A study on synthesis of benzodiazepine scaffolds using biologically active chalcones as precursors

Bhathiwal, Anirudh Singh; Bendi, Anjaneyulu; Tiwari, Aditi

doi:10.1016/j.molstruc.2022.132649

Cited by 15 publications

(7 citation statements)

References 81 publications

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“…Members of the diazepine family are extensively used for their anticonvulsant, anxiolytic, analgesic, sedative, antidepressant, and hypnotic effects. 162,163 Chalcone 120 and o-phenylenediamine 121 were reported to produce a range of benzodiazepines 122 164,165 (Scheme 40). 4.2.1.6.5.Aza-Michael addition of azides to chalcones to form triazoles…”

Section: Organic and Biomolecular Chemistry Reviewmentioning

confidence: 99%

Synthesis, reactions and application of chalcones: a systematic review

2023

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Section: Organic and Biomolecular Chemistry Reviewmentioning

confidence: 99%

Synthesis, reactions and application of chalcones: a systematic review

2023

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“…The interaction with chiral catalysts shows the relevance of chalcones in the development of novel stereoselective reactions. [48] Apart from Michael additions, chalcones have been extensively used for the synthesis of biologically active 5-and 6membered azaheterocycles, including pyrrole, [49] isoxazole, [50] pyrazole, [51] benzodiazepine, [52] triazole, [53] and pyrimidine. [54] The most common reactants, illustrated in Scheme 6, are among the many that exist for achieving such transformations.…”

Section: Reactivity Of Chalconesmentioning

confidence: 99%

Chalcones, a Privileged Scaffold: Highly Versatile Molecules in [4+2] Cycloadditions

Mastachi-Loza

Ramírez-Candelero²,

Benítez‐Puebla

et al. 2022

Chemistry An Asian Journal

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Chalcones are aromatic ketones found in nature as the central core of many biological compounds. They have a wide range of biological activity and are biogenetic precursors of other important molecules such as flavonoids. Their pharmacological relevance makes them a privileged scaffold, advantageous for seeking alternative therapies in medicinal chemistry. Due to their structural diversity and ease of synthesis, they are often employed as building blocks for chemical transformations. Chalcones have a carbonyl conjugated system with two electrophilic centers that are commonly used for nucleophilic additions, as described in numerous articles. They can also participate in Diels-Alder reactions, which are [4 + 2] cycloadditions between a diene and a dienophile. This microreview presents a chronological survey of studies on chalcones as dienes and dienophiles in Diels-Alder cycloadditions. Although these reactions occur in nature, isolation of chalcones from plants yields very small quantities. Contrarily, synthesis leads to large quantities at a low cost. Hence, novel methodologies have been developed for [4 + 2] cycloadditions, with chalcones serving as a 2π or 4π electron system.

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“…The circumdatins are a group of benzodiazepine alkaloids, first discovered in 1999 from a terrestrial isolate of the fungus A. ochraceus ( Rahbæk and Breinholt, 1999 ). Structurally, the core chemical structure of benzodiazepines is the fusion of a benzene ring and a diazepine ring ( Bhathiwal et al, 2022 ). Until now, thirteen compounds in the circumdatin family have been reported (circumdatins A-N).…”

Section: Secondary Metabolites From a Ochraceusmentioning

confidence: 99%

The Secondary Metabolites and Biosynthetic Diversity From Aspergillus ochraceus

Chen

et al. 2022

Front. Chem.

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Aspergillus ochraceus, generally known as a food spoilage fungus, is the representative species in Aspergillus section Circumdati. A. ochraceus strains are widely distributed in nature, and usually isolated from cereal, coffee, fruit, and beverage. Increasing cases suggest A. ochraceus acts as human and animal pathogens due to producing the mycotoxins. However, in terms of benefits to mankind, A. ochraceus is the potential source of industrial enzymes, and has excellent capability to produce diverse structural products, including polyketides, nonribosomal peptides, diketopiperazine alkaloids, benzodiazepine alkaloids, pyrazines, bis-indolyl benzenoids, nitrobenzoyl sesquiterpenoids, and steroids. This review outlines recent discovery, chemical structure, biosynthetic pathway, and bio-activity of the natural compounds from A. ochraceus.

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A study on synthesis of benzodiazepine scaffolds using biologically active chalcones as precursors

Cited by 15 publications

References 81 publications

Synthesis, reactions and application of chalcones: a systematic review

Synthesis, reactions and application of chalcones: a systematic review

Chalcones, a Privileged Scaffold: Highly Versatile Molecules in [4+2] Cycloadditions

The Secondary Metabolites and Biosynthetic Diversity From Aspergillus ochraceus

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