US2003162960A1PendingUtilityA1
Colormetric sensor compositions and methods
Priority: May 28, 1999Filed: Aug 16, 2002Published: Aug 28, 2003
Est. expiryMay 28, 2019(expired)· nominal 20-yr term from priority
C07D 403/14C07D 487/22C07D 471/14C07D 207/333
36
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Claims
Abstract
The present invention provides novel compounds exemplified by pyrrolic nitrogens used as anion and neutral species recognition elements with an aromatic core as a signal group. Described are methods for the synthesis of various pyrrole aryl compounds as well as various applications for these compounds. Methods of use include the binding and detection of specific analytes in a mixture and, in some examples, the separation of the analyte from the mixture. Additional methods of use include the transport of therapeutic agents and the sensing of components, degradants, and impurities in foodstuffs.
Claims
exact text as granted — not AI-modifiedWhat is claimed is:
1 . A pyrrole-aryl compound of the general formulas,
wherein Ar is an aryl group, wherein R 1 -R 6 , individually at each occurrence, are the same or different, and are hydrogen, alkyl, hydroxyalkyl, glycol, polyglycol, amino, nitro, halo, cyano, aryl, heteroaryl, thio, thioalkyl, amide, ester, acyl, aldehyde, or carboxy, and provided, however, that if Ar is an unsubstituted quinoxaline group then R 1 -R 6 cannot each be hydrogen.
2 . A pyrrole-aryl compound of the general formula:
wherein R 1 -R 10 , individually at each occurrence, are the same or different and are hydrogen, alkyl, hydroxyalkyl, glycol, polyglycol, amino, nitro, halo, cyano, aryl, heteroaryl, thio, thioalkyl, amide, ester, acyl, aldehyde, or carboxy, provided, however, that R 1 -R 10 cannot each be hydrogen.
3 . The compound of claim 2 , wherein R 1 ═R 2 ═OCH 3 .
4 . The compound of claim 2 , wherein R 1 ═R 2 ═NO 2 .
5 . The compound of claim 2 , wherein R 1 ═R 2 ═CH 3 .
6 . The compound of claim 2 , wherein R 1 ═R 2 ═O(CH 2 CH 2 O) 3 CH 3 .
7 . The compound of claim 2 , wherein R 1 ═R 2 ═O(CH 2 ) n CH 3 , and wherein n is 0-20.
8 . The compound of claim 2 , wherein R 1 ═H, R 2 ═NO 2 .
9 . The compound of claim 2 , wherein R 1 ═NH 2 , R 2 ═NO 2 .
10 . The compound of claim 2 , wherein R 1 ═NH 2 , R 2 ═NH 2 .
11 . The compound of claim 2 wherein R 1 and R 2 are part of a cyclic group and further wherein said compound is selected from the group consisting of:
12 . The compound of any one of claims 1 - 11 in which one or more of the pyrrole nitrogens exist in anionic form.
13 . A compound of the general formulas,
wherein individually at each occurrence, each of R 1 , -R 6 are the same or different, and are hydrogen, alkyl, hydroxyalkyl, glycol, polyglycol, amino, nitro, halo, cyano, aryl, heteroaryl, thio, thioalkyl, amide, ester, acyl, aldehyde, or carboxy.
14 . The compound of claim 13 , wherein R 1 ═CO 2 CH 2 CH 3 , R 2 ═CH 3 , R 3 ═CH 3 .
15 . The compound of claim 13 , wherein R 1 ═CO 2 CH 2 CH 3 , R 2 ═CH 2 CH 3 , R 3 ═CH 2 CH 3 .
16 . The compound of claim 13 , wherein R 1 ═CH 3 , R 2 ═COCH 3 , R 3 ═CH 3 .
17 . The compound of claim 13 , wherein R 1 ═CH 3 , R 2 ═CO(CH 2 ) n CH 3 , R 3 ═CH 3 , and wherein n is 0-20.
18 . The compound of claim 13 , wherein R 1 ═H, R 2 ═CH 3 , R 3 ═CH 3 .
19 . The compound of claim 13 , wherein R 1 ═H, R 2 ═CH 2 CH 3 , R 3 ═CH 2 CH 3 .
20 . The compound of claim 13 , wherein R 1 ═H, R 2 ═R 3 ═CH 2 (CH 2 ) 2 CH 3 .
21 . The compound of any one of claims 13 - 20 in which one or more of the pyrrole nitrogens exist in anionic form.
22 . A compound of the general formula,
wherein individually at each occurrence, each of R 1 , -R 7 are the same or different and are hydrogen, alkyl, hydroxyalkyl, glycol, polyglycol, amino, nitro, halo, cyano, aryl, heteroaryl, thio, thioalkyl, amide, ester, acyl, aldehyde, or carboxy, and n=0-10, and further wherein each of R 1 -R 7 on either side of the axis of the diketone bridge may be the same or different from the corresponding R 1 -R 7 on the opposite side of the diketone bridge and further wherein each R 4 and R 5 of the n subunits of pyrrole may be the same or different from corresponding R 4 and R 5 of any other subunits of pyrrole.
23 . The compound of claim 22 , wherein each of R is H and wherein n=0.
24 . A compound of the general formula:
wherein individually at each occurrence, each of R 1 , -R 11 are the same or different and are hydrogen, alkyl, hydroxyalkyl, glycol, polyglycol, amino, nitro, halo, cyano, aryl, heteroaryl, thio, thioalkyl, amide, ester, acyl, aldehyde, or carboxy, and n=0-10, and further wherein each of R 1 -R 7 on either side of the axis of the quinoxaline bridge may be the same or different from the corresponding R 1 -R 7 on the opposite side of the quinoxaline bridge and further wherein each R 4 and R 5 of the n subunits of pyrrole may be the same or different from corresponding R 4 and R 5 of any other subunits of pyrrole.
25 . The compound of claim 24 wherein n=1.
26 . The compound of claim 24 wherein n=2.
27 . A pyrrole-aryl compound of the general structure:
wherein individually at each occurrence, R 1 , -R 10 are the same or different and are hydrogen, alkyl, hydroxyalkyl, glycol, polyglycol, amino, nitro, halo, cyano, aryl, heteroaryl, thio, thioalkyl, amide, ester, acyl, aldehyde, or carboxy and M is Li, B, Na, Mg, Al, Si, K, As, Rb, Sb, Cs, La, Hf, Bi, Pr, Eu, Yb, or Th.
28 . A pyrrole-aryl compound of the general structure:
wherein R 1 , -R 8 individually at each occurrence, are the same or different and are hydrogen, alkyl, hydroxyalkyl, glycol, polyglycol, amino, nitro, halo, cyano, aryl, heteroaryl, thio, thioalkyl, amide, ester, acyl, aldehyde, or carboxy; and further wherein Ar is selected from the group consisting of:
and further wherein X, Y, and Z are selected from the group consisting of hydrogen, aldehyde, nitro, and amino.
29 . A pyrrole-quinoxaline compound of the general structure:
wherein R 1 , -R 8 individually at each occurrence, are the same or different and are hydrogen, alkyl, hydroxyalkyl, glycol, polyglycol, amino, nitro, halo, cyano, aryl, heteroaryl, thio, thioalkyl, amide, ester, acyl, aldehyde, or carboxy, and wherein TMS is a trimethylsilyl group.
30 . The compound of claim 1 , 2 , 24 , 27 , or 28 in which one or more of the pyrrole nitrogens exist in anionic form.
31 . The compound of claim 1 , 2 , 24 , 27 , or 28 incorporated into a macrocyclic molecule.
32 . The compound of claim 31 selected from the group consisting of the following structures:
wherein all R, individually at each occurrence, are the same or different and are hydrogen, alkyl, hydroxyalkyl, glycol, polyglycol, amino, nitro, halo, cyano, aryl, heteroaryl, thio, thioalkyl, amide, ester, acyl, aldehyde, or carboxy and n=1-10.
33 . A pyrrole-aryl compound of the following general formulas:
wherein R 1 -R 6 , individually at each occurrence, are the same or different and are hydrogen, alkyl, hydroxyalkyl, glycol, polyglycol, amino, nitro, halo, cyano, aryl, heteroaryl, thio, thioalkyl, amide, ester, acyl, aldehyde, or carboxy.
34 . A method for the analysis of an anion or neutral species comprising:
(a) obtaining a pyrrole-aryl compound; (b) contacting the pyrrole-aryl compound with a sample containing an anion or neutral species; and (c) optically monitoring the pyrrole-aryl compound in the presence of the sample.
35 . The method of claim 34 wherein said pyrrole-aryl compound is a pyrrole-quinoxaline compound.
36 . The method of claim 34 or 35 , wherein the pyrrole-aryl compound is the compound of claim 2 .
37 . The method of claim 36 , wherein R 1 ═R 2 ═NO 2 .
38 . The method of claim 36 , wherein R 1 ═H, R 2 ═NO 2 .
39 . The method of claim 34 or 35 wherein the anion is an anion of fluoride, cyanide, phenolate, carboxylate, sulfate, sulfite, sulfide, sulfonate, nitrate, nitrite, bromide, iodide, pertechtenate, perrhenate, phosphate, phosphonates, nucleobase, nucleotide or oligonucleotide.
40 . The method of claim 39 , wherein the anion is fluoride or chloride.
41 . The method of claim 34 or 35 wherein the neutral species is cis-3-hexenal.
42 . The method of claim 34 or 35 , wherein the optically monitoring is fluorescence excitation, fluorescence emission, visual detection or ultraviolet or visible absorption.
43 . The method of claim 34 or 35 , wherein the pyrrole-aryl compound is attached to a solid support.
44 . The method of claim 34 or 35 , wherein the optical monitoring is performed by the means of a spectroscopic apparatus comprising a fiber optic.
45 . The method of claim 34 or 35 , in which the analysis is carried out in vivo, in vitro, or in situ.
46 . A method of using a pyrrole-aryl compound in vivo, in vitro, or in situ to selectivlely transport therapeutic agents.
47 . A method of using a pyrrole-aryl compound as a sensing element in the analysis of foodstuffs.Join the waitlist — get patent alerts
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