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《Acta Chimica Sinica》 1959-06
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PAN PEI-CHAUN JEN YUN-FENG WANG YUEN-YIN KAO YEE-SHENG (Institute of Materia Medica,Academia Sinica,Shanghai)  
The preparation of two kinds of nitrogen mustards related to local anesthetics wasdescribed.The compounds were(1).β-diethyl-amino-ethyl-ρ-bis-(2-chloroethyl)aminobenzoate(Ⅳ,procaine-mustard),in which the ρ-amino-group of procaine(Ⅱ)wasreplaced by bis-(2-chloroethyl)amino group(Ⅰ).Similarly,nitrogen mustards Ⅴ,Ⅶ,Ⅷ,Ⅸa.Ⅸb and Ⅸc related to thiocaine and other anesthetics have also been prepared.(2).N-β-diethylamino-ethyl 2-n-butoxy-6-bis-(2-chloroethyl)amino-cinchoninic acid amide(ⅩⅥ,percaine-mustard),which was obtained by introducing Ⅰ to the molecule of percaine(ⅩⅢ).By doing so,the authors are in the hope to obtain a drug which,when applingdirectly to tumour tissue will not only act locally so as to prevent the normal tissue frombeing poisoned but will exert also the pain-relieving action.Compound Ⅳ was obtained by the following ways:(1)Ⅱ was condensed withethylene oxide to give ρ-bis(2-hydroxyethyl)amino-compound(Ⅲ),which was then treatedwith thionyl chloride to form Ⅳ.(2).ρ-bis(2-chloroethyl)amino-benzoyl chloride(Ⅵ)was reacted directly with diethylamnio-ethanol.Compounds Ⅴ,Ⅶ,Ⅷ and Ⅸa(or Ⅸb or Ⅸc)were obtained by treatment of Ⅵwith dimethylamino-ethanol,diethylamino-ethyl mercaptan,diethylaminoethyl-amine,andn-propanol(or n-butanol or iso-pentanol)respectively.The compound ⅩⅥ was prepared by a 5-step synthesis starting from 2-chloro-6-nitro-cinchoninic acid chloride(Ⅹ)which was treated with diethylamine to form N-β-diethyl-amino-ethyl 2-chloro-6-nitro cinchoninic acid amide(Ⅺ).The latter was then converted toN-β-diethylamino-ethyl 2-n-butoxy-6-nitrocinchoninic acid amide(Ⅻ)by treating with sodiumhutoxylate.By direct nitration of percaine(ⅩⅢ)there was also formed Ⅻ,which uponcatalytic hydrogenation led to the formation of the corresponding 6-amino-compound(ⅩⅣ).The latter,on treatment with ethylene oxide,gave 6-his(2-chloroethyl)amino compond(ⅩⅤ)Which formed the desired product ⅩⅥ after being reacted with phosphorus oxychlo-ride.Compound Ⅻ exhibited quite strong local anesthetic activity;procaine-mustard Ⅳand percaine-mustard ⅩⅥ still retain the local anesthetic action as the parent compounds,but the corresponding bis(2-hydroxyethyl)amino compounds Ⅲ and ⅩⅤ were inactive.Compounds Ⅳ,Ⅴ,Ⅶ,Ⅷ and ⅩⅥ were active in vitro against tumour cells,S.180and Ehrlich ascites tumour.Pharmacological examinations are in progress.
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【Secondary References】
Chinese Journal Full-text Database 8 Hits
1 LIANG Pei,QIN Yong chao,JIANG Zu cheng and XIONG Chao mei (College of Chemistry and Environmental Science,Wuhan University,Wuhan 430072),Fenxi Shiyanshi,2000,19(3):56~59;Separation and Determination of Four Fluoroquinolone Antibiotics by RP HPLC[J];ANALYTICAL LABORATORY;2000-03
2 Wang Bin ,Wang Jiesheng,Liang Yanyu (Department of Development,Kunshan Double Crane Pharmaceutical Co.Ltd.,Kunshan 215315),Huaxue Shiji,2001,23(4),243;245;Synthesis of 2-acetonyloxo-3,4-difluoro-nitrobenzene[J];Chemical Reagents;2001-04
3 SUN Hui1, DONG Xiangchao1, L Xianyu2, WANG Haibo1, HAN Jianfang1 (1. Department of Chemistry, Nankai University, Tianjin 300071, China; 2. College of Life Science, Nankai University, Tianjin 300071, China);Separation and Determination of Fluoroquinolones with a Molecularly Imprinted Polymer[J];Chinese Journal of Chromatography;2003-03
4 ZHANG Yi,DONG Xiang-chao (College of Chemistry,Nankai University,Tianjin 300071,China);Evaluation of Enrofloxacin Imprinted Polymeric Microspheres Synthesized with Living/Controlled Radical Polymerization[J];Journal of Instrumental Analysis;2008-10
5 Yang Yushe(Yang YS), Ji Ruyun(Ji RY), Chen Kaixian(Chen KX) and Ding Jian(Ding J) (Shanghai Institute of Materia Medica, Shanghai 200031);STUDIES ON SYNTHESIS ANTIBACTERIAL AND ANTITUMOR ACTIVITY OF (S) (-) OFLOXACIN ANALOGUES[J];ACTA PHARMACEUTICA SINICA;1999-02
6 HU Wei-xiao,SUN Nan,YANG Zhong-yu (Institute of Pharmaceutical Engineering,Zhejiang University of Technology,Hangzhou 310032,China);A Study on Synthesis and Anticancer Activity of Thiosemicarbazones[J];Chinese Journal of Medicinal Chemistry;2001-03
7 TIAN Meng chao,QU Ling bo,XIE Jian gang,CHEN Rong feng (Department of Chemistry,Zhengzhou University,Zhengzhou 450052,China);Syntheses and antibacterial activity of 1-alkyl-6-fluoro-7-(4-acyl-1-piperazinyl)-1,4-dihydro-4-oxo- quinoline-3-carboxylic acid and its derivatives[J];Chinese Journal of Medicinal Chemistry;2002-05
8 LI Mei, QI JianJuna, GUO HuiYuana (Centre for Drug Evaluation, Ministry of Public Health, Beijing 100050;a Institute of Medicinal Biotechnology, Chinese Academy of Medical Sciences, Beijing 100050);RECENT PROGRESS OF RESEARCH AND DEVELOPMENT OF QUINOLONE ANTIBACTERIAL AGENTS IN CHINA[J];CHINESE JOURNAL OF PHARMACEUTICALS;1999-06
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