雷兴翰, 章丽珠, 徐懋丽, 张秀平, 郑克勤, 颜闵, 邵葆若, 萧树华, 湛崇清. 关于血吸虫病化学治疗的研究Ⅰ.β-(5-硝基-2-呋喃)丙烯酰胺及其酯类衍生物的合成J. 药学学报, 1963, 10(7): 418-435.
引用本文: 雷兴翰, 章丽珠, 徐懋丽, 张秀平, 郑克勤, 颜闵, 邵葆若, 萧树华, 湛崇清. 关于血吸虫病化学治疗的研究Ⅰ.β-(5-硝基-2-呋喃)丙烯酰胺及其酯类衍生物的合成J. 药学学报, 1963, 10(7): 418-435.
LEI HSING-HAN, CHANG LI-CHU, HS MOU-LI, CHANG SIU-PING, TZIN KA-CHIN AND YEN MING Shao Bao-ruo, Xiao Shu-hua , Zhan Chang-qing, . CHEMOTHERAPEUTIC STUDIES ON SCHISTOSOMIASIS Ⅰ. THE SYNTHESIS OF DERIVATIVES OF β-(5-NITRO-2-FURYL) ACRYLAMIDES AND ESTERSJ. Acta Pharmaceutica Sinica, 1963, 10(7): 418-435.
Citation: LEI HSING-HAN, CHANG LI-CHU, HS MOU-LI, CHANG SIU-PING, TZIN KA-CHIN AND YEN MING Shao Bao-ruo, Xiao Shu-hua , Zhan Chang-qing, . CHEMOTHERAPEUTIC STUDIES ON SCHISTOSOMIASIS Ⅰ. THE SYNTHESIS OF DERIVATIVES OF β-(5-NITRO-2-FURYL) ACRYLAMIDES AND ESTERSJ. Acta Pharmaceutica Sinica, 1963, 10(7): 418-435.

关于血吸虫病化学治疗的研究Ⅰ.β-(5-硝基-2-呋喃)丙烯酰胺及其酯类衍生物的合成

CHEMOTHERAPEUTIC STUDIES ON SCHISTOSOMIASIS Ⅰ. THE SYNTHESIS OF DERIVATIVES OF β-(5-NITRO-2-FURYL) ACRYLAMIDES AND ESTERS

  • 摘要: 本文报导合成了硝基呋喃丙烯酰胺及其酯类衍生物107个.这类化合物的合成是从糠醛經Perkin反应制备β-呋喃丙烯酸,然后硝化成β-(5-硝基-2-呋喃)丙烯酸,再經酰氯与相应的胺类或氨基酸等縮合为酰胺。酯类则直接用酸与相应的醇酯化而得.經动物篩选后发現其中有33个化合物对感染日本血吸虫病小白鼠有显著作用.尤以β-(5-硝基-2-呋喃)丙烯酰异丙胺(I4,F-30066)及β-(5-硝基-2-呋喃)丙烯酰甘氨酸乙酯(Ⅵ17,F-30069)具有强烈杀虫效力,均已試用于临床,証明有一定疗效。

     

    Abstract: Compounds with high phenol coefficient have been used as effective remedies in the treatment of many diseases caused by certain kinds of worms in human body. In many instances the anthelmintic activity has paralled the antibacterial activity. These facts led the authors to prepare a number of compounds for the purpose of screening tests against Schistosomiasis Japonica. In 1958 the authors found Furacin and Xie-30 (hexachlorodiphenyl methane) to be effective in animal tests against Schistosomiasis Japonica. This encouraged the authors to study further along this line. In this paper the syntheses of 107 derivatives of β-(5-nitro-2-furyl) acrylamides and esters are described. The amides were prepared by the condensation of β-(5-nitro-2-furyl) acryloyl chloride with various amines (alkyl, aromatic and substituted aromatic, amino acids, etc.) while esters were obtained directly from β-(5-nitro-2-furyl) acrylic acid and alcohols in suitable conditions. β-(5-nitro-2-furyl) acrylic acid was directly prepared by nitration of β-(2-furyl) acrylic acid which was obtained from furfural and sodium acetate by means of Perkin's reaction, and the corresponding acid chloride was prepared with phosphorus pentachloride or thionyl chloride under mild conditions. In screening with mice, 33 compounds were found to possess pronounced anthelmintic activity against Schistosomiasis Japonica, among which N-(iso-propyl)-β-(5-nitro-2-furyl) acrylamide (F-30066), N-(ethyl-glycinyl)-β-(5-nitro-2-furyl) acrylamide (F-30069) and N-(cyclohexyl)-β-(5-nitro-2-furyl) acrylamide (20112) were shown to be the most effective and have passed on to clinical trials with favourable results reported.

     

/

返回文章
返回