Synthesis of some N, n′-diacylhydrazine derivatives with radical-scavenging and antifungal activity

Chemical Biology and Drug Design

Volumn 73, Issue 3, 2009, Pages 320-327

  Liu, Xing Hai ^a   Shi, Yan Xia ^b   Ma, Yi ^a   He, Guo Rong ^c   Dong, Wei Li ^a   Zhang, Chuan Yu ^a   Wang, Bao Lei ^a   Wang, Su Hua ^a   Li, Bao Ju ^b   Li, Zheng Ming ^a  

^a NANKAI UNIVERSITY   (China)

^b INSTITUTE OF PLANT PROTECTION   (China)

^c INSTITUTE OF MATERIA MEDICA   (China)

Author keywords

1,1 diphenyl 2 picrylhydrazyl radical scavenging activity; Antifungal activities; Comparative molecular field analysis; Diacylhydrazines

Indexed keywords

2 CHLORO N' (CYCLOPROPANECARBONYL)BENZOHYDRAZIDE; 2,4 DICHLORO N' (CYCLOPROPANECARBONYL)BENZOHYDRAZIDE; 3,4 DICHLORO N' (CYCLOPROPANECARBONYL)BENZOHYDRAZIDE; 4 CHLORO N' (CYCLOPROPANECARBONYL)BENZOHYDRAZIDE; ANTIFUNGAL AGENT; ASCORBIC ACID; CHLOROTHALONIL; DIMETHANCHLON; FUNGICIDE; HYDRAZINE DERIVATIVE; JINGGANGMYCIN; N' (CYCLOPROPANECARBONYL) 2 FLUOROBENZOHYDRAZIDE; N' (CYCLOPROPANECARBONYL) 2 HYDROXYBENZOHYDRAZIDE; N' (CYCLOPROPANECARBONYL) 2 METHOXYLBENZOHYDRAZIDE; N' (CYCLOPROPANECARBONYL) 2 METHYLBENZOHYDRAZIDE; N' (CYCLOPROPANECARBONYL) 2,4 DIMETHYLTHIAZOLE 5 CARBOHYDRAZIDE; N' (CYCLOPROPANECARBONYL) 3 METHYLBENZOHYDRAZIDE; N' (CYCLOPROPANECARBONYL) 4 METHOXY BENZOHYDRAZIDE; N' (CYCLOPROPANECARBONYL) 4 NITROBENZOHYDRAZIDE; N' (CYCLOPROPANECARBONYL)BENZOHYDRAZIDE; N' (CYCLOPROPANECARBONYL)FURAN 2 CARBOHYDRAZIDE; N' (CYCLOPROPANECARBONYL)ISONICOTINOHYDRAZIDE; N' (CYCLOPROPANECARBONYL)NICOTINOHYDRAZIDE; N' BUTYRYLCYCLOPROPANECARBOHYDRAZIDE; PYRIMETHANIL; SCAVENGER; THIOPHANATE METHYL; UNCLASSIFIED DRUG;

ANTIFUNGAL ACTIVITY; ARMYWORM; ARTICLE; BIOASSAY; BOTRYTIS CINEREA; COMPARATIVE MOLECULAR FIELD ANALYSIS; CONTROLLED STUDY; DRUG ACTIVITY; DRUG MECHANISM; DRUG SCREENING; DRUG STRUCTURE; DRUG SYNTHESIS; FUNGAL SCLEROTIUM; FUNGICIDAL ACTIVITY; FUSARIUM OXYSPORUM; HYPHOMYCETES; IN VITRO SELECTION; NONHUMAN; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; QUANTITATIVE ANALYSIS; STRUCTURE ACTIVITY RELATION;

ANTIFUNGAL AGENTS; ASCORBIC ACID; FREE RADICAL SCAVENGERS; FUNGI; HYDRAZINES; MODELS, CHEMICAL; QUANTITATIVE STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 60349127319     PISSN: 17470277     EISSN: None     Source Type: Journal    
DOI: 10.1111/j.1747-0285.2009.00779.x     Document Type: Article

References (43)

1. Lamson D.W., Brignall M.S. (1999) Antioxidants in cancer therapy, their actions and interactions with oncologic therapies. Med Rev 4 : 304 329.
2. Brash D.E., Havre P.A. (2002) New careers for antioxidants. Proc Natl Acad Sci USA 99 : 13969 13971.
3. Asghar Z., Masood Z. (2008) Evaluation of antioxidant properties of silymarin and its potential to inhibit peroxyl radicals in vitro. Pakistan J Pharm Sci 21 : 249 254.
4. Chen J., Hu T., Zheng R. (2007) Antioxidant activities of Sophora subprostrata polysaccharide in immunosuppressed mice. Int Immunopharmacol 7 : 547 553.
5. Ziakas G.N., Rekka E.A., Gavalas A.M., Eleftheriou P.T., Kourounakis P.N. (2006) New analogues of butylated hydroxytoluene as anti-inflammatory and antioxidant agents. Bioorg Med Chem 14 : 5616 5624.
6. Flamm E.S., Demopoulos H.B., Seligman M.L., Poser R.G., Ransohoff J. (1978) Free radicals in cerebral ischemia. Stroke 9 : 445 447.
7. Green A.R., Shuaib A. (2006) Therapeutic strategies for the treatment of stroke. Drug Discov Today 11 : 681 693.
8. Sarkhail P., Fadyevatan S., Abdollahi M. (2008) Antioxidant effect of Phlomis persica Boiss. in rats with streptozotocin-induced diabetes. Planta Med 74 : 980 980.
9. Belleville J. (2003) Nature and level of dietary proteins and lipids in food intake Ocl-Oleagineux. Corps Gras Lipides 10 : 31 40.
10. Sapcanin A., Sofic E., Tahirovic I., Gavrankapetanovic I., alcher K. (2007) Antioxidant capacity in the lipophilic fraction of Alzheimer's brain tissues. Bosnian J Basic Med Sci 7 : 317 321.
11. Zhao B.L. (2008) Protective effects of green tea polyphenols against Parkinson's disease. Prog Biochem Biophys 35 : 735 743.
12. Duarte C.D., Tributino J.L.M., Lacerda D.I., Martins M.V., Alexandre-Moreira M.S., Dutra F., Bechara E.J.H. et al. (2007) Synthesis, pharmacological evaluation and electrochemical studies of novel 6-nitro-3,4-methylenedioxyphenyl-N-acylhydrazone derivatives: discovery of LASSBio-881, a new ligand of cannabinoid receptors Bioorg. Med Chem 15 : 2421 2433.
13. Tabrizchi R. (2000) Edaravone Mitsubishi-Tokyo. Curr Opin Investig Drugs 1 : 347 354.
14. Ayhan-kilcigil G., Kus C., Çoban T., Can-Eke B., Iscan M. (2004) Synthesis and antioxidant properties of novel benzimidazole derivatives. J Enzym Inhib Med Chem 19 : 129 135.
15. Ashiqa U., Araa R., Mahroof-Tahir M., Maqsooda Z.T., Khanc K.M., Khanc S.N., Siddiquic H., Choudharyc M.I. (2008) Synthesis, spectroscopy, and biological properties of vanadium(IV)-hydrazide complexes. Chem Biodivers 5 : 82 92.
16. Alkan M., Yüksek H., Gürsoy-Kol Ö., Calapog̀lu M. (2008) Synthesis, acidity and antioxidant properties of some novel 3,4-disubstituted-4,5-dihydro-1H-1,2,4-triazol-5-one derivatives. Molecules 13 : 107 121.
17. Sueishi K., Mishima K., Makino K., Itoh Y., Tsuruya K., Hirakata H., Oishi R. (2002) Protection by a radical scavenger edaravone against cisplatin-induced nephrotoxicity in rats. Eur J Pharmacol 451 : 203 208.
18. Yanagi M., Watanabe T., Masui A. (1992) ANS-118: A novel insecticide. Brighton Crop Prot Conf Pests Dis 2000 2 : 27 32.
19. Heller J.J., Mattioda H., Klein E., Sagenmuller A. (1992) Field evalution of RH-5992 on lepidopterous pests in Europe. Brighton Crop Prot Conf Pests Dis 1 : 59 66.
20. Le D.P., Thirugnanam M., Lidert Z., Carlson G.R., Ryan J.B. (1996) RH-2485: a new selective insecticide for caterpillar control. Brighton Crop Prot Conf Pests Dis 2 : 481 486.
21. Zhao Q.Q., Ou X.M., Huang Z.Q., Bi F.C., Huang R.Q., Wang Q.M. (2008) Synthesis and insecticidal activities of novel N-sulfenyl-N′-tert-butyl-N, N′-diacylhydrazines. 3. N-(alkyldithio), N-(aminothio), and N,N-dithio derivatives. J Agr Food Chem 56 : 10799 10804.
22. Ohno N., Fujimoto K., Mizutani Y., Mizutani T., Hirano M., Itaya N., Honda T., Yoshioka H. (1974) New class of pyrethroidal insecticides. α-Substituted phenylacetic acid esters. Agric Biol Chem 38 : 881 883.
23. Lee Y.T., Hang T.T., Duggleby R.G. (2005) Cyclopropane-1,1-dicarboxylate is a slow-tight-binding inhibitor of rice ketol-acid reductoisomerase. Plant Sci 168 : 1035 1040.
24. Liu X.H., Chen P.Q., Wang B.L., Li Y.H., Wang S.H., Li Z.M. (2007) Synthesis bioactivity theoretical and molecular docking study of 1-cyano-N-substituted-cyclopropanecarboxamide as ketol-acid reductoisomerase inhibitor. Bioorg Med Chem Lett 17 : 3784 3788.
25. Liu X.H., Chen P.Q., He F.Q., Li Y.H., Wang S.H., Li Z.M. (2007) Structure bioactivity and theoretical study of 1-cyano-N-p-tolylcyclo- propanecarboxamide. Struct Chem 5 : 563 568.
26. Liu X.H., Zhang C.Y., Guo W.C., Li Y.H., Chen P.Q., Wang T., Dong W.L., Sun H.W., Li Z.M. (2008) Synthesis bioactivity and SAR study of N′-(5-substituted-1,3,4-thiadiazol-2-yl)-N-cyclopropyformyl-thiourea as ketol-acid reductoisomerase inhibitor. J Enzym Inhib Med Chem. DOI:.
27. Macaev F., Rusu G., Pogrebnoi S., Gudima A., Stingaci E., Vlad L., Shvets N., Kandemirli F., Dimoglo A., Reynolds R. (2005) Synthesis of novel 5-aryl-2-thio-1,3,4-oxadiazoles and the study of their structure- antimycobacterial activities. Bioorg Med Chem 13 : 4842 4850.
28. Nesterova E.Y., Voevudsky M.V., Samukha A.V., Zubatyuk R.I., Shishkin O.V. (2005) Study of the acylation reaction of 2,6-dimethyl-3,5- pyridinedicarboxylic acid hydrazides. Chem Heterocycl Compd 41 : 1511 1520.
29. Haksar C.N., Malhotra R.C., Ramachandran P.K. (1979) Oxidation of hydrazides of salicylic and substituted salicylic acids with active manganese dioxide. Indian J Chem 17B : 191 193.
30. Goswami B.N., Kataky J.C.S., Baruah J.N., Nath S.C. (1984) Synthesis of 3,5-disubstituted 1,3,4-oxadiazole-2-thiones as potential fungicidal agents. J Heterocycl Chem 21 : 205 208.
31. Clemence F., Joliveau-Maushart C., Meier J., Cerede J., Delevallee F., Benzoni J., Deraedt R. (1985) Synthesis and analgesic activity in the 1,2,4-triazole series. Eur J Med Chem 20 : 257 266.
32. Werbel L.M., McNamara D.J., Colbry N.L., Johnson J.L., Degnan M.J., Whitney B. (1979) Antimalarial drugs. 42 Synthesis and antimalarial effects of N,N-dialkyl-6-(substituted phenyl)-1,2,4,5-tetrazin-3-amines. J Heterocycl Chem 16 : 881 894.
33. Omodei-Sale A., Consonni P., Galliani G. (1983) A new class of nonhormonal pregnancy-terminating agents. Synthesis and contragestational activity of 3,5-diaryl-s-triazoles. J Med Chem 26 : 1187 1192.
34. Zamani K., Faghihi K., Tofighi T., Shariatzadeh M.R. (2004) Synthesis and antimicrobial activity of some pyridyl and naphthyl substituted 1,2,4-triazole and 1,3,4-thiadiazole derivatives. Turk J Chem 28 : 95 100.
35. Holt J., Andreassen T., Bakke J.M., Fiksdahl A. (2005) Nitropyridyl isocyanates. J Heterocycl Chem 42 : 259 264.
36. 2-derivatized hydrazines: denticity effects redox switches and reductant-driven redox-cycling. Med Chem 1 : 159 171.
37. Auge J., Lubin-Germain N. (2000) Glycosylhydrazides a new class of sugar surfactants. Preparation and amphiphilic properties of 1-glycosyl-2- acylhydrazines. J Carbohydr Chem 19 : 379 392.
38. Gyamfi M.A., Yonamine M., Aniya Y. (1999) Free-radical scavenging action of medicinal herbs from Ghana Thonningia sanguinea on experimentally induced liver injuries. Gen Pharm 32 : 661 667.
39. Shi Y.X., Yuan L.P., Zhang Y.B., Li B.J. (2007) Fungicidal activity of novel fungicide chlorphenomizole and efficacy in controlling main diseases on vegetable in field. Chin J Pest Sci 9 : 126 130.
40. Zhao Q.Q., Shang J., Huang Z.Q., Wang K.Y., Bi F.C., Huang R.Q., Wang Q.M. (2008) Synthesis and insecticidal activities of novel N-Sulfenyl-N′- tert-butyl-N,N′-diacylhydrazines. 2. N-substituted phenoxysulfenate derivatives. J Agr Food Chem 56 : 5254 5259.
41. Zhao W.G., Wang J.G., Li Z.M., Yang Z. (2006) Synthesis and antiviral activity against tobacco mosaic virus and 3D-QSAR of alpha-substituted-1,2,3- thiadiazoleacetamides. Bioorg Med Chem 16 : 6107 6111.
42. Bush B.L., Nachbar R.B. (1993) Sample-distance partial least-squares PLS optimized for many variables, with application to CoMFA. J Comput-Aided Mol Des 7 : 587 619.
43. Chen Q., Zhu X.L., Jiang L.L., Liu Z.M., Yang G.F. (2008) Synthesis antifungal activity and CoMFA analysis of novel l,2,4-triazolo[1,5-a]pyrimidine derivatives. Eur J Med Chem 43 : 595 603.