Synthesis of novel pyrazolo[3,4-d]pyrimidinone derivatives as cytotoxic inhibitors

Authors

  • Ameur Rahmouni Laboratoire de Chimie Hétérocyclique, Produits Naturels et Réactivité, Equipe: Chimie Médicinale et Produits Naturels, Faculté des Sciences de Monastir, Université de Monastir, Avenue de l’Environnement, 5019 Monastir, Tunisie
  • Anis Romdhane Laboratoire de Chimie Hétérocyclique, Produits Naturels et Réactivité, Equipe: Chimie Médicinale et Produits Naturels, Faculté des Sciences de Monastir, Université de Monastir, Avenue de l’Environnement, 5019 Monastir, Tunisie
  • Malek Besbes Laboratoire des maladies transmissibles et des substances biologiquement actives, Faculté de Pharmacie, 5000 Monastir, Tunisie
  • Nicolas Elie Centre de Recherche de Gif, Institut de Chimie des Substances Naturelles, CNRS, Avenue de la Terrasse, 91198 Gif-sur-Yvette Cedex, France
  • David Touboul Centre de Recherche de Gif, Institut de Chimie des Substances Naturelles, CNRS, Avenue de la Terrasse, 91198 Gif-sur-Yvette Cedex, France
  • Hichem Ben Jannet Laboratoire de Chimie Hétérocyclique, Produits Naturels et Réactivité, Equipe: Chimie Médicinale et Produits Naturels, Faculté des Sciences de Monastir, Université de Monastir, Avenue de l’Environnement, 5019 Monastir, Tunisie

DOI:

https://doi.org/10.13171/mjc.2.4.2014.11.02.23

Abstract

Various α-fonctionalized iminoethers 2 were easily prepared from ethyl 5-amino-3-substituted-1-phenyl-1H-pyrazole-4-carboxylate 1. The reaction of iminoethers 2 with ammonia afforded 3-substitued-1-phenyl-1H-pyrazolo[3,4-d] pyrimidin-4(5H)-ones 3 which were also synthesized by the addition of formamide to ethyl 5-amino-3-substituted-1-phenyl-1H-pyrazole-4-carboxylate 1. The 5-amino-3-substitued-1-phenyl-1H-pyrazolo[3,4-d]pyrimidin-4(5H)-ones 4 were obtained from hydrazonolysis of iminoethers 2. Otherwise, the condensation of these intermediates 2 with a series of some primary amines and hydroxylamine led respectively, to the corresponding 3,5-disubstitued-1-phenyl-1H-pyrazolo[3,4-d]pyrimidin-4(5H)-ones 5 and the 3-substitued-5-hydroxy-1-phenyl-1H-pyrazolo[3,4-d] pyrimidin-4-(5H)-ones 6. The synthesized compounds 1-6 were completely characterized by 1H NMR, 13C NMR, IR and HRMS. Some synthesized compounds were evaluated for their cytotoxic effect using the Human cervical adenocarcinoma Hela cell line.

References

- J. K. Gupta, C. Anshu, D. Rupesh, V. Kumari, P. K. Sharma, P. K. Verma, International Journal of Pharmaceutical Sciences and Research, 2010, 5, 0975-8232.

- M. H. Elnagdi, E. M. Kandeel, E. M. Zayed, Z. E. Kandeel, J. Heterocycl. Chem., 1977, 14, 155-157.

- A. E. Rashad, M. I. Hegab, R. E. Abdel-Megeid, N. Fathalla, F. M. E. Abdel-Megeid, Eur. J. Med. Chem., 2009, 44, 3285-3292.

- N. C. Desai , V.V. Joshi, K. M. Rajpara, H. V. Vaghani, H. M. Satodiya, Journal of Fluorine Chemistry, 2012, 142, 67-78.

- R. A. Mekheimer, E. A. Ahmed, K. U. Sadek, Tetrahedron, 2012, 68, 1637-1667.

- H. A. Stefani, C. M. P. Pereira, R. B. Almeida, R. C. Braga, K. P. Guzen, R. Cella, Tetrahedron Lett.,2005, 46, 6833-6837.

- A. M. Youssef, E. G. Neeland, E. B. Villanueva, M. S. White, I. M. El-Ashmawy, B. Patrick, A. Klegeris, A. S. Abd-El-Aziz, Bioorg. Med. Chem, 2010, 18, 5685-5696.

- J. P. Colomer, E.L. Moyano, Tetrahedron Lett.,2011, 52, 1561-1565.

- B. S. Holla, M. Mahalinga, M. S. Karthikeyan,P. M. Akberalib, N. S. Shetty, Bioorg. Med. Chem., 2006, 14, 2040-2047.

- M. M. El-Enany, M. M. Kamel, O. M. Khalil, H. B. El-Nassan, Eur. J. Med. Chem., 2010, 45, 5286-5291.

- D. C. Kim, Y. R. Lee, B. S. Yang, K. J. Shin, D. J. Kim, B. Y. Chung, K. H. Yoo, Eur. J. Med. Chem., 2003, 38, 525-532.

- S. Schenone, C. Brullo, O. Bruno,F. Bondavalli, L. Mosti, G. Maga,E. Crespan, F. Carraro, F. Manetti, C. Tintori, M. Botta, Eur .J. Med. Chem., 2008, 43, 2665-2676.

- M. M. Ghorab, F. A. Ragab, S. I. Alqasoumi, A. M. Alafeefy, S. A. Aboulmagd, Eur. Med. Chem., 2010, 45, 171-178.

- M. Ge, E. Cline, L. Yang, Tetrahedron Lett.,2006, 47, 5797-5799.

- K. M. Al-Taisan, H. M. Al-Hazimi, S. Al-Shihry, Molecules, 2010,15, 3932-3957.

- E. I. Al-Afleq, S. A. Abubshait, Molecules, 2001, 6, 621-638.

- P. G. Baraldi, H. El-Kashef, A. Farghaly, P. Vanelle, F. Fruttarolo, Tetrahedron, 2004, 60,5093-5098.

- A. M. F. Oliveira-Campos, A. M. Salaheldin, L. M. Rodrigues, ARKIVOC, 2007, (xvi), 92-100.

- S. Gupta, L. M. Rodrigues, A. P. Esteves, A. M. F. Oliveira-Campos, M. S. J. Nascimento, N. Nazareth, H. Cidade, M. P. Neves, E. Fernandes, M. Pinto, N. M. F. S. A. Cerqueira, N. Bras, Eur. J. Med. Chem., 2008, 43, 771-780.

- M. S. Nermien, M. M. Hany, E. S. A. E. H. Khattab, S. S. Motlaq, A. M. El-Agrody, Eur. J. Med. Chem., 2011, 46, 765-772.

- R. Yan, Y. Yang, Y. Zeng, G. Zou, J. Ethnopharmacol., 2009, 121, 451-455.

Downloads

Published

2014-02-11

Issue

Vol. 2 No. 6 (2014)

Section

Inorganic Chemistry

License

Authors who publish with this journal agree to the following terms:

    1. Authors retain copyright and grant the journal right of first publication with the work simultaneously licensed under a Creative Commons Attribution License that allows others to share the work with an acknowledgement of the work's authorship and initial publication in this journal
    2. Authors are able to enter into separate, additional contractual arrangements for the non-exclusive distribution of the journal's published version of the work (e.g., post it to an institutional repository or publish it in a book), with an acknowledgement of its initial publication in this journal
    3. Authors are permitted and encouraged to post their work online (e.g., in institutional repositories or on their website) prior to and during the submission process, as it can lead to productive exchanges, as well as earlier and greater citation of published work (See The Effect of Open Access).