First synthesis of merged hybrids phosphorylated azirino[2,1-b]benzo[e][1,3]oxazine derivatives as anticancer agents

Carramiñana, Victor; Retana, Ana M. Ochoa de; Santos, Jesús M. de los; Palacios, Francisco

doi:10.1016/j.ejmech.2019.111771

Cited by 24 publications

(14 citation statements)

References 65 publications

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“…On the other hand, 1,3‐thiazine derivatives, an important class of heterocyclic compounds, have a wide range of biological properties[ 66 , 67 ] including antiproliferative,[ 68 , 69 , 70 , 71 , 72 ] analgesic, [73] anticonvulsant,[ 74 , 75 ] anti‐inflammatory, [76] antibiotic, [77] antimicrobial,[ 75 , 78 , 79 , 80 ] antimalarial, [81] and antihypertensive [82] properties. A literature survey revealed that also 1,3‐oxazine moieties exhibit a broad range of pharmacological activities,[ 83 , 84 ] such as anticancer,[ 85 , 86 , 87 , 88 , 89 ] antimicrobial[ 90 , 91 ] and anti‐inflammatory[ 92 , 93 ] effects, which showed their potential value in developing new therapeutic agents.…”

Section: Introductionmentioning

confidence: 99%

Antiproliferative Activity of (−)‐Isopulegol‐based 1,3‐Oxazine, 1,3‐Thiazine and 2,4‐Diaminopyrimidine Derivatives

Bamou

Tayeb

et al. 2022

ChemistryOpen

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A series of novel heterocyclic structures, namely 1,3‐oxazines, 1,3‐thiazines and 2,4‐diaminopyrimidines, were designed and synthesised. The bioassay tests demonstrated that, among these analogues, 2,4‐diaminopyridine derivatives showed significant antiproliferative activity against different human cancer cell lines (A2780, SiHa, HeLa, MCF‐7 and MDA‐MB‐231). Pyrimidines substituted with N 2 ‐( p ‐trifluoromethyl)aniline, in particular, displayed a potent inhibitory effect on the growth of cancer cells. Structure–activity relationships were also studied from the aspects of stereochemistry on the aminodiol moiety as well as exploring the effects of substituents on the pyrimidine scaffold.

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Section: Introductionmentioning

confidence: 99%

Antiproliferative Activity of (−)‐Isopulegol‐based 1,3‐Oxazine, 1,3‐Thiazine and 2,4‐Diaminopyrimidine Derivatives

Bamou

Tayeb

et al. 2022

ChemistryOpen

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“…All these reactions yielded imidazolidin-2-ones or oxazolidin-2-imines compounds which generate great interest in medicinal and pharmaceutical chemistry since they represent classes of heterocyclic compounds with a broad variety of biological activities [ 26 , 27 ]. In the last few years we have been involved in the chemistry related to phosphorylated 2 H -azirines for the preparation of α- or β-aminophosphonic acid derivatives [ 28 , 29 , 30 ], pyrroles [ 31 , 32 ], oxazoles [ 33 ], 1 H -benzo[ d ]azepines [ 31 ], or hybrid molecules such as azirino [2,1- b ]benzo[ e ][ 1 , 3 ]oxazines [ 34 ], among others. Additionally, organophosphorus derivatives are fascinating compounds from a biological point of view, due to the fact that these substituents may regulate relevant biological functions modifying the reactivity of heterocyclic systems [ 35 ].…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Antiproliferative Activity of Phosphorus Substituted 4-Cyanooxazolines, 2-Aminocyanooxazolines, 2-Iminocyanooxazolidines and 2-Aminocyanothiazolines by Rearrangement of Cyanoaziridines

et al. 2021

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Several phosphorus-substituted N-acylated cyanoaziridines 2 and N-carbamoylated cyanoziridines 5 were prepared in good to high yields. N-Acylated cyanoaziridines 2 were used, after ring expansion, in an efficient synthesis of oxazoline derivative 3a and in a completely regio-controlled reaction in the presence of NaI. Conversely, N-carbamoyl cyanoaziridines 5 reacted with NaI to obtain a regioisomeric mixture of 2-aminocyanooxazolines 7. Mild acidic conditions can be used for the isomerization of N-thiocarbamoyl cyanoaziridine 6a into a 2-aminocyanothiazoline derivative 8a by using BF3·OEt2 as a Lewis acid. Likewise, a one pot reaction of NH-cyanoaziridines 1 with isocyanates obtained 2-iminocyanooxazolidines 9 regioselectively. This synthetic methodology involves the addition of isocyanates to starting cyanoaziridines to obtain N-carbamoyl cyanoaziridines 5, which after the ring opening, reacts with a second equivalent of isocyanate to give the final 2-imino cyanooxazolidines 9. In addition, the cytotoxic effect on the cell lines derived from human lung adenocarcinoma (A549) was also screened. 2-Iminooxazolidines 9 exhibited moderate activity against the A549 cell line in vitro. Furthermore, a selectivity towards cancer cells (A549) over non-malignant cells (MCR-5) was detected.

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“…Likewise, we have been recently involved in the development of strategies for the preparation of fluorine [ 41 , 42 , 43 , 44 ] and phosphorus [ 45 , 46 , 47 , 48 , 49 ] containing derivatives, as well as for the design of new biologically active simple and fused heterocycles with anticancer and antileishmanial activity [ 50 , 51 , 52 , 53 , 54 , 55 , 56 ]. Due to the potential of five-membered heterocycles containing the 1,5-dihydro-2 H -pyrrol-2-one skeleton as anticancer agents, we thought that γ-lactam derivatives, obtained by multicomponent methodologies, may be excellent candidates for the development of new antiproliferative agents.…”

Section: Introductionmentioning

confidence: 99%

A Multicomponent Protocol for the Synthesis of Highly Functionalized γ-Lactam Derivatives and Their Applications as Antiproliferative Agents

et al. 2021

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An efficient synthetic methodology for the preparation of 3-amino 1,5-dihydro-2H-pyrrol-2-ones through a multicomponent reaction of amines, aldehydes, and pyruvate derivatives is reported. In addition, the densely substituted lactam substrates show in vitro cytotoxicity, inhibiting the growth of carcinoma human tumor cell lines HEK293 (human embryonic kidney), MCF7 (human breast adenocarcinoma), HTB81 (human prostate carcinoma), HeLa (human epithelioid cervix carcinoma), RKO (human colon epithelial carcinoma), SKOV3 (human ovarian carcinoma), and A549 (carcinomic human alveolar basal epithelial cell). Given the possibilities in the diversity of the substituents that offer the multicomponent synthetic methodology, an extensive structure-activity profile is presented. In addition, both enantiomers of phosphonate-derived γ-lactam have been synthesized and isolated and a study of the cytotoxic activity of the racemic substrate vs. its two enantiomers is also presented. Cell morphology analysis and flow cytometry assays indicate that the main pathway by which our compounds induce cytotoxicity is based on the activation of the intracellular apoptotic mechanism.

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First synthesis of merged hybrids phosphorylated azirino[2,1-b]benzo[e][1,3]oxazine derivatives as anticancer agents

Cited by 24 publications

References 65 publications

Antiproliferative Activity of (−)‐Isopulegol‐based 1,3‐Oxazine, 1,3‐Thiazine and 2,4‐Diaminopyrimidine Derivatives

Antiproliferative Activity of (−)‐Isopulegol‐based 1,3‐Oxazine, 1,3‐Thiazine and 2,4‐Diaminopyrimidine Derivatives

Synthesis and Antiproliferative Activity of Phosphorus Substituted 4-Cyanooxazolines, 2-Aminocyanooxazolines, 2-Iminocyanooxazolidines and 2-Aminocyanothiazolines by Rearrangement of Cyanoaziridines

A Multicomponent Protocol for the Synthesis of Highly Functionalized γ-Lactam Derivatives and Their Applications as Antiproliferative Agents

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