Recent advances in synthesis and medicinal chemistry of benzodiazepines

Arora, Nidhi; Dhiman, Prashant; Kumar, Shiva; Singh, Gurpreet; Monga, Vikramdeep

doi:10.1016/j.bioorg.2020.103668

Cited by 69 publications

(46 citation statements)

References 111 publications

Supporting

Mentioning

Contrasting

Unclassified

Order By: Relevance

“…There are quite a few methods for the synthesis of the benzodiazepine skeleton [9]. But these days more and more research groups significantly shift their efforts towards the wide applica-tion of a tandem synthetic approach to solve different matters.…”

Section: Introductionmentioning

confidence: 99%

Effective microwave-assisted approach to 1,2,3-triazolobenzodiazepinones via tandem Ugi reaction/catalyst-free intramolecular azide–alkyne cycloaddition

Mazur¹,

Zhelavskyi²,

Zviagin³

et al. 2021

Beilstein J. Org. Chem.

View full text Add to dashboard Cite

A novel catalyst-free synthetic approach to 1,2,3-triazolobenzodiazepinones has been developed and optimized. The Ugi reaction of 2-azidobenzaldehyde, various amines, isocyanides, and acids followed by microwave-assisted intramolecular azide–alkyne cycloaddition (IAAC) gave a series of target heterocyclic compounds in moderate to excellent yields. Surprisingly, the normally required ruthenium-based catalysts were found to not affect the IAAC, only making isolation of the target compounds harder while the microwave-assisted catalyst-free conditions were effective for both terminal and non-terminal alkynes.

show abstract

Section: Introductionmentioning

confidence: 99%

Effective microwave-assisted approach to 1,2,3-triazolobenzodiazepinones via tandem Ugi reaction/catalyst-free intramolecular azide–alkyne cycloaddition

Mazur¹,

Zhelavskyi²,

Zviagin³

et al. 2021

Beilstein J. Org. Chem.

View full text Add to dashboard Cite

show abstract

“…Benzodiazepine (BZD) drugs are a family of compounds widely used in the treatment of neurological pathologies that offer similar pharmacological properties, with anxiolytic, sedative, hypnotic, skeletal muscle relaxant, amnesic, and anticonvulsant effects [ 1 , 2 ], with a very well-established mechanism of action and metabolization in the organism [ 3 ]. These drugs have a chemical structure based on a core formed by the fusion of benzene and diazepine rings [ 4 , 5 ], and they act as positive allosteric modulators of the GABA A receptor complex present in neural tissue [ 6 , 7 ]. They are commonly used in the treatment of sleep and anxiety disorders, with safe use in the short term [ 8 ].…”

Section: Introductionmentioning

confidence: 99%

Benzodiazepines: Drugs with Chemical Skeletons Suitable for the Preparation of Metallacycles with Potential Pharmacological Activity

Silva

Meneghetti

2021

Molecules

View full text Add to dashboard Cite

The synthesis of organometallic compounds with potential pharmacological activity has attracted the attention of many research groups, aiming to take advantage of aspects that the presence of the metal-carbon bond can bring to the design of new pharmaceutical drugs. In this context, we have gathered studies reported in the literature in which psychoactive benzodiazepine drugs were used as ligands in the preparation of organometallic and metal complexes and provide details on some of their biological effects. We also highlight that most commonly known benzodiazepine-based drugs display molecular features that allow the preparation of metallacycles via C-H activation. These organometallic compounds merit further attention regarding their potential biological effects, not only in terms of psychoactive drugs but also in the search for drug replacements, for example, for cancer treatments.

show abstract

“…[9] Benzodiazepines, dinitrogenated benzofused members, are classified depending on the relative position of both nitrogens in the azepine ring as 1,2-, 1,3-, 1,4-1,5-and 2,3-benzodiazepines ( Figure 2). [10] They are suitable drugs to affect the binding to human receptors such as GABA A, [11] AMPA (e. g., Nerisopam), [12] even DNA (e. g., Anthramycin) [13] as well as inhibitors of bromodomains. [14] For instance, 1,4-benzodiazepines are one of the most common drugs owing to their extensive use to treat anxiety, [15] insomnia, [16] or cancer, [17] 1,2-benzodiazepines are highlighted as cancer inhibitors (e. g., CB-6644), [18] and 1,5-benzodiazepines are potent CNS active agents (e. g., Clobazam).…”

Section: Introductionmentioning

confidence: 99%

Recent Advances in Transition‐Metal‐Catalyzed Oxidative Annulations to Benzazepines and Benzodiazepines

2020

View full text Add to dashboard Cite

Benzazepines and benzodiazepines, benzofused seven-membered N-heterocycles, compose an important family of natural products and pharmaceuticals. Although certainly important and effectives, classical synthetic methods of these cyclic compounds involve methodologies that often require multistep procedures, with generation of waste materials and lack of sustainability. By contrast, cycloadditions based on transition metal catalyzed CÀ H bond activations (oxidative annulations) have emerged as appealing strategies for more sustainable synthetic processes. In this review, we focus our attention to describe the state-of-the-art transitionmetal-catalyzed annulations via CÀ H activations to benzazepines and benzodiazepines.

show abstract

Recent advances in synthesis and medicinal chemistry of benzodiazepines

Cited by 69 publications

References 111 publications

Effective microwave-assisted approach to 1,2,3-triazolobenzodiazepinones via tandem Ugi reaction/catalyst-free intramolecular azide–alkyne cycloaddition

Effective microwave-assisted approach to 1,2,3-triazolobenzodiazepinones via tandem Ugi reaction/catalyst-free intramolecular azide–alkyne cycloaddition

Benzodiazepines: Drugs with Chemical Skeletons Suitable for the Preparation of Metallacycles with Potential Pharmacological Activity

Recent Advances in Transition‐Metal‐Catalyzed Oxidative Annulations to Benzazepines and Benzodiazepines

Contact Info

Product

Resources

About