Acylated and alkylated benzo(crown-ethers) form ion-dependent ion channels in biological membranes

Carrasquel-Ursulaez, Willy; Dehghany, Mahzad; Jones, Carl J.; Idikuda, Vinaykumar; Lu, Brian; Schomaker, Jennifer M.; Chanda, Baron

doi:10.1016/j.bpj.2022.01.026

Cited by 3 publications

(3 citation statements)

References 39 publications

(69 reference statements)

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“…The strategy of our protocol is to use N,N'-(2-hydroxypropane-1,3-diyl)bis(2-hydroxybenzamide) (7) as the key precursor for designing the desired lariat macrocycles. Thus, a good yield of 7 was obtained by reacting two equivalents of phenyl salicylate (11) with 1,3-diamino-2-hydroxypropane (12) in isopropyl alcohol containing TEA.…”

Section: Resultsmentioning

confidence: 99%

“…Crown ethers have been discovered by Pedersen in 1967 [1] . Since then, synthetic macrocycle chemistry for supramolecular host‐guest complexation has advanced rapidly for a variety of applications, including the development of optically active sensors and mobile ion carriers [2–7] . In this regard, various crown ligands have been synthesized by making various modifications to the basic crown ether structure.…”

Section: Introductionmentioning

confidence: 99%

“…[1] Since then, synthetic macrocycle chemistry for supramolecular host-guest complexation has advanced rapidly for a variety of applications, including the development of optically active sensors and mobile ion carriers. [2][3][4][5][6][7] In this regard, various crown ligands have been synthesized by making various modifications to the basic crown ether structure. This includes the synthesis of aza-crown ethers in which one or more nitrogen atoms have been added to the macrocyclic ring in an attempt to modify its ligating properties.…”

Section: Introductionmentioning

confidence: 99%

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Synthesis of novel macrocyclic di‐ and tetralactams and their corresponding C‐pivot lariat derivatives

Abbas

2023

ChemistrySelect

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A synthesis of novel C‐pivot lariat macrocycles incorporated amide linkages is described. The dipotassium salt of N,N′‐(2‐hydroxypropane‐1,3‐diyl)bis(2‐hydroxybenzamide) is first reacted with a variety of bis(chloro) compounds, and then the hydroxyl groups of these macrocycles are acylated with chloroacetyl chloride to give the corresponding (chloroacetoxy) derivatives. The desired products were produced in good yields through subsequent amination of the latter compounds with morpholine.

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Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%