Synthesis Characterization and Antibacterial, Antifungal Activity of N-(Benzyl Carbamoyl or Carbamothioyl)-2-hydroxy Substituted Benzamide and 2-Benzyl Amino-Substituted Benzoxazines.

International Journal of Medicinal Chemistry Pub Date : 2013-01-01 Epub Date: 2013-10-31 DOI:10.1155/2013/436397
Tyson Belz, Saleh Ihmaid, Jasim Al-Rawi, Steve Petrovski
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引用次数: 9

Abstract

New N-(benzyl carbamothioyl)-2-hydroxy substituted benzamides 13, 20, and 21 were synthesized using sodium bicarbonate and benzyl amine with 2-thioxo-substituted-1,3-benzoxazines 6, 10a, b, 11c, and 12a-n. The 2-thioxo-substituted-1,3-oxazines 6, 10a-b, 11d 12a-n, and 26 were converted to the corresponding 2-methylthio-substituted-1,3-oxazines 14a-l and 24 which were then converted to 2-benzyl amino-substituted-benzoxazines 15a-i by refluxing with benzylamine. Products 15a, b, e, f, and g were also synthesized by boiling the corresponding N-(benzyl carbamothioyl)-2-hydroxy substituted benzamides 13a, b, f, l, and m in acetic acid. 2-Oxo-substituted-1,3-benzoxazines 22 and 25 were prepared by treating the corresponding 2-methylthio-substituted-1,3-oxazines 14 and 24 with dilute HCl. The N-(benzyl carbamoyl)-2-hydroxy substituted benzamide 23 was synthesized from the reaction of 2-oxo-substituted-1,3-benzoxazine 22 with benzylamine. The new products were characterized using IR, (1)H, and (13)C NMR in addition to microanalysis. Selected compounds were tested in vitro for antibacterial and antifungi activity and the most active compounds were found to be the 4-(substituted-benzylamino)-2-hydroxy benzoic acids 9a and d (M. chlorophenolicum, MIC 50 and 25 µgm L(-1), resp.), N1, N3-bis (benzyl carbamothioyl)-4,6-dihydroxy-substituted phthalamides 20a and 20c (B. subtilis MIC 12.5, 50 µgm L(-1), resp.) and 21 (M. chlorophenolicum, MIC 50 µgm L(-1)).

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N-(苄基氨基甲酰基或氨基甲酰基)-2-羟基取代苯甲酰胺和2-苄基氨基取代苯并恶嗪的合成、表征及抗菌活性研究。
以碳酸氢钠和苯胺为原料,用2-硫氧基取代-1,3-苯并恶嗪6、10a、b、11c和12a-n合成了新的N-(苄基氨基甲氧基)-2-羟基取代苯并酰胺13、20和21。2-硫代取代-1,3-恶嗪6、10a-b、11d、12a-n和26分别转化为相应的2-甲基硫代取代-1,3-恶嗪14a-l和24,再与苄胺回流转化为2-苄基氨基取代-苯并恶嗪15a-i。产物15a、b、e、f和g也通过在乙酸中煮沸相应的N-(苄基氨基甲氧基)-2-羟基取代苯酰胺13a、b、f、1和m来合成。用稀盐酸对相应的2-甲基硫代-1,3-恶嗪14和24进行处理,制备了2-氧取代-1,3-苯并恶嗪22和25。以2-氧取代-1,3-苯并恶嗪22与苄胺为原料,合成了N-(苄基氨基甲酰基)-2-羟基取代苯并酰胺23。新产物通过IR、(1)H和(13)C核磁共振以及微量分析进行了表征。筛选出的化合物体外抗菌和抗真菌活性最高的是4-(取代-苄基)-2羟基苯甲酸9a和d (M. chlorophenolicum, MIC 50和25µgm L(-1), resp.), N1, n3 -二(苄基氨基)-4,6-二羟基取代邻苯二胺20a和20c (B. subtilis MIC 12.5, 50µgm L(-1), resp.)和21 (M. chlorophenolicum, MIC 50µgm L(-1))。
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期刊介绍: International Journal of Medicinal Chemistry is a peer-reviewed, Open Access journal that publishes original research articles as well as review articles in all areas of chemistry associated with drug discovery, design, and synthesis. International Journal of Medicinal Chemistry is a peer-reviewed, Open Access journal that publishes original research articles as well as review articles in all areas of chemistry associated with drug discovery, design, and synthesis.
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