New derivatives and ring systems of annulated pyrrolobenzo[1,4]diazepines

Schmidt, Andreas; Lindner, Anika Sabine; Shilabin, Abbas Gholipour; Nieger, Martin

doi:10.1016/j.tet.2007.12.044

Cited by 15 publications

(7 citation statements)

References 44 publications

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“…[4b, 7] However, unlike the related oxazolones, new asymmetric methods involving imidazolidinones are scarce in the literature. There have been several recent reports involving the use of alkylidene oxazolones in enantioselective processes, [8] likely due the ability to access unnatural amino acids from these readily available precursors.…”

mentioning

confidence: 99%

Enantioselective N‐Heterocyclic Carbene Catalyzed Annulation Reactions with Imidazolidinones

McCusker

Scheidt

2013

Angew Chem Int Ed

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confidence: 99%

Enantioselective N‐Heterocyclic Carbene Catalyzed Annulation Reactions with Imidazolidinones

McCusker

Scheidt

2013

Angew Chem Int Ed

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“…Preparation of 1-(2-methyl-3H-benzo[b] [1,4]diazepin-4-yl) hydrazine (6). A mixture of 2 (1.92 g, 0.01 mol) and hydrazine hydrate (0.5 mL, 0.01 mol) in 30 mL ethanol containing 0.1 mL triethylamine was refluxed at 80 C for 4 h. The reaction mixture was concentrated under reduced pressure, and the residue washed with acidified cold water and then triturated with methanol.…”

Section: Resultsmentioning

confidence: 99%

“…Benzodiazepines form a well-known and widely applied class of biologically active compounds and are representatives of the family of privileged structures (PBDs) that can recognize and bind to specific sequences of DNA. They are potential regulators of gene expression with possible application as therapeutic agents in treatment of genetic disorders including cancer [6]. Heterocyclic scaffolds containing the diazepine moiety, which show additional bioactivities, oral fibrinogen antagonists are also interesting compounds [7,8].…”

Section: Introductionmentioning

confidence: 99%

Synthesis of Some New Benzo[b][1,4]diazepine Based Heterocycles

Azab

2013

Journal of Heterocyclic Chem

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Preparation of 4‐chloro‐3H‐benzo[b][1,4]diazepine‐2‐carbaldehyde 5, which is used as a key intermediate in the synthesis of chalcones derivatives, via its condensation with some aromatic acetophenone derivatives under ethanol piperidine condition was described. Also illustrated was the reaction of such chalcones with available nucleophilics and reagents of active methylene group to afford new series of fused and isolated pyrazoles, isoxazolines pyrimidines, pyridines, triazolo[1,5‐a]pyrimidines, benzo[1,4]oxa(thia)zepines, and pyrido[1,2‐a]benzimidazoles incorporating 4‐chloro‐3H‐benzo[b][1,4]diazepine moiety, which have a potential pharmaceutical interest. Furthermore, condensation reaction of 4‐chloro‐3H‐benzo[b][1,4]diazepine‐2‐carbaldehyde with aromatic amine derivatives to afford the Schiff's bases was described. The C═N double bond of the latter compounds has been reacted with chloroketene to give β‐lactams and with sulfanylacetic acid to give the 2‐(4‐oxo‐1,3‐thiazolidinyl)‐substituted derivative. The structures of the newly prepared compounds were established by elemental analysis, IR, MS, and 1H NMR spectral analysis.

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“…In continuation to our previous attempts to discover novel bioactive PBDs and improvement of their efficacy [ 13 , 14 , 15 , 16 ], we became interested in the synthesis and characterization of a new class of tetracyclic PBD derivatives with fused heterocyclic moiety. We evaluated a panel of thirteen novel PBD's for in vitro cytotoxicity using NCI-60 cell lines screening.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and biological activity of fused tetracyclic Pyrrolo[2,1-c][1,4]benzodiazepines

Annor-Gyamfi

Jarrett

Osazee

et al. 2018

Heliyon

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Cancer remains the second major cause of death in the world. Thus, there is a pressing need to identify potential synthetic route for the development of novel anticancer agents which will serve as lead compounds to effectively combat this life-threatening epidemic. Pyrrolo[2,1-c][1,4]benzodiazepines (PBDs) have sparked a great interest as lead compounds because of their cancerostatic and anti-infective properties. The twisted molecular structure of PBD analogs provides both helical and chiral elements. In an effort to expand novel PBDs that interact with the key exocyclic amino group of the DNA-guanine base, we hypothesized that construction of a fused cyclic active system, would likely serve as an electrophilic site when compared to traditional electrophilic C11-N10 imine group. To examine our theory, we report herein the synthesis and cell viability/cytotoxicity of a series of PBD analogs using NCI-60 cell lines screening. Thus, compounds 1–13 were synthesized and fully characterized. The selected PBDs were found to have marginal inhibition of growth, up to 30%, for certain cell lines.

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New derivatives and ring systems of annulated pyrrolobenzo[1,4]diazepines

Cited by 15 publications

References 44 publications

Enantioselective N‐Heterocyclic Carbene Catalyzed Annulation Reactions with Imidazolidinones

Enantioselective N‐Heterocyclic Carbene Catalyzed Annulation Reactions with Imidazolidinones

Synthesis of Some New Benzo[b][1,4]diazepine Based Heterocycles

Synthesis and biological activity of fused tetracyclic Pyrrolo[2,1-c][1,4]benzodiazepines

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