Rubrolide analogues and their derived lactams as potential anticancer agents

Pereira, Ulisses Alves; Moreira, Thaís Altoé; Barbosa, Luiz C. A.; Maltha, Célia R. A.; Bomfim, Igor S.; Maranhão, Sarah Sant’ Anna; Moraes, Manoel Odoríco de; Pessoa, Cláudia; Barros-Nepomuceno, Francisco Washington Araújo

doi:10.1039/c5md00459d

Cited by 25 publications

(15 citation statements)

References 41 publications

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“…RMN de 1 H (300 MHz, CDCl 3 ) δ 3,84 (s, 3H, 7'), 3,88 (s, 3H, 7''), 6,92 (d, J 3',2' = J 5',6' = 8,4 Hz, 2H, 3' e 5'), 6,97 (d, J 3'',2'' = J 5'',6'' = 8,5 Hz, 2H, 3'' e 5''), 7,62 (d, J 2',3' = J 6',5' = 8,4 Hz, 2H, 2' e 6'), 8,18 (d, J 2'',3'' = J 6'',5'' = 8,5 Hz, 2H, 2'' e 6''). RMN de 13 C (75 MHz, CDCl 3 ) δ 55,5 (7'), 55,6 (7''), 86,8 (2), 93,5 (1), 112,1 (1'), 113,8 (3'' e 5''), 114,4 (3' e 5'), 130,4 (1''), 131,9 (2'' e 6''), 135,0 (2' e 6'), 161,5 (4'), 164,3 (4''), 176,8 (3) 14), 239 (12), 238 (71), 224 (16), 223 (100), 195 (28), 180 (12), 163 (7), 160 (7), 159 (71), 152 (29), 151 (10), 144 (18), 135 (20), 131 (6), 126 (7), 119 (35), 116 (23), 107 (7), 92 (24), 88 (21), 87 (8), 77 (43), 76 (11), 75 (13), 74 (11), 64 (24), 63 (36), 62 (23), 51 (15), 50 (14).…”

Section: -(3-bromo-4-metoxifenil)-1-(35-dibromo-4-metoxifenil)prop-mentioning

confidence: 99%

“…35 e anteriormente empregadas com sucesso para o preparo de vários análogos de nostoclídeos [36][37][38][39] e rubrolídeos. [19][20][21][22][23][24] Para isso, as lactonas foram submetidas à reação com os aldeídos na presença de TBDMSOTf e DIPEA. Esse procedimento resulta na formação de um sililfurano intermediário que condensa com o aldeído resultando na formação de um sililéter intermediário.…”

Section: Sínteseunclassified

“…Nos últimos anos, nosso grupo tem relatado a síntese de vários butenolídeos análogos a compostos naturais e que apresentam atividades antibacteriana, 19,20 herbicida 21 , inibidora de fotossíntese [21][22][23] e citotóxica. 24 Dando continuidade a essa linha de pesquisa, e considerando que os cadiolídeos ainda foram pouco investigados em termos de atividade antimicrobiana, no presente artigo descrevemos a síntese de 21 novos análogos aos cadiolídeos empregando adaptações da metodologia desenvolvida por Boukouvalas e Thibault. 18 Foram obtidos compostos com diferentes padrões de substituição nos três anéis benzênicos e a atividade antimicrobiana dos mesmos foi avaliada sobre os microrganismos patogênicos Candida albicans, Staphylococcus aureus, Bacillus cereus, Escherichia coli e Salmonella typhimurium.…”

Section: Introductionunclassified

“…EM, m/z (%) 754 ([M +. ], C 27 H 18 Br 4 O 6 , 15), 755 ([M+1] + , 5), 756 ([M+2] + , 55), 757 ([M+3] + , 16), 758 ([M+4] + , 79), 759 ([M+5] + , 23), 760 ([M+6] + , 53), 761 ([M+7] + , 15), 762 ([M+8] + , 15), 679(9), 677 (9), 411 (13), 410(5), 409(24), 407(13), 295 (49), 294(10), 293 (100), 291 (52), 250(10), 248 (5), 239(16), 237(19), 235(10), 228 (59), 226(60), 215 (29), 213 (47), 211 (20), 200 (11), 199 (10), 198 (10), 119 (54), 103 (11), 89 (15), 77 (8), 76 (9), 75 (10), 63 (5), 57 (6). HRMS [ESI(+), IT-TOF]: calculado [C 27 H 19 Br 4 O 6 ] + 754,7910; encontrado 754,7905.…”

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confidence: 99%

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Inibição Do Crescimento De Microrganismos Patogênicos Induzida Por Butenolídeos Análogos Aos Cadiolídeos

Mairink

Barbosa

Maltha

et al. 2019

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INHIBITORY EFFECT ON GROWTH OF PATHOGENIC MICROORGANISMS INDUCED BY BUTENOLIDES RELATED TO CADIOLIDES. The increasing number of antibiotic resistant microorganisms requires the development of new drugs. In this context, natural cadiolides are promising leads as they present potent antimicrobial activity and low cytotoxicity. In this work we report the synthesis of 21 new cadiolide analogues. The synthesis involved a Diels−Alder cycloaddition/ cycloreversion reaction between an oxazole and different ynones, affording four intermediate butenolides (14a-d) in 61-81% yield. These intermediates were subjected to a vinylogous Knoevenagel condensation, followed by demethylation of the methoxylated compounds, affording all 21 analogues in good yields. The antibiotic activity of all compounds was evaluated against a panel of five microorganisms. The bioassays on the microbial growth showed that the cadiolides are more active for Gram-positive than Gram-negative bacteria, and have low activity against the fungus C. albicans. The most active compounds (14b, 15b, 15c and 16e) were effective against S. aureus showing IC 50 in the range of 1.8-6.0 µg mL-1. The results also indicated that the nature and position of substituent groups on the aromatic moieties have some effect on the activities.

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Section: -(3-bromo-4-metoxifenil)-1-(35-dibromo-4-metoxifenil)prop-mentioning

confidence: 99%

Section: Sínteseunclassified

Section: Introductionunclassified

mentioning

confidence: 99%

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Inibição Do Crescimento De Microrganismos Patogênicos Induzida Por Butenolídeos Análogos Aos Cadiolídeos

Mairink

Barbosa

Maltha

et al. 2019

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“…In 2016, Barbosa and coworkers found that compound 91n caused a decrease in HL-60 cell viability followed by an increase in the apoptoric and necrotic cells in a concentration dependent manner [179].…”

Section: Scheme 92 Synthesis Of (Z)-5-(1-arylmethylene)-3bromo-4-(5-mentioning

confidence: 99%

Synthesis and Biological Properties of 2(5H)-Furanones Featuring Bromine Atoms on the Heterocyclic Ring and/or Brominated Substituents

Rossi

Lessi

Manzini

et al. 2017

COC

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This review deals with the synthesis of unnatural and natural 2(5H)-furanone derivatives featuring bromine atoms on the heterocyclic ring and/or brominated substituents, which have been described in the literature since 1951 up to February 2016. The review has been organized on the basis of six classes of brominated furanone derivatives that were synthesized: i) 2(5H)-furanone derivatives with one bromine atom on the heterocyclic ring; ii) 2(5H)-furanone derivatives with two bromine atoms on the heterocyclic ring; iii) 2(5H)-furanone derivatives featuring one bromine atom on the heterocyclic ring and monobrominated substituents; iv) 2(5H)- furanone derivatives featuring one bromine atom on the heterocyclic ring and dibrominated substituents; v) 2(5H)-furanone derivatives with monobrominated substituents; and vi) 2(5H)-furanones featuring dibrominated substituents. Where possible, experimental details of the syntheses have been reported. Furthermore, the biological properties of the target compounds, including their mutagenic, cytotoxic, enzymatic, anti-inflammatory and photosynthetic inhibitory activities have been summarized, paying particular attention on the compounds that have demonstrated antimicrobial properties via inhibition of quorum sensing and biofilm formation

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Antibacterial and Cytotoxic Activity of Ruthenium‐p‐cymene Complexes with 2‐Methylquinolin‐8‐ol Derivatives

et al. 2021

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Eight 5‐aryl‐2‐methylquinolin‐8‐ol ligands (2–9) were prepared by a cross‐coupling Suzuki reaction from precursors brominated at position 5 (10), and positions 5 and 7 (11). These ligands were converted into new ruthenium(II)‐p‐cymene complexes (12–22) (51–94 %). The cytotoxic and antimicrobial activities of all compounds were investigated. Ligands showed higher cytotoxicity (EC50=3.1–4.8 μM) than ruthenium complexes (EC50=5.2–7.8 μM) against human melanoma cancer cells (A375). The most potent compound 7 has been shown to act via apoptosis. Some compounds were more potent as anticancer than cisplatin. Several ruthenium complexes selectively inhibited S. typhimurium and S. aureus (IC50=4.64–146.15 and 9.37–125.95 μg/mL, respectively), while most ligands were potent against C. albicans. Molecular docking studies with a protein from S. aureus suggest four key amino acids interactions, in agreement with the inhibitory potential against this bacterium.

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Rubrolide analogues and their derived lactams as potential anticancer agents

Abstract: Analogues of rubrolides were synthesized and shown to be cytotoxic to several cancer cell lines and not toxic to L929 normal cells. The cytotoxicity involved the induction of cell death by apoptosis.

Cited by 25 publications

References 41 publications

Inibição Do Crescimento De Microrganismos Patogênicos Induzida Por Butenolídeos Análogos Aos Cadiolídeos

Inibição Do Crescimento De Microrganismos Patogênicos Induzida Por Butenolídeos Análogos Aos Cadiolídeos

Synthesis and Biological Properties of 2(5H)-Furanones Featuring Bromine Atoms on the Heterocyclic Ring and/or Brominated Substituents

Antibacterial and Cytotoxic Activity of Ruthenium‐p‐cymene Complexes with 2‐Methylquinolin‐8‐ol Derivatives

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