메뉴 건너뛰기




Volumn 22, Issue 7, 2013, Pages 3428-3433

Oxadiazolo pyrrolidine carboxamides as enoyl-ACP reductase inhibitors: Design, synthesis and antitubercular activity screening

Author keywords

Antitubercular activities; Docking; Enoyl acyl carrier protein (ACP); Oxadiazole; Pyrrolidine carboxamides; Reductase inhibitors

Indexed keywords

5 OXO 1 PHENYL N (5 PHENYL 1,3,4 OXADIAZOL 2 YL) PYRROLIDINE 3 CARBOXAMIDE; AMIDE; CARBOXYLIC ACID; ENOYL ACYL CARRIER PROTEIN REDUCTASE INHIBITOR; N [5 (4 CHLOROPHENYL) 1,3,4 OXADIAZOL 2 YL] 5 OXO 1 PHENYLPYRROLIDINE 3 CARBOXAMIDE; N [5 (4 METHOXYPHENYL) 1,3,4 OXADIAZOL 2 YL] 5 OXO 1 PHENYLPYRROLIDINE 3 CARBOXAMIDE; N [5 (4 METHYLPHENYL) 1,3,4 OXADIAZOL 2 YL] 5 OXO 1 PHENYLPYRROLIDINE 3 CARBOXAMIDE; N [5 (4 NITROPHENYL) 1,3,4 OXADIAZOL 2 YL] 5 OXO 1 PHENYLPYRROLIDINE 3 CARBOXAMIDE; OXADIAZOLE DERIVATIVE; OXIDOREDUCTASE INHIBITOR; TUBERCULOSTATIC AGENT; UNCLASSIFIED DRUG;

EID: 84878884350     PISSN: 10542523     EISSN: 15548120     Source Type: Journal    
DOI: 10.1007/s00044-012-0340-3     Document Type: Article
Times cited : (23)

References (17)
  • 2
    • 0037311637 scopus 로고    scopus 로고
    • Isoniazid activation defects in recombinant Mycobacterium tuberculosis catalase-peroxidase (KatG) mutants evident in InhA inhibitor production
    • 10.1128/AAC.47.2.670-675.2003
    • Chih-Jen W, Benfang L, James MM, Shiao-Chun T (2003) Isoniazid activation defects in recombinant Mycobacterium tuberculosis catalase-peroxidase (KatG) mutants evident in InhA inhibitor production. Antimicrob Agents Chemother 47(2):670-675
    • (2003) Antimicrob Agents Chemother , vol.47 , Issue.2 , pp. 670-675
    • Chih-Jen, W.1    Benfang, L.2    James, M.M.3    Shiao-Chun, T.4
  • 3
    • 16344385633 scopus 로고    scopus 로고
    • Can DOTS control multidrug-resistant tuberculosis?
    • 15811438 10.1016/S0140-6736(05)74788-7
    • Espinal MA, Dye C (2005) Can DOTS control multidrug-resistant tuberculosis? Lancet 365:1206-1209
    • (2005) Lancet , vol.365 , pp. 1206-1209
    • Espinal, M.A.1    Dye, C.2
  • 4
    • 13244287939 scopus 로고    scopus 로고
    • Synthesis and tuberculostatic activity of some (4-phenylpiperazin-1- ylmethyl)-1,3,4-oxadiazole and (4-phenylpiperazin-1-ylmethyl)-1,2,4-triazole derivatives
    • 15794341 1:CAS:528:DC%2BD2MXjtVKjsr0%3D
    • Foks H, Pancechowska-Ksepko D, Janowiec M, Zwolska Z, Augustynowicz-Kopeć E (2004) Synthesis and tuberculostatic activity of some (4-phenylpiperazin-1-ylmethyl)-1,3,4-oxadiazole and (4-phenylpiperazin-1- ylmethyl)-1,2,4-triazole derivatives. Acta Pol Pharm 61(6):473-476
    • (2004) Acta Pol Pharm , vol.61 , Issue.6 , pp. 473-476
    • Foks, H.1    Pancechowska-Ksepko, D.2    Janowiec, M.3    Zwolska, Z.4    Augustynowicz-Kopeć, E.5
  • 5
    • 77954309707 scopus 로고    scopus 로고
    • Synthesis and antibacterial activity of some transition metal complexes of oxime, semicarbazone and phenylhydrazone
    • 10.1155/2009/204714 1:CAS:528:DC%2BD1MXhsVSltrzF
    • Hania MM (2009) Synthesis and antibacterial activity of some transition metal complexes of oxime, semicarbazone and phenylhydrazone. E-J Chem 6(S1):S508-S514
    • (2009) E-J Chem , vol.6 , Issue.S1
    • Hania, M.M.1
  • 6
    • 0032515066 scopus 로고    scopus 로고
    • Broad spectrum antimicrobial biocides target the FabI component of fatty acid synthesis
    • 9804793 10.1074/jbc.273.46.30316 1:CAS:528:DyaK1cXnsVyrtb4%3D
    • Heath RJ, Yu YT, Shapiro MA, Olson E, Rock CO (1998) Broad spectrum antimicrobial biocides target the FabI component of fatty acid synthesis. J Biol Chem 273(46):30316-30320
    • (1998) J Biol Chem , vol.273 , Issue.46 , pp. 30316-30320
    • Heath, R.J.1    Yu, Y.T.2    Shapiro, M.A.3    Olson, E.4    Rock, C.O.5
  • 7
    • 0030993176 scopus 로고    scopus 로고
    • Biochemistry and molecular genetics of cell-wall lipid biosynthesis in mycobacteria
    • 9159514 10.1046/j.1365-2958.1997.3361705.x 1:CAS:528:DyaK2sXjt1SjsbY%3D
    • Kolattukudy PE, Fernandes ND, Azad AK, Fitzmaurice AM, Sirakova TD (1997) Biochemistry and molecular genetics of cell-wall lipid biosynthesis in mycobacteria. Mol Microbiol 24:263-270
    • (1997) Mol Microbiol , vol.24 , pp. 263-270
    • Kolattukudy, P.E.1    Fernandes, N.D.2    Azad, A.K.3    Fitzmaurice, A.M.4    Sirakova, T.D.5
  • 9
    • 18144398613 scopus 로고    scopus 로고
    • Antimycobacterial activity of new 3-substituted 5-(pyridine-4-yl)-3H-1,3, 4-oxadiazol-2-one and 2-thione derivatives - Preliminary molecular modeling investigations
    • 10.1016/j.bmc.2005.03.013
    • Maria GM, Daniele Z, Luciano V, Maurizio F, Marco F, Sabrina P, Guiditta S, Elena B (2005) Antimycobacterial activity of new 3-substituted 5-(pyridine-4-yl)-3H-1,3,4-oxadiazol-2-one and 2-thione derivatives - preliminary molecular modeling investigations. Bioorg Med Chem 13:3797-3809
    • (2005) Bioorg Med Chem , vol.13 , pp. 3797-3809
    • Maria, G.M.1    Daniele, Z.2    Luciano, V.3    Maurizio, F.4    Marco, F.5    Sabrina, P.6    Guiditta, S.7    Elena, B.8
  • 10
    • 34848927285 scopus 로고    scopus 로고
    • Extensively drug-resistant Mycobacterium tuberculosis, India
    • 18252133 10.3201/eid1309.070443
    • Mondal R, Jain A (2007) Extensively drug-resistant Mycobacterium tuberculosis, India. Emerg Infect Dis 13:1429-1431
    • (2007) Emerg Infect Dis , vol.13 , pp. 1429-1431
    • Mondal, R.1    Jain, A.2
  • 11
    • 33748278900 scopus 로고    scopus 로고
    • Synthesis and antibacterial activity of new oxadiazolo [1, 3, 5]-triazine, 1,2,4 triazolo and thiadiazolo 1,3,4 oxadiazole derivatives
    • 1:CAS:528:DC%2BD28XotVSisrc%3D
    • Mulwad VV, Chaskar AC (2006) Synthesis and antibacterial activity of new oxadiazolo [1, 3, 5]-triazine, 1,2,4 triazolo and thiadiazolo 1,3,4 oxadiazole derivatives. Indian J Chem 45B:1710-1715
    • (2006) Indian J Chem , vol.45 , pp. 1710-1715
    • Mulwad, V.V.1    Chaskar, A.C.2
  • 12
    • 2342554253 scopus 로고
    • The reaction of itaconic acid with primary amines
    • 10.1021/ja01159a520 1:CAS:528:DyaG3cXjtVWhtA%3D%3D
    • Paytash PL, Sparrow E, Gathe JC (1950) The reaction of itaconic acid with primary amines. J Am Chem Soc 72:1415-1416
    • (1950) J Am Chem Soc , vol.72 , pp. 1415-1416
    • Paytash, P.L.1    Sparrow, E.2    Gathe, J.C.3
  • 13
    • 0345133299 scopus 로고    scopus 로고
    • The isoniazid-NAD adduct is a slow, tight-binding inhibitor of InhA, the Mycobacterium tuberculosis enoyl reductase: Adduct affinity and drug resistance
    • 10.1073/pnas.2235848100
    • Richa R, Adrian W, Peter JT (2003) The isoniazid-NAD adduct is a slow, tight-binding inhibitor of InhA, the Mycobacterium tuberculosis enoyl reductase: adduct affinity and drug resistance. Proc Natl Acad Sci USA 100(24):13881-13886
    • (2003) Proc Natl Acad Sci USA , vol.100 , Issue.24 , pp. 13881-13886
    • Richa, R.1    Adrian, W.2    Peter, J.T.3
  • 14
    • 0032472224 scopus 로고    scopus 로고
    • Modification of the NADH of the isoniazid target (InhA) from Mycobacterium tuberculosis
    • 9417034 10.1126/science.279.5347.98 1:CAS:528:DyaK1cXjsFGgtA%3D%3D
    • Rozwarski DA, Gregory AG, Derek HR, William RJ, James CS (1998) Modification of the NADH of the isoniazid target (InhA) from Mycobacterium tuberculosis. Science 279:98-102
    • (1998) Science , vol.279 , pp. 98-102
    • Rozwarski, D.A.1    Gregory, A.G.2    Derek, H.R.3    William, R.J.4    James, C.S.5
  • 15
    • 0014841450 scopus 로고
    • Inhibition by isoniazid of synthesis of mycolic acids in Mycobacterium tuberculosis
    • 5500025 10.1099/00221287-63-1-41 1:CAS:528:DyaE3MXpsF2ktg%3D%3D
    • Winder FG, Collins PB (1970) Inhibition by isoniazid of synthesis of mycolic acids in Mycobacterium tuberculosis. J Gen Microbiol 63:41-48
    • (1970) J Gen Microbiol , vol.63 , pp. 41-48
    • Winder, F.G.1    Collins, P.B.2
  • 16
    • 33750111588 scopus 로고    scopus 로고
    • Pyrrolidine carboxamides as a novel class of inhibitors of enoyl acyl carrier protein reductase from Mycobacterium tuberculosis
    • 10.1021/jm060461g
    • Xin H, Akram A, Robert S, Paul ROM (2006) Pyrrolidine carboxamides as a novel class of inhibitors of enoyl acyl carrier protein reductase from Mycobacterium tuberculosis. J Med Chem 49:6308-6323
    • (2006) J Med Chem , vol.49 , pp. 6308-6323
    • Xin, H.1    Akram, A.2    Robert, S.3    Paul, R.O.M.4


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.