Synthesis of Highly Functionalised Enantiopure Bicyclo[3.2.1]- octane Systems from Carvone

Abad, Antonio; Agulló, Consuelo; Cuñat, Ana C.; Alfonso, Ignacio; Navarro, Ismael; Vera, Noelia

doi:10.3390/90500287

Cited by 12 publications

(6 citation statements)

References 14 publications

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“…Thus, heating a solution of 11 in toluene at 190 °C gave 12 as a single product. The addition of propylene oxide as acid scavenger to the reaction mixture proved vital to prevent hydrolysis of the starting material over the course of the reaction . Subsequent in situ reduction of the ester with DIBAL-H and quenching with aqueous HCl yielded hydroxyketone 3 (85%).…”

Section: Resultsmentioning

confidence: 99%

Total Synthesis of (−)-Mitrephorone A

et al. 2018

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The first synthesis of (−)-mitrephorone A is disclosed along with discussion and study of synthetic strategies. The natural product includes a highly congested hexacyclic ent-trachylobane diterpenoid framework featuring a rare, embedded oxetane. The synthetic analysis presented dissects a number of approaches for the synthesis of the central oxetane, including carbonyl-olefin photocycloadditions, Prins-type cyclizations, and oxidative ring closures. In the successful route, three [4 + 2] cycloadditions enable rapid construction of all carbocycles. A novel late-stage oxidative cyclization of a hydroxy diosphenol with Koser's reagent furnishes the pivotal oxetane moiety.

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Section: Resultsmentioning

confidence: 99%

Total Synthesis of (−)-Mitrephorone A

et al. 2018

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“…The bicyclo[3.2.1]octane skeleton is a common subunit in many natural products. It is present in diterpene families of compounds, such as the kaurenes and the gibberellins, and also in many sesquiterpenes [13]. One of the more interesting properties of the bicyclo[3.2.1]octane skeleton is its rigidity, which promotes specific coordination of two or more ligands on it, which can be of great value to medicinal chemists in the search for biological activity [14][15][16][17].…”

Section: Introductionmentioning

confidence: 99%

“…Antioxidant properties of these compounds (1)(2)(3)(4)(5)(6)(7)(8)(9)(10)(11)(12)(13)(14)(15) were investigated as a part of this study but were proven to be negligible and hence will not be discussed in great detail. The table with the results is given in the Supporting material (Table S1).…”

Section: Introductionmentioning

confidence: 99%

Acetyl- and butyrylcholinesterase inhibitory activity of selected photochemicallysynthesized polycycles

Šagud¹,

Škorić²,

Vuk³

et al. 2019

Turk J Chem

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Alzheimer's disease (AD) is a progressive neurodegenerative disorder and the main cause of dementia in the elderly population. Since the treatment of AD has been associated with the activity of acetylcholinesterase (AChE) and butyrylcholinesterase (BChE), their inhibitors remain the main focus of AD investigations. In this study we evaluated cholinesterase inhibitory activity of 14 bicyclo[3.2.1]octene/octadiene derivatives and naturally occurring sesquiterpene alcohol cedrol. These 14 compounds have been efficiently and ecologically prepared by a photochemical approach in batch photochemical reactors. Various compounds with the bicyclo[3.2.1]octene skeleton have already been successfully evaluated for treatment of central nervous system disorders and AD. Among the tested polycyclic derivatives, compounds 4-[(9 S)-tricyclo[6.3.1.0 2,7 ]dodeca-2,4,6,10-tetraen-9-yl]pyridine (3) and (11 S)-11-(4-chlorophenyl)-12-[(E)-2-(4-chlorophenyl)ethenyl]tricyclo[6.3.1.0 2,7 ]dodeca-2,4,6,9-tetraene (6) showed the best inhibitory activity on BChE (IC 50 = 8.8 µ M) and AChE (IC 50 = 17.5 µ M), respectively.

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“…[2] Purine analogues, pyrimidine analogues and antifolates are cytostatic compounds that inhibit cell proliferation and are used in cancer treatment, as well as for autoimmune disorders. [3][4][5] In general the oxazole moiety [6] and the bicyclo[3.2.1]-core [7] are important building blocks for the synthesis of many biologically active molecules. Some of the fused polycyclic compounds with the oxazole ring have shown antibacterial and antituberculosis [8] activities as well as anticancer activitiy [9] and some have been tested for antioxidant activity.…”

Section: Introductionmentioning

confidence: 99%

Antiinflammatory and Antiproliferative Activity of Naphthoxazole, Fused Hetero-benzoxazole and Bridged Benzobicyclic Photoproducts

Šagud

Ratković

Cedilak

et al. 2019

Croat. chem. acta (Online)

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Biological activity of naphthoxazoles, fused hetero-benzoxazoles and benzobicyclo[3.2.1]-derivatives was investigated in proliferation and inflammation based assays. The tested compounds were prepared by photocylization or photocycloaddition reactions. Effect of compounds on proliferation of several cancer cell lines was determined by measuring cell metabolic activity through time. Lipopolysaccharide (LPS) stimulation of peripheral blood mononuclear cells (PBMC) was used to investigate antiinflammatory properties of the compounds. Several naphthoxazoles and fused hetero-benzoxazoles inhibited TNFα protein expression in LPS stimulated PBMC, indicating possible antiinflammatory role which would be interesting to further investigate. Physico-chemical properties of tested compounds have been also studied using chromatographic lipophilicity measure, chrom logD and logP was calculated as the importance of physico-chemical properties of compounds at early stage of discovery of new drugs is well established. The similarities in structure and activity of some representative compounds affirm the need to further address their antiinflammatory properties.

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Synthesis of Highly Functionalised Enantiopure Bicyclo[3.2.1]- octane Systems from Carvone

Cited by 12 publications

References 14 publications

Total Synthesis of (−)-Mitrephorone A

Total Synthesis of (−)-Mitrephorone A

Acetyl- and butyrylcholinesterase inhibitory activity of selected photochemicallysynthesized polycycles

Antiinflammatory and Antiproliferative Activity of Naphthoxazole, Fused Hetero-benzoxazole and Bridged Benzobicyclic Photoproducts

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