Recent publications and patent

P49. Bayraktar, G.; Marchand, P.; Barbosa, E.G.; da Silva, M.C.; Weber, K.C.; Cojean, S.; Saylam, M.; Istanbullu, H. Biological properties and in silico studies of thiazolopyrimidine derivatives active against visceral and cutaneous Leishmania spp. amastigote forms. Eur. J. Med. Chem. Rep. 2024, 12, 100228; doi: 10.1016/j.ejmcr.2024.100228.

P48. Kohlmann, P.; Krylov, S.N.; Marchand, P.; Jose, J. FRET Assays for the Identification of C. albicans HSP90-Sba1 and Human HSP90α-p23 Binding Inhibitors. Pharmaceuticals 2024, 17, 516; doi: 10.3390/ph17040516.

P47. Soltani,S; Koubaa, I.; Cojean, S.; Picot, C.; Marchand, P.; Allouche, N. Phytochemical, antileishmanial, antifungal and cytotoxic profiles of Thymelaea tartonraira (L.) All. extracts. Nat. Prod. Res. 2024, 38, 3481-3487; doi: 10.1080/14786419.2023.2252153

P46. Primas, N.; Castera-Ducros, C.; Paoli-Lombardo, R.; Curti, C.; Mathias, F.; Rathelot, P.; Marchand, P.; Vanelle, P. 31^st Annual GP₂A Medicinal Chemistry Conference. Drugs Drug Candidates 2024, 3, 209-243; doi: 10.3390/ddc3010013.

P45. Rouges, C.; Asad, M.; Laurent, A.D.; Marchand, P.; Le Pape, P. Is the C-terminal domain an effective and selective target for the design of Hsp90 inhibitors against Candida yeast? Microorganisms 2023, 11, 2837; doi.org/10.3390/microorganisms11122837.

P44. Gonçalves de Lima Neto, R.; Saraiva de Araújo Neta, M.; Tiburcio Valeriano, C. A.; Pereira Neves, R.; Lacerda, A. M.; Ferraz, C. E.; Inácio, C. P.; Le Pape, P.; Ourliac-Garnier, I.; de Faria, A. R.; da Silva, T. G.; Alves Pereira, V. R. ; Marchand, P. Antifungal efficacy of imidazo[1,2-a]pyrazine based thiosemicarbazones and thiazolidinediones against Sporothrix species. Future Microbiol. 2023, 18, 1225-1233; doi: 10.2217/fmb-2023-0044.

P43. O’Boyle, N. M.; Helesbeux, J.-J.; Meegan, M. J.; Sasse, A.; O’Shaughnessy, E.; Qaisar, A.; Clancy, A.; McCarthy, F.; Marchand, P. 30^th Annual GP₂A Medicinal Chemistry Conference. Pharmaceuticals 2023, 16, 432; doi: 10.3390/ph16030432.

P42. Soltani, S.; Koubaa, I.; Dhouib, I.; Khemakham, B.; Marchand, P., Allouche, N. New specific α‑glucosidase inhibitor flavonoid from Thymelaea tartonraira leaves: structure elucidation, biological and molecular docking studies. Chem. Biodivers. 2023, 20, e202200944; doi: 10.1016/j.phytol.2022.05.004.

P41. Núñez-Mojica, G.; Hernández-Carrillo, M. L.; Avalos-Alanísa, F. G.; Garza-González, E.; Rivas-Galindo, V. M.; Silva-Mares, D. A.; Bazin, M.-A.; Marchand, P.*; Camacho-Corona, M. R.* Amino ether analogues of 4,4′-dihydroxy-3-methoxy-6,7′-cyclolignan and their activity against drug-resistant bacteria. Phytochem. Lett. 2022, 50, 57-60; doi: 10.1016/j.phytol.2022.05.004.

P40. de Lima Porto Ramos, K. R.; Cabral da Silva, S.; Marchand, P.; Barreto Mota, F. V.; de Assis Correia, J. C.; Gomes da Silva, J. A.; Santana, M. A.; da Silva Moura, W. C.; dos Santos, V. L.; Moura, R. O.; da Silva, T. G. Effects of acylhydrazone derivatives on experimental pulmonary inflammation by chemical sensitization. Antiinflamm. Antiallergy Agents Med. Chem. 2022, 21, 135-151; doi: 10.2174/1871523021666220729141608.

P39. Mota, F. V. B.; Coutinho, F. N.; de Carvalho, V. M. F.; de Assis Correia, J. C.; Bastos, I. V. G. A.; Neto, P. P. M.; Ximenes, R. M.; Brondani, D. J.; de Faria, A. R.; Marchand, P.; da Silva, T. G. Antinociceptive effects of aza-bicyclic isoxazoline-acylhydrazone derivatives in different models of nociception in mice. Curr. Top. Med. Chem. 2022, 22, 247-258; doi: 10.2174/1568026622666220105102508.

P38. da Silva Almeida, J. R. G.; Grougnet, R.; Quintans Junior, L. J.; Chevalier, S.; Feuilloley, M.; Robert, T.; Bach, S.; Gonçalves de Oliveira Junior, R.; Thiéry, V.; Bazureau, J.-P.; Mongin, F.; Kritsanida, M.; Sol, V.; de Oliveira Costa, V. C.; Bourgougnon, N.; Marchand, P.; Picot, L. The Franco-Brazilian Network on Natural Products (FB2NP): a new network promoting cooperation and exchanges in natural products research. Letter to the Editor, Quim. Nova 2022, 45, 1–3; doi: 10.21577/0100-4042.20170847.

P37. Helesbeux, J.-J.; Carro, L.; McCarthy, F. O.; Moreira, V. M.; Giuntini, F.; O’Boyle, N.; Matthews, S. E.; Bayraktar, G.; Bertrand, S.; Rochais, C.; Marchand, P. 29^th Annual GP2A Medicinal Chemistry Conference. Pharmaceuticals 2021, 14, 1278; doi: 10.3390/ph14121278.

P36. Dao, V. H.; Ourliac-Garnier, I.; Logé, C.; McCarthy, F. O.; Bach, S.; da Silva, T. G.; Denevault-Sabourin, C.; Thiéfaine, J.; Baratte, B.; Robert, T.; Gouilleux, F.; Brachet-Botineau, M.; Bazin M.-A.; Marchand, P. Dibenzofuran derivatives inspired from cercosporamide as dual inhibitors of Pim and CLK1 kinases. Molecules 2021, 26, 6572; doi: 10.3390/molecules26216572.

P35. Rodrigues Oliveira, A.; Alves dos Santos, F.; de Lima Ferreira, L. P.; da Rocha Pitta, M. G.; de Oliveira Silva, M. V.; de Oliveira Cardoso, M. V.; Ferreira Pinto, A.; Marchand, P.; Barreto de Melo Rêgo, M. J.; Lima Leite, A. C. Synthesis, anticancer activity and mechanism of action of new phthalimido-1,3-thiazole derivatives. Chem. Biol. Interact. 2021, 347, 109597; doi: 10.1016/j.cbi.2021.109597.

P34. Núñez-Mojica, G.; Vázquez-Ramírez, A. L.; García, A.; Rivas-Galindo, V. M.; Garza-González, E.; Cuevas González-Bravo, G. E.; Toscano, R. A.; Moo-Puc, R. E.; Villanueva-Toledo, J. R.; Marchand, P.; Camacho-Corona, M. R. New cyclolignans of Larrea tridentata and their antibacterial and cytotoxic activities. Phytochem. Lett. 2021, 43, 212-218; doi: 10.1016/j.phytol.2021.04.013.

P33. Rodini Garcia Princival, I. M.; Princival, J. L.; Dias da Silva, E.; de Arruda Lima, S. M.; Carvalho Carregosa, J.; Wisniewski Jr, A.; Oliveira de Lucena, C. C.; Halwass, F.; Alves Franca, J. A.; Gomes Rebello Ferreira, L. F.; Zaldini Hernandes, M.; Alcântara Saraiva, K. L.; Alves Peixoto, C.; Baratte, B.; Robert, T.; Bach, S.; Correia Gomes, D.; Guedes Paiva, P. M.; Marchand, P.; do Desterro Rodrigues, M.; Gonçalves da Silva, T. Streptomyces hygroscopicus UFPEDA 3370: a valuable source of the potent cytotoxic agent nigericin and its evaluation against human colorectal cancer cells. Chem. Biol. Interact. 2021, 333, 109316; doi: 10.1016/j.cbi.2020.109316.

P32. Bazin, M.-A.; Cojean, S.; Pagniez, F.; Bernadat, G.; Cavé, C.; Ourliac-Garnier, I.; Nourrisson, M.-R.; Morgado, C.; Picot, C.; Leclercq, O.; Baratte, B.; Robert, T.; Späth, G.F.; Rachidi, N.; Bach, S.; Loiseau, P.M.; Le Pape, P.; Marchand, P. In vitro identification of imidazo[1,2-a]pyrazine-based antileishmanial agents and evaluation of L. major casein kinase 1 inhibition. Eur. J. Med. Chem. 2021, 210, 112956; doi: 10.1016/j.ejmech.2020.112956.

P31. Núñez-Mojica, G.; Rivas-Galindo, V. M.; Garza-González, E.; Miranda, L. D.; Romo-Pérez, A.; Pagniez, F.; Picot, C.; Le Pape, P.; Bazin, M.-A.; Marchand, P.*; Camacho-Corona, M. R.* Antimicrobial and anti-leishmanial activities of extracts and some constituents from the leaves of Solanum chrysotrichum Schldl. Med. Chem. Res. 2021, 30, 152-162; doi: 10.1007/s00044-020-02648-8.

P30. Loidreau, Y.; Nourrisson, M.-R.; Fruit, C.; Corbière, C.; Marchand, P.*; Besson, T.* Microwave-assisted synthesis of potential bioactive benzo-, pyrido- or pyrazino-thieno[3,2-d]pyrimidin-4-amine analogs of MPC-6827. Pharmaceuticals 2020, 13, 202; doi: 10.3390/ph13090202.

P29. Loidreau, Y.; Dubouilh-Benard, C.; Nourrisson, M.-R.; Loaëc, N.; Meijer, L.; Besson, T.; Marchand, P. Exploring kinase inhibition properties of 9H-pyrimido[5,4-b]- and [4,5-b]indol-4-amine derivatives. Pharmaceuticals 2020, 13, 89; doi: 10.3390/ph13050089.

P28. Aldholmi, M.; Marchand, P.; Ourliac-Garnier, I.; Le Pape, P.; Ganesan, A. A decade of antifungal leads from natural products: 2010-2019. Pharmaceuticals 2019, 12, 182; doi:10.3390/ph12040182.

P27. Mistry, S. N.*; Marchand, P.*; Kellam, B. 27th Annual GP2A Medicinal Chemistry Conference. Pharmaceuticals - Meeting Report. 2019, 12, 179; doi:10.3390/ph12040179.

P26. Nascimento da Cruz, A. C.; Brondani, D .J.; I´talo de Santana, T.; Oliveira da Silva, L.; da Oliveira Borba, E. F.; de Faria, A. R.; Ferreira Cavalcanti de Albuquerque, J.; Piessard, S.; Matos Ximenes, R.; Baratte, B.; Bach, S.; Ruchaud, S.; Bezerra Mendonça Junior, F. J.; Bazin, M.-A.; Montenegro Rabello, M.; Hernandes, M. Z.; Marchand, P.*; Gonçalves da Silva, T*. Biological evaluation of arylsemicarbazone derivatives as potential anticancer agents. Pharmaceuticals 2019, 12, 169; doi:10.3390/ph12040169.

P25. Pereira, P. S.; de Lima, M. D. C. A.; Neto, P. P. M.; Oliveira-Tintino, C. D. D. M.; Tintino, S. R.; Menezes, I. R. D. A.; de Oliveira, J. F.; Marchand, P.; Coutinho, H. D. M.; Rodrigues, M. D. D.; da Silva, T. G. Thiazolidinedione and thiazole derivatives potentiate Norfloxacin activity against NorA efflux pump overexpression in Staphylococcus aureus 1199B strains. Bioorg. Med. Chem. 2019, 27, 3797-3804.

P24. Roque Marques, K. M.; do Desterro, M. R.; de Arruda, S. M.; de Araújo Neto, L. N.; de Lima, M. D. C. A.; de Almeida, S. M. V.; da Silva, E. C. D.; de Aquino, T. M.; da Silva Júnior, E. F. ; de Araújo-Júnior, J. X.; Silva, M. M.; de A. Dantas, M. D.; Santos, J. C. C.; Figueiredo, I. M.; Bazin, M.-A.; Marchand, P.; da Silva, T. G.; Mendonça Junior, F. J. B. 5-Nitro-thiophene-thiosemicarbazone derivatives present antitumor activity mediated by apoptosis and DNA intercalation. Curr. Top. Med. Chem. 2019, 19, 1075-1091.

P23. Barreto Mota, F. V.; Saraiva de Araújo Neta, M.; de Souza Franco, E.; Gomes Alves Bastos, I. V.; Cardoso Correia da Araújo, L.; Cabral da Silva, S.; Bezerra de Oliveira, T.; Souza, E. K.; Moraes de Almeida, V.; Matos Ximenes, R.; de Sousa Maia, M. B.; Mendonça Junior, F. J. B.; Marchand, P.; de Faria, A. R.; da Silva, T. G. Evaluation of anti-inflammatory activity and molecular docking study of new aza-bicyclic isoxazoline acylhydrazone derivatives. Med. Chem. Commun. 2019, 10, 1916-1925.

P22. de Oliveira Pedrosa Rolim, M.; Rodrigues de Almeida, A.; Galdino da Rocha Pitta, M.; Barreto de Melo Rêgo, M. J.; Quintans-Júnior, L. J.; de Souza Siqueira Quintans, J.; Heimfarth, L.; Scotti, L.; Scotti, M. T.; Marques Duarte da Cruz, R.; Nóbrega de Almeida, R.; da Silva, T. G.; de Oliveira, J. A.; de Campos, M. L.; Marchand, P.; Mendonça Junior, F. J. B. Synthesis and pharmacological evaluation of CVIB, a codrug of carvacrol and ibuprofen as a novel anti-inflammatory agent. Int. Immunopharmacol. 2019, 76, 105856; doi:10.1016/j.intimp.2019.105856.

P21. Dallemagne, P.; Rochais, C.; Marchand, P.*; Besson, T. 26th Annual GP2A Medicinal Chemistry Conference & 32nd Journées Franco-Belges de Pharmacochimie. Pharmaceuticals - Meeting Report. 2019, 12, 73; doi:10.3390/ph12020073.

P.20. Winfield, H. J.; Cahill, M. M.; O’Shea, K. D.; Pierce, L. T.; Robert, T.; Ruchaud, S.; Bach, S.; Marchand, P.; McCarthy, F. O. Synthesis and anticancer activity of novel bisindolylhydroxymaleimide derivatives with potent GSK-3 kinase inhibition. Bioorg. Med. Chem. 2018, 26, 4209-2024.

P19. Dao, V. H.; Ourliac-Garnier, I.; Bazin, M.-A.; Jacquot, C.; Baratte, B.; Ruchaud, S.; Bach, S.; Grovel, O.; Le Pape, P.; Marchand, P. Benzofuro[3,2-d]pyrimidines inspired from cercosporamide CaPkc1 inhibitor: synthesis and evaluation of fluconazole susceptibility restoration. Bioorg. Med. Chem. Lett. 2018, 28, 2250-2255.

P18. Reynoso, J. E.; Salgado-Zamora, H.; Bazin, M.-A.; Campos-Aldrete, M. E.; Marchand, P. Design and synthesis of imidazo[1,2-a]pyridines with carboxamide group substitution and in silico evaluation of their interaction with a LuxR-type quorum sensing receptor. J. Heterocycl. Chem. 2018, 55, 1101-1111.

P17. Arruda Lima, S.; Gonçalves Melo, J.; Gadelha Militão, G. C.; Souza Lima, G. M.; Alves Lima, M. C.; Santos Aguiar, J.; Mendonça Araújo, J.; Braz-Filho, R.; Marchand, P.; Araújo, J. M.; Gonçalves Silva, T. Characterization of the biochemical, physiological, and medicinal properties of Streptomyces hygroscopicus ACTMS-9H isolated from the Amazon (Brazil). Appl. Microbiol. Biotechnol. 2017, 101, 711-723.

P16. Bazin, M.-A.; Rousseau, B.; Marhadour, S.; Tomasoni, C.; Evenou, P.; Piessard, S.; Vaisberg, A. J.; Ruchaud, S.; Bach, S.; Roussakis, C.; Marchand, P. Discovery of (imidazo[1,2-a]pyrazin-6-yl)ureas as antiproliferative agents targeting P53 in non-small cell lung cancer cell lines. Anticancer Res. 2016, 36, 1621-1630.

P15. Antoine, M.; Schuster, T.; Seipelt, I.; Aicher, B.; Teifel, M.; Günther, E.; Gerlach, M.; Marchand, P. Efficient synthesis of novel disubstituted pyrido[3,4-b]pyrazines for the design of protein kinase inhibitors. Med. Chem. Commun. 2016, 7, 224-229.

P14. Marchand, P.; Bazin, M.-A.; Pagniez, F.; Rivière, G.; Bodero, L.; Marhadour, S.; Nourrisson, M.-R.; Picot, C.; Ruchaud, S.; Bach, S.; Baratte, B.; Sauvain, M.; Castillo Pareja, D.; Vaisberg, A. J.; Le Pape, P. Synthesis, antileishmanial activity and cytotoxicity of 2,3-diaryl- and 2,3,8-trisubstituted imidazo[1,2-a]pyrazines. Eur. J. Med. Chem. 2015, 103, 381-395.

P13. Loidreau, Y.; Deau, E.; Marchand, P.; Nourrisson, M.-R.; Logé, C.; Coadou, G.; Loaëc, N.; Meijer, L.; Besson, T. Synthesis and molecular modelling studies of 8-arylpyrido[3',2':4,5]thieno[3,2-d]pyrimidin-4-amines as multitarget Ser/Thr kinases inhibitors. Eur. J. Med. Chem. 2015, 92, 124-134.

P12. Defaux, J.; Antoine, M.; Logé, C.; Le Borgne, M.; Schuster, T.; Seipelt, I.; Aicher, B.; Teifel, M.; Günther, E.; Gerlach, M.; Marchand, P. Discovery of (7-aryl-1,5-naphthyridin-2-yl)ureas as dual inhibitors of ERK2 and Aurora B kinases with antiproliferative activity against cancer cells. Bioorg. Med. Chem. Lett. 2014, 24, 3748-3752.

P11. Defaux, J.; Antoine, M.; Le Borgne, M.; Schuster, T.; Seipelt, I.; Aicher, B.; Teifel, M.; Günther, E.; Gerlach, M.; Marchand, P. Discovery of 7-aryl-substituted (1,5-naphthyridin-4-yl)ureas as Aurora kinase inhibitors. ChemMedChem 2014, 9, 217-232.

P10. Deau, E.; Loidreau, Y.; Marchand, P.; Nourrisson, M.-R.; Loaëc, N.; Meijer, L.; Levacher, V.; Besson, T. Synthesis of novel 7-substituted pyrido[2',3':4,5]furo[3,2-d]pyrimidin-4-amines and their N-aryl analogues and evaluation of their inhibitory activity against Ser/Thr Kinases. Bioorg. Med. Chem. Lett. 2013, 23, 6784-6788.
P8. Bazin, M.-A.; Marhadour, S.; Tonnerre, A.; Marchand, P. Exploration of versatile reactions on 2-chloro-3-nitroimidazo[1,2-a]pyridine: expanding structural diversity of C2- and C3-functionalized imidazo[1,2-a]pyridines. Tetrahedron Lett. 2013, 54, 5378-5382.

P7. Loidreau, Y.; Marchand, P.; Dubouilh-Benard, C.; Nourrisson, M.-R.; Duflos, M.; Loaëc, N.; Meijer, L.; Besson, T. Synthesis and biological evaluation of N-aryl-7-methoxybenzo[b]furo[3,2-d]pyrimidin-4-amines and their N-arylbenzo[b]thieno[3,2-d]pyrimidin-4-amine analogues as dual inhibitors of CLK1 and DYRK1A kinases. Eur. J. Med. Chem.2013, 59, 283-295.

P6. Loidreau, Y.; Dubouilh-Benard, C.; Marchand, P.; Nourrisson, M.-R.; Duflos, M.; Buquet, C.; Corbière, C.; Besson, T. Efficient new synthesis of N-arylbenzo[b]furo[3,2-d]pyrimidin-4-amines and their benzo[b]thieno[3,2-d]pyrimidin-4-amine analogues via a microwave assisted Dimroth rearrangement. J. Heterocycl. Chem. 2013, 50, 1187-1197.
P4. Loidreau, Y.; Marchand, P.; Dubouilh-Benard, C.; Nourrisson, M.-R.; Duflos, M.; Lozach, O.; Loaec, N.; Meijer, L.; Besson, T. Synthesis and biological evaluation of N-arylbenzo[b]thieno[3,2-d]pyrimidin-4-aminesand their pyrido and pyrazino analogues as Ser/Thr kinase inhibitors. Eur. J. Med. Chem. 2012, 58, 171-183.

P3. Loidreau, Y.; Marchand, P.; Dubouilh-Benard, C.; Nourrisson, M.-R., Duflos, M.; Besson, T. First synthesis of 4-aminopyrido[2',3':4,5]furo[3,2-d]pyrimidines. Tetrahedron Lett. 2012, 53, 944-947.

P2. Marhadour, S.; Bazin, M.-A.; Marchand, P. An efficient access to 2,3-diarylimidazo[1,2-a]pyridines via imidazo[1,2-a]pyridine-2-yltriflate through a Suzuki cross-coupling reaction-direct arylation sequence. Tetrahedron Lett. 2012, 53, 297-300.

P1. Antoine, M.; Gerlach, M.; Günther, E.; Schuster, T.; Czech, M.; Seipelt, I.; Marchand, P. A convenient synthesis of novel 2,8-disubstituted pyrido[3,4-b]pyrazines possessing biological activity. Synthesis 2012, 44, 69-82.

 

Patents :

Gerlach, M.; Schuster, T.; Marchand, P.; Defaux, J.; Seipelt, I.; Polymeropoulos, E.; Müller, G.; Günther, E. Novel Naphthyridine derivatives and the use thereof as kinase inhibitors. PCT Int. Appl. WO 2011064250, 2011.