Synthesis of Fused 9,10‐Dihydro‐6H‐Azepino‐ and 9,10‐Dihydro‐6H‐[1,3]Diazepino[1,2‐e]Purines via Ring Closing Metathesis as Antilipid Peroxidation Agents

Thalassitis, Andreas; Hadjipavlou‐Litina, Dimitra; Litinas, Κonstantinos E.

doi:10.1002/jhet.2049

Cited by 9 publications

(7 citation statements)

References 59 publications

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“…It could be easily replaced by their 5‐ and 6‐membered ring analogues. Compounds having hypoglycemic, 310 diuretic, 311 antilipidic peroxidation, 312 andantidyslipidemia 313 activities are displayed in Figure 39.…”

Section: Activity On Unknown Targetsmentioning

confidence: 99%

1,3‐Diazepine: A privileged scaffold in medicinal chemistry

Malki

Martinez

Masurier

2021

Medicinal Research Reviews

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Privileged structures have been widely used as effective templates for drug discovery. While benzo‐1,4‐diazepine constitutes the first historical example of such a structure, the 1,3 analogue is just as rich in terms of applications in medicinal chemistry. The 1,3‐diazepine moiety is present in numerous biological active compounds including natural products, and is used to design compounds displaying a large range of biological activities. It is present in the clinically used anticancer compound pentostatin, in several recent FDA approved β‐lactamase inhibitors (e.g., avibactam) and also in coformycin, a natural product known as a ring‐expanded purine analogue displaying antiviral and anticancer activities. Several other 1,3‐diazepine containing compounds have entered into clinical trials. This heterocyclic structure has been and is still widely used in medicinal chemistry to design enzyme inhibitors, GPCR ligands, and so forth. This review endeavours to highlight the main use of the 1,3‐diazepine scaffold and its derivatives, and their applications in medicinal chemistry, drug design, and therapy. We will focus more particularly on the development of enzyme inhibitors incorporating this scaffold, with a strong emphasis on the molecular interactions involved in the inhibition mechanism.

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Section: Activity On Unknown Targetsmentioning

confidence: 99%

1,3‐Diazepine: A privileged scaffold in medicinal chemistry

Malki

Martinez

Masurier

2021

Medicinal Research Reviews

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“…[21] Thalassitis et al used lower concentrations of the catalyst (5 mol %), but a longer reaction time was necessary to obtain compounds 47 in high yields (Scheme 11C). [22] 2.2. Two-bond formation: intermolecular reactions 1,3-Diazepines can also be made by intermolecular reactions involving the simultaneous formation of two bonds in a single transformation.…”

Section: Cà C Bond Formation Between Positions 5 Andmentioning

confidence: 99%

“…When a double bond is present in the diazepine ring, another approach is possible. A ring closure metathesis (RCM) can then occur between two alkene groups, using a Grubb's first or second [21,22] generation catalyst. The metathesis reaction is compatible with various functions and was used to prepare numerous substituted 1,3-diazepines.…”

Section: Cà C Bond Formation Between Positions 5 Andmentioning

confidence: 99%

1,3‐Diazepine Derivatives: Strategies for Synthesis

2021

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“…The biological importance of naturally occurring purines has led to an interest in studies of the biological activities of synthetically modified purines . A wide range of purine derivatives, such as purine, purines nucleosides, and their analogs, have been developed, and have exhibited potential activity as enzyme inhibitors , cytotoxic , antiviral , antihyperglycemic , immunostimulator , anticonvulsant , antimalarial , anticancer , anti‐inflammatory , anti‐lipid peroxidation , antifungal , and antibacterial activities.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Antibacterial Activity of Novel Substituted Purine Derivatives

Gao

Hong

et al. 2015

Journal of Heterocyclic Chem

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A series of novel N‐substituted‐2‐(6‐morpholino‐9H‐purin‐9‐yl)acetamide and 4‐(9‐((5‐substituted‐1,3,4‐oxadiazole/thiadiazole‐2‐yl)methyl)‐9H‐purin‐6‐yl)‐morpholine derivatives were synthesized and evaluated their antibacterial activities against rice bacterial leaf blight and tobacco bacterial wilt caused by Xanthomonas oryzae pv. oryzae (Xoo) and Ralstonia solanacearum (R. solanacearum) via the turbidimeter test in vitro. Antibacterial bioassay indicated that most compounds demonstrated good inhibitory effect against Xoo and R. solanacearum. Especially, compound 6a demonstrated the best inhibitory effect against Xoo with half‐maximal effective concentration (EC50) value of 8.39 μg/mL, which was even better than those of commercial agents Bismerthiazol and Thiodiazole copper. The synthesized purine derivatives containing amide and 1,3,4‐oxadiazole/thiadiazole moieties exhibited excellent antibacterial activities against Xanthomonas oryzae pv. oryzae and R. solanacearum in vitro.

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Synthesis of Fused 9,10‐Dihydro‐6H‐Azepino‐ and 9,10‐Dihydro‐6H‐[1,3]Diazepino[1,2‐e]Purines via Ring Closing Metathesis as Antilipid Peroxidation Agents

Abstract: New compounds are tested as inhibitors of lipid peroxidation.

Cited by 9 publications

References 59 publications

1,3‐Diazepine: A privileged scaffold in medicinal chemistry

1,3‐Diazepine: A privileged scaffold in medicinal chemistry

1,3‐Diazepine Derivatives: Strategies for Synthesis

Synthesis and Antibacterial Activity of Novel Substituted Purine Derivatives

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