Venting-while-heating microwave-assisted synthesis of 3-arylthioindoles

ACS Combinatorial Science

Volumn 14, Issue 4, 2012, Pages 258-262

  La Regina, Giuseppe ^a   Gatti, Valerio ^a   Famiglini, Valeria ^a   Piscitelli, Francesco ^a   Silvestri, Romano ^a  

^a SAPIENZA UNIVERSITY OF ROME   (Italy)

Author keywords

3 arylthioindoles; dielectric heating, venting while heating; indole; microwave assisted organic synthesis; sulfenylation

Indexed keywords

INDOLE DERIVATIVE; THIOL DERIVATIVE;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; COMBINATORIAL CHEMISTRY; HEAT; MICROWAVE RADIATION; MOLECULAR LIBRARY; STEREOISOMERISM; SYNTHESIS;

COMBINATORIAL CHEMISTRY TECHNIQUES; HOT TEMPERATURE; INDOLES; MICROWAVES; MOLECULAR STRUCTURE; SMALL MOLECULE LIBRARIES; STEREOISOMERISM; SULFHYDRYL COMPOUNDS;

EID: 84859727783     PISSN: 21568952     EISSN: None     Source Type: Journal    
DOI: 10.1021/co200165j     Document Type: Article

References (33)

1. Sprouse, J. S.; Soeby, K. K.; Anderson, N. [2-(6-Fluoro-1 H -indol-3-ylsulfanyl)benzyl]methyl amine for the treatment of affective disorders. PCT Int. Appl. WO 2009112541 A2, September 17, 2009.
2. Zhou, N.; Zeller, W.; Krohn, M.; Anderson, H.; Zhang, J.; Onua, E.; Kiselyov, A. S.; Ramirez, J.; Halldorsdottir, G.; Andresson, T.; Gurney, M. E.; Singh, J. 3,4-Disubstituted indole acylsulfonamides: A novel series of potent and selective human EP3 receptor antagonists Bioorg. Med. Chem. Lett. 2009, 19, 123-126
3. Ainge, D.; Butters, M.; Merifield, E.; Ramakrishnan, R.; Rayapati, R. N.; Sharma, P. R.; Thomson, C. Intermediates and processes for the preparation of 4-(acetylamino)-3-[(4-chlorophenyl)thio]-2-methyl-1 H -indole-1-acetic Acid. PCT Int. Appl. WO 2011004182 A1, January 13, 2011.
4. De Martino, G.; La Regina, G.; Coluccia, A.; Edler, M. C.; Barbera, M. C.; Brancale, A.; Wilcox, E.; Hamel, E.; Artico, M.; Silvestri, R. Arylthioindoles, Potent Inhibitors of Tubulin Polymerization J. Med. Chem. 2004, 47, 6120-6123 (Pubitemid 39599903)
5. Hamel, E.; Silvestri, R.; Brancale, A. Arylthioindole tubulin polymerization inhibitors and their preparation, pharmaceutical compositions, and methods of treating or preventing cancer using them. PCT Int. Appl. WO 2006041961 A1, April 20, 2006.
6. De Martino, G.; Edler, M. C.; La Regina, G.; Coluccia, A.; Barbera, M. C.; Barrow, D.; Nicholson, R. I.; Chiosis, G.; Brancale, A.; Hamel, E.; Artico, M.; Silvestri, R. New Arythioindoles, Potent Inhibitors of Tubulin Polymerization. 2. Structure Activity Relationship and Molecular Modeling Studies J. Med. Chem. 2006, 49, 947-954 (Pubitemid 43221643)
7. La Regina, G.; Edler, M. C.; Brancale, A.; Kandil, S.; Coluccia, A.; Piscitelli, F.; Hamel, E.; De Martino, G.; Matesanz, R.; Díaz, J. F.; Scovassi, A. I.; Ennio, P.; Lavecchia, A.; Novellino, E.; Artico, M.; Silvestri, R. New Arylthioindoles Inhibitors of Tubulin Polymerization. 3. Biological Evaluation, Structure-Activity Relationships and Molecular Modeling Studies J. Med. Chem. 2007, 50, 2865-2874 (Pubitemid 46980857)
8. La Regina, G.; Sarkar, T.; Bai, R.; Edler, M. C.; Saletti, R.; Coluccia, A.; Piscitelli, F.; Minelli, L.; Gatti, V.; Mazzoccoli, C.; Palermo, V.; Mazzoni, C.; Falcone, C.; Scovassi, A. I.; Giansanti, V.; Campiglia, P.; Porta, A.; Maresca, B.; Hamel, E.; Brancale, A.; Novellino, E.; Silvestri, R. New Arylthioindoles and Related Bioisosteres at the Sulfur Bridging Group. 4. Synthesis, Tubulin Polymerization, Cell Growth Inhibition, and Molecular Modeling Studies J. Med. Chem. 2009, 52, 7512-7527
9. Giansanti, V.; Piscitelli, P.; Camboni, T.; Prosperi, E.; La Regina, G.; Parks, M.; Silvestri, R.; Scovassi, A. I. Arylthioindoles: Promising compounds against cancer cell proliferation Oncology Lett. 2010, 1, 109-112
10. Atkinson, J. G.; Hamel, P.; Girard, Y. A New Synthesis of 3-Arylthioindoles Synthesis 1988, 6, 480-481
11. Fang, X.-L.; Tang, R.-Y.; Zhong, P.; Li, J.-H. Iron-catalyzed Sulfenylation of Indoles with Disulfides Promoted by a Catalytic Amount of Iodine Synthesis 2009, 24, 4183-4189
12. Shirani, H.; Janosik, T. Synthesis of 3-(Arylthio)indoles and Related Compounds by Reactions of Metalated Aromatics or Heterocycles with Protected 3,3′-Dithiobisindoles Synthesis 2007, 17, 2690-2698 (Pubitemid 47414262)
13. Matsugi, M.; Murata, K.; Gotanda, K.; Nambu, H.; Anilkumar, G.; Matsumoto, K.; Kita, Y. Facile and Efficient Sulfenylation Method Using Quinone Mono- O, S -Acetals under Mild Conditions J. Org. Chem. 2001, 66, 2434-2441 (Pubitemid 32867439)
14. Matsugi, M.; Murata, K.; Nambu, H.; Kita, Y. An efficient sulfenylation of aromatics using highly active quinone mono O, S -acetal bearing a pentafluorophenylthio group Tetrahedron Lett. 2001, 42, 1077-1080 (Pubitemid 32149848)
15. 1H Nuclear Magnetic Resonance Spectra of 3-(Arylthio)indoles J. Org. Chem. 1980, 45, 1688-1691
16. Gilow, H. M.; Brown, C. S.; Copeland, J. N.; Kelly, K. E. Sulfenylation of Some Pyrroles and Indoles J. Heterocycl. Chem. 1991, 28, 1025-1034
17. Silvestri, R.; De Martino, G.; La Regina, G.; Artico, M.; Massa, S.; Vargiu, L.; Mura, M.; Loi, A. G.; Marceddu, T.; La Colla, P. Novel Indolyl Aryl Sulfones Active against HIV-1 Carrying NNRTI Resistance Mutations: Synthesis and SAR Studies J. Med. Chem. 2003, 46, 2482-2493 (Pubitemid 36637932)
18. Tudge, M.; Tamiya, M.; Savarin, C.; Humphrey, G. R. Development of a Novel, Highly Efficient Halide-Catalyzed Sulfenylation of Indoles Org. Lett. 2006, 8, 565-568 (Pubitemid 43341961)
19. 3 as a catalyst for the synthesis of 3-sulfenyl indoles Tetrahedron Lett. 2010, 51, 2014-2016
20. Schlosser, K. M.; Krasutsky, A. P.; Hamilton, H. W.; Reed, J. E.; Sexton, K. A Highly Efficient Procedure for 3-Sulfenylation of Indole-2-Carboxylates Org. Lett. 2004, 6, 819-821 (Pubitemid 38387983)
21. Hamilton, H. W.; Krasutsky, A. P.; Reed, J. E.; Schlosser, K. M. 3-Sulfenylation of Indole-2-Carboxylates. U.S. Patent US 20040133014 A1, July 8, 2004.
22. Maeda, Y.; Koyabu, M.; Nishimura, T.; Uemura, S. Vanadium-Catalyzed Sulfenylation of Indoles and 2-Naphthols with Thiols under Molecular Oxygen J. Org. Chem. 2004, 69, 7688-7693 (Pubitemid 39403356)
23. Yadav, J. S.; Reddy, B. V. S.; Reddy, Y. J. A rapid synthesis of 3-sulfenyl indoles using Selectfluor Tetrahedron Lett. 2007, 48, 7034-7037 (Pubitemid 47331550)
24. Wu, G.; Wu, J.; Wu, J.; Wu, L. Oxone-Mediated Oxidative 3-Arylthio Substitution of Indoles Synth. Commun. 2008, 38, 1036-1043 (Pubitemid 351364145)
25. Yadav, J. S.; Reddy, B. V. S.; Reddy, Y. J.; Praneeth, K. Iron(III) Chloride: a Versatile Catalyst for the Practical Synthesis of 3-Sulfenylindoles Synthesis 2009, 9, 1520-1524
26. Guo, Y.-J.; Tang, R.-Y.; Li, J.-H.; Zhong, P.; Zhang, X.-G. Palladium-Catalyzed Annulation of 2-(1-Alkynyl)benzenamines with Disulfides: Synthesis of 3-Sulfenylindoles Adv. Synth. Catal. 2009, 351, 2615-2618
27. 4NI-Induced Electrophilic Cyclization Org. Lett. 2009, 11, 173-176
28. 4NI-Induced Electrophilic Cyclization J. Org. Chem. 2009, 74, 6802-6811
29. Bhattacharyya, B.; Panda, D.; Gupta, S.; Banerjee, M. Anti-Mitotic Activity of Colchicine and the Structural Basis for Its Interaction with Tubulin Med. Res. Rev. 2008, 28, 155-183 (Pubitemid 350274963)
30. La Regina, G.; Gatti, V.; Piscitelli, F.; Silvestri, R. Open Vessel and Cooling while Heating Microwave-Assisted Synthesis of Pyridinyl N -Aryl Hydrazones ACS Comb. Sci. 2011, 13, 2-6
31. CEM Corporation, U.S.A.; http://www.cem.com/page199.html (accessed January 08, 2012).
32. Hayes, B. L. Microwave Synthesis: Chemistry at the Speed of Light; CEM Publishing: Matthews, NC, 2002; pp 29-76.
33. Alam, A.; Takaguchi, Y.; Tsuboi, S. Simple, extremely fast, and high-yielding oxidation of thiols to disulfides Synth. Commun. 2005, 35, 1329-1333 (Pubitemid 40734318)