Synthetic receptors for hydrosulfide

Patent metadata

Field	Value
Publication number	US-11187690-B2
Application number	US-201715612848-A
Country	US
Kind code	B2
Filing date	Jun 2, 2017
Priority date	Jun 3, 2016
Publication date	Nov 30, 2021
Grant date	Nov 30, 2021

Abstract

A method for detecting for the presence of H2S or HS− anion in a system, comprising contacting a sample from the system with a compound, or a protonate or salt thereof, having a structure represented by:wherein Y represents an aromatic group or a substituted aromatic group;n is 1 or 2;R is independently H, alkyl, substituted alkyl, a polyether moiety, carboxyl, substituted carboxyl, carbamate, substituted carbonate, carbonyloxy, alkoxy, substituted alkoxy, haloalkyl, halogen, nitro, amino, amido, aryloxy, cyano, hydroxyl, or sulfonyl;R1 is H, substituted lower alkyl, lower alkyl, substituted aralkyl or aralkyl;R2 is selected from H, acyl, substituted aralkyl, aralkyl, phosphonyl, —SO2R3; —C(O)R5; —C(O)OR7 or —C(O)NR9R10;R3; R5; R7; R9 and R10 are each independently selected from H, substituted lower alkyl, lower alkyl, substituted aralkyl, aralkyl, substituted aryl or aryl.

First claim

What is claimed is:

1. A method for detecting for the presence of HS − in an aqueous system, comprising contacting a sample from the system with a compound, or a protonate or salt thereof, thereby detecting the presence of HS − in the system, wherein the compound, or the protonate or salt thereof, has a structure represented by:

wherein Y is selected from:

wherein R 20 , R 50 , R 52 , and R 53 are each independently selected from hydrogen, alkyl, substituted alkyl, a polyether moiety, carboxyl, substituted carboxyl, carbamate, substituted carbonate, carbonyloxy, alkoxy, substituted alkoxy, haloalkyl, halogen, nitro, amino, aryloxy, cyano, hydroxyl, or sulfonyl, and R 51 , R 54 and R 55 are each hydrogen;
each R 15 is independently H, alkyl, substituted alkyl, a polyether moiety, carboxyl, substituted carboxyl, carbamate, substituted carbonate, carbonyloxy, alkoxy, substituted alkoxy, haloalkyl, halogen, nitro, amino, amido, aryloxy, cyano, hydroxyl, or sulfonyl;
each X is independently halogen, alkoxy, substituted alkoxy, alkyl, substituted alkyl or a polyether moiety; and
m is 0 to 5.

2. The method of claim 1 , wherein Y is

wherein R 50 is halogen, and R 51 is hydrogen.

3. The method of claim 1 , wherein Y is

wherein R 20 is hydrogen.

4. The method of claim 1 , wherein at least one R 15 is lower alkyl.

5. The method of claim 4 , wherein m is 1, and X is lower alkoxy.

6. The method of claim 1 , wherein each R 15 is lower alkyl, and each R 15 is in a para position relative to the position of the —NH— group.

7. The method of claim 1 , wherein at least one R 15 is tert-butyl.

8. The method of claim 1 , wherein m is 1, and X is lower alkoxy.

9. The method of claim 1 , wherein m is 1, and X is methoxy.

10. The method of claim 1 , wherein m is 1 and the X group is in a para position relative to the position of the —NH— group.

11. The method of claim 10 , wherein each R 15 is lower alkyl, and each R 15 is in a para position relative to the position of the —NH— group.

12. The method of claim 1 , wherein the compound is:

13. A method for detecting for the presence of HS − in a biological system, comprising contacting a sample from the system with a compound, or a protonate or salt thereof, thereby detecting the presence of HS − in the system, wherein the compound, or the protonate or salt thereof, has a structure represented by:

wherein Y is selected from:

wherein R 20 , R 50 , R 52 , and R 53 are each independently selected from hydrogen, alkyl, substituted alkyl, a polyether moiety, carboxyl, substituted carboxyl, carbamate, substituted carbonate, carbonyloxy, alkoxy, substituted alkoxy, haloalkyl, halogen, nitro, amino, aryloxy, cyano, hydroxyl, or sulfonyl, and R 51 , R 54 and R 55 are each hydrogen;
each R 15 is independently H, alkyl, substituted alkyl, a polyether moiety, carboxyl, substituted carboxyl, carbamate, substituted carbonate, carbonyloxy, alkoxy, substituted alkoxy, haloalkyl, halogen, nitro, amino, amido, aryloxy, cyano, hydroxyl, or sulfonyl;
each X is independently halogen, alkoxy, substituted alkoxy, alkyl, substituted alkyl or a polyether moiety; and
m is 0 to 5.

14. The method of claim 13 , wherein Y is

wherein R 50 is halogen, and R 51 is hydrogen.

15. The method of claim 13 , wherein Y is

wherein R 20 is hydrogen.

16. The method of claim 13 , wherein at least one R 15 is lower alkyl.

17. The method of claim 16 , wherein m is 1, and X is lower alkoxy.

18. The method of claim 13 , wherein each R 15 is lower alkyl, and each R 15 is in a para position relative to the position of the —NH— group.

19. The method of claim 13 , wherein at least one R 15 is tert-butyl.

20. The method of claim 13 , wherein m is 1, and X is lower alkoxy.

21. The method of claim 13 , wherein m is 1, and X is methoxy.

22. The method of claim 13 , wherein m is 1 and the X group is in a para position relative to the position of the —NH— group.

23. The method of claim 22 , wherein each R 15 is lower alkyl, and each R 15 is in a para position relative to the position of the —NH— group.

24. The method of claim 13 , wherein the compound is:

Assignees

• Univ Oregon

Inventors

• Haley Michael M
• Pluth Michael
• Johnson Darren W
• Fontenot Sean

Classifications

• C07C275/28

  having nitrogen atoms of urea groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton · CPC title

• G01N27/414

  Ion-sensitive or chemical field-effect transistors, i.e. ISFETS or CHEMFETS · CPC title

• C07C275/34

  having nitrogen atoms of urea groups and singly-bound oxygen atoms bound to carbon atoms of the same non-condensed six-membered aromatic ring · CPC title

• Y10T436/156666

  Sulfur containing · CPC title

• G01N33/0044 Primary

  Sulphides, e.g. H2S · CPC title