Medium-ring aminocyclitols: a concise synthesis of nine-membered aminocarbasugar analogs and the solid-state supramolecular architectures of two key precursors

Mehta, Goverdhan; Mohanrao, Raja; Katukojvala, Sreenivas; Landais, Yannick; Sen, Saikat

doi:10.1016/j.tetlet.2011.03.141

Cited by 19 publications

(7 citation statements)

References 35 publications

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“…Deprotonation of 22 with barium hydroxide followed by the addition of aldehyde 21 gave enone 26 . Removal of the acetonide protecting group in 26 with HCl in H 2 O/THF gave authentic ( R )-niphatenone B ( 8 ) . Repeating the synthesis with ( R )-4-hydroxymethyl-2,2-dimethyl-1,3-dioxolane as the starting material gave authentic ( S )-niphatenone B ( 4 ).…”

Section: Synthesis Of Niphatenones a (3) And B (4)mentioning

confidence: 99%

“…The niphatenones contain enone functionalities that are potential Michael acceptors. In order to probe if covalent bonding of the niphatenones to the AR played a role in their biological activity, ( R )-dihydroniphatenone B ( 28 ) was prepared from acetonide 26 via catalytic hydrogenation to give the saturated ketone 27 , followed by acid catalyzed hydrolysis of the acetonide as shown in Scheme …”

Section: Synthesis Of Analogues Of Niphatenones a And Bmentioning

confidence: 99%

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Niphatenones, Glycerol Ethers from the Sponge Niphates digitalis Block Androgen Receptor Transcriptional Activity in Prostate Cancer Cells: Structure Elucidation, Synthesis, and Biological Activity

et al. 2011

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Extracts of the marine sponge Niphates digitalis collected in Dominica showed strong activity in a cell-based assay designed to detect antagonists of the androgen receptor (AR) that could act as lead compounds for the development of a new class of drugs to treat castration recurrent prostate cancer (CRPC). Assay-guided fractionation showed that niphatenones A (3) and B (4), two new glycerol ether lipids, were the active components of the extracts. The structures of 3 and 4 were elucidated by analysis of NMR and MS data and confimed via total synthesis. Biological evaluation of synthetic analogues of the niphatenones has shown that the enantiomers 7 and 8 are more potent than the natural products in the screening assay and defined preliminary SAR for the new AR antagonist pharmacophore, including the finding that the Michael acceptor enone functionality is not required for activity. Niphatenone B (4) and its enantiomer 8 blocked androgen-induced proliferation of LNCaP prostate cancer cells but had no effect on the proliferation of PC3 prostate cancer cells that do not express functional AR, consistent with activity as AR antagonists. Use of the propargyl ether 44 and Click chemistry showed that niphatenone B binds covalently to the activation function-1 (AF1) region of the AR N-terminus domain (NTD).

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Section: Synthesis Of Niphatenones a (3) And B (4)mentioning

confidence: 99%

Section: Synthesis Of Analogues Of Niphatenones a And Bmentioning

confidence: 99%

Niphatenones, Glycerol Ethers from the Sponge Niphates digitalis Block Androgen Receptor Transcriptional Activity in Prostate Cancer Cells: Structure Elucidation, Synthesis, and Biological Activity

et al. 2011

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“…Many methods have been previously reported for the synthesis of aminocyclitols containing five- and six-membered rings, along with their diverse biological activities [ 1 – 3 16 – 26 ]. However, only a limited number of synthetic methods are available for the synthesis of seven- [ 27 – 28 ], eight- [ 29 – 38 ], and nine- [ 35 ] membered aminocyclitols. Therefore, we were inspired to work on the development of the first synthesis of some C8-amino- and chloro-substituted cyclitols.…”

Section: Introductionmentioning

confidence: 99%

Stereoselective syntheses of 3-aminocyclooctanetriols and halocyclooctanetriols

Salamci¹,

Zozik²

2021

Beilstein J. Org. Chem.

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The efficient synthesis of two new stereoisomeric 3-aminocyclooctanetriols and their new halocyclitol derivatives starting from cis,cis-1,3-cyclooctadiene are reported. Reduction of cyclooctene endoperoxide, obtained by photooxygenation of cis,cis-1,3-cyclooctadiene, with zinc yielded a cyclooctene diol followed by acetylation of the hydroxy group, which gave dioldiacetate by OsO4/NMO oxidation. The cyclooctane dioldiacetate prepared was converted to the corresponding cyclic sulfate via the formation of a cyclic sulfite in the presence of catalytic RuO4. The reaction of this cyclic sulfate with a nucleophilic azide followed by the reduction of the azide group provided the target, 3-aminocyclooctanetriol. The second key compound, bromotriol, was prepared by epoxidation of the cyclooctenediol with m-chloroperbenzoic acid followed by hydrolysis with HBr(g) in methanol. Treatment of bromotriol with NaN3 and the reduction of the azide group yielded the other desired 3-aminocyclooctanetriol. Hydrolysis of the epoxides with HCl(g) in methanol gave stereospecifically new chlorocyclooctanetriols.

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“…Furthermore, there are covalent‐type glycosidase inhibitors, including naturally occurring carbohydrates like acarbose and nojirimycin, as well as hydroxy‐ and amino‐substituted bioactive aminoglicosides . The nuclei of these inhibitors are involved in many biological processes, from cellular communication to inhibition of glucosidase …”

Section: Introductionmentioning

confidence: 99%

rac‐ and meso‐Cyclohexanoids: Their α‐, β‐glycosidases, antibacterial, antifungal activities, and molecular docking studies

Karakılıç

Baran

Öğütçü

et al. 2020

Archiv der Pharmazie

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An efficient and versatile synthesis method has been postulated for hydroxymethylated rac‐ and meso‐cyclohexanoid derivatives. The synthesis of these stereoisomers was achieved easily with traditional methods using hexahydroisobenzofuran 6, prepared from commercially available cis‐hydrophthalic anhydride. The study, involving diastereoselective epoxidation and cis‐hydroxylation, was conducted to obtain epoxy‐, cis‐, and trans‐diol‐furans 7, 8, and 9. After sulfamic acid‐catalyzed ring‐opening reaction of the epoxide and furan rings, rac‐ and meso‐tetraacetates 14, 15, and 16 were afforded. Hydrolysis of acetate groups with ammonia in absolute methanol yielded the desired tetrols rac‐17, meso‐18, and meso‐19. All structures, after purification by chromatographic methods and elucidation by spectral techniques, were screened against α‐ and β‐glucosidases. Compounds 7, 8, 10, 17, 18, and 19 were also evaluated for their antibacterial and antifungal activity against some selected synthesized compounds with varying degrees of inhibitory effects on the growth of different pathogenic microorganisms by the well‐diffusion method. In addition, Saccharomyces cerevisiae α‐glucosidase molecular modeling studies were performed for all rac‐ and meso‐compounds 7, 8, 10, 17, 18, and 19.

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Medium-ring aminocyclitols: a concise synthesis of nine-membered aminocarbasugar analogs and the solid-state supramolecular architectures of two key precursors

Cited by 19 publications

References 35 publications

Niphatenones, Glycerol Ethers from the Sponge Niphates digitalis Block Androgen Receptor Transcriptional Activity in Prostate Cancer Cells: Structure Elucidation, Synthesis, and Biological Activity

Niphatenones, Glycerol Ethers from the Sponge Niphates digitalis Block Androgen Receptor Transcriptional Activity in Prostate Cancer Cells: Structure Elucidation, Synthesis, and Biological Activity

Stereoselective syntheses of 3-aminocyclooctanetriols and halocyclooctanetriols

rac‐ and meso‐Cyclohexanoids: Their α‐, β‐glycosidases, antibacterial, antifungal activities, and molecular docking studies

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