Synthesis and biological evaluation of benzo[b]furo[3,4-e][1,4]diazepin-1-one derivatives as anti-cancer agents

Malayeri, Sina Omid; Tayarani‐Najaran, Zahra; Behbahani, Fatemeh Shaebani; Rashidi, Roghayeh; Delpazir, Saeedeh; Ghodsi, Razieh

doi:10.1016/j.bioorg.2018.07.023

Cited by 11 publications

(2 citation statements)

References 24 publications

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“…Benzoxazepines and benzodiazepines are benzo-fused sevenmembered heterocyclic compounds constituting two important classes of building blocks in drug discovery due to a wide range of their biological activities such as anti-psychotic, [1][2][3][4] anti-convulsant, [5][6][7][8] anti-cancer, [9][10][11] anti-HIV1, [12][13] antibacterial, [14] and progesterone receptor agonists. [15] Representative examples of some biologically important benzoxazepines and benzodiazepines are illustrated in Scheme 1.…”

Section: Introductionmentioning

confidence: 99%

Environmentally Benign One‐pot Synthesis of Benzo‐Fused Seven‐Membered Heterocyclic Compounds Using UiO‐66 Metal‐Organic Framework as Efficient and Reusable Catalyst

Mirhosseini‐Eshkevari

Zamani

Ghasemzadeh

2020

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A series of biologically relevant 1,4‐benzoxazepine and 1,4‐benzodiazepine derivatives were synthesized via a one‐pot three‐component reaction of 2‐aminophenol or ortho‐phenylenediamine, dimedone, and aromatic aldehydes catalyzed by UiO‐66 metal‐organic framework (MOF). This methodology provides excellent yields, simple procedure, short reaction time, low‐cost catalyst, and mild reaction conditions. The UiO‐66 MOF, which was characterized by different spectroscopic techniques such as XRD, FT‐IR, and TEM, could be recovered and reused up to eight times with no significant loss of catalytic performance.

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Section: Introductionmentioning

confidence: 99%

Environmentally Benign One‐pot Synthesis of Benzo‐Fused Seven‐Membered Heterocyclic Compounds Using UiO‐66 Metal‐Organic Framework as Efficient and Reusable Catalyst

Mirhosseini‐Eshkevari

Zamani

Ghasemzadeh

2020

ChemistrySelect

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“…This includes anxiolytic, anticonvulsant, antiepileptic, muscle relaxant, antidepressant, sedative, and hypnotic activities [8][9][10][11][12][13][14][15][16], mainly ascribed to the 1,4-benzodiazepines but also to the 1,5-benzodiazepines. Furthermore, the application of benzodiazepines has been extended to the treatment of bipolar disorder [17,18] and chronic back pain [19] and several studies make them potential candidates for use in anti-cancer [20][21][22][23][24], anti-infective [20,21], and anti-HIV [25,26] drugs. Moreover, particularly 1,4-benzodiazepines are present in many natural alkaloids [27][28][29].…”

Section: Introductionmentioning

confidence: 99%

Palladium-Catalyzed Benzodiazepines Synthesis

2020

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This review is focused on palladium-catalyzed reactions as efficient strategies aimed at the synthesis of different classes of benzodiazepines. Several reaction typologies are reported including hydroamination, amination, C–H arylation, N-arylation, and the Buchwald–Hartwig reaction, depending on the different substrates identified as halogenated starting materials (activated substrates) or unactivated unsaturated systems, which then exploit Pd(0)- or Pd(II)-catalytic species. In particular, the use of the domino reactions, as intra- or intermolecular processes, are reported as an efficient and eco-compatible tool to obtain differently functionalized benzodiazepines. Different domino reaction typologies are the carboamination, aminoarylation, aminoacethoxylation, aminohalogenation, and aminoazidation.

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