How to cite this paper
El-Sayed, M., Mahmoud, K & Hilgeroth, A. (2014). Glacial acetic acid as an efficient catalyst for simple synthesis of dindolylmethanes.Current Chemistry Letters, 3(1), 7-14.
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1. (a) Morteza S, Mohammad Z., Hendrik G., Zahra T. (2010) Bis- and trisindolylmethanes (BIMs and TIMs), Chem Rev. 110(4), 2250-2293. (b) Maciejewska, D.; Szpakowska, I.; Wolska, I.; Niemyjska, M.;Mascini, M.; Maj-Zurawska, M. (2006) DNA-based electrochemical biosensors for monitoring of bis-indoles as potential antitumoral agents, chemistry, X-ray crystallography, Bio electrochemistry, 69,1-9.
2. Maciejewska, D.; Niemyjska, M.; Wolska, I.; Waostowski, M.;Rasztawicka, M. (2004) Synthesis, Spectroscopic Studies and Crystal Structure of 5,5’-Dimethoxy-3,3’-methanediyl-bis-indole as the Inhibitor of Cell Proliferation of Human Tumors, Z. Naturforsch., B: Chem. Sci.59, 1137-1142.
3. Maciejewska, D.; Wolska, I.; Niemyjska, M.; Zero, P. (2005) Structure in solid state of 3,30-diindolylmethane derivatives, potent cytotoxic agents against human tumor cells, followed X-ray diffraction and 13C CP/MAS NMR analyses, J. Mol. Struct. 753, 53-60.
4. Mason, M. R.; Fneich, B. N.; Kirschbaum, K. (2003) Titanium and Zirconium Amido Complexes Ligated by 2,2 & apos; -Di(3-methylindolyl)methanes: Synthesis, Characterization, and Ethylene Polymerization Activity. Inorg. Chem. 42, 6592-6594.
5. Mason, M. R. (2003) Di- and Triindolylmethanes: Versatile Ligands for Main Group and Transition Elements, Chemtracts, 16, 272-289.
6. Barnard, T. S.; Mason, M. R. (2001) Hindered Axial-Equatorial Carbonyl Exchange in an Fe(CO)4(PR3) Complex of a Rigid Bicyclic Phosphine, Inorg. Chem. 40, 5001-5009.
7. Barnard, T. S.; Mason, M. R. (2001) Synthesis, Structure and Coordination Chemistry of the Bicyclic p-Acid Phosphatri(3-methylindolyl)methane, Organometallics, 20, 206-214.
8. Tanski, J. M.; Parkin, G. (2003) Tantalum Amido and Imido Complexes Supported by Tris[(2-indolyl)methyl]amine, a Tetradentate Trianionic Ligand with Reduced ?-Donor Character, Inorg. Chem. 42, 264-266.
9. Black, D. S. (1993) New Dimensions in Indole Chemistry from Ligand Design to Natural Products Synlett 246-252.
10. Raju, B. C.; Rao, J. M.,(2008) An Easy and Efficient Synthesis of Bisindolylmethanes and Tetraindolylmethane Tr?ger’s Base Catatlyzed by AgBF4, Indian J. Chem. 47B, 899-905.
11. Sujatha, K.; Perumal, P. T.; Muralidharan, D.; Rajendran, M. (2009) Synthesis and Biological Evaluation of some novel Heterocyclic Derivatives of Paraacetamole as Potential Analgesic and Antipyretic Agents, Indian J. Chem. 48B, 267-269.
12. Nagarajan, R.; Perumal, P. T. (2004) Expedient Synthesis of Bis-indolylmethanes, Chem. Lett. 33, 150-159.
13. Chakrabarty, M.; Mukherjee, R.; Mukherji, A.; Arima, S.; Harigaya, Y. (2006) Phosphoric Acid-on-Silica Gel: A Green Catalyst for the Synthesis of Symmetrical Bis(indolyl)alkanes, Heterocycle 68, 1659-1668.
14. Yu, L.; Chen, D.; Li, J.; Wang, P. G.(1997) Preparation, Characterization, and Synthetic Uses of Lanthanide(III) Catalysts Supported on Ion Exchange Resins, J. Org. Chem. 62, 3575-3581.
15. Karthik, M.; Tripathi, A. K.; Gupta, N. M.; Palanichamy, M.; Murugesan, V. (2004) A highly efficient, eco-friendly, room temperature synthesis of bis(indol-3-yl)methanes using the mesoporous titanosilicate Ti-TUD-1: electrophilic substitution reactions of indoles Part XXIII Catal. Commun. 5, 209-216.
16. Penieres-Carrillo, G.; Garc?´a-Estrada, J. G.; Gutie´rrez-Ram?´reza, J. L.; Alvarez-Toledanob, C. (2003) Infrared-assisted eco-friendly selective synthesis of diindolylmethanes Green Chem.5, 337-339.
17. Maiti, A. K.; Bhattacharyya, P. (1997) Montmorillonite Clay-catalysed Synthesis of Bis(indol-3-yl)-methanes and 1,2-Bis(indol-3-yl)ethanes J. Chem. Res. 424-425.
18. Banerji, J.; Dutta, U.; Basak, B.; Saha, M.; Budzikiewicz, H.; Chatterjee, A.(2001) A facile Ph3P/CO2 mediated, one-pot synthesis of 2-oxazolidinones from 1,2-azido alcohols via phosphazene and isocyanate intermediates Indian J. Chem. 40B, 978-984.
19. Ramesh, C.; Ravindranath, N.; Das, B. (1999) Coordination Networks with 1,3-Bis(4-pyridyl)propane. A Flexible Ligand Exhibiting Supramolecular Isomerism J. Chem. Res. (S) 72. DOI: 10.1039/a805819i
20. Nagawade, R. R.; Shinde, D. B., (2005) PCL5 as A Mild and Efficient Catalyst for the Synthesis of Bisindolylmethanes and Di-bisindolylmethanes Bull. Korean Chem. Soc. 26, 453-458.
21. Bandgar, B. P.; Shaikh, K. A.(2004) SnCl2.2H2O; a precious addition to catalyst range for synthesis of bis(indolyl)methanes J. Chem. Res. 34, 730-736.
22. Mohammadpoor-Baltork, I.; Memarian, H. R.; Khosropour, A. R.; Nikoofar, K. (2006) BiOClO4.xH2O and Bi(OTf)3 as Efficient and Environmentally Benign Catalysts for Synthesis of Bis(indolyl)methanes in Solution and Under Ultrasound Irradiation Lett. Org. Chem.3, 768-772.
23. Thirupathi Reddy, Y.; Narsimha Reddy, P.; Sunil Kumar, B.; Rajitha, B. (2005) Efficient synthesis of bisindolylmethanes catalyzed by TiCl4 Indian, J. Chem. 44B, 2393-2395.
24. Kamal, A.; Khan, M. N. A.; Reddy, K. S.; Srikanth, Y. V. V.; Ahmed, S. K.; Kumar, K. P.; Murthy, U. S. N. (2009) An efficient synthesis of bis(indolyl)methanes and evaluation of their antimicrobial activities J. Enzyme Inhib. Med. Chem 24, 559-565.
25. Kruber (1941) Isolated from Isolierung aus Steinkohlenteer Chem. Ber 74, 1688 - 1692.
26. (a): Segall, A.; Pappa, H.; Pizzorno, M. T.; Radice, M.; Amoroso, A.; Gutkind, G. O. (1996) antimicrobial activity of 5,6-Dihydrobenzo-[A]-carbazoles .2. Farmaco Ed. Sci. 51, 513 - 516. (b): Pappa, H.; Segall, A.; Pizzorno, M. T.; Radice, M.; Amoroso, A.; Gutkind, G. O. (1994) Antimicrobial Activity of 5,6-Dihydrobenzo-[A]-carbaoles Farmaco Ed. Sci.49, 333 - 336.
27. Amoroso, A.; Radice, M.; Segall, A.; Rodero, L.; Hochenfellner, F.; Pizzorno, M. T.; Moretton, J.; Garrido, D.;Gutkind, G. (2000) Antitumoral activity of trisubstituted dihydrobenzo(a)carbazoles Pharmazie 55, 151 - 152.
28. Segall, A.; Pizzorno, M. T. (2000) Antitumoral activity of trisubstituted dihydrobenzo(a)carbazoles. Part III Pharmazie 55, 766 - 767.
29. Golob, T.; Biberger, C.; Walter, G.; Angerer, E. (2000) Antiestrogenic activities of 3,8-dihydroxy-6,11-dihydrobenzo[a]carbazoles with sulfur-containing side chains Arch.Pharm. 2000, 333, 305 - 311.
30. Frederich, M.; Jacquier, M.-J.; Thepenier, P.; Mol, P. D.; Tits, M.; Philippe, G.; Delaude, C.; Angenot, L.; Zeches-Hanrot, M. (2002) Antiamoebic and antiplasmodial activities of alkaloids ... alkaloids from Strychnos icaja. J. Nat. Prod. 65, 1381 - 1386.
31. Fertuck, K. C.; Kumar, S.; Sikka, H. C.; Matthews, J. B.;Zacharewski, T. R., (2001) Interaction of PAH-related compounds with the isoforms of the estrogen receptor, Toxicol. Lett. 121, 167 - 178.
32. Brown, D. W.; Graupner, P. R.; Sainsbury, M.; Shertzer, H.G. (1991) New Antioxidants Incorporating Indole and indoline Chromophores Tetrahedron 1991, 47, 4383 - 4408.
33. Butera, J. A.; Antane, S. A.; Hirth, B.; Lennox, J. R.; Sheldon, J. H.; Norton, N. W.; Warga, D.; Argentieri, T. M.; (2001) Indazolylamino quinazolines and pyridopyrimidines as inhibitors of the EGFr and C-erbB-2 Bioorg. Med. Chem. Lett. 11, 2093 - 2098.
34. Cerri, R.; Boatto, G.; Pau, A.; Sparatore, F.; Cima, L. (1991) Synthesis and Cytotoxicity Studies of Cyclohepta[b]indoles, Benzo[6,7]cyclohepta[1,2-b]indoles, Indeno[1,2-b]indoles, and Benzo[a]carbazoles Farmaco Ed. Sci. 46, 369 - 378.
35. Cerri, R.; Boatto, G.; Pau, A.; Sparatore, F.; Manca, P. (1988) Synthesis, antimicrobial and antioxidant activities of some indole analogues containing naphthyridine and pyrimidonaphthyridine systems Farmaco Ed. Sci.43, 113 - 124.
36. Kuehm-Caubere, C.; Caubere, P.; Jamart-Gregoire, B.; Pfeiffer,B.; Guardiola-Lemaitre, B. (1999) Synthesis and reactivity of styrylchromonesEur. J. Med. Chem. Chim. Ther.34, 51 - 62.
37. Joseph, B.; Chapellier, V.; Merour, J.-Y.; Leonce, S. (1998) Synthesis, Cytotoxicity, DNA Interaction and Topoisomerase II Inhibition Properties of Etrahydropyrrole[3,4-a]carbazole-1,3-dione and Tetrahydropyrido[3,2-b]pyrrole[3,4-g]indole-1,3-dione Heterocycles 48, 1423 -1430.
38. Joseph, B.; Alagille, D.; Merour, J.-Y.; Leonce, S. (2000) 2-Chloro-7,8,9,10-tetrahydrocyclohepta[b]indol-6(5H)-one, Chem.Pharm. Bull. 2000, 48, 1872 - 1876.
39. Bor-Cherng H., Yea-Fen J., Yi-Ling C. and Shiow L., (2006) Synthesis and Cytotoxicity Studies of Cyclohepta[b]indoles,Benzo[6,7]cyclohepta[1,2-b]indoles, Indeno[1,2-b]indoles, and Benzo[a]carbazoles, J.Chin. Chem. Soc. 53, No. 3, 647–662.
2. Maciejewska, D.; Niemyjska, M.; Wolska, I.; Waostowski, M.;Rasztawicka, M. (2004) Synthesis, Spectroscopic Studies and Crystal Structure of 5,5’-Dimethoxy-3,3’-methanediyl-bis-indole as the Inhibitor of Cell Proliferation of Human Tumors, Z. Naturforsch., B: Chem. Sci.59, 1137-1142.
3. Maciejewska, D.; Wolska, I.; Niemyjska, M.; Zero, P. (2005) Structure in solid state of 3,30-diindolylmethane derivatives, potent cytotoxic agents against human tumor cells, followed X-ray diffraction and 13C CP/MAS NMR analyses, J. Mol. Struct. 753, 53-60.
4. Mason, M. R.; Fneich, B. N.; Kirschbaum, K. (2003) Titanium and Zirconium Amido Complexes Ligated by 2,2 & apos; -Di(3-methylindolyl)methanes: Synthesis, Characterization, and Ethylene Polymerization Activity. Inorg. Chem. 42, 6592-6594.
5. Mason, M. R. (2003) Di- and Triindolylmethanes: Versatile Ligands for Main Group and Transition Elements, Chemtracts, 16, 272-289.
6. Barnard, T. S.; Mason, M. R. (2001) Hindered Axial-Equatorial Carbonyl Exchange in an Fe(CO)4(PR3) Complex of a Rigid Bicyclic Phosphine, Inorg. Chem. 40, 5001-5009.
7. Barnard, T. S.; Mason, M. R. (2001) Synthesis, Structure and Coordination Chemistry of the Bicyclic p-Acid Phosphatri(3-methylindolyl)methane, Organometallics, 20, 206-214.
8. Tanski, J. M.; Parkin, G. (2003) Tantalum Amido and Imido Complexes Supported by Tris[(2-indolyl)methyl]amine, a Tetradentate Trianionic Ligand with Reduced ?-Donor Character, Inorg. Chem. 42, 264-266.
9. Black, D. S. (1993) New Dimensions in Indole Chemistry from Ligand Design to Natural Products Synlett 246-252.
10. Raju, B. C.; Rao, J. M.,(2008) An Easy and Efficient Synthesis of Bisindolylmethanes and Tetraindolylmethane Tr?ger’s Base Catatlyzed by AgBF4, Indian J. Chem. 47B, 899-905.
11. Sujatha, K.; Perumal, P. T.; Muralidharan, D.; Rajendran, M. (2009) Synthesis and Biological Evaluation of some novel Heterocyclic Derivatives of Paraacetamole as Potential Analgesic and Antipyretic Agents, Indian J. Chem. 48B, 267-269.
12. Nagarajan, R.; Perumal, P. T. (2004) Expedient Synthesis of Bis-indolylmethanes, Chem. Lett. 33, 150-159.
13. Chakrabarty, M.; Mukherjee, R.; Mukherji, A.; Arima, S.; Harigaya, Y. (2006) Phosphoric Acid-on-Silica Gel: A Green Catalyst for the Synthesis of Symmetrical Bis(indolyl)alkanes, Heterocycle 68, 1659-1668.
14. Yu, L.; Chen, D.; Li, J.; Wang, P. G.(1997) Preparation, Characterization, and Synthetic Uses of Lanthanide(III) Catalysts Supported on Ion Exchange Resins, J. Org. Chem. 62, 3575-3581.
15. Karthik, M.; Tripathi, A. K.; Gupta, N. M.; Palanichamy, M.; Murugesan, V. (2004) A highly efficient, eco-friendly, room temperature synthesis of bis(indol-3-yl)methanes using the mesoporous titanosilicate Ti-TUD-1: electrophilic substitution reactions of indoles Part XXIII Catal. Commun. 5, 209-216.
16. Penieres-Carrillo, G.; Garc?´a-Estrada, J. G.; Gutie´rrez-Ram?´reza, J. L.; Alvarez-Toledanob, C. (2003) Infrared-assisted eco-friendly selective synthesis of diindolylmethanes Green Chem.5, 337-339.
17. Maiti, A. K.; Bhattacharyya, P. (1997) Montmorillonite Clay-catalysed Synthesis of Bis(indol-3-yl)-methanes and 1,2-Bis(indol-3-yl)ethanes J. Chem. Res. 424-425.
18. Banerji, J.; Dutta, U.; Basak, B.; Saha, M.; Budzikiewicz, H.; Chatterjee, A.(2001) A facile Ph3P/CO2 mediated, one-pot synthesis of 2-oxazolidinones from 1,2-azido alcohols via phosphazene and isocyanate intermediates Indian J. Chem. 40B, 978-984.
19. Ramesh, C.; Ravindranath, N.; Das, B. (1999) Coordination Networks with 1,3-Bis(4-pyridyl)propane. A Flexible Ligand Exhibiting Supramolecular Isomerism J. Chem. Res. (S) 72. DOI: 10.1039/a805819i
20. Nagawade, R. R.; Shinde, D. B., (2005) PCL5 as A Mild and Efficient Catalyst for the Synthesis of Bisindolylmethanes and Di-bisindolylmethanes Bull. Korean Chem. Soc. 26, 453-458.
21. Bandgar, B. P.; Shaikh, K. A.(2004) SnCl2.2H2O; a precious addition to catalyst range for synthesis of bis(indolyl)methanes J. Chem. Res. 34, 730-736.
22. Mohammadpoor-Baltork, I.; Memarian, H. R.; Khosropour, A. R.; Nikoofar, K. (2006) BiOClO4.xH2O and Bi(OTf)3 as Efficient and Environmentally Benign Catalysts for Synthesis of Bis(indolyl)methanes in Solution and Under Ultrasound Irradiation Lett. Org. Chem.3, 768-772.
23. Thirupathi Reddy, Y.; Narsimha Reddy, P.; Sunil Kumar, B.; Rajitha, B. (2005) Efficient synthesis of bisindolylmethanes catalyzed by TiCl4 Indian, J. Chem. 44B, 2393-2395.
24. Kamal, A.; Khan, M. N. A.; Reddy, K. S.; Srikanth, Y. V. V.; Ahmed, S. K.; Kumar, K. P.; Murthy, U. S. N. (2009) An efficient synthesis of bis(indolyl)methanes and evaluation of their antimicrobial activities J. Enzyme Inhib. Med. Chem 24, 559-565.
25. Kruber (1941) Isolated from Isolierung aus Steinkohlenteer Chem. Ber 74, 1688 - 1692.
26. (a): Segall, A.; Pappa, H.; Pizzorno, M. T.; Radice, M.; Amoroso, A.; Gutkind, G. O. (1996) antimicrobial activity of 5,6-Dihydrobenzo-[A]-carbazoles .2. Farmaco Ed. Sci. 51, 513 - 516. (b): Pappa, H.; Segall, A.; Pizzorno, M. T.; Radice, M.; Amoroso, A.; Gutkind, G. O. (1994) Antimicrobial Activity of 5,6-Dihydrobenzo-[A]-carbaoles Farmaco Ed. Sci.49, 333 - 336.
27. Amoroso, A.; Radice, M.; Segall, A.; Rodero, L.; Hochenfellner, F.; Pizzorno, M. T.; Moretton, J.; Garrido, D.;Gutkind, G. (2000) Antitumoral activity of trisubstituted dihydrobenzo(a)carbazoles Pharmazie 55, 151 - 152.
28. Segall, A.; Pizzorno, M. T. (2000) Antitumoral activity of trisubstituted dihydrobenzo(a)carbazoles. Part III Pharmazie 55, 766 - 767.
29. Golob, T.; Biberger, C.; Walter, G.; Angerer, E. (2000) Antiestrogenic activities of 3,8-dihydroxy-6,11-dihydrobenzo[a]carbazoles with sulfur-containing side chains Arch.Pharm. 2000, 333, 305 - 311.
30. Frederich, M.; Jacquier, M.-J.; Thepenier, P.; Mol, P. D.; Tits, M.; Philippe, G.; Delaude, C.; Angenot, L.; Zeches-Hanrot, M. (2002) Antiamoebic and antiplasmodial activities of alkaloids ... alkaloids from Strychnos icaja. J. Nat. Prod. 65, 1381 - 1386.
31. Fertuck, K. C.; Kumar, S.; Sikka, H. C.; Matthews, J. B.;Zacharewski, T. R., (2001) Interaction of PAH-related compounds with the isoforms of the estrogen receptor, Toxicol. Lett. 121, 167 - 178.
32. Brown, D. W.; Graupner, P. R.; Sainsbury, M.; Shertzer, H.G. (1991) New Antioxidants Incorporating Indole and indoline Chromophores Tetrahedron 1991, 47, 4383 - 4408.
33. Butera, J. A.; Antane, S. A.; Hirth, B.; Lennox, J. R.; Sheldon, J. H.; Norton, N. W.; Warga, D.; Argentieri, T. M.; (2001) Indazolylamino quinazolines and pyridopyrimidines as inhibitors of the EGFr and C-erbB-2 Bioorg. Med. Chem. Lett. 11, 2093 - 2098.
34. Cerri, R.; Boatto, G.; Pau, A.; Sparatore, F.; Cima, L. (1991) Synthesis and Cytotoxicity Studies of Cyclohepta[b]indoles, Benzo[6,7]cyclohepta[1,2-b]indoles, Indeno[1,2-b]indoles, and Benzo[a]carbazoles Farmaco Ed. Sci. 46, 369 - 378.
35. Cerri, R.; Boatto, G.; Pau, A.; Sparatore, F.; Manca, P. (1988) Synthesis, antimicrobial and antioxidant activities of some indole analogues containing naphthyridine and pyrimidonaphthyridine systems Farmaco Ed. Sci.43, 113 - 124.
36. Kuehm-Caubere, C.; Caubere, P.; Jamart-Gregoire, B.; Pfeiffer,B.; Guardiola-Lemaitre, B. (1999) Synthesis and reactivity of styrylchromonesEur. J. Med. Chem. Chim. Ther.34, 51 - 62.
37. Joseph, B.; Chapellier, V.; Merour, J.-Y.; Leonce, S. (1998) Synthesis, Cytotoxicity, DNA Interaction and Topoisomerase II Inhibition Properties of Etrahydropyrrole[3,4-a]carbazole-1,3-dione and Tetrahydropyrido[3,2-b]pyrrole[3,4-g]indole-1,3-dione Heterocycles 48, 1423 -1430.
38. Joseph, B.; Alagille, D.; Merour, J.-Y.; Leonce, S. (2000) 2-Chloro-7,8,9,10-tetrahydrocyclohepta[b]indol-6(5H)-one, Chem.Pharm. Bull. 2000, 48, 1872 - 1876.
39. Bor-Cherng H., Yea-Fen J., Yi-Ling C. and Shiow L., (2006) Synthesis and Cytotoxicity Studies of Cyclohepta[b]indoles,Benzo[6,7]cyclohepta[1,2-b]indoles, Indeno[1,2-b]indoles, and Benzo[a]carbazoles, J.Chin. Chem. Soc. 53, No. 3, 647–662.