Versatile synthesis of ibotenic acid analogues with potential for activity at glutamate receptors by use of a homochiral β-lactam template in our ‘ring switching’ strategy

Papadopoulos, Konstantinos; Young, Douglas W.

doi:10.1016/s0040-4039(02)00590-7

Cited by 19 publications

(6 citation statements)

References 10 publications

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“…Several synthetic approaches to the Dihydrobenzo[4,5]imidazo[1,2- a ]pyrimidin-4-one scaffold 1 have been found in the literature [ 17 , 18 , 19 , 20 , 21 , 22 ]. All of them utilize the reactivity of 2-aminobenzimidazole 2 with 1,3-dielectrophiles of several types.…”

Section: Resultsmentioning

confidence: 99%

Generation of 500-Member Library of 10-Alkyl-2-R1,3-R2-4,10-Dihydrobenzo[4,5]imidazo[1,2-α]pyrimidin-4-ones

et al. 2009

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Representative benzimidazopyrimidinones were previously reported to be intercalating antitumor agents. In this work, we used 2-substituted 4,10-dihydrobenzo Dihydrobenzo[4,5]imidazo[1,2-a]pyriminin-4-ones for their diversification by regioselective alkylation. Under the conditions established, the alkylation gave 10-alkyl derivatives which permitted the parallel generation of a 500-member library of the title compounds.

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Section: Resultsmentioning

confidence: 99%

Generation of 500-Member Library of 10-Alkyl-2-R1,3-R2-4,10-Dihydrobenzo[4,5]imidazo[1,2-α]pyrimidin-4-ones

et al. 2009

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“…Besides, the stimulation of base caused the SP isomer of SP-OX-NO 2 to undergoaring-switching( spiral ring to oxazine ring) process to OX isomer. [41][42][43] Interestingly,ametastable cis-MC isomer was involved in the isomerization of MC or SP to OX necessarily.T he new moleculeS P-OX-NO 2 not only preserved the bidirectionals witching property under visible light and base stimuli in solution, but also showed high contrast in both visible and fluorescent color.F urthermore, the application of SP-OX-NO 2 with photochromic and basochromic properties in multicolor rewritable paper was achieved.…”

Section: Introductionmentioning

confidence: 99%

“…Through proper molecular modification with nitro functional groups, both SP and OX isomers could be achieved separately upon exposure to different stimuli to give out different colors. Besides, the stimulation of base caused the SP isomer of SP‐OX‐NO 2 to undergo a ring‐switching (spiral ring to oxazine ring) process to OX isomer . Interestingly, a metastable cis ‐MC isomer was involved in the isomerization of MC or SP to OX necessarily.…”

Section: Introductionmentioning

confidence: 99%

Photo‐/Baso‐Chromisms and the Application of a Dual‐Addressable Molecular Switch

Liu

et al. 2019

Chemistry An Asian Journal

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Twot ypical molecular switches of spiropyran (SP) and benzoxazine (OX) were fused by sharing an indole to achieve an ew dual-addressable molecular switch (SP-OX-NO 2 ). Through properm olecular modification with NO 2 ,t he transformation from merocyanine (MC) to ring-closed SP or ring-closedO Xc an be controlled separately with visible light or base stimuli in solution,r espectively,a nd these processes are verifiedb yU V-vis and NMR spectroscopy as well as control experiments.T he cis-merocyanine( cis-MC) form is in-volved in the basochromic process in solution. DFT calculation suggests that the bidirectional switchingp roperty of the fused SP-OX molecular switch can be controlled separately,w hen the OX isomer is more stable than the deprotonated SP isomer.B ecause of the significant color variations in solution,t he simple dual-addressable switch has been further successfully appliedt oc onstruct am ulticolor reversible display on paper. Scheme1.Illustrationoft he design of the (a) linked dual-switchable system and the (b) fused dual-switchable molecule. (c) Photo-/ baso-chromisms of at ypical (c)nitrospiropyrana nd (d) oxazine. (e) Design and control of the transformation of SP-OX-NO 2 among its multiples tates.

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“…The isoxazole rings are found in natural products like the ibotonic acid – an active constituent of the psychotropic fly agaric mushroom Amanita muscaria – acting as ionotropic and metabotropic (G‐protein linked) glutamate receptor subtypes . (+)‐Neopeltolide was isolated from a taxonomically uncharacterized sponge of the Neopeltidae family, order ‘Lithistida’ collected in deep water of the Jamaica's coast .…”

Section: Introductionmentioning

confidence: 99%

“…[2] The isoxazole rings are found in natural products like the ibotonic acid -an active constituent of the psychotropic fly agaric mushroom Amanita muscaria -acting as ionotropic and metabotropic (G-protein linked) glutamate receptor subtypes. [3] (+)-Neopeltolide was isolated from a taxonomically uncharacterized sponge of the Neopeltidae family, order 'Lithistida' collected in deep water of the Jamaica's coast. [4] The compound was assigned structurally as macrolide with an isoxazole ring on a side chain and showed some similarities in the structure to the compound previously known, leucascandrolide A.…”

Section: Introductionmentioning

confidence: 99%

Isoxazoles: synthesis, evaluation and bioinformatic design as acetylcholinesterase inhibitors

Gutiérrez

Matus

Poblete

et al. 2013

Journal of Pharmacy and Pharmacology

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Our research provided enough evidence of the efficacy of isoxazoles as AChE inhibitors. The isoxazoles were synthesized and evaluated as inhibitors of AChE. The docking study based on a novel series of complexes isoxazole with AChE from Electroporus electricus has demonstrated that the ligand bind is similar to the compounds used as reference. To find new candidates with the isoxazole core that act as inhibitors of AChE, part of the structure of the compound 9 was used for de-novo design. Molecular docking models of the ligand-AChE complexes suggest that the compound 10 is located on the periphery of the AChE active site.

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Versatile synthesis of ibotenic acid analogues with potential for activity at glutamate receptors by use of a homochiral β-lactam template in our ‘ring switching’ strategy

Cited by 19 publications

References 10 publications

Generation of 500-Member Library of 10-Alkyl-2-R1,3-R2-4,10-Dihydrobenzo[4,5]imidazo[1,2-α]pyrimidin-4-ones

Generation of 500-Member Library of 10-Alkyl-2-R1,3-R2-4,10-Dihydrobenzo[4,5]imidazo[1,2-α]pyrimidin-4-ones

Photo‐/Baso‐Chromisms and the Application of a Dual‐Addressable Molecular Switch

Isoxazoles: synthesis, evaluation and bioinformatic design as acetylcholinesterase inhibitors

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