1,3-戊二烯。将D-A加合物转化为9-菲啶酮缩酮将为动力霉素A核心结构开辟一条新的合成路线。我们发现了一种有效的合成方法,通过酰氯与三烷基铝反应制备β-不饱和酮(1/3摩尔当量)在AlCl 3存在下(1摩尔当量)。II.从L-丝氨酸立体选择性地合成了L-苏型和D-苏型-1-苯基-2-棕榈酰氨基-3-吗啉代-1-丙醇(PPMP)和癸酰基衍生物(PsR)。III.通过X-射线衍射确定了Vsr核酸内切酶的晶体结构。IV.实现了试剂控制的对映选择性Pictet-Spengler反应的第一个实例。在手性刘易斯酸催化下,Nb-羟色胺与醛的Pictet-Spengler反应得到了90%ee的2-羟基四氢-β-咔啉,手性联萘酚衍生的Brphindted酸辅助的刘易斯酸催化下,也实现了对映选择性的Pictet-Spengler反应,ee高达91%ee.
项目成果
期刊论文数量(31)
专著数量(0)
科研奖励数量(0)
会议论文数量(0)
专利数量(0)
Tomohiko Kawate, Hideki Yamada, Than Soe, and Masako Nakagawa: "Enantioselective Asymmetric Pictet-Spengler Reaction Catalyzed by Diisopinocampheylchloroborane." Tetrahedron : Asymmetry. 7(5). 1249-1252 (1996)
Tomohiko Kawate、Hideki Yamada、Than Soe 和 Masako Nakakawa:“二异松蒎基氯硼烷催化的对映选择性不对称 Pictet-Spengler 反应”。
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Mitsuhiro Arisawa, Yasuhiro Torisawa, Michiaki Kawahara, Masamichi Yamanaka, Atsushi Nishida, and Masako Nakagawa: "Lewis Acid-Promoted Coupling Reactions of Acid Chlorides with Organoaluminum and Organozinc Reagents." The Journal of Organic Chemistry. 62
Mitsuhiro Arisawa、Yasuhiro Torisawa、Michiaki Kawahara、Masamichi Yamanaka、Atsushi Nishida 和 Masako Nakakawa:“刘易斯酸促进酰基氯与有机铝和有机锌试剂的偶联反应。”
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Tomohiko Kawate, Natsuko Fukuta, Atsushi Nishida, and Masako Nakagawa: "Synthesis of Sphingosine Analogues : Stereoselective Synthesis of 3-Deoxysphingosine and cis-Isomers." Chemical Pharmaceutical Bulletin. 45(12). 2116-2118 (1997)
Tomohiko Kawate、Natsuko Fukuta、Atsushi Nishida 和 Masako Nakakawa:“鞘氨醇类似物的合成:3-脱氧鞘氨醇和顺式异构体的立体选择性合成。”
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Yasuhiro Torisawa, Than Soe, Chiaki Katoh, Yumiko Motohashi, Atsushi Nishida, Tohru Hino, and Masako Nakagawa: "A Facile Aldol-Isomerization Route to 3-Alkyldihydropyridinone with A Chiral Azocine Ring." Heterocycles. 47(2). 655-659 (1998)
Yasuhiro Torisawa、Than Soe、Chiaki Katoh、Yumiko Motohashi、Atsushi Nishida、Tohru Hino 和 Masako Nakakawa:“具有手性偶氮辛环的 3-烷基二氢吡啶酮的简便羟醛异构化路线。”
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Hideharu Uchida, Atsushi Nishida, and Masako Nakagawa: "An Efficient Access to the Optically Active Manzamine Tetracyclic Ring System." Tetrahedron Letters. 40(1). 113-116 (1999)
Hideharu Uchida、Atsushi Nishida 和 Masako Nakakawa:“有效获取光学活性曼扎明四环系统。”
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NAKAGAWA Masako其他文献
NAKAGAWA Masako的其他文献
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{{ truncateString('NAKAGAWA Masako', 18)}}的其他基金
Synthesis of Antitumor Manzamine Alkaloid Isolated from Sponge and Development of Highly Bioactive Molecule
海绵抗肿瘤曼扎明生物碱的合成及高生物活性分子的开发
- 批准号:
11470467 - 财政年份:1999
- 资助金额:
$ 1.66万 - 项目类别:
Grant-in-Aid for Scientific Research (B).
Synthetic studies on Antitumor Antibiotic and Biological Activity
抗肿瘤抗生素及其生物活性的综合研究
- 批准号:
05671865 - 财政年份:1993
- 资助金额:
$ 1.66万 - 项目类别:
Grant-in-Aid for General Scientific Research (C)
Synthesis of Biologically Active Nitrogen Containing Aliphatic Compounds Using Nitroethanol as a Synthon.
使用硝基乙醇作为合成物合成具有生物活性的含氮脂肪族化合物。
- 批准号:
01571140 - 财政年份:1989
- 资助金额:
$ 1.66万 - 项目类别:
Grant-in-Aid for General Scientific Research (C)
Synthesis of Sphingosines and Cerebrosides
鞘氨醇和脑苷脂的合成
- 批准号:
61570993 - 财政年份:1986
- 资助金额:
$ 1.66万 - 项目类别:
Grant-in-Aid for General Scientific Research (C)
相似国自然基金
Manzamine A 的全合成研究
- 批准号:21372221
- 批准年份:2013
- 资助金额:80.0 万元
- 项目类别:面上项目
相似海外基金
SYNTHESIS OF MANZAMINE A VIA NOVEL DIELS-ALDER REACTION
通过新型狄尔斯-阿尔德反应合成曼扎胺
- 批准号:
2172971 - 财政年份:1996
- 资助金额:
$ 1.66万 - 项目类别:
SYNTHESIS OF MANZAMINE A VIA NOVEL DIELS-ALDER REACTION
通过新型狄尔斯-阿尔德反应合成曼扎胺
- 批准号:
2020969 - 财政年份:1996
- 资助金额:
$ 1.66万 - 项目类别:
SYNTHESIS OF MANZAMINE A USING A NOVEL REARRANGEMENT
使用新颖的重排合成曼扎胺 A
- 批准号:
2104004 - 财政年份:1994
- 资助金额:
$ 1.66万 - 项目类别:
SYNTHESIS OF MANZAMINE A USING A NOVEL REARRANGEMENT
使用新颖的重排合成曼扎胺 A
- 批准号:
2104005 - 财政年份:1994
- 资助金额:
$ 1.66万 - 项目类别:
Synthetic Study on Antitumor Antivacterial Marine Alkaloid Manzamine A
抗肿瘤抗菌海洋生物碱曼扎明A的合成研究
- 批准号:
04671283 - 财政年份:1992
- 资助金额:
$ 1.66万 - 项目类别:
Grant-in-Aid for General Scientific Research (C)