新型噻唑基甲氧基苯基嘧啶的合成及其嘧啶、异恶唑啉和吡唑啉类似物的抗高血糖活性评价
Synthesis of new thiazolylmethoxyphenyl pyrimidines and antihyperglycemic evaluation of the pyrimidines, analogues isoxazolines and pyrazolines.
作者信息
Bhosle Manisha R, Deshmukh Amarsinh R, Pal Savita, Srivastava Arvind K, Mane Ramrao A
机构信息
Department of Chemistry, Dr. Babasaheb Ambedkar Marathwada University, Aurangabad 431004, Maharashtra, India.
Division of Biochemistry, CSIR-Central Drug Research Institute, Lucknow 226031, India.
出版信息
Bioorg Med Chem Lett. 2015 Jun 1;25(11):2442-6. doi: 10.1016/j.bmcl.2015.03.068. Epub 2015 Apr 11.
New thiazolylmethoxyphenyl pyrimidines (7a-g) have been conveniently synthesized with better yields by cyclocondensing 3-(4-((2-phenylthiazol-4-yl)methoxy)phenyl)-1-(4-substituted phenyl)prop-2-en-1-ones (4a-g) with thiourea in aqueous emulsion of tetradecyltrimethylammonium bromide (TTAB) at 80 °C. Antihyperglycemic activity of the new thiazolylmethoxyphenyl pyrimidines (7a-d), thiazolylmethoxyphenyl pyrazolines (5a-d) and thiazolylmethoxyphenyl isoxazolines (6a-d) has been evaluated in sucrose loaded rat model. Among these compounds; 5a, 5c, 6b, 7c and 7d have displayed noticeable antihyperglycemic activity. Pyrimidines and pyrazolines have displayed better antihyperglycemic activity than the analogues isoxazolines.
通过在80℃下，使3-(4-((2-苯基噻唑-4-基)甲氧基)phenyl)-1-(4-取代苯基)丙-2-烯-1-酮(4a-g)与硫脲在十四烷基三甲基溴化铵(TTAB)的水乳液中进行环缩合反应，已方便地合成了新型噻唑基甲氧基苯基嘧啶(7a-g)，产率更高。在蔗糖负荷大鼠模型中评估了新型噻唑基甲氧基苯基嘧啶(7a-d)、噻唑基甲氧基苯基吡唑啉(5a-d)和噻唑基甲氧基苯基异恶唑啉(6a-d)的降血糖活性。在这些化合物中，5a、5c、6b、7c和7d表现出显著的降血糖活性。嘧啶和吡唑啉表现出比类似的异恶唑啉更好的降血糖活性。
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