The reaction of cyanoacetic acid hydrazide with 2-acetylfuran: Synthesis of coumarin, pyridine, thiophene and thiazole derivatives with potential antimicrobial activities

Simple item page
dc.AffiliationOctober University for modern sciences and Arts (MSA)
dc.contributor.authorMohareb R.M.
dc.contributor.authorEl-Arab E.E.
dc.contributor.authorEl-Sharkawy K.A.
dc.contributor.otherFaculty of Pharmacy
dc.contributor.otherOctober University for Modern Sciences and Arts
dc.contributor.otherElwahaat Road
dc.contributor.otherOctober City
dc.contributor.otherEgypt; Faulty of Science
dc.contributor.otherChemistry Department
dc.contributor.otherCairo University
dc.contributor.otherEgypt; National Organization of Drug Control and Research (NODCAR)
dc.contributor.otherP.O. 29
dc.contributor.otherCairo
dc.contributor.otherEgypt
dc.date.accessioned2020-01-25T19:58:34Z
dc.date.available2020-01-25T19:58:34Z
dc.date.issued2009
dc.descriptionScopus
dc.description.abstractThe hydrazide-hydrazone derivative 1 was formed through the reaction of cyanoacetic acid hydrazide with 2-acetylfuran. Compound 1 underwent a series of hetrocyclization reactions through its reaction with different chemical reagents to produce arylidene, coumarin, aryl hydrazone, pyridine, thiophene and thiazole derivatives 2-10. The MIC values for the newly synthesized products were tested against E. coli, B. cereus, B. subtilis and C. albicans compared with ampicilline and cycloheximide as reference drugs. � Mohareb et al.; licensee �sterreichische Apotheker-Verlagsgesellschaft m. b. H.en_US
dc.description.urihttps://www.scimagojr.com/journalsearch.php?q=22212&tip=sid&clean=0
dc.identifier.doihttps://doi.org/10.3797/scipharm.0901-20
dc.identifier.issn368709
dc.identifier.otherhttps://doi.org/10.3797/scipharm.0901-20
dc.identifier.urihttps://t.ly/0Mge3
dc.language.isoEnglishen_US
dc.relation.ispartofseriesScientia Pharmaceutica
dc.relation.ispartofseries77
dc.subjectAntimicrobialen_US
dc.subjectPyridineen_US
dc.subjectThiazoleen_US
dc.subjectThiopheneen_US
dc.subject2 cyano n '(1 furan 2 ylethylidene) 3 (4 methoxyphenyl)prop 2 enehydrazideen_US
dc.subject2 cyano n (1 furan 2 ylethylidene) 3 phenylprop 2 enehydrazideen_US
dc.subject2 cyano n' (1 furan 2 ylethylidene) 2 (phenylhydrazono)acetohydrazideen_US
dc.subject2 cyano n' (1 furan 2 ylethylidene) 2 [(4 methoxyphenyl)hydrazono]acetohydrazideen_US
dc.subject2 cyano n' (1 furan 2 ylethylidene) 2 [(4 methylphenyl)hydrazono]acetohydrazideen_US
dc.subject3 (4 chlorophenyl) 2 cyano n' (1 furan 2 ylethylidene)prop 2 enehydrazideen_US
dc.subject3 amino n' (1 furan 2 ylethylidene) 4,5,6,7 tetrahydro 1 benzothiophene 2 carbohydrazideen_US
dc.subject3,5 diamino 4 cyano n' (1 furan 2 ylethylidene)thiophene 2 carbohydrazideen_US
dc.subject4 amino n' (1 furan 2 ylethylidene) 3 phenyl 2 thioxo 2,3 dihydro 1,3 thiazole 5 carbohydrazideen_US
dc.subject4,6 diamino 1 [(1 furan 2 ylethylidene)amino] 2 oxo 1,2 dihydropyridine 3 carbonitrileen_US
dc.subject6 amino 1 [(1 furan 2 ylethylidene)amino] 2 oxo 4 phenyl 1,2 dihydropyridine 3,5 dicarbonitrileen_US
dc.subjectacetic acid derivativeen_US
dc.subjectampicillinen_US
dc.subjectantiinfective agenten_US
dc.subjectcoumarin derivativeen_US
dc.subjectcycloheximideen_US
dc.subjectethyl 2 amino 5 cyano 1 [(1 furan 2 ylethylidene)amino] 6 oxo 4 phenyl 1,6 dihydropyridine 3 carboxylateen_US
dc.subjectethyl 2,4 diamino 5 [[2 (1 furan 2 ylethylidene)hydrazino]carbonyl]thiophene 3 carboxylic aciden_US
dc.subjectethyl 4 amino 5 cyano 1 [(1 furan 2 ylethylidene)amino] 6 oxo 1,6 dihydropyridine 2 carboxylic aciden_US
dc.subjectfuran derivativeen_US
dc.subjecthydrazide derivativeen_US
dc.subjecthydrazone derivativeen_US
dc.subjectn' (1 furan 2 ylethylidene) 2 oxo 2h chromene 3 carbohydrazideen_US
dc.subjectpyridine derivativeen_US
dc.subjectthiazole derivativeen_US
dc.subjectthiophene derivativeen_US
dc.subjectunclassified drugen_US
dc.subjectantimicrobial activityen_US
dc.subjectarticleen_US
dc.subjectBacillus cereusen_US
dc.subjectBacillus subtilisen_US
dc.subjectCaenorhabditis elegansen_US
dc.subjectchemical reactionen_US
dc.subjectcontrolled studyen_US
dc.subjectdrug synthesisen_US
dc.subjectEscherichia colien_US
dc.subjectminimum inhibitory concentrationen_US
dc.subjectnonhumanen_US
dc.titleThe reaction of cyanoacetic acid hydrazide with 2-acetylfuran: Synthesis of coumarin, pyridine, thiophene and thiazole derivatives with potential antimicrobial activitiesen_US
dc.typeArticleen_US
dcterms.isReferencedByKaregoudar, P., Parasa, D.J., Ashok, M., Mahalinga, M., Poojary, B., Holla, B.S., Synthesis, antimicrobial and ant-inflammatory activities of some 1,2,4-triazolo[3,4-b][1,3,4]thiazoles and 1,2,4-triazolo[3,4-b]thiadiazines bearing trichlorophenyl moiety (2008) Eur J Med Chem, 43, pp. 208-815. , doi:10.1016/j.ejmech.2007.06.026; Pomarnacka, E., Bednarski, P.J., Reszka, P., Borys, E.D., Bienczak, A., Werel, W., Halasa, R., Synthesis and biological activity of new 2-amino-8-chloro-5,5-dioxo[1,2, 4]triazolo[2,3- B][1,4,2]benzodithiazines (2006) Eur J Med Chem, 41, pp. 633-639. , doi:10.1016/j.ejmech.2005.11.009; Padmavathi, V., Reddy, G.S., Padmaia, A., Kondaiah, P., Shazia, A., Synthesis, antimicrobial and cytotoxic activities of 1,3,4-oxadiazoles, 1,3,4-thiadiazoles and 1,2,4- Triazoles (2009) Eur J Med Chem, 44, pp. 206-2112. , doi:10.1016/j.ejmech.2008.10.012; Ragavendran, J.V., Sriram, D., Patel, S.K., Reddy, I.V., Bharathwajan, N., Stables, J., Yogeeswari, P., Design and synthesis of anticonvulsants from a combined phthalimide-GABA-anilide and hydrazone pharmacophore (2007) European Journal of Medicinal Chemistry, 42 (2), pp. 146-151. , DOI 10.1016/j.ejmech.2006.08.010, PII S022352340600290X; Rahman, V.P.M., Mukhtar, S., Ansari, W.H., Lemiere, G., Synthesis, stereochemistry and biological activity of some novel long alkyl chain substituted thiazolidin-4-ones and thiazan-4-one from 10-undecenoic acid hydrazide (2005) European Journal of Medicinal Chemistry, 40 (2), pp. 173-184. , DOI 10.1016/j.ejmech.2004.10.003, PII S0223523404002181; Zora, M., Gormen, M., Synthesis of ferrocenyl pyrazoles by the reaction of (2-formyl-1- chlorovinyl)ferrocene with hydrazines (2007) Journal of Organometallic Chemistry, 692 (22), pp. 5026-5032. , DOI 10.1016/j.jorganchem.2007.07.029, PII S0022328X07005487; Ito, T., Fraser, I.P., Yeo, Y., Highley, C.B., Bellas, E., Kohane, D.S., Anti-inflammatory function of an in situ cross-linkable conjugate hydrogel of hyaluronic acid and dexamethasone (2007) Biomaterials, 28 (10), pp. 1778-1786. , DOI 10.1016/j.biomaterials.2006.12.012, PII S0142961206010325; Acharya, B.N., Saraswat, D., Kaushik, M.P., Pharmacophore based discovery of potential antimalarial agent targeting haem detoxification pathway (2008) Eur J Med Chem, 43, pp. 2840-2852. , doi:10.1016/j.ejmech.2008.02.005; Yong, X., Fan, C.D., Zhao, B.X., Zhao, J., Shin, D.S., Miao, J.Y., Synthesis and structure relationships of novel 1-arylmethyl-3-aryl-1H- pyrazole-5-carbohydrazide hydrazone derivatives as potential agents against A549 lung cancer cells (2008) Eur J Med Chem, 43, pp. 2347-2353. , doi:10.1016/j.ejmech.2008.01.021; Imramovsky, A., Polanc, S., Vinsova, J., Kocevar, M., Jampilek, J., Reckova, Z., Kaustova, J., A new modification of anti-tubercular active molecules (2007) Bioorganic and Medicinal Chemistry, 15 (7), pp. 2551-2559. , DOI 10.1016/j.bmc.2007.01.051, PII S0968089607000776; Dumciute, J., Martynaitis, V., Holzer, W., Mangelinckx, S., Kimpe, N.D., Sackus, A., Synthesis and ring transformations of 1-amino-1,2,3,9a-[1,2-a]indol-2(9H) -ones (2006) Tetrahedron, 62, pp. 3309-3319. , doi:10.1016/j.tet.2006.01.054; Bedia, K.B., Elcin, O., Deda, U., Fatma, K., Nathaly, S., Sevim, R., Dimoglo, A., Synthesis and characterization of novel hydrazide-hydrazones and the study of their structureantituberculosis (2006) Eur J Med Chem, 41, pp. 1253-1261. , doi:10.1016/j.ejmech.2006.06.009; Melnyk, P., Leroux, V., Sergheraert, C., Grellier, P., Design, synthesis and in vitro antimalarial activity of an acylhydrazone library (2006) Bioorganic and Medicinal Chemistry Letters, 16 (1), pp. 31-35. , DOI 10.1016/j.bmcl.2005.09.058, PII S0960894X05012254; Richardson, D.R., Ponka, R., Pyridoxal isonicotinoyl hydrazone and its analogs: Potential orally effective iron-chelating agents for the treatment of iron overload disease (1998) Journal of Laboratory and Clinical Medicine, 131 (4), pp. 306-314; Kucukguzel, G., Kocatepe, A., Clercq, E.D., Sahin, F., Gulluce, M., Synthesis and biological activity of 4-thiazolidinones, thiosemicarbazides derived from diflunisal hydrazide (2006) Eur J Med Chem, 41, pp. 353-359. , doi:10.1016/j.ejmech.2005.11.005; Zhou, J.F., Gong, G.X., Zhu, F.X., Zhi, S.J., Microwave promoted one-pot synthesis of 3-(2?-amino-3?-cyano- 4?-arylpyrid-6?-yl) coumarins (2009) Chin Chem Lett, 20, pp. 37-39. , doi:10.1016/j.cclet.2008.10.006; Volmajer, J., Toplak, R., Leban, I., Le Marechal, A.M., Synthesis of new iminocoumarins and their transformations into N-chloro and hydrazono compounds (2005) Tetrahedron, 61 (29), pp. 7012-7021. , DOI 10.1016/j.tet.2005.05.020, PII S0040402005007982; McKibben, B.P., Cartwright, C.H., Castelhano, A.L., Practical synthesis of tetrasubstituted thiophenes for use in compound libraries (1999) Tetrahedron Letters, 40 (30), pp. 5471-5474. , DOI 10.1016/S0040-4039(99)01108-9, PII S0040403999011089; Scrowston, R.M., Recent advances in the chemistry of benzo[b]thiophenes (1981) Adv Heterocycl Chem, 29, pp. 171-249. , doi:10.1016/S0065-2725(08)60788-60796; Tormos, G.V., Khodorkovsky, Y.U., Neilands, O.Y., Belyakov, S.V., A novel cyclocondensation of xanthates containing active methylene groups with isothiocyanates.Spectral data and X-ray structures of the products (1992) Tetrahedron, 48, pp. 6863-6874. , doi:10.1016/S0040-4020(01)
dcterms.sourceScopus

Files

Original bundle

Now showing 1 - 2 of 2
Thumbnail Image
Name:
avatar_scholar_256.png
Size:
6.31 KB
Format:
Portable Network Graphics
Description:
Download
Thumbnail Image
Name:
scipharm-77-00355.pdf
Size:
218.89 KB
Format:
Adobe Portable Document Format
Description:
Download

Collections

Faculty Of Pharmacy Research Paper