US2011015396A1PendingUtilityA1
Tunable phenylacetylene hosts
Assignee: STATE OF OREGON ON BEHALF OF THE UNIVERSITY OF OREGONPriority: Dec 14, 2006Filed: Sep 28, 2010Published: Jan 20, 2011
Est. expiryDec 14, 2026(~0.4 yrs left)· nominal 20-yr term from priority
Inventors:Michael M. HaleyDarren W. JohnsonOrion B. BerrymanCharles A. JohnsonCalden Nathaniel Carroll Stimpson
C07D 401/04C07D 213/22C07D 513/22C07D 333/20
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Claims
Abstract
Disclosed herein is a class of tunable phenylacetylene compounds as well as compositions and methods for their use as host compounds for ligand binding. In certain examples the hosts report binding events by exhibiting altered spectroscopic properties, such as different fluorescent emission spectra.
Claims
exact text as granted — not AI-modified1 . A compound or salt thereof comprising the formula
wherein Y represents an optionally substituted aromatic group;
n is 1 or 2;
R is H or lower alkyl;
R 1 is H, lower alkyl or aralkyl;
R 2 is selected from H, acyl aralkyl, phosphonyl, —SO 2 R 3 , —(R 4 )C(O)R 5 ; —N(R 6 )C(O)OR 7 , and —N(R 8 )C(O)NR 9 R 10 ;
R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , and R 10 independently are selected from H, lower alkyl, aralkyl, and aryl;
provided that Y is not a pyridyl or bipyridyl.
2 . The compound of claim 1 wherein Y comprises a heteroaromatic group.
3 . The compound of claim 1 , wherein Y is a 5- or 6-membered ring.
4 . The compound of claim 1 , wherein Y comprises a polycyclic group.
5 . The compound of claim 1 , wherein Y comprises a group selected from pyrazinyl, pyrimidinyl, pyrrole, imidazole, triazole, thiophene, thiazole, furyl, and oxazolyl.
6 . The compound of claim 1 , wherein Y is
7 . The compound of claim 1 , according to the formula
wherein R is selected from H and lower alkyl; and
X is selected from —N(H)SO 2 R 3 , —N(R 4 )C(O)R 5 , —N(R 6 )C(O)OR 7 , and —N(R 8 )C(O)NR 9 R 10 ;
R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , and R 10 independently are selected from H, lower alkyl, aralkyl, and aryl.
8 . The compound of claim 1 , according to the formula
wherein X is selected from —N(H)SO 2 R 3 , —N(R 4 )C(O)R 5 , —N(R 6 )C(O)OR 7 , and —N(R 8 )C(O)NR 9 R 10 ; and
R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , and R 10 independently are selected from H, lower alkyl, aralkyl, and aryl.
9 . The compound of claim 1 , according to the formula
wherein R is lower alkyl;
X is halogen, —OR 11 , alkyl sulfide, nitro, sulfonyl, phosphonyl, phosphate, sulfate, or lower alkyl;
and R 11 is H, acyl, or optionally substituted lower alkyl.
10 . The compound of claim 9 , wherein X comprises an alkoxy or alkyl sulfide moiety.
11 . The compound of claim 10 , wherein X has the formula —OR 11 or —SR 11 and R is optionally substituted lower alkyl.
12 . The compound claim 1 , having the formula
or
13 . The compound of claim 1 , wherein the compound is macrocyclic.
14 . A method for binding a ligand, comprising providing a host compound according to claim 1 and exposing the compound to the ligand, thereby binding the ligand.
15 . The method of claim 14 , wherein the ligand is an ionic ligand.
16 . The method of claim 14 , wherein the ligand is an anionic ligand.
17 . The method of claim 16 , wherein the host is protonated.
18 . The method of claim 16 , wherein the ligand is chloride, sulfate, hydrogen sulfate, perchlorate, pertechnetate, or nitrate.
19 . The method of claim 14 , wherein the ligand is an inorganic ligand.
20 . The method of claim 14 , wherein the ligand comprises a metal selected from the group consisting of Pb, As, Zn, U, Ca, Cd, Hg, and combinations thereof.
21 . The method of claim 14 , wherein binding the ligand induces a change in the fluorescence emission spectrum of the host compound.
22 . The method of claim 14 , wherein binding the ligand occurs in a stoichiometry of about two host compound molecules per ligand.
23 . A crystalline complex comprising a compound of claim 1 .
24 . A method for preparing a host compound, comprising:
providing a compound of the formula
and converting it to a compound of the formula
25 . The method of claim 24 , comprising
providing a compound of the formula
and converting it to a compound of the formulaJoin the waitlist — get patent alerts
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