“Anti-Michael” and Michael Additions in the Reactions of 2-Arylmethyliden-1,3-Indandiones with 2-Aminothiophenol
Departamento de Química Orgánica, Universidad Nacional Autónoma de México, Facultad de Química, Cd. Universitaria, Ciudad de México, México
,
Departamento de Química Orgánica, Universidad Nacional Autónoma de México, Facultad de Química, Cd. Universitaria, Ciudad de México, México
,
Departamento de Química Orgánica, Universidad Nacional Autónoma de México, Facultad de Química, Cd. Universitaria, Ciudad de México, México
,
Departamento de Química Orgánica, Universidad Nacional Autónoma de México, Facultad de Química, Cd. Universitaria, Ciudad de México, México
,
Instituto de Química, Universidad Nacional Autónoma de México, Facultad de Química, Cd. Universitaria, Ciudad de México, México
,
Departamento de Química Orgánica, Universidad Nacional Autónoma de México, Facultad de Química, Cd. Universitaria, Ciudad de México, México
1 Departamento de Química Orgánica, Universidad Nacional Autónoma de México, Facultad de Química, Cd. Universitaria, Ciudad de México, México
2 Departamento de Química Orgánica, Universidad Nacional Autónoma de México, Facultad de Química, Cd. Universitaria, Ciudad de México, México
3 Departamento de Química Orgánica, Universidad Nacional Autónoma de México, Facultad de Química, Cd. Universitaria, Ciudad de México, México
4 Departamento de Química Orgánica, Universidad Nacional Autónoma de México, Facultad de Química, Cd. Universitaria, Ciudad de México, México
5 Instituto de Química, Universidad Nacional Autónoma de México, Facultad de Química, Cd. Universitaria, Ciudad de México, México
6 Departamento de Química Orgánica, Universidad Nacional Autónoma de México, Facultad de Química, Cd. Universitaria, Ciudad de México, México
A novel 2-indano[2,3b]-2-ferrocenyl- and 2-indano[2,3b]-2-( p -methoxy-phenyl)[1,5]benzo-2,5-dihydrothiazepine 5a,b (addition Michael/cyclization) (~30.32%), indano[2,3b]-2-ferrocenyl- and 2-( p -methoxyphenyl)[1,4] benzothiazine 4a,b (addition “anti-Michael”/cyclization) (~45.43%), respectively, were obtained by the condensation of 2-ferrocenyl-and 2-( p -methoxy-phenyl)methyliden-1,3-indandiones 1a,b with o -aminothiophenol 2 in the presence of AcOH and HCl. A new “anti-Michael” addition reaction of 1,4- bis -heteronucleophile 2 into 2-arylmethyliden-1,3-indandiones was reported. As a result of this reaction the product 1a,b was obtained. The structures of the resultant compounds were elucidated by IR, 1 H and 13 C NMR spectroscopy, mass spectrometry, elemental and X-ray diffraction analysis. The in vitro antitumor activity of the obtained products was researched using the following human cancer cell lines: glioblastoma (CNS U-251), prostatic adenocarcinoma (PC-3), chronic myelogenous leukemia (K562), colorectal adenocarcinoma (HCT-15), mammary adenocarcinoma (MCF-7), and small cell lung cancer (SKLU) and the sulforhodamine B (SRB) method. Among these new compounds some thiazine and thiazepine derivatives showed compelling in vitro antitumor effects on cell lines K-562, HCT-15, SKLU-1 and MCF-7.
Bariwal, J.B., Upadhyay, K.D., Manvar, A.T., Trivedi, J.C., Singh, J.S., Jain, K.S. and Shah, A.K. (2008) 1, 5-Benzothiazepine, a Versatile Pharmacophore: A Review. European Journal of Medicinal Chemistry, 43, 2279-2290. https://doi.org/10.1016/j.ejmech.2008.05.035
Hekmatshoar, R., Sadjadi, S., Shiri, S., Heravi, M.M. and Beheshtiha, Y.S. (2009) Green Protocol for Synthesis of 1,5-Benzodiazepines and 1,5-Benzothiazepines in the Presence of Nanocrystalline Aluminum Oxide. Synthetic Communications, 39, 2549-2259. https://doi.org/10.1080/00397910802657925
Nardi, M., Cozza, A., Maiuolo, L., Oliverio, M. and Procopio, A. (2008) Ga (OTf) 3-Promoted Condensation Reactions for 1, 5-Benzodiazepines and 1, 5-Benzothia- zepines. Tetrahedron Letters, 49, 5302-5308. https://doi.org/10.1016/j.tetlet.2008.06.082
Nikalje, A.P. and Vyawahare, D. (2011) Facile Green Synthesis of 2,4-substituted- 2,3-dihydro-1,5 Benzothiazepine Derivatives as Novel Anticonvulsant and Central Nervous System (CNS) Depressant Agents. African Journal of Pure and Applied Chemistry, 5, 422-428.
Pommier, Y., Garafalo, A., Brizzi, A., Campiani, G., Fiornini, I. and Nacci, V. (1999) Thiazolothiazepine Inhibitors of HIV-1 Integrase. Journal of Medicinal Chemistry, 42, 3334-3341.
Upadhyay, K., Manvar, A., Rawal, K., Joshi, S., Trivedi, J., Chaniyara, R. and Shah, A. (2012) Evaluation of Structurally Diverse Benzoazepines Clubbed with Coumarins as Mycobacterium tuberculosis Agents. Chemical Biology & Drug Design, 80, 1003-1008. https://doi.org/10.1111/j.1747-0285.2012.01436.x
Arya, K. and Dandia, A. (2008) The Expedient Synthesis of 1,5-benzothiazepines as a Family of Cytotoxic Drugs. Bioorganic & Medicinal Chemistry Letters, 18, 114- 119. https://doi.org/10.1016/j.bmcl.2007.11.002
Singh, G., Kumar, N., Yadav, A.K. and Mishra, A.K. (2002) Syntheses of Some New 1,5-Benzothiazepine Derivatives and Their Ribofuranosides as Antimicrobial Agents. Heteroatom Chemistry, 13, 620-625. https://doi.org/10.1002/hc.10051
Dandia, A., Singh, R., Singh, D., Laxkar, A. and Sivpuri, A. (2010) Regioselective Synthesis of Diltiazem Analogue Pyrazolo[4,3-c][1,5]benzothiazepines and Antifungal Activity. Phosphorus, Sulfur and Silicon, 185, 2472-2479. https://doi.org/10.1080/10426501003713064
“Anti-Michael” and Michael Additions in the Reactions of 2-Arylmethyliden-1,3-Indandiones with 2-Aminothiophenol — Oak Academic Publishing
Ansari, F.I., Kalsoom, S., Zaheer-ul-Haq, Ali, Z. and Jabeen, F. (2012) In Silico Studies on 2,3-dihydro-1,5-benzothiazepines as Cholinesterase Inhibitors. Medicinal Chemistry Research, 21, 2329-2339. https://doi.org/10.1007/s00044-011-9754-6
Saini, R.K., Joshi, Y.C. and Joshi, P. (2008) Solvent-Free Synthesis of Some 1,5- Benzothiazepines and Benzodiazepines and Their Antibacterial Activity. Phosphorus, Sulfur and Silicon, 183, 2181-2190. https://doi.org/10.1080/10426500701852661
Kopf-Maier, P. and Kopf, H. (1987) Non-Platinum Group Metal Antitumor Agents. History, Current Status, and Perspectives. Chemical Reviews, 87, 1137-1152. https://doi.org/10.1021/cr00081a012
Willy, B. and Müller, T.J.J. (2010) Three-Component Synthesis of benzo[b][1,5]thiazepines via Coupling-Addition-Cyclocondensation Sequence. Molecular Diversity, 14, 443-453. https://doi.org/10.1007/s11030-009-9223-z
Klimova, M.A., Gallardo Vega, J.J., Sánchez García, M., Flores-Alamo, J.M. and Méndez Stivalet, J. (2015) 4-Aryl-2-ferrocenyl- and 2-Aryl-4-ferrocenyl- 2,3-dihydro-1,5-benzothiazepines with Potentially Biological Activities: Synthesis, Characterization, X-ray Diffraction Studies. Journal of Heterocyclic Chemistry, ID JHET-15-0038. https://doi.org/10.1002/jhet.2519
Katritzky, A.R., Odens, H.H. and Zhang, S. (2001) Novel Syntheses of 2,3-Dihy- dro-1,5-benzothiazepin-4(5H)-ones and 2H-1,4-Benzothiazin-3(4H)-ones. The Journal of Organic Chemistry, 66, 6792-6796. https://doi.org/10.1021/jo0101959
Salisova, M., Prokesova, M., Kubrikanova, M. and Toma, S. (1993) Reactions of Ferrocenecarboxylic Acid and Omega Ferrocenyl-Omega-Oxoalkanoic Acids with 2-Aminothiophenol. Chemical Papers—Chemicke Zvesti, 47, 183-185.
Arslan, H. and Algül, Ö. (2007) Synthesis and Ab Initio/DFT Studies on 2- (4-methoxyphenyl)benzo[d]thiazole. International Journal of Molecular Sciences, 8, 760-776. https://doi.org/10.3390/i8080760
Roth, H.J. and Kok, W. (1976) Zur Kenntnis der Ninhydrin-Reaktion, 3. Mitt. Reaktion mit Dimethoxyanilinen und reaktiven Aromaten. Archiv der Pharmazie, 309, 81-86. https://doi.org/10.1002/ardp.19763090202
CrysAlis, C.C.D. and CrysAlis, R. (2009) Crystal Structure Solution. Oxford Difraction, Abingdon.
Sheldrick, G.M. (1990) SHELXS-97, Crystal Structure Solution. University of Göttingen, Göttingen.
Sheldrick, G. (1997) M.SHELXS-97, Crystal Structure Refinament. University of Göttingen, Göttingen.
Monks, A., Scudiero, D., Skehan, P., Shoemaker, R., Paul, K., Vistica, D., Hose, C., Langley, J., Cronise, P., Vaigro-Wolff, A., Gray-Goodrich, M., Campbell, H., Mayo, J. and Boyd, M. (1991) Feasibility of a High-Flux Anticancer Drug Screen Using a Diverse Panel of Cultured Human Tumor Cell Lines. Journal of the National Cancer Institute, 83, 757-766. https://doi.org/10.1093/jnci/83.11.757
Eicher, S. Hauptmann, A. Speicher, (2012) The Chemistry of Heterocycles. Structures, Reactions, Synthesis and Applications. Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim, 529-545.
Stankovic, E., Elecko, P. and Toma, S. (1996) Knoevenagel Condensation of Ferrocenecarbaldehyde with Some Methylene Active Reagents on Inorganic Supports. Chemical Papers, 50, 68-71.
Cooke, G., Palmer, H.M. and Schulz, O. (1995) Novel Ferrocene Derivatives From Precursors Derived From Alumina-Catalysed Knoevenagel Reactions of Ferrocenecarboxaldehyde. Synthesis, 1995, 1415-1418. https://doi.org/10.1055/s-1995-4125
Wu, D., Ren, Z., Cao, W. and Tong, W. (2005) Solvent-Free Synthesis of 2-Aryli- deneindan-1,3-diones in the Presence of Magnesium Oxide or Silica Gel Under Grinding. Synthetic Communications, 35, 3157-3162. https://doi.org/10.1080/00397910500282968
Sánchez García, J.J., Gallardo Vaga, M.A., Flores-Álamo, M., Méndez Stivalet, J.M. and Klimova, E.I. (2015) 1,4-dinitrogen Nucleophiles in the Breaking of the Cα=Cβ Multiple Bond in 2-ferrocenylmethylidene-β-dicarbonyl Compounds. Simple Method for the Preparation of the Al(III) Complexes with β-diketones and β-ketoesters. Journal of Applied Chemical Science International, 2, 147-158.