Synthesis on N-Alkylated Maleimides

Clevenger, Randell C.; Turnbull, Kenneth

doi:10.1080/00397910008087165

Cited by 43 publications

(46 citation statements)

References 46 publications

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“…1). The protected maleimide31 was attached to an ω-substituted alkylene chain through reaction with Br(CH 2 ) n OH. The hydroxyl group of the resulting intermediate was then substituted with bromide and subsequently converted to pyridinium or piperidine.…”

Section: Resultsmentioning

confidence: 99%

Novel Selective and Irreversible Mosquito Acetylcholinesterase Inhibitors for Controlling Malaria and Other Mosquito-Borne Diseases

Dou

Park

Rana

et al. 2013

Sci Rep

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We reported previously that insect acetylcholinesterases (AChEs) could be selectively and irreversibly inhibited by methanethiosulfonates presumably through conjugation to an insect-specific cysteine in these enzymes. However, no direct proof for the conjugation has been published to date, and doubts remain about whether such cysteine-targeting inhibitors have desirable kinetic properties for insecticide use. Here we report mass spectrometric proof of the conjugation and new chemicals that irreversibly inhibited African malaria mosquito AChE with bimolecular inhibition rate constants (kinact/KI) of 3,604–458,597 M−1sec−1 but spared human AChE. In comparison, the insecticide paraoxon irreversibly inhibited mosquito and human AChEs with kinact/KI values of 1,915 and 1,507 M−1sec−1, respectively, under the same assay conditions. These results further support our hypothesis that the insect-specific AChE cysteine is a unique and unexplored target to develop new insecticides with reduced insecticide resistance and low toxicity to mammals, fish, and birds for the control of mosquito-borne diseases.

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Section: Resultsmentioning

confidence: 99%

Novel Selective and Irreversible Mosquito Acetylcholinesterase Inhibitors for Controlling Malaria and Other Mosquito-Borne Diseases

Dou

Park

Rana

et al. 2013

Sci Rep

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“…However, the ring closure is often inefficient and thus only poor yields of the desired maleimide derivatives are obtained. A newly developed approach [21] utilizes nucleophilic substitution of alkyl bromide with a maleimide (PM) protected with furan by a Diels-Adler reaction [22,23] and subsequent deprotection to afford a high yield of N-substituted maleimide. We used w-bromoundecene and PM as starting materials (see Scheme 2b), and obtained a high yield (80 %) of 11-maleimido-undecene (MU), which is comparable with the yields reported.…”

Section: Resultsmentioning

confidence: 99%

“…The white crystalline product that separated after cooling to 4 8C was recrystallized with ethyl acetate to yield the product (0.25 g; 20.7 %). Protected maleimido-undecene (PMU): 11-(3,6-endoxo-D 4 -tetrahydrophthalimide)undecene: [21] In an oven-dried (at 200 8C for 12 h, closed by a stopper and subsequently cooled to room temperature) round-bottom flask, PM (0.131 g, 0.8 mmol) and BU (0.2 mL, 0.8 mmol) were dissolved in anhydrous DMF (8 mL, dried over 4 molecular sieve) along with K 2 CO 3 (0.55 g, 5 equiv). The entire reaction mixture was stirred under N 2 at 55 8C for 2.5 h. The entire reaction mixture was diluted with ethyl acetate (150 mL), washed (water, saturated sodium bicarbonate solution), and dried over Na 2 SO 4 .…”

Section: -Bromo-1-undecene (Bu)mentioning

confidence: 99%

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Maleimido‐Terminated Self‐Assembled Monolayers

Wang

Cai

Rauscher

et al. 2005

Chemistry A European J

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Four approaches have been explored for the preparation of maleimido-functionalized self-assembled monolayers (SAMs) on silicon. SAMs prepared by self-assembly of maleimido-functionalized alkyltrichlorosilanes (11-maleimido-undecyl-trichlorosilane) on oxide-covered silicon yield higher signals from maleimido functionalities in ATR-IR (attenuated total reflection IR) spectroscopy and XPS (X-ray photoelectron spectroscopy) than the other three methods. The surface composition of maleimido groups was tailored further by the formation of mixed monolayers with nonfunctionalized alkyltrichlorosilanes (decyltrichlorosilane). The order of the alkyl chains within the monolayers only slightly depends on the composition of the mixed monolayers. We utilized the maleimido-terminated SAMs to bind various nucleophilic compounds, alkylamines, alkylthiols, and thiol-tagged DNA oligonucleotides by means of conjugate addition.

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“…[19d] Monomers 1 [17c] and 2, [26] exo-7-oxabicycloA C H T U N G T R E N N U N G [2.2.1]hept-5-ene-2,3-dicarboximide, [26] N-butylthymine, [28] 2,6-bis(acetylamino)pyridine, [21] and 2,6-bis(benzoylaminopyridine) [21] were synthesized according to literature procedures. N-Hexylthymine was prepared by using the same procedure as N-butylthymine.…”

Section: Methodsmentioning

confidence: 99%

Molecule‐Responsive Block Copolymer Micelles

Ishihara

Bazzi

Toader

et al. 2007

Chemistry A European J

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Ring-opening metathesis polymerization was used to generate an ABC triblock copolymer, containing complementary diamidopyridine (DAP) and thymine (THY) outer blocks, which assembles into spherical aggregates held together by DAP-THY noncovalent interactions. Addition of THY-containing small guest molecules results in complete opening and deaggregation of the block copolymer micelle. This molecular recognition and macroscopic response shows high selectivity to the guest structure, and tolerates only a small amount of conformational mobility in the THY guest. On the other hand, addition of a small DAP-containing guest does not break the aggregates, but instead, results in new micelles which show a different selectivity profile from the parent morphology. We have examined the effect of a number of structural features in the block copolymers, on both the extent and selectivity of their macroscopic response to guests (that is, opening of the micelle). This study has resulted in a set of structural guidelines, which help in the design of effective molecule-responsive micelles for applications in selective drug delivery, sensing, and surface patterning.

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Synthesis on N-Alkylated Maleimides

Cited by 43 publications

References 46 publications

Novel Selective and Irreversible Mosquito Acetylcholinesterase Inhibitors for Controlling Malaria and Other Mosquito-Borne Diseases

Novel Selective and Irreversible Mosquito Acetylcholinesterase Inhibitors for Controlling Malaria and Other Mosquito-Borne Diseases

Maleimido‐Terminated Self‐Assembled Monolayers

Molecule‐Responsive Block Copolymer Micelles

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