Citation: FENG Yang, LI Chuanbi, ZHAO Liting, LI Jiaqi, WEI Ya'nan. Synthesis, Crystal Structure and Antimicrobial Activities of Novel Aroylhydrazones Containing Barbituric Acid Moiety[J]. Chinese Journal of Applied Chemistry, ;2016, 33(8): 913-922. doi: 10.11944/j.issn.1000-0518.2016.08.150386 shu

Synthesis, Crystal Structure and Antimicrobial Activities of Novel Aroylhydrazones Containing Barbituric Acid Moiety

1.
Department of Chemistry, Jilin Normal University, Siping, Jilin 136000, China

Corresponding author: LI Chuanbi,
Received Date: 3 November 2015
Available Online: 24 March 2016
Fund Project:

A series of novel acylhydrazone compounds was synthesized by a simple and efficient condensation of 1,3-dimethy-5-formyllbarbituric acids with aryloxy/arylamino acetylhydrazides and nitrogen-containing heterocyclic acetylhydrazides under microwave irradiation. The structures of all new compounds were confirmed by elemental analysis, IR, ¹H NMR, mass spectrometry and single-crystal X-ray diffraction analysis. In vitro antimicrobial activity evaluation results show that some of the target compounds exhibit superior antimicrobial activities compared with ciprofloxacin. Structure-activity relationship analysis shows that when the aryl group is a nitrogen-containing heterocyclic compound, its antibacterial activity is significantly stronger than that of a benzene ring compound. One of target compounds 2t shows the strongest activities against S.Aureus with the minimum inhibitory concentration(MIC) of 0.8 g/L and against E.Coli with the MIC of 1.6 g/L.
- barbituric acid,
- aryl acetohydrazide,
- microwave irradiation,
- crystal structure,
- antimicrobial activity
1. [1]
  [1] Habibi A,Tarameshloo Z. A New and Convenient Method for Synthesis of Barbituric Acid Derivatives[J]. J Iran Chem Soc,2011,8(1):287-291.
2. [2]
  [2] Jursic B S,Stevens D E. Transition Metal Free Reductive Dimerization of Nitrogen Containing Barbituric Acid Benzylidenes[J]. J Heterocycl Chem,2003,40(4):701-706.
3. [3]
  [3] Al-Najjar H J,Barakat A,Al-Majid A M,et al. A Greener, Efficient Approach to Michael Addition of B-arbituric Acid to Nitroalkene in Aqueous Diethylamine Medium[J]. Molecules,2014,19(1):1150-1162.
4. [4]
  [4] Barakat A,Al-Majid A M,Al-Ghamdi A M,et al. Tandem Aldol-Michael Reactions in Aqueous Diethylamine Medium:A Greener and Efficient Approach to Dimedone-Barbituric Acid Derivatives[J]. Chem Cent J,2014,8(1):9-16.
5. [5]
  [5] Nevagi R J,Dighe S N,Dighe S N,et al. Use of Ionic Liquids as Neoteric Solvents in the Synthesis of Fused Heterocycles[J]. Arch Pharm,2014,347(8):540-551.
6. [6]
  [6] Alizadeh A,Khodaei M M,Fakhari M,et al. Chemo and Regioselective Serendipitous Electrochemically Initiated Spirocyclization of Caffeic Acid Esters with Barbituric Acid Derivatives[J]. Electrochim Acta,2015,178(2):533-540.
7. [7]
  [7] Cunha T M,Roman-Campos D,Lotufo C M,et al. Morphine Peripheral Analgesia Depends on Activation of the PI3Kγ/AKT/nNOS/NO/KATP Signaling Pathway[J]. Proc Natl Acad Sci USA,2010,107(9):4442-4447.
8. [8]
  [8] Refat M S,Adam A M A. Structural, Thermal, Kinetic and Pharmacology in Vitro Studies of H-Bonded Complexes Formed Between the Sedative-Hypnotic Drug 5,5-Diethylbarbituratic Acid with Various Acceptors Liquid and Solid Characterization[J]. J Mol Liq,2014,196(2):142-152.
9. [9]
  [9] Siddiqui Z N,Farooq F,Musthafa T N M,et al. Synthesis, Characterization and Antimicrobial Evaluation of Novel Halopyrazole Derivatives[J]. J Saudi Chem Soc,2013,17(2):237-243.
10. [10]
  [10] Neumann D M,Cammarata A,Backes G,et al. Synthesis and Antifungal Activity of Substituted 2,4,6-Pyrimidinetrione Carbaldehyde Hydrazones[J]. Bioorg Med Chem,2014,22(2):813-826.
11. [11]
  [11] El-Hashash M A,Sherif S M,Badawy A A,et al. Facial Synthesis of Some New Pyrazolopyridine, Barbituric and Thiobarbituric Acid Derivatives with Antimicrobial Activities[J]. Int J Adv Res,2014,2(1):900-913.
12. [12]
  [12] Teimouri M B,Akbari-Moghaddam P,Motaghinezhad M. Urotropine Bromine Promoted Synthesis of Funct-ionalized Oxaspirotricyclic Furopyrimidines via a Domino Knoevenagel Condensation/Michael Addition/α-Bromination/Williamson Cycloetherification Sequence in Water[J]. Tetrahedron,2013,69(33):6804-6809.
13. [13]
  [13] XIA Qingchun,HE Qizhuang,SHEN Zhihui,et al. Synthesis and Characterization of Arylacethydrazide[J]. J Shanghai Normal Univ(Nat Sci),2009,38(5):507-510(in Chinese).夏庆春,何其庄,沈智慧,等. 芳酰肼的制备及表征[J]. 上海师范大学学报(自然科学版),2009,38(5):507-510.
14. [14]
  [14] Palaska E,Sahin G,Kelicen P,et al. Synthesis and Anti-Inflammatory Activity of 1-Acylthiosemicarbazides,1,3,4-Oxadiazoles, 1,3,4-Thiadiazoles and 1,2,4-Triazole-3-thiones[J]. Il Farmaco,2002,57(2):101-107.
15. [15]
  [15] Husain A,Ahmad A,Alam M M,et al. Fenbufen Based 3-[5-(Substitutedaryl)-1,3,4-oxadiazol-2-yl]-1-(bi-phenyl-4-yl) Propan-1-Ones as Safer Antiinflammatory and Analgesic Agents[J]. Eur J Med Chem,2009,44(9):3798-3804.
16. [16]
  [16] Siddiqui N,Alam M,Ahsan W. Synthesis, Anticonvulsant and Toxicity Evaluation of 2-(1H-indol-3-yl) Acetyl-N-(substituted phenyl) hydrazine Carbothioamides and Their Related Heterocyclic Derivatives[J]. Acta Pharm,2008,58(4):445-454.
17. [17]
  [17] Jadav S S,Kaptein S,Timiri A,et al. Design, Synthesis, Optimization and Antiviral Activity of a Class of Hybrid Dengue Virus E Protein Inhibitors[J]. Bioorg Med Chem Lett,2015,25(8):1747-1752.
18. [18]
  [18] SONG Bin,ZHENG Changzheng,ZHANG Mingkai,et al. Synthesis, Luminescence Property and Antibacterial Activities of 2-Furoyhydrazone Derivatives[J]. Chinese J Appl Chem,2014,31(7):794-798(in Chinese).宋斌,郑长征,张铭凯,等. 2-呋喃甲酰腙衍生物的合成、荧光性质及抑菌活性[J]. 应用化学,2014,31(7):794-798.
19. [19]
  [19] Kandpal B,Meshram J,Mohanram I,et al. Evaluation of Newly Synthesized Quinazolinone Derivatives of Hydrazones as Potent Anti-Inflammatory and Antibacterial Agents[J]. Med Chem Res,2015,24(4):1419-1426.
20. [20]
  [20] Bhaskarachar R K,Revanasiddappa V G,Hegde S,et al. Design, Synthesis and Anticancer Activity of Functionalized Spiro-Quinolines with Barbituric and Thiobarbituric Acids[J]. Med Chem Res,2015,24(9):3516-3528.
21. [21]
  [21] Khurana J M,Vij K. Nickel Nanoparticles Catalyzed Knoevenagel Condensation of Aromatic Aldehydes with Barbituric Acids and 2-Thiobarbituric Acids[J]. Catal Lett,2010,138(1):104-110.
22. [22]
  [22] Manlove A,Groziak M P. Six-Membered Ring Systems:Diazines and Benzo Derivatives[J]. Prog Heterocycl Chem,2009,20(4):333-363.
23. [23]
  [23] Sathisha K R,Khanum S A,Chandra J N N S,et al. Synthesis and Xanthine Oxidase Inhibitory Activity of 7-Methyl-2-(phenoxymethyl)-5H-[1,3,4] Thiadiazolo [3,2-a] Pyrimidin-5-One Derivatives[J]. Bioorg Med Chem,2011,19(1):211-220.
24. [24]
  [24] Singh H H,Nagar S,Chaudhari A,et al. Inhibition of Pyruvic Acid Oxidation by 2,5-Substituted 1,3,4-Oxadiazoles[J]. J Pharm Sci,1973,62(3):504-507.
25. [25]
  [25] More U A,Joshi S D,Aminabhavi T M,et al. Design, Synthesis, Molecular Docking and 3D-QSAR Studies of Potent Inhibitors of Enoyl-Acyl Carrier Protein Reductase as Potential Antimycobacterial Agents[J]. Eur J Med Chem,2014,71(4):199-218.
26. [26]
  [26] Hiremath S P,Biradar J S,Kudari S M. Synthesis of Substituted Oxadiazoles, Thiadiazoles and Triazoles and Evaluation of Their Biological-Activity[J]. J Indian Chem Soc,1984,61(1):74-76.
27. [27]
  [27] SHEN Guanxin. Microbiology and Immunology[M]. Beijing:People's Medical Publishing House,2007:327(in Chinese).沈关心. 微生物学与免疫学[M]. 北京:人民卫生出版社,2007:327.
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