1,4-Diazepines: A Review on Synthesis, Reactions and Biological Significance

Abstract

Background: 1,4-Diazepines are two nitrogen containing seven membered heterocyclic compounds and associated with a wide range of biological activities. Due to its medicinal importance, scientists are actively involved in the synthesis, reactions and biological evaluation of 1,4-diazepines since number of decades. Objective: The primary purpose of this review is to discuss the synthetic schemes and reactivity of 1,4- diazepines. This article also describes biological aspects of 1,4-diazepine derivatives, that can be usefully exploited for the pharmaceutical sector. Conclusion: This review summarizes the abundant literature on synthetic routes, chemical reactions and biological attributes of 1,4-diazepine derivatives. We concluded that 1,4-diazepines have significant importance due to their biological activities like antipsychotic, anxiolytic, anthelmintic, anticonvulsant, antibacterial, antifungal and anticancer. 1,4-diazepine derivatives with significant biological activities could be explored for potential use in the pharmaceutical industries.

One-Pot Four-Component Coupling Approach to Polyheterocycles: 6H-Furo[3,2-f]pyrrolo[1,2-d][1,4]diazepine

“…In summary, a one-pot four-component coupling of readily available starting materials under eco-friendly conditions allowed rapid access to a new 5–7–5 heterocyclic chemical space through a domino process where five new bonds (three C–C, one C–O, and one C–N) were formed with consecutive construction of furan and diazepine. Novel heterocyclic scaffolds described herein should be useful for further biochemical exploration, given the importance of fused diazepine ring systems . Further synthetic efforts to generate new polyheterocyclic chemical space through multicomponent domino reactions as well as the biological application of the derivatives are currently in progress.…”

One-pot strategy to synthesize seven–membered 1,4-diazepine heterocyclic scaffolds assisted by zinc oxide nanoparticles as heterogeneous catalytic support system

“…[1][2][3][4][5][6][7][8][9][10] Diazepines are considered the biologically active epitope antigenic determinant and the useful building blocks in the construction of various pharmaceutically significant lead molecules. 11 Their derivatives are imperious types of compounds that have been widely explored for pharmacological activities such as antibacterial, antiviral, antioxidant, anticancer, antitumor [12][13] , antiparasitic 14 , antiemetic, antihistaminic, spasolytic 15 , antagonistic, anticonvulsive, anti-inflammatory and anti-fungicidal. [14][15][16] Some of them are an integral component of antimalarial drug therapy, anti-HIV, and other various pharmaceutical applications.…”

“…11 Their derivatives are imperious types of compounds that have been widely explored for pharmacological activities such as antibacterial, antiviral, antioxidant, anticancer, antitumor [12][13] , antiparasitic 14 , antiemetic, antihistaminic, spasolytic 15 , antagonistic, anticonvulsive, anti-inflammatory and anti-fungicidal. [14][15][16] Some of them are an integral component of antimalarial drug therapy, anti-HIV, and other various pharmaceutical applications. 17 Certain drugs embracing azepine nucleus are used for the treatment of Parkinson's and Alzheimer's disease since they exhibit anticonvulsant activity and may be used as tranquilizers.…”

“…23 Therefore, keeping in view such a wide range of pharmaceutical profiles and industrial applications associated with such an important seven-membered aza-scaffold, the development of mild and efficient protocols for their preparation continues to be a challenging endeavor for synthetic organic chemists. [24][25] Some commonly reported literature methods include cycloaddition reactions, 26 imino-annulation, 27 ring-closing metatheses [RCM], 28, and coupling reactions. [29][30][31] However a large number of methods reported in the literature suffer from several bottlenecks viz the use of drastic conditions, lesser yields, and typical product isolation procedures.…”

Copper‐Catalyzed Coupling of Arylethynes and Aryltriazenes to Access Libraries of 1,2‐Diketones and Their Efficacy in Synthesis of Triaryloxazoles, Imidazoles and Diaryl‐Diazepines

“…There is ongoing interest in 1,4-diazepine derivatives due to their rich biological activity and medicinal application. [22] The 2,3-diaryl-6,7-dihydro-5H-1,4-diazepines possess anticancer and antiplatelet activities. [23] Condensation of diaryl-1,2-diketones with trimethylenediamine represents a logical method for the synthesis of these compounds, however limited studies have been reported and the yields are generally modest to poor.…”