Synthesis, Characterization and Bioactivity of Propranolol and it's Derivatives

Sheetal Sihag, P. Devi, Rajvir Singh, Sushila Singh
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Abstract

Herein, the conventional method used for β-blocker synthesis is initiated by refluxing biphenyl-2-ol (1) with an epoxy ring (2) in the presence of K2CO3 to obtain 2-[(biphenyl-2-yloxy)methyl]oxirane (3). Compound (3) was then reacted with 99% isopropylamine (4) and various substituted phenols (6a-i) to form 1-(biphenyl-2-yloxy)-3-(propan-2-ylamino)propan-2-ol (5) and 1-(2,6-dimethyl-/4-methoxy- /4-chloro-3-hydroxy-/2,6-dimethoxy-/3,4-dimethyl-/4-amine-/4-bromo/3,4-dinitro-/2,4- dihydroxyphenoxy)-3-(biphenyl-2-yloxy)-propan-2-ols (7a-i), respectively. The synthesized compounds were analyzed by 1H NMR and FTIR spectroscopy to determine their structure and also evaluated for their antifungal activity against Rhizoctonia solani and Aspergillus niger using the food poison technique. From the activity data, it was found that compound 1-(biphenyl-2-yloxy)-3-(propan- 2-ylamino)-propan-2-ol (5) was most active against both the fungi Rhizoctonia solani and Aspergillus niger. The antibacterial activity was also determined against Bacillus species by zone of inhibition method. The compounds (5, 7a-i) were also evaluated for its herbicidal activity.
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心得安及其衍生物的合成、表征及生物活性研究
在此,合成β阻断剂的常规方法是在K2CO3存在下,用环氧环(2)回流联苯-2-醇(1)得到2-[(联苯-2-基氧基)甲基]氧环(3),然后化合物(3)与99%异丙胺(4)和各种取代的酚(6a-i)反应生成1-(联苯-2-基氧基)-3-(丙基-2-基氨基)丙烷-2-醇(5)分别为1-(2,6-二甲基-/4-甲氧基-/4-氯-3-羟基-/2,6-二甲氧基-/3,4-二甲基-/4-胺-/4-溴/3,4-二硝基-/2,4-二羟基苯氧基)-3-(联苯-2-乙氧基)-丙烷-2-醇(7a-i)。采用1H NMR和FTIR对合成的化合物进行了结构分析,并采用食毒法对其抑菌活性进行了评价。从活性数据来看,化合物1-(联苯-2-氧基)-3-(丙基-2-氨基)-丙基-2-醇(5)对真菌solani Rhizoctonia和Aspergillusniger的活性均最高。用抑制带法测定了其对芽孢杆菌的抑菌活性。并对化合物(5,7 a-i)的除草活性进行了评价。
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