Quinolone antibacterials: preparation and activity of bridged bicyclic analogues of the C7-piperazine

Kiely, John S.; Hutt, Marland P.; Culbertson, Townley P.; Bucsh, Ruth A.; Worth, Donald F.; Lesheski, Lawrence E.; Gogliotti, Rocco D.; Sesnie, Josephine C.; Solomon, Marjorie S.; Mich, Thomas F.

doi:10.1021/jm00106a029

Cited by 17 publications

(6 citation statements)

References 5 publications

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“…Rigid bicycles are relevant ring systems in medicinal chemistry. , Access to the bridged bicyclic sulfoximine skeleton 9 required the synthesis of the bridged bicyclic thiomorpholine 10 , which was constructed according to a procedure described in the literature (Scheme ). Starting with commercially available N -( tert -butoxycarbonyl)pyrrole 11 , bis-carbomethoxylation occurred under the conditions developed by Donohoe and co-workers and gave diester 12 in 53% yield.…”

Section: Resultsmentioning

confidence: 99%

Polycyclic Sulfoximines as New Scaffolds for Drug Discovery

et al. 2018

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The design and synthesis of three novel polycyclic scaffolds containing sulfoximines are presented in this work, which exemplify that sulfoximines represent a real opportunity for the discovery of new drug candidates. Additionally, the structures present at least two points of diversification and contain a high level of sp-character, hence being very interesting 3D scaffolds. The compounds synthesized were added to the compound collection of the European Lead Factory.

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Section: Resultsmentioning

confidence: 99%

Polycyclic Sulfoximines as New Scaffolds for Drug Discovery

et al. 2018

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“…Therefore, in spite of bridge-imparted rigidity, the hexagonal ring of 2,5-diazabicyclo[2.2.1]heptane can be affected by some geometric distortions. The framework of 2,5-diazabicyclo[2.2.1]heptane is frequently considered to be the bicyclic counterpart of piperazine where the occurrence of the C1-C7-C4 bridge imparts rigidity to the hexagonal ring (Kiely et al, 1991;Beinat et al, 2013;. It is worth noting that the bicyclic bridged structure of 2,5-diazabicyclo[2.2.1]heptane determines the boat conformation of its cage (Fig.…”

Section: Structural Commentarymentioning

confidence: 99%

Crystal structure of (1S,4S)-2,5-diazoniabicyclo[2.2.1]heptane dibromide

Britvin

Rumyantsev

2017

Acta Cryst E

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The cage of 2,5-diazabicyclo[2.2.1]heptane is frequently employed in synthetic chemistry as a rigid bicyclic counterpart of the piperazine ring. The 2,5-diazabicyclo[2.2.1]heptane scaffold is incorporated into a variety of compounds having pharmacological and catalytic applications. The unsubstituted parent ring of the system, 2,5-diazabicyclo[2.2.1]heptane itself, has not been structurally characterized. We herein report on the molecular structure of the parent ring in (1S,4S)-2,5-diazoniabicyclo[2.2.1]heptane dibromide, C 5 H 12 N 2 2+ Á2Br À . The asymmetric unit contains two crystallographically independent cages of 2,5-diazabicyclo[2.2.1]heptane. Each cage is protonated at the two nitrogen sites. The overall charge balance is maintained by four crystallographically independent bromide ions. In the crystal, the components of the structure are linked via a complex three-dimensional network of N-HÁ Á ÁBr hydrogen bonds.

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“…All the derivatives showed similar potency as compared with the parent 7‐piperazinyl analogs. The best activity was found to be associated with endo‐7‐(3‐amino‐8‐azabicyclo[3.2.1]oct‐8‐yl)‐1‐cyclopropyl‐6,8‐difluoro‐1,4‐dihydro‐4‐oxo‐3‐quinolinecarboxylic acid ( 40 ), which displayed activity surpassing that of the piperazine parent compound . Esters of 2‐methyl‐1,8‐naphthyridine‐3‐carbamic acid ( 41 ) have exhibited antifungal properties against Alternaria alternata , Fusarium oxysporum , and Curvularia lunata .…”

Section: Biological Properties Of 18‐naphthyridine Derivativesmentioning

confidence: 99%

1,8‐Naphthyridine Derivatives: A Review of Multiple Biological Activities

Madaan

Verma

Kumar

et al. 2015

Archiv der Pharmazie

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The 1,8-naphthyridine group of compounds have gained special attention of researchers on account of their demonstrating a variety of interesting biological activities. A wide range of biological properties establishes them as potent scaffolds in therapeutic and medicinal research. The broad spectrum of activities primarily includes antimicrobial, antiviral, anticancer, anti-inflammatory, and analgesic activities. 1,8-Naphthyridine derivatives have also exhibited potential applications in neurological disorders such as Alzheimer's disease, multiple sclerosis, and depression. In addition, these synthetic derivatives have been found to possess activities such as anti-osteoporotic (α(v)β(3) antagonists), anti-allergic, antimalarial, gastric antisecretory, bronchodilator, anticonvulsant, anti-hypertensive, platelet aggregation inhibition, anti-oxidant, EGFR inhibition, protein kinase inhibition, ionotropic agent, β-3 antagonist, MDR modulator, adenosine receptor agonist, adrenoceptor antagonist, and pesticide activities. In spite of the widespread application of the 1,8-naphythyridine scaffolds, only a limited number of review articles are available till date. In this review, we attempt to compile and discuss the key data available in the literature for the multiple biological activities of 1,8-naphthyridine derivatives, in a chronological manner. This review compilation (with 199 references) may be helpful in understanding the diverse biological properties of 1,8-naphthyridines and provide insights into their mechanism of action. This may direct future research in the synthesis of new derivatives and exploring this scaffold for other possible biological activities.

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Quinolone antibacterials: preparation and activity of bridged bicyclic analogues of the C7-piperazine

Cited by 17 publications

References 5 publications

Polycyclic Sulfoximines as New Scaffolds for Drug Discovery

Polycyclic Sulfoximines as New Scaffolds for Drug Discovery

Crystal structure of (1S,4S)-2,5-diazoniabicyclo[2.2.1]heptane dibromide

1,8‐Naphthyridine Derivatives: A Review of Multiple Biological Activities

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