论文标题:苯氧羧酸类和异噻唑啉酮类化合物的合成与生物活性研究
Studies on the Synthesis and Biological Activities of Phenoxy Carboxylic Acid and Isothiazolone Derivatives
论文作者 张佩玉
论文导师 王玉良,论文学位 硕士,论文专业 有机化学
论文单位 四川大学,点击次数 135,论文页数 57页File Size781k
2005-05-09论文网 http://www.lw23.com/lunwen_350540957/ 苯氧羧酸; 异噻唑啉酮; 二苯醚;衍生物;合成; 生物活性
phenoxy carboxylic acid; isothiazolone; diphenyl ethers; derivatives; synthesis; bactericidal activities
苯氧羧酸类化合物和异噻唑啉酮类化合物均具有重要的生物活性,其中苯氧羧酸类化合物因其具有强选择性,迅速内吸性,良好的展着性、对环境危害小和使用安全等优点,被广泛应用在农林、环保等方面;而异噻唑啉酮类化合物因其抗菌能力强、应用剂量小、相容性好,毒性低,并且对多种细菌都具有有很强的抗菌作用,成为高效而经济的防腐、防霉用之首选,被广泛应用于工业循环冷却水、粘合剂、纺织、涂料、造纸、建材、制革、轻工、金属加工油、农林环保等领域。寻找效能更高,应用范围更广,选择性更好而毒性更低的具有生物活性的目标物,一直是化学和药物学等相关专业的科技工作者所关注的方向。本文致力于具有新型结构的苯氧羧酸类化合物和异噻唑啉酮类化合物的合成研究工作,合成苯氧羧酸类化合物14 个,其中11 个为未见文献报道的新化合物;合成异噻唑啉酮类化合物10 个,其中7 个为未见文献报道的新化合物,所有目标物的结构经核磁共振、红外、质谱以及元素分析等方法得到证实,取得了以下一些具有创新性的研究结果: (1)以各种取代羟基二苯醚为母体,合成了苯氧基苯氧乙酸酯类化合物5个。(2)以各种取代羟基二苯醚为母体,合成了苯氧基苯氧丙酸酯类化合物8个, (3)以氯代哒嗪氧基苯酚为母体,合成杂环氧基苯氧丙酸酯类化合物1个,此类化合物至今在国内外均未见报道。(4)以丙烯酸甲酯为起始原料,通过硫化、胺解、氯环化,得到无卤代异噻唑啉酮化合物1 个,一氯代异噻唑啉酮化合物2 个,二氯代异噻唑啉酮化
The phenoxy carboxylic acid and the isothiazolone derivatives have important biological activities. The phenoxy carboxylic acid derivatives have extensive application and the research values in the agriculture, forestry and environment. The isothiazolone derivatives have extensive application and the research values in the medicine, agriculture, cosmetics, textile product etc. It is a very important target to obtain more compounds which have higher effect, wider application, better selectivity and lower toxicity. This article concentrates on the synthesis of the phenoxy carboxylic acid derivatives and the synthesis and biological activities of the isothiazolone derivatives. 14 phenoxy carboxylic acid derivatives including 11 new compounds have been synthesized; 10 isothiazolone derivatives including 7 new compounds have been synthesized. All of the target compounds have been isolated and characterized by IR, 1HNMR, MS and elemental analysis. The following innovated results were achieved: (1) 5 phenoxy acetic acid derivatives have been designed and synthesized. 3 of them were reported for the first time and their structures have been confirmed by 1H NMR, elemental analysis, MS and IR. (2) 8 phenoxy propionic acid derivatives have been designed and synthesized. 7 of them were reported for the first time and their structures have been confirmed by 1H NMR, MS, IR and elemental analysis. (3) One new heterocyclic phenoxy propionic acid derivatives were synthesized isolated and characterized by IR, 1HNMR, MS and elemental analysis. The study gives a good basis to expand the research and applications of the phenoxy carboxylic acid ester derivatives. (4) One non-haloid isothiazolone compound, 2 chlorin-substituted isothiazolone derivatives and one dichlorin-substituted isothiazolone derivative have been synthesized. 3 of them were reported for the first time and their structures have been confirmed by 1H NMR, MS, IR and elemental analysis. (5) 3 bromine-substituted isothiazolone derivatives and 3 bromine-and chlorine-substituted isothiazolone derivatives have been synthesized. 4 of them were reported for the first time and their structures have been confirmed by 1H NMR, MS, IR and elemental analysis. (6) Anti-bacteria activity of eight isothiazolone compounds against five bacteria was tested and the following results were obtained: a) all of the tested compounds have strong anti-bacteria activity. b) It is always advantageous to the anti-bacteria activity to increase the number of halogen atom in the molecule. c) The bigger group on 2-position is advantageous to enhance the anti-bacteria activity of molecule.
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