메뉴 건너뛰기




Volumn 24, Issue 2, 2009, Pages 559-565

An efficient synthesis of bis(indolyl)methanes and evaluation of their antimicrobial activities

Author keywords

Aluminium triflate; Antibacterial activity; Antifungal activity; Bis(indolyl)methanes

Indexed keywords

3,3' BISINDOLYL (4 METHOXYPHENYL)METHANE; 3,3' BISINDOLYL (4 NITROPHENYL)METHANE; 3,3' BISINDOLYL (5 NITROFURFURYL)METHANE; 3,3' BISINDOLYL (5 NITROTHIENYL)METHANE; 3,3' BISINDOLYLETHANE; 3,3' BISINDOLYLFURFURYLMETHANE; 3,3' BISINDOLYLPENTANE; 3,3' BISINDOLYLPHENYLMETHANE; 3,3' BISINDOLYLPROPANE; 3,3' BISINDOLYLTHIENYLMETHANE; ALUMINUM DERIVATIVE; ALUMINUM TRIFLATE; ANTIINFECTIVE AGENT; BIS(INDOLYL)METHANE DERIVATIVE; INDOLE DERIVATIVE; UNCLASSIFIED DRUG; DRUG DERIVATIVE; METHANE;

EID: 68049101302     PISSN: 14756366     EISSN: 14756374     Source Type: Journal    
DOI: 10.1080/14756360802292974     Document Type: Article
Times cited : (95)

References (43)
  • 1
    • 0025875228 scopus 로고
    • Nortopsentins A, B, C. Cytotoxic and antifungal imidazolediyl bis[indoles] from the sponge Spongosorites ruetzleri
    • Sakemi S, Sun HH. Nortopsentins A, B, and C. Cytotoxic and antifungal imidazolediyl bis[indoles] from the sponge Spongosorites ruetzleri. J Org Chem 1991;56: 4304-4307.
    • (1991) J Org Chem , vol.56 , pp. 4304-4307
    • Sakemi, S.1    Sun, H.H.2
  • 3
    • 0026669966 scopus 로고
    • A new bis- (indole) alkaloid from a deep-water marine sponge of the genus Spongosorites
    • Wright AE, Pomponi SA, Ctross SS, McCarthy PJ. A new bis- (indole) alkaloid from a deep-water marine sponge of the genus Spongosorites. J Org Chem 1992;57: 4772-4775.
    • (1992) J Org Chem , vol.57 , pp. 4772-4775
    • Wright, A.E.1    Pomponi, S.A.2    Ctross, S.S.3    McCarthy, P.J.4
  • 4
    • 0027948295 scopus 로고
    • Hamacanthins A and B, new antifungal bis indole alkaloids from the deepwater marine sponge, Hamacantha Sp
    • Gunasekera SP, McCarthy PJ, Kelly-Borges M. Hamacanthins A and B, new antifungal bis indole alkaloids from the deepwater marine sponge, Hamacantha Sp. J Nat Prod 1994;57: 1437-1441.
    • (1994) J Nat Prod , vol.57 , pp. 1437-1441
    • Gunasekera, S.P.1    McCarthy, P.J.2    Kelly-Borges, M.3
  • 5
    • 0029856385 scopus 로고    scopus 로고
    • From inactive nortopsentin D, a novel bis(indole) alkaloid isolated from the axinellid sponge Dragmacidon sp. from deep waters south of new caledonia, to a strongly cytotoxic derivative
    • Mancini I, Guella G, Pietra F, Debitus C, Waikedre J. From inactive nortopsentin D, a novel bis(indole) alkaloid isolated from the axinellid sponge Dragmacidon sp. from deep waters south of new caledonia, to a strongly cytotoxic derivative. Helv Chim Acta 1996;79: 2075-2082.
    • (1996) Helv Chim Acta , vol.79 , pp. 2075-2082
    • Mancini, I.1    Guella, G.2    Pietra, F.3    Debitus, C.4    Waikedre, J.5
  • 6
    • 0025998158 scopus 로고
    • 6-Bromotryptamine derivatives from the Gulf of California tunicate Didemnum candidum
    • Fahy E, Potts BCM, Faulkner DJ, Smith K. 6-Bromotryptamine derivatives from the Gulf of California tunicate Didemnum candidum. J Nat Prod 1991;54: 564-569.
    • (1991) J Nat Prod , vol.54 , pp. 564-569
    • Fahy, E.1    Potts, B.C.M.2    Faulkner, D.J.3    Smith, K.4
  • 7
    • 0028605225 scopus 로고
    • Vibrindole A, a metabolite of the marine bacterium, Vibrio parahaemolyticus, isolated from the toxic mucus of the boxfish Ostracion cubicus
    • Bell R, Carmeli S, Sar N. Vibrindole A, a metabolite of the marine bacterium, Vibrio parahaemolyticus, isolated from the toxic mucus of the boxfish Ostracion cubicus. J Nat Prod 1994; 57: 1587-1590.
    • (1994) J Nat Prod , vol.57 , pp. 1587-1590
    • Bell, R.1    Carmeli, S.2    Sar, N.3
  • 9
    • 0036007872 scopus 로고    scopus 로고
    • Marine natural products
    • Faulkner DJ.Marine natural products. Nat Prod Rep 2002;19: 1-49.
    • (2002) Nat Prod Rep , vol.19 , pp. 1-49
    • Faulkner, D.J.1
  • 12
    • 0032718416 scopus 로고    scopus 로고
    • Synthesis and antimicrobial activities of monoindolyl- and bisindolyloximes
    • Prudhomme M, Sancelme M, Bonnefoy A, Fabbro D, Meyer T. Synthesis and antimicrobial activities of monoindolyl- and bisindolyloximes. Eur J Med Chem 1999;34: 161-165.
    • (1999) Eur J Med Chem , vol.34 , pp. 161-165
    • Prudhomme, M.1    Sancelme, M.2    Bonnefoy, A.3    Fabbro, D.4    Meyer, T.5
  • 16
    • 0015838036 scopus 로고
    • Nitrofuryl heterocyclics. 3
    • Islip PJ, Johnson MR. Nitrofuryl heterocyclics. 3. J Med Chem 1973;16: 1308-1310.
    • (1973) J Med Chem , vol.16 , pp. 1308-1310
    • Islip, P.J.1    Johnson, M.R.2
  • 17
    • 0015946924 scopus 로고
    • Nitrofurfuryl heterocycles. 12. 4-Amino-6-(5-nitro-2-furyl)isoxazolo[5,4- d ]pyrimidines and 4-amino-2-(5-nitro-2-furyl) pyrimido[4,5-d ]pyrimidines
    • Burch HA, Benjamin LE, Russell HE, Freedman R. Nitrofurfuryl heterocycles. 12. 4-Amino-6-(5-nitro-2-furyl)isoxazolo[ 5,4-d ]pyrimidines and 4-amino-2-(5-nitro-2-furyl) pyrimido[4,5-d ]pyrimidines. J Med Chem 1974;17: 451-453.
    • (1974) J Med Chem , vol.17 , pp. 451-453
    • Burch, H.A.1    Benjamin, L.E.2    Russell, H.E.3    Freedman, R.4
  • 19
    • 34247581707 scopus 로고    scopus 로고
    • A new class of nifuroxazide analogues: Synthesis of 5-nitrothiophene derivatives with antimicrobial activity against multidrug-resistant Staphylococcus aureus
    • DOI 10.1016/j.bmc.2007.03.068, PII S0968089607002684
    • Masunari A, Tavares LC. A new class of nifuroxazide analogues: Synthesis of 5-nitrothiophene derivatives with antimicrobial activity against multidrug-resistant Staphylococcus aureus. Bioorg Med Chem 2007;15: 4229-4236. (Pubitemid 46678838)
    • (2007) Bioorganic and Medicinal Chemistry , vol.15 , Issue.12 , pp. 4229-4236
    • Masunari, A.1    Tavares, L.C.2
  • 20
    • 0141918781 scopus 로고    scopus 로고
    • Synthesis and in vitro antibacterial evaluation of N-[5-(5-nitro-2- thienyl)-1,3,4-thiadiazole-2-yl] piperazinyl quinolones
    • DOI 10.1016/S0223-5234(03)00148-X
    • Foroumadi A, Mansouri S, Kiani Z, Rahmani A. Synthesis and in vitro antibacterial evaluation of N-[5-(5-nitro-2-thienyl)- 1,3,4-thiadiazole-2-yl] piperazinyl quinolones. Eur J Med Chem 2003;38: 851-854. (Pubitemid 37244048)
    • (2003) European Journal of Medicinal Chemistry , vol.38 , Issue.9 , pp. 851-854
    • Foroumadi, A.1    Mansouri, S.2    Kiani, Z.3    Rahmani, A.4
  • 21
    • 0035950063 scopus 로고    scopus 로고
    • Investigation of 5-nitrofuran derivatives: Synthesis, antibacterial activity, and quantitative structure-activity relationships
    • Pires JR, Saito C, Gomes SL, Giesbrecht AM, Amaral AT. Investigation of 5-nitrofuran derivatives: Synthesis, antibacterial activity, and quantitative structure-activity relationships. JMed Chem 2001;44: 3673-3681.
    • (2001) JMed Chem , vol.44 , pp. 3673-3681
    • Pires, J.R.1    Saito, C.2    Gomes, S.L.3    Giesbrecht, A.M.4    Amaral, A.T.5
  • 22
    • 19444364335 scopus 로고    scopus 로고
    • Conformational analysis, electronic properties and molecular electrostatic potential of nitrofurans derivatives with antibacterial activity
    • Monasterios M, Escorche M, Avendano M. Conformational analysis, electronic properties and molecular electrostatic potential of nitrofurans derivatives with antibacterial activity. J Mol Structure 2005;748: 49-55.
    • (2005) J Mol Structure , vol.748 , pp. 49-55
    • Monasterios, M.1    Escorche, M.2    Avendano, M.3
  • 23
    • 0035664023 scopus 로고    scopus 로고
    • Studies on nitrophenylfuran derivatives: Part XII. Synthesis, characterization, antibacterial and antiviral activities of some nitrophenylfurfurylidene- 1,2,4-triazolo[3,4-b ]-1,3,4-thiadiazines
    • Holla BS, Akberali PM, Shivananda MK. Studies on nitrophenylfuran derivatives: Part XII. Synthesis, characterization, antibacterial and antiviral activities of some nitrophenylfurfurylidene- 1,2,4-triazolo[3,4-b ]-1,3,4-thiadiazines. II Farmaco 2001;56: 919-927.
    • (2001) II Farmaco , vol.56 , pp. 919-927
    • Holla, B.S.1    Akberali, P.M.2    Shivananda, M.K.3
  • 24
    • 0023892307 scopus 로고
    • The metabolic activation of nitroheterocyclic therapeutic agents
    • Kedderis GL, Miwa GT. The metabolic activation of nitroheterocyclic therapeutic agents. Drug Metab Rev 1988; 19: 33-62.
    • (1988) Drug Metab Rev , vol.19 , pp. 33-62
    • Kedderis, G.L.1    Miwa, G.T.2
  • 25
    • 0342954805 scopus 로고    scopus 로고
    • Studies on arylfuran derivatives: Part XI. Synthesis, characterisation and biological studies on some mannich bases carrying 2,4- dichlorophenylfurfural moiety
    • Holla BS, Rao BS, Shridhara K, Akberali PM. Studies on arylfuran derivatives: Part XI. Synthesis, characterisation and biological studies on some mannich bases carrying 2,4- dichlorophenylfurfural moiety. II Farmaco 2000;55: 338-344.
    • (2000) II Farmaco , vol.55 , pp. 338-344
    • Holla, B.S.1    Rao, B.S.2    Shridhara, K.3    Akberali, P.M.4
  • 26
    • 0033838079 scopus 로고    scopus 로고
    • Studies on arylfuran derivatives: Part X. Synthesis and antibacterial properties of arylfuryl-D2-pyrazolines
    • Holla BS, Akberali PM, Shivananda MK. Studies on arylfuran derivatives: Part X. Synthesis and antibacterial properties of arylfuryl-D2-pyrazolines. II Farmaco 2000;55: 256-263.
    • (2000) II Farmaco , vol.55 , pp. 256-263
    • Holla, B.S.1    Akberali, P.M.2    Shivananda, M.K.3
  • 27
    • 0035042642 scopus 로고    scopus 로고
    • Lithium perchlorate catalyzed reactions of indoles: An expeditious synthesis of bis(indolyl)methanes
    • Yadav JS, Reddy BVS, Murthy CVSR, Kumar GM, Madan Ch. Lithium perchlorate catalyzed reactions of indoles: An expeditious synthesis of bis(indolyl)methanes. Synthesis 2001;5: 783-787.
    • (2001) Synthesis , vol.5 , pp. 783-787
    • Yadav, J.S.1    Reddy, B.V.S.2    Cvsr, M.3    Kumar, G.M.4    Madan, Ch.5
  • 29
    • 0002062728 scopus 로고
    • Cyclizative condensation. I. 2- methylindole with acetone and methyl ethyl ketone
    • Roomi M, Macdonald S. Cyclizative condensation. I. 2- methylindole with acetone and methyl ethyl ketone. Can J Chem 1970;48: 139-143.
    • (1970) Can J Chem , vol.48 , pp. 139-143
    • Roomi, M.1    MacDonald, S.2
  • 30
    • 0026008696 scopus 로고
    • Photochemical synthesis of diindolylmethanes
    • Auria M. Photochemical synthesis of diindolylmethanes. Tetrahedron 1991;47: 9225-9230.
    • (1991) Tetrahedron , vol.47 , pp. 9225-9230
    • Auria, M.1
  • 32
    • 33947473792 scopus 로고
    • Cyclizative condensations. I. 2-Methylindole with acetone and methyl ethyl ketone
    • Noland WE, Venkiteswaran MR, Richards CG. Cyclizative condensations. I. 2-Methylindole with acetone and methyl ethyl ketone. J Org Chem 1961;26: 4241-4248.
    • (1961) J Org Chem , vol.26 , pp. 4241-4248
    • Noland, W.E.1    Venkiteswaran, M.R.2    Richards, C.G.3
  • 33
    • 0030600171 scopus 로고    scopus 로고
    • Lewis acid-catalyzed reactions in protic media. Lanthanide-catalyzed reactions of indoles with aldehydes or ketones
    • Chen DP, Yu LB, Wang PG. Lewis acid-catalyzed reactions in protic media. Lanthanide-catalyzed reactions of indoles with aldehydes or ketones. Tetrahedron Lett 1996;37: 4467-4470.
    • (1996) Tetrahedron Lett , vol.37 , pp. 4467-4470
    • Chen, D.P.1    Yu, L.B.2    Wang, P.G.3
  • 34
    • 0037016927 scopus 로고    scopus 로고
    • InCl3 and In(OTf)3 catalyzed reactions: Synthesis of 3-acetyl indoles, bisindolylmethane and indolylquinoline derivatives
    • Nagarajan R, Perumal PT. InCl3 and In(OTf)3 catalyzed reactions: Synthesis of 3-acetyl indoles, bisindolylmethane and indolylquinoline derivatives. Tetrahedron 2002;58: 1229-1232.
    • (2002) Tetrahedron , vol.58 , pp. 1229-1232
    • Nagarajan, R.1    Perumal, P.T.2
  • 35
    • 2342483570 scopus 로고    scopus 로고
    • Dy(OTf)3 in ionic liquid: An efficient catalytic system for reactions of indole with aldehydes/ketones or imines
    • Mi XL, Luo SZ, He JQ, Chen JP. Dy(OTf)3 in ionic liquid: An efficient catalytic system for reactions of indole with aldehydes/ketones or imines. Tetrahedron Lett 2004;45: 4567-4570.
    • (2004) Tetrahedron Lett , vol.45 , pp. 4567-4570
    • Mi, X.L.1    Luo, S.Z.2    He, J.Q.3    Chen, J.P.4
  • 36
    • 1042298780 scopus 로고    scopus 로고
    • Facile synthesis of bis(indolyl)methanes using catalytic amount of iodine at room temperature under solvent-free conditions
    • Ji SJ, Wang SY, Zhang Y, Loh TT. Facile synthesis of bis(indolyl)methanes using catalytic amount of iodine at room temperature under solvent-free conditions. Tetrahedron 2004; 60: 2051-2055.
    • (2004) Tetrahedron , vol.60 , pp. 2051-2055
    • Ji, S.J.1    Wang, S.Y.2    Zhang, Y.3    Loh, T.T.4
  • 37
    • 31444448205 scopus 로고    scopus 로고
    • An efficient and clean synthesis of bis(indolyl)methanes in a protic solvent at room temperature
    • Bhuyan JP, Deb ML. An efficient and clean synthesis of bis(indolyl)methanes in a protic solvent at room temperature. Tetrahedron Lett 2006;47: 1441-1443.
    • (2006) Tetrahedron Lett , vol.47 , pp. 1441-1443
    • Bhuyan, J.P.1    Deb, M.L.2
  • 38
    • 0023996553 scopus 로고
    • Friedel-Crafts chemistry. 11. Boron, aluminum, and gallium tris(trifluoromethanesulfonate) (triflate): Effective new Friedel-Crafts catalysts
    • Olah GA, Farooq O, Farnia SMF, Olah JA. Friedel-Crafts chemistry. 11. Boron, aluminum, and gallium tris(trifluoromethanesulfonate) (triflate): Effective new Friedel-Crafts catalysts. J Am Chem Soc 1988;110: 2560-2565.
    • (1988) J Am Chem Soc , vol.110 , pp. 2560-2565
    • Olah, G.A.1    Farooq, O.2    Farnia, S.M.F.3    Olah, J.A.4
  • 39
    • 34247582284 scopus 로고    scopus 로고
    • Al(OTf)3 as a highly efficient catalyst for the rapid acetylation of alcohols, phenols and thiophenols under solvent-free conditions
    • Kamal A, Khan MNA, Reddy KS, Srikanth YVV, Krishnaji T. Al(OTf)3 as a highly efficient catalyst for the rapid acetylation of alcohols, phenols and thiophenols under solvent-free conditions. Tetrahedron Lett 2007;48: 3813-3818.
    • (2007) Tetrahedron Lett , vol.48 , pp. 3813-3818
    • Kamal, A.1    Khan, M.N.A.2    Reddy, K.S.3    Srikanth, Y.V.V.4    Krishnaji, T.5
  • 40
    • 0037273188 scopus 로고    scopus 로고
    • Aluminium trifluromethanesulfonate [Al(OTf) 3] as a highly efficient and chemoselective catalyst for thioacetalization of carbonyl compounds under mild conditions
    • Firouzabadi H, Iranpoor N, Kohmareh G. Aluminium trifluromethanesulfonate [Al(OTf)3] as a highly efficient and chemoselective catalyst for thioacetalization of carbonyl compounds under mild conditions. Synth Commun 2003; 33: 167-173.
    • (2003) Synth Commun , vol.33 , pp. 167-173
    • Firouzabadi, H.1    Iranpoor, N.2    Kohmareh, G.3
  • 41
    • 26444553613 scopus 로고    scopus 로고
    • Aluminium triflate: A remarkable Lewis acid catalyst for the ring opening of epoxides by alcohols
    • Williams DBG, Lawton M. Aluminium triflate: A remarkable Lewis acid catalyst for the ring opening of epoxides by alcohols. Org Biomol Chem 2005;3: 3269-3272.
    • (2005) Org Biomol Chem , vol.3 , pp. 3269-3272
    • Williams, D.B.G.1    Lawton, M.2
  • 42
    • 33746820989 scopus 로고    scopus 로고
    • Aluminium triflate: An efficient recyclable Lewis acid catalyst for the aminolysis of epoxides
    • Williams DBG, Lawton M. Aluminium triflate: An efficient recyclable Lewis acid catalyst for the aminolysis of epoxides. Tetrahedron Lett 2006;47: 6557-6560.
    • (2006) Tetrahedron Lett , vol.47 , pp. 6557-6560
    • Williams, D.B.G.1    Lawton, M.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.