메뉴 건너뛰기




Volumn 77, Issue 2, 2009, Pages 355-366

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

Author keywords

Antimicrobial; Pyridine; Thiazole; Thiophene

Indexed keywords

2 CYANO N '(1 FURAN 2 YLETHYLIDENE) 3 (4 METHOXYPHENYL)PROP 2 ENEHYDRAZIDE; 2 CYANO N (1 FURAN 2 YLETHYLIDENE) 3 PHENYLPROP 2 ENEHYDRAZIDE; 2 CYANO N' (1 FURAN 2 YLETHYLIDENE) 2 (PHENYLHYDRAZONO)ACETOHYDRAZIDE; 2 CYANO N' (1 FURAN 2 YLETHYLIDENE) 2 [(4 METHOXYPHENYL)HYDRAZONO]ACETOHYDRAZIDE; 2 CYANO N' (1 FURAN 2 YLETHYLIDENE) 2 [(4 METHYLPHENYL)HYDRAZONO]ACETOHYDRAZIDE; 3 (4 CHLOROPHENYL) 2 CYANO N' (1 FURAN 2 YLETHYLIDENE)PROP 2 ENEHYDRAZIDE; 3 AMINO N' (1 FURAN 2 YLETHYLIDENE) 4,5,6,7 TETRAHYDRO 1 BENZOTHIOPHENE 2 CARBOHYDRAZIDE; 3,5 DIAMINO 4 CYANO N' (1 FURAN 2 YLETHYLIDENE)THIOPHENE 2 CARBOHYDRAZIDE; 4 AMINO N' (1 FURAN 2 YLETHYLIDENE) 3 PHENYL 2 THIOXO 2,3 DIHYDRO 1,3 THIAZOLE 5 CARBOHYDRAZIDE; 4,6 DIAMINO 1 [(1 FURAN 2 YLETHYLIDENE)AMINO] 2 OXO 1,2 DIHYDROPYRIDINE 3 CARBONITRILE; 6 AMINO 1 [(1 FURAN 2 YLETHYLIDENE)AMINO] 2 OXO 4 PHENYL 1,2 DIHYDROPYRIDINE 3,5 DICARBONITRILE; ACETIC ACID DERIVATIVE; AMPICILLIN; ANTIINFECTIVE AGENT; COUMARIN DERIVATIVE; CYCLOHEXIMIDE; ETHYL 2 AMINO 5 CYANO 1 [(1 FURAN 2 YLETHYLIDENE)AMINO] 6 OXO 4 PHENYL 1,6 DIHYDROPYRIDINE 3 CARBOXYLATE; ETHYL 2,4 DIAMINO 5 [[2 (1 FURAN 2 YLETHYLIDENE)HYDRAZINO]CARBONYL]THIOPHENE 3 CARBOXYLIC ACID; ETHYL 4 AMINO 5 CYANO 1 [(1 FURAN 2 YLETHYLIDENE)AMINO] 6 OXO 1,6 DIHYDROPYRIDINE 2 CARBOXYLIC ACID; FURAN DERIVATIVE; HYDRAZIDE DERIVATIVE; HYDRAZONE DERIVATIVE; N' (1 FURAN 2 YLETHYLIDENE) 2 OXO 2H CHROMENE 3 CARBOHYDRAZIDE; PYRIDINE DERIVATIVE; THIAZOLE DERIVATIVE; THIOPHENE DERIVATIVE; UNCLASSIFIED DRUG;

EID: 67149139963     PISSN: 00368709     EISSN: 22180532     Source Type: Journal    
DOI: 10.3797/scipharm.0901-20     Document Type: Article
Times cited : (35)

References (20)
  • 1
    • 41449111442 scopus 로고    scopus 로고
    • 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
    • doi:10.1016/j.ejmech.2007.06.026
    • Karegoudar P, Parasa DJ, Ashok M, Mahalinga M, Poojary B, Holla BS. 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. Eur J Med Chem. 2008; 43: 208-815. doi:10.1016/j.ejmech.2007.06.026
    • (2008) Eur J Med Chem , vol.43 , pp. 208-815
    • Karegoudar, P.1    Parasa, D.J.2    Ashok, M.3    Mahalinga, M.4    Poojary, B.5    Holla, B.S.6
  • 2
    • 33646761622 scopus 로고    scopus 로고
    • Synthesis and biological activity of new 2-amino-8-chloro-5,5-dioxo[1,2, 4]triazolo[2,3- B][1,4,2]benzodithiazines
    • doi:10.1016/j.ejmech.2005.11.009
    • Pomarnacka, E, Bednarski PJ, 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. Eur J Med Chem. 2006; 41: 633-639. doi:10.1016/j.ejmech.2005.11.009
    • (2006) Eur J Med Chem , vol.41 , pp. 633-639
    • Pomarnacka, E.1    Bednarski, P.J.2    Reszka, P.3    Borys, E.D.4    Bienczak, A.5    Werel, W.6    Halasa, R.7
  • 3
    • 62549153106 scopus 로고    scopus 로고
    • Synthesis, antimicrobial and cytotoxic activities of 1,3,4-oxadiazoles, 1,3,4-thiadiazoles and 1,2,4- Triazoles
    • doi:10.1016/j.ejmech.2008.10.012
    • Padmavathi V, Reddy GS, 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. Eur J Med Chem. 2009; 44: 206-2112. doi:10.1016/j.ejmech. 2008.10.012
    • (2009) Eur J Med Chem , vol.44 , pp. 206-2112
    • Padmavathi, V.1    Reddy, G.S.2    Padmaia, A.3    Kondaiah, P.4    Shazia, A.5
  • 5
    • 13444302530 scopus 로고    scopus 로고
    • Synthesis, stereochemistry and biological activity of some novel long alkyl chain substituted thiazolidin-4-ones and thiazan-4-one from 10-undecenoic acid hydrazide
    • DOI 10.1016/j.ejmech.2004.10.003, PII S0223523404002181
    • Rahman VP, Mukhtar S, Ansari WH, Lemiere G. Syhthesis,stereochemistry and biological activity of some novel long alkyl chain substituted thiazolidin- 4-ones and thiazan-4-one from 10-undecenoic acid hydrazide. Eur J Med Chem. 2005; 40: 173-184. doi:10.1016/j.ejmech.2004.10.003 (Pubitemid 40203158)
    • (2005) European Journal of Medicinal Chemistry , vol.40 , Issue.2 , pp. 173-184
    • Rahman, V.P.M.1    Mukhtar, S.2    Ansari, W.H.3    Lemiere, G.4
  • 6
    • 34548794722 scopus 로고    scopus 로고
    • Synthesis of ferrocenyl pyrazoles by the reaction of (2-formyl-1- chlorovinyl)ferrocene with hydrazines
    • DOI 10.1016/j.jorganchem.2007.07.029, PII S0022328X07005487
    • Zora M, Gormen M. Synthesis of ferrocenyl pyrazoles by the reaction of (2-formyl-1-chlorovinyl)ferrocene. J Organomet Chem. 2007; 692: 5026-5032. doi:10.1016/j.jorganchem.2007.07.029 (Pubitemid 47430145)
    • (2007) Journal of Organometallic Chemistry , vol.692 , Issue.22 , pp. 5026-5032
    • Zora, M.1    Gormen, M.2
  • 7
    • 33846441633 scopus 로고    scopus 로고
    • Anti-inflammatory function of an in situ cross-linkable conjugate hydrogel of hyaluronic acid and dexamethasone
    • DOI 10.1016/j.biomaterials.2006.12.012, PII S0142961206010325
    • Ito T, Fraser IP, Yeo Yoon, Highley CB, Bellas E, Kohane DS. Anti-inflammatory function of an in situ cross-linkable conjugate hydrogel of hyaluronic acid and dexamethasone. Biomaterials. 2007; 28: 1778-1786. doi:10.1016/j.biomaterials.2006.12.012 (Pubitemid 46137996)
    • (2007) Biomaterials , vol.28 , Issue.10 , pp. 1778-1786
    • Ito, T.1    Fraser, I.P.2    Yeo, Y.3    Highley, C.B.4    Bellas, E.5    Kohane, D.S.6
  • 8
    • 56949083948 scopus 로고    scopus 로고
    • Pharmacophore based discovery of potential antimalarial agent targeting haem detoxification pathway
    • doi:10.1016/j.ejmech.2008.02.005
    • Acharya BN, Saraswat D, Kaushik MP. Pharmacophore based discovery of potential antimalarial agent targeting haem detoxification pathway. Eur J Med Chem. 2008; 43: 2840-2852. doi:10.1016/j.ejmech.2008.02.005
    • (2008) Eur J Med Chem , vol.43 , pp. 2840-2852
    • Acharya, B.N.1    Saraswat, D.2    Kaushik, M.P.3
  • 9
    • 54049104981 scopus 로고    scopus 로고
    • Synthesis and structure relationships of novel 1-arylmethyl-3-aryl-1H- pyrazole-5-carbohydrazide hydrazone derivatives as potential agents against A549 lung cancer cells
    • doi:10.1016/j.ejmech.2008.01.021
    • Xia Yong, Fan CD, Zhao BX, Zhao J, Shin DS, Miao JY. Synthesis and structure relationships of novel 1-arylmethyl-3-aryl-1H-pyrazole-5- carbohydrazide hydrazone derivatives as potential agents against A549 lung cancer cells. Eur J Med Chem. 2008; 43: 2347-2353. doi:10.1016/j.ejmech.2008.01. 021
    • (2008) Eur J Med Chem , vol.43 , pp. 2347-2353
    • Yong, X.1    Fan, C.D.2    Zhao, B.X.3    Zhao, J.4    Shin, D.S.5    Miao, J.Y.6
  • 11
    • 33644886098 scopus 로고    scopus 로고
    • Synthesis and ring transformations of 1-amino-1,2,3,9a-[1,2-a]indol-2(9H) -ones
    • doi:10.1016/j.tet.2006.01.054
    • Dumciute J, Martynaitis V, Holzer W, Mangelinckx S, Kimpe ND, Sackus A. Synthesis and ring transformations of 1-amino-1,2,3,9a-[1,2-a]indol-2(9H)-ones. Tetrahedron. 2006; 62: 3309-3319. doi:10.1016/j.tet.2006.01.054
    • (2006) Tetrahedron , vol.62 , pp. 3309-3319
    • Dumciute, J.1    Martynaitis, V.2    Holzer, W.3    Mangelinckx, S.4    Kimpe, N.D.5    Sackus, A.6
  • 12
    • 33751032349 scopus 로고    scopus 로고
    • Synthesis and characterization of novel hydrazide-hydrazones and the study of their structureantituberculosis
    • doi:10.1016/j.ejmech.2006.06.009
    • Bedia KB, 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. Eur J Med Chem. 2006; 41: 1253-1261. doi:10.1016/j.ejmech.2006.06.009
    • (2006) Eur J Med Chem , vol.41 , pp. 1253-1261
    • Bedia, K.B.1    Elcin, O.2    Deda, U.3    Fatma, K.4    Nathaly, S.5    Sevim, R.6    Dimoglo, A.7
  • 13
    • 27744587111 scopus 로고    scopus 로고
    • Design, synthesis and in vitro antimalarial activity of an acylhydrazone library
    • DOI 10.1016/j.bmcl.2005.09.058, PII S0960894X05012254
    • Melnyk P, Leroux V, Sergheraert C, Grellier P. Design, synthesis and in vitro antimalarial of an acylhydrazone library. Bioorg Med Chem Lett. 2006; 16: 31-35. doi:10.1016/j.bmcl.2005.09.058 (Pubitemid 41625635)
    • (2006) Bioorganic and Medicinal Chemistry Letters , vol.16 , Issue.1 , pp. 31-35
    • Melnyk, P.1    Leroux, V.2    Sergheraert, C.3    Grellier, P.4
  • 14
    • 0032055861 scopus 로고    scopus 로고
    • Pyridoxal isonicotinoyl hydrazone and its analogs: Potential orally effective iron-chelating agents for the treatment of iron overload disease
    • Richardson DR, Ponka P. Pyridoxal isonicotinoyl hydrazone and its analogs: Potential orally effective iron-chelating agents for the treatment of iron overload disease. J Lab. Clin Med. 1998; 131: 306-315. doi:10.1016/S0022- 2143(98)90180-90189 (Pubitemid 28209557)
    • (1998) Journal of Laboratory and Clinical Medicine , vol.131 , Issue.4 , pp. 306-314
    • Richardson, D.R.1    Ponka, R.2
  • 15
    • 33646447042 scopus 로고    scopus 로고
    • Synthesis and biological activity of 4-thiazolidinones, thiosemicarbazides derived from diflunisal hydrazide
    • doi:10.1016/j.ejmech.2005.11.005
    • Kucukguzel G, Kocatepe A, Clercq ED, Sahin F, Gulluce M. Synthesis and biological activity of 4-thiazolidinones, thiosemicarbazides derived from diflunisal hydrazide. Eur J Med Chem. 2006; 41: 353-359. doi:10.1016/j.ejmech. 2005.11.005
    • (2006) Eur J Med Chem , vol.41 , pp. 353-359
    • Kucukguzel, G.1    Kocatepe, A.2    Clercq, E.D.3    Sahin, F.4    Gulluce, M.5
  • 16
    • 57349170656 scopus 로고    scopus 로고
    • Microwave promoted one-pot synthesis of 3-(2′-amino-3′-cyano- 4′-arylpyrid-6′-yl) coumarins
    • doi:10.1016/j.cclet.2008.10.006
    • Zhou JF, Gong GX, Zhu FX, Zhi SJ. Microwave promoted one-pot synthesis of 3-(2′-amino-3′-cyano-4′-arylpyrid-6′-yl) coumarins. Chin Chem Lett. 2009; 20: 37-39. doi:10.1016/j.cclet.2008.10.006
    • (2009) Chin Chem Lett , vol.20 , pp. 37-39
    • Zhou, J.F.1    Gong, G.X.2    Zhu, F.X.3    Zhi, S.J.4
  • 17
    • 20444490441 scopus 로고    scopus 로고
    • Synthesis of new iminocoumarins and their transformations into N-chloro and hydrazono compounds
    • DOI 10.1016/j.tet.2005.05.020, PII S0040402005007982
    • Volmajer J, Toplak R, Leban I, Le Marechal AM. Synthesis of new iminocoumarins and their transformations into N-chloro and hydrazono compounds. Tetrahedron. 2005; 61: 7012-7021. doi:10.1016/j.tet.2005.05.020 (Pubitemid 40814103)
    • (2005) Tetrahedron , vol.61 , Issue.29 , pp. 7012-7021
    • Volmajer, J.1    Toplak, R.2    Leban, I.3    Le Marechal, A.M.4
  • 18
    • 0033165866 scopus 로고    scopus 로고
    • Practical synthesis of tetrasubstituted thiophenes for use in compound libraries
    • DOI 10.1016/S0040-4039(99)01108-9, PII S0040403999011089
    • Mckibben BP, Cartwright CH, Castelhano L. Practical synthesis of tetrasubstituted thiophenes for use in compound libraries. Tetrahedron Lett.1999; 40: 5471-5474. doi:10.1016/S0040-4039(99)01108-1109 (Pubitemid 29325186)
    • (1999) Tetrahedron Letters , vol.40 , Issue.30 , pp. 5471-5474
    • McKibben, B.P.1    Cartwright, C.H.2    Castelhano, A.L.3
  • 19
    • 77957043510 scopus 로고
    • Recent advances in the chemistry of benzo[b]thiophenes
    • doi:10.1016/S0065-2725(08)60788-60796
    • Scrowston RM. Recent advances in the chemistry of benzo[b]thiophenes. Adv Heterocycl Chem. 1981; 29: 171-249. doi:10.1016/S0065-2725(08)60788-60796
    • (1981) Adv Heterocycl Chem , vol.29 , pp. 171-249
    • Scrowston, R.M.1
  • 20
    • 0026760454 scopus 로고
    • A novel cyclocondensation of xanthates containing active methylene groups with isothiocyanates.Spectral data and X-ray structures of the products
    • doi:10.1016/S0040-4020(01)
    • Tormos GV, Khodorkovsky YU, Neilands OY, Belyakov SV. A novel cyclocondensation of xanthates containing active methylene groups with isothiocyanates.Spectral data and X-ray structures of the products. Tetrahedron. 1992; 48: 6863-6874. doi:10.1016/S0040-4020(01)
    • (1992) Tetrahedron , vol.48 , pp. 6863-6874
    • Tormos, G.V.1    Khodorkovsky, Y.U.2    Neilands, O.Y.3    Belyakov, S.V.4


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.