Synthesis of tetrahydrobenzoxazepine acetals with electron-withdrawing groups on the nitrogen atom. Novel scaffolds endowed with anticancer activity against breast cancer cells

Díaz‐Gavilán, Mónica; Rodríguez-Serrano, Fernando; Gómez-Vidal, José A.; Marchal, Juan A.; Aránega, Antonia; Gallo, Miguel Á.; Espinosa, Antonio; Campos, Joaquı́n M.

doi:10.1016/j.tet.2004.09.072

Cited by 49 publications

(36 citation statements)

References 24 publications

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“…As part of an Anticancer Drug Programme, we were interested in the preparation of the heterocycles 3a-b ( Figure 2) that could be useful intermediates for the synthesis of novel bioactive compounds. Figure 2 shows the synthesis of derivatives 3a-b [19]. The Mitsunobu reaction is a versatile method for the transformation of aliphatic alcohols into alkylating agents in situ and under mild conditions [20].…”

Section: (Rs)-26-dichloro-9-[1-(o-or P-nitrobenzenesulfonyl)-1235mentioning

confidence: 99%

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Bozepinib: A Promising Selective Derivative Targeting Breast Cancer Stem Cells

Campos¹,

Conejo‐García²,

Cruz‐López³

2021

Translational Research in Cancer

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Bozepinib is a potent antitumour compound that shows an IC 50 of 0.166 μM against MDA-MB-231 human breast cancer cell line. It is also a very selective drug that presents a therapeutic index (TI) of 11.0 against MDA-MB-231 in relation to the normal MCF-10A. It is important to identify new cancer stem-like cells (CSCs) anticancer drugs to struggle against the resistance and the high risk of relapse in patients. In the present chapter, we show how bozepinib demonstrated selectivity on cancer cells and showed an inhibitory effect over kinases involved in carcinogenesis, proliferation and angiogenesis. Bozepinib inhibits HER-2 signaling pathway and JNK and ERK kinases. In addition, it has an inhibitory effect on AKT and VEGF together with anti-angiogenic and anti-migratory activities. Interestingly, bozepinib suppresses the formation of both mammo-and colonospheres and eliminated ALDH+ CSC subpopulations at a low micromolar range similar to salinomycin. It also induces the downregulation of SOX2, c-MYC and β-CATENIN and upregulation of the GLI-3 Hedgehog signaling repressor. Finally, bozepinib shows in vivo antitumor and anti-metastatic efficacy in xenotransplanted nude mice without presenting subacute toxicity. However, further studies in cancer patients are needed to confirm the therapeutic potential of bozepinib.

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Section: (Rs)-26-dichloro-9-[1-(o-or P-nitrobenzenesulfonyl)-1235mentioning

confidence: 99%

“…Actually, the derivative 8 was isolated when the reaction was carried out using triethylamine (TEA) as a hydrochloride acid scavenger and 1.1 equiv. of the sulfonyl chloride was added ( Figure 3) [19].…”

Section: (Rs)-26-dichloro-9-[1-(o-or P-nitrobenzenesulfonyl)-1235mentioning

confidence: 99%

Bozepinib: A Promising Selective Derivative Targeting Breast Cancer Stem Cells

Campos¹,

Conejo‐García²,

Cruz‐López³

2021

Translational Research in Cancer

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“…The lipophilic character of R 1 increased the activity and no limit of volume had been observed for the studied groups. The electron-withdrawing character of R 1 could help to increase the activity (Díaz-Gavilán et al, 2004). Carbonyl derivatives were more potent than the sulfonyl ones.…”

Section: Anticancer and Sar Studies On (1235-tetrahydro-41-benzoxmentioning

confidence: 99%

Benzo-Fused Seven- and Six-Membered Derivatives Linked to Pyrimidines or Purines Induce Apoptosis of Human Metastatic Breast Cancer MCF-7 Cells In Vitro

Campos¹,

Núñez²,

Conejo‐García³

et al. 2011

Breast Cancer - Current and Alternative Therapeutic Modalities

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“…This combination has led to them being of interest as sorbents and solid supports in catalysis. [5] The benzo [b][1,4]oxazepine derivatives show various forms of bioactivity such as allergic bronchitis, treating of bronchial asthma, [6] anxiolytic activity, antidepressive, [7] antihistaminic and antiserotoninergic [8] effects, anticancer activity against breast cancer cells [9] and progesterone receptor agonists. [10] The common methods for the syntheses of benzo [b][1,4]oxazepines involve Nalkylation of N-methylanthranilic acid with an α-chloroacid [11] and N-alkylation of 2-aminobenzhydrol, in the presence of ethanolic sodium solution.…”

Section: Introductionmentioning

confidence: 99%

Eco‐friendly synthesis of benzoxazepine and malonamide derivatives in aqueous media

Babazadeh

Hosseinzadeh‐Khanmiri

Zakhireh

2016

Applied Organom Chemis

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A special, efficient and reusable heterogeneous catalytic system is reported for the one-pot three-component synthesis of a series of malonamide and 2,3,4,5-tetrahydrobenzo[b] [1,4]oxazepine derivatives in the presence of a heterogeneous material composed of MCM-48/H 5 PW 10 V 2 O 40 in aqueous media and at room temperature. The products were identified using physical data (melting points) by comparison with those reported in the literature. Also, the structures of the new compounds were characterized by means of infrared, 1 H NMR, 13 C NMR and CHN analyses.

show abstract

Synthesis of tetrahydrobenzoxazepine acetals with electron-withdrawing groups on the nitrogen atom. Novel scaffolds endowed with anticancer activity against breast cancer cells

Cited by 49 publications

References 24 publications

Bozepinib: A Promising Selective Derivative Targeting Breast Cancer Stem Cells

Bozepinib: A Promising Selective Derivative Targeting Breast Cancer Stem Cells

Benzo-Fused Seven- and Six-Membered Derivatives Linked to Pyrimidines or Purines Induce Apoptosis of Human Metastatic Breast Cancer MCF-7 Cells In Vitro

Eco‐friendly synthesis of benzoxazepine and malonamide derivatives in aqueous media

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