Citation: Yang Dan, Wang Ping, Wu Hanfu, Li Jilan. Syntheses and Antimicrobial Activities of Novel Quinazolin-2, 4-dione Acetyl Hydrazones[J]. Chemistry, ;2017, 80(6): 544-552. shu

Syntheses and Antimicrobial Activities of Novel Quinazolin-2, 4-dione Acetyl Hydrazones

Liupanshui Normal University, Liupanshui 553004

Received Date: 21 September 2016
Accepted Date: 29 December 2016

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Abstract Methyl 2-aminobenzoate was reacted with iodomethane to get methyl N-methylanthranilate. The key intermediate 2-(6-chloro-1-methyl-2, 4-dioxo-1, 2-dihydroquinazolin-3(4H)-yl)acetohydrazide (7) was synthesized from methyl N-methylanthranilate via substitution, hydrolysis, cyclization and hydrazinolysis reactions. Then the key intermediate 7 was reacted with various substituted aromatic aldehydes or ketones to afford a series of quinazolin-2, 4-dione acetyl hydrazone compounds 9a~9t. The structures of all target compounds were characterized by means of ¹H NMR, ¹³C NMR and MS. The preliminary bioassay indicated that the as-synthesized compounds had certain antibacterial activities against the tested strains. At the same time, some of them showed better antibacterial activities than the commercial drugs such as streptomycin sulfate and polyoxin B.
- Quinazolin-2, 4-dione,
- Acetohydrazone,
- Synthesis,
- Antifungal,
- Antibacterial
1. [1]
  F Oger, A Lecorgne, E Sala et al. J. Med. Chem., 2010, 53:1937~1950.
2. [2]
  R A Reinke, P J King, J G Victoria et al. J. Med. Chem., 2002, 45:3669~3683.
3. [3]
  M A H Ismail, S Barker, D A A E Ella et al. J. Med. Chem., 2006, 49:1526~1535.
4. [4]
  J Feng, Z Y Zhang, M B Wallace et al. J. Med. Chem., 2007, 50:2297~2300.
5. [5]
  I V Ukrainets, L V Sidorenko, O V Gorokhova et al. Chem. Heterocycl. Compd., 2006, 42(4):475~487.
6. [6]
  I V Ukrainets, V V Kravtsova1, A A Tkach1 et al. Chem. Heterocycl. Compd., 2010, 46(1):96~105.
7. [7]
  C K Ryu, J Y Shim, Y J Yi et al. Arch. Pharm. Res., 2004, 27(10):990~996.
8. [8]
  K J Aldred, S A McPherson, P Wang et al. Biochem., 2012, 51(1):370~381.
9. [9]
  S Goto, H Tsuboi, M Kanoda et al. Org. Process. Res. Dev., 2003, 7:700~706.
10. [10]
  A Arranz, S F D Betoño, C Echevarria et al. J. Pharm. Biomed. Anal., 1999, 21:797~807.
11. [11]
  Y Guan, C Y Miao, D F Su. Blackwell. Sci. Fund. Clinic. Pharmacol., 2001, 15:221~226.
12. [12]
  A S Lee, M J Su. J. Biomed. Sci., 2008, 15:239~249.
13. [13]
  C Trilok, G Neha, L Suman et al. Eur. J. Med. Chem., 2010,45(5):1772~1776.
14. [14]
  M M Burbuliene, E Udrenaite, P Gaidelis et al. Pol. J. Chem., 2002,76(4):557~563.
15. [15]
  B Chai, S Cao, H D Liu et al. Heterocycl. Commun., 2002, 8(6):601~606.
16. [16]
  K J Keshari, S Abdul, K Yatendra et al. Eur. J. Med. Chem., 2010, 45(11):4963~4967.
17. [17]
  鲍小平, 熊启中, 邹林波等. 合成化学, 2013, 21(1):53~57.
18. [18]
  张刚, 高光宇, 李清寒等. 化学试剂, 2014, 36(7):594~598.
19. [19]
  王应红, 杨录, 刘志昌. 有机化学, 2013, 33:154~158.
20. [20]
  沈生强, 孙晓红, 刘源发等.化学通报, 2014, 77(3):265~269.
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16. [16]
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沈阳化工大学材料科学与工程学院沈阳 110142