US2009286968A1PendingUtilityA1
2-Quinoxalinol Salen Compounds and Uses Thereof
Est. expiryApr 25, 2028(~1.7 yrs left)· nominal 20-yr term from priority
C07D 241/44C07D 241/52
56
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Claims
Abstract
Disclosed are 2-quinoxalinol salen compounds and in particular 2-quinoxalinol salen Schiff-base ligands. The disclosed 2-quinoxalinol salen compounds may be utilized as ligands for forming complexes with cations, and further, the formed complexes may be utilized as catalysts for oxidation reactions. The disclosed 2-quinoxalinol salen compounds also may be conjugated to solid supports and utilized in methods for selective solid-phase extraction or detection of cations.
Claims
exact text as granted — not AI-modified1 . A compound having a formula:
wherein:
R 1 is an amino acid side chain moiety; and
R 2 and R 3 are hydrogen, hydroxyl, C 1-6 alkyl which may be straight chain or branched, C 1-6 alkoxy which may be straight chain or branched, ether, or amine; and
R 2 and R 3 are the same or different.
2 . The compound of claim 1 , wherein R 1 is selected from:
3 . The compound of claim 1 , wherein R 1 is selected from:
4 . The compound of claim 1 , wherein R 1 is an aromatic amino acid side chain moiety.
5 . The compound of claim 1 , wherein R 2 and R 3 are the same.
6 . The compound of claim 1 , wherein R 2 and R 3 are different.
7 . The compound of claim 1 , wherein at least one of R 2 and R 3 are hydrogen.
8 . The compound of claim 1 , wherein both of R 2 and R 3 are hydrogen.
9 . The compound of claim 1 , wherein at least one of R 2 and R 3 are hydroxyl.
10 . The compound of claim 1 , wherein both of R 2 and R 3 are hydroxyl.
11 . The compound of claim 1 , wherein at least one of R 2 and R 3 is 3-OH.
12 . The compound of claim 1 , wherein at least one of R 2 and R 3 is 5-OH.
13 . The compound of claim 1 , wherein at least one of R 2 and R 3 is 3-C 1-6 straight chain or branched alkyl.
14 . The compound of claim 1 , wherein both of R 2 and R 3 are 3-C 1-6 straight chain or branched alkyl.
15 . The compound of claim 1 , wherein at least one of R 2 and R 3 is 3-tert-butyl
16 . The compound of claim 1 , wherein at least one of R 2 and R 3 is 3,5-Di-tert butyl.
17 . The compound of claim 1 complexed to a divalent cation.
18 . The compound of claim 1 , wherein the divalent cation is selected from a group consisting of Cu 2+ , Mn 2+ , Co 2+ , Ni 2+ , and UO 2 2+ .
19 . The compound of claim 1 , conjugated to a solid support.
20 . The compound of claim 19 , wherein the solid support is a functionalized polystyrene resin selected from a group consisting of aminomethyl polystyrene resin, 2-chrlotrityl chloride resin, DHP HM resin, HMPA-AM resin, Knorr resin, Knorr-2-chlorotrityl resin, MBHA resin, Merrifield resin, oxime resin, PAM resin, Rink amide-AM resin, Rink amide-MBHA resin, Sieber resin, Wang resin, Weinreb AM resin, Boc-Ser-Merrifield resin, and Boc-Gly-Merrifield resin.
21 . The compound of claim 1 , wherein the compound is conjugated via an acylating linker compound.
22 . The compound of claim 21 , wherein the acylating linker compound is an anhydride compound.
23 . The compound of claim 22 , wherein the anhydride compound is an acid anhydride.
24 . The compound of claim 1 , conjugated to a fluorophore.
25 . A method of making the compound of claim 1 , comprising reacting a mixture comprising a 2-quinoxalinol compound having a formula:
wherein R 1 is an amino acid side chain moiety; and
a salicylic aldehyde compound having a formula:
wherein R 2 is hydrogen, hydroxyl, C 1-6 alkyl which may be straight chain or branched, C 1-6 alkoxy which may be straight chain or branched, ether, or amine.
26 . The method of claim 25 , wherein the mixture further comprises an alcohol and reacting the mixture comprises heating the mixture.
27 . A method of removing a divalent cation from a solution, comprising contacting the solution with the compound of claim 1 .
28 . The method of claim 27 , wherein the divalent cation is selected from a group consisting of Cu 2+ , Mn 2+ , Co 2+ , Ni 2+ , and UO 2 2+ .
29 . A method of removing a divalent compound from a solution, comprising contacting the solution with the compound of claim 19 .
30 . The method of claim 29 , wherein the divalent cation is selected from a group consisting of Cu 2+ , Mn 2+ , Co 2+ , Ni 2+ , and UO 2 2+ .
31 . A method for detecting a divalent cation in a solution, the method comprising
(a) contacting the solution with the compound of claim 1 , wherein if the solution comprises the divalent cation, the compound forms a complex with the divalent cation; and (b) detecting the complex in the solution.
32 . The method of claim 31 , wherein detecting the complex comprises at least one of determining an absorption maximum for the solution via UV-Vis spectra analysis; detecting a change in fluorescence for the solution; and detecting a change in electrochemical properties of the solution.
33 . A method for detecting a divalent cation in a solution, the method comprising:
(a) contacting the solution with a complex comprising a complexed cation, which complex optionally may be conjugated to a solid support or a fluorophore, where if the solution comprises the cation, the solution cation displaces the complexed cation from the compound and forms a new complex with the compound; and (b) detecting the new complex or detecting the displaced cation.
34 . The method of claim 33 , wherein detecting the new complex or displaced cation comprises at least one of determining an absorption maximum for the solution via UV-Vis spectra analysis; detecting a change in fluorescence for the solution; and detecting a change in electrochemical properties of the solution.
35 . A method of oxidizing a compound comprising reacting the compound with an oxidizing agent and the compound of claim 17 .
36 . The method of claim 35 , wherein the compound is a methylene compound.Join the waitlist — get patent alerts
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