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Research Article

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

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Pages 559-565 | Received 05 Jun 2007, Accepted 28 Sep 2007, Published online: 01 Apr 2009

References

  • S Sakemi, and HH Sun. (1991). Nortopsentins A, B, and C. Cytotoxic and antifungal imidazolediyl bis[indoles] from the sponge Spongosorites ruetzleri. J Org Chem 56:4304–4307.
  • B Bao, Q Sun, X Yao, J Hong, CO Lee, CJ Sim, KS Im, and JH Jung. (2005). Cytotoxic bisindole alkaloids from a marine sponge Spongosorites sp. J Nat Prod 68:711–715.
  • AE Wright, SA Pomponi, SS Ctross, and PJ McCarthy. (1992). A new bis-(indole) alkaloid from a deep-water marine sponge of the genus Spongosorites. J Org Chem 57:4772–4775.
  • SP Gunasekera, PJ McCarthy, and M Kelly-Borges. (1994). Hamacanthins A and B, new antifungal bis indole alkaloids from the deep-water marine sponge, Hamacantha Sp. J Nat Prod 57:1437–1441.
  • I Mancini, G Guella, F Pietra, C Debitus, and J Waikedre. (1996). 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 79:2075–2082.
  • E Fahy, BCM Potts, DJ Faulkner, and K Smith. (1991). 6-Bromotryptamine derivatives from the Gulf of California tunicate Didemnum candidum. J Nat Prod 54:564–569.
  • R Bell, S Carmeli, and N Sar. (1994). Vibrindole A, a metabolite of the marine bacterium, Vibrio parahaemolyticus, isolated from the toxic mucus of the boxfish Ostracion cubicus. J Nat Prod 57:1587–1590.
  • TR Garbe, M Kobayashi, N Shimizu, N Takesue, M Ozawa, and H Yukawa. (2000). Indolyl carboxylic acids by condensation of indoles with α-keto acids. J Nat Prod 63:596–598.
  • DJ Faulkner. (2002). Marine natural products. Nat Prod Rep 19:1–49.
  • JCA Tanaka, CC da Silva, AJB de Oliveria, CV Nakamura, and BPD Filho. (2006). Antibacterial activity of indole alkaloids from Aspidosperma ramiflorum. Braz J Med Bio Res 39:387–391.
  • K-B Oh, W Mar, S Kim, J-Y Kim, T-H Lee, J-G Kim, D Shin, CJ Sim, and J Shin. (2006). Antimicrobial activity and cytotoxicity of bis(indole) alkaloids from the sponge Spongosorites sp. Biol Pharm Bull 29:570–573.
  • M Prudhomme, M Sancelme, A Bonnefoy, D Fabbro, and T Meyer. (1999). Synthesis and antimicrobial activities of monoindolyl- and bisindolyloximes. Eur J Med Chem 34:161–165.
  • RK Tiwari, D Singh, J Singh, V Yadav, AK Pathak, R Dabur, AK Chhillar, R Singh, GL Sharma, R Chandra, and AK Verma. (2006). Synthesis and antibacterial activity of substituted 1,2,3,4-tetrahydropyrazino[1,2-a]indoles. Bioorg Med Chem Lett 16:413–416.
  • E Szarvasi, L Fontaine, and A Betbeder-Matibet. (1973). Antimicrobials. New nitrofuran derivatives. J Med Chem 16:281–287.
  • W Hoyle, GP Roberts, and O Meth-Cohn. (1973). Potential antimicrobial furans. J Med Chem 16:709–710.
  • PJ Islip, and MR Johnson. (1973). Nitrofuryl heterocyclics. 3. J Med Chem 16:1308–1310.
  • HA Burch, LE Benjamin, HE Russell, and R Freedman. (1974). 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 17:451–453.
  • CY Wang, CW Chiu, K Muraoka, PD Michie, and GT Bryan. (1975). Antibacterial activity of nitropyrroles, nitrothiophenes, and aminothiophenes in vitro. Antimicrob Agents Chemother 8:216–219.
  • A Masunari, and LC Tavares. (2007). A new class of nifuroxazide analogues: Synthesis of 5-nitrothiophene derivatives with antimicrobial activity against multidrug-resistant Staphylococcus aureus. Bioorg Med Chem 15:4229–4236.
  • A Foroumadi, S Mansouri, Z Kiani, and A Rahmani. (2003). 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 38:851–854.
  • JR Pires, C Saito, SL Gomes, AM Giesbrecht, and AT Amaral. (2001). Investigation of 5-nitrofuran derivatives: Synthesis, antibacterial activity, and quantitative structure–activity relationships. J Med Chem 44:3673–3681.
  • M Monasterios, M Escorche, and M Avendano. (2005). Conformational analysis, electronic properties and molecular electrostatic potential of nitrofurans derivatives with antibacterial activity. J Mol Structure 748:49–55.
  • BS Holla, PM Akberali, and MK Shivananda. (2001). 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 56:919–927.
  • GL Kedderis, and GT Miwa. (1988). The metabolic activation of nitroheterocyclic therapeutic agents. Drug Metab Rev 19:33–62.
  • BS Holla, BS Rao, K Shridhara, and PM Akberali. (2000). Studies on arylfuran derivatives: Part XI. Synthesis, characterisation and biological studies on some mannich bases carrying 2,4-dichlorophenylfurfural moiety. II Farmaco 55:338–344.
  • BS Holla, PM Akberali, and MK Shivananda. (2000). Studies on arylfuran derivatives: Part X. Synthesis and antibacterial properties of arylfuryl-Δ2-pyrazolines. II Farmaco 55:256–263.
  • JS Yadav, BVS Reddy, CVSR Murthy, GM Kumar, and Ch Madan. (2001). Lithium perchlorate catalyzed reactions of indoles: An expeditious synthesis of bis(indolyl)methanes. Synthesis 5:783–787.
  • BV Gregorovich, K Liang, M Clugston, and S Macdonald. (1968). Reductive C-alkylation. Can J Chem 46:3291–3300.
  • M Roomi, and S Macdonald. (1970). Cyclizative condensation. I. 2-methylindole with acetone and methyl ethyl ketone. Can J Chem 48:139–143.
  • M Auria. (1991). Photochemical synthesis of diindolylmethanes. Tetrahedron 47:9225–9230.
  • A Chatterjee, S Manna, J Benerji, C Pascard, T Prange, and J Shoolery. (1980). Lewis-acid-induced electrophilic substitution in indoles with acetone. Part 2. J Chem Soc Perkin Trans 1:553–555.
  • WE Noland, MR Venkiteswaran, and CG Richards. (1961). Cyclizative condensations. I. 2-Methylindole with acetone and methyl ethyl ketone. J Org Chem 26:4241–4248.
  • DP Chen, LB Yu, and PG Wang. (1996). Lewis acid-catalyzed reactions in protic media. Lanthanide-catalyzed reactions of indoles with aldehydes or ketones. Tetrahedron Lett 37:4467–4470.
  • R Nagarajan, and PT Perumal. (2002). InCl3 and In(OTf)3 catalyzed reactions: Synthesis of 3-acetyl indoles, bis-indolylmethane and indolylquinoline derivatives. Tetrahedron 58:1229–1232.
  • XL Mi, SZ Luo, JQ He, and JP Chen. (2004). Dy(OTf)3 in ionic liquid: An efficient catalytic system for reactions of indole with aldehydes/ketones or imines. Tetrahedron Lett 45:4567–4570.
  • SJ Ji, SY Wang, Y Zhang, and TT Loh. (2004). Facile synthesis of bis(indolyl)methanes using catalytic amount of iodine at room temperature under solvent-free conditions. Tetrahedron 60:2051–2055.
  • JP Bhuyan, and ML Deb. (2006). An efficient and clean synthesis of bis(indolyl)methanes in a protic solvent at room temperature. Tetrahedron Lett 47:1441–1443.
  • GA Olah, O Farooq, SMF Farnia, and JA Olah. (1988). Friedel–Crafts chemistry. 11. Boron, aluminum, and gallium tris(trifluoromethanesulfonate) (triflate): Effective new Friedel–Crafts catalysts. J Am Chem Soc 110:2560–2565.
  • A Kamal, MNA Khan, KS Reddy, YVV Srikanth, and T Krishnaji. (2007). Al(OTf)3 as a highly efficient catalyst for the rapid acetylation of alcohols, phenols and thiophenols under solvent-free conditions. Tetrahedron Lett 48:3813–3818.
  • H Firouzabadi, N Iranpoor, and G Kohmareh. (2003). Aluminium trifluromethanesulfonate [Al(OTf)3] as a highly efficient and chemoselective catalyst for thioacetalization of carbonyl compounds under mild conditions. Synth Commun 33:167–173.
  • DBG Williams, and M Lawton. (2005). Aluminium triflate: A remarkable Lewis acid catalyst for the ring opening of epoxides by alcohols. Org Biomol Chem 3:3269–3272.
  • DBG Williams, and M Lawton. (2006). Aluminium triflate: An efficient recyclable Lewis acid catalyst for the aminolysis of epoxides. Tetrahedron Lett 47:6557–6560.
  • ME Linday. Practical introduction to microbiology. London: E & F.N. Spon Ltd; (1962). p 177.

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