Compounds and compositions for use as alkylating agent sensors and methods of use thereof

Patent metadata

Field	Value
Publication number	US-9638690-B2
Application number	US-201514927836-A
Country	US
Kind code	B2
Filing date	Oct 30, 2015
Priority date	Nov 7, 2014
Publication date	May 2, 2017
Grant date	May 2, 2017

Abstract

This invention provides compound having a structure of Formula I:

Uses of such compounds and compositions comprising the compounds as alkylating agent sensors.

First claim

What is claimed is:

1. A compound of Formula 1:

wherein
A 1 is selected from H, Me, Et, Pr, Bu, F, Br, I, OH, OJ, OC(O)J, CF 3 , CCl 3 , CN, SO 3 H, C(O)OH, CHO, C(O)OJ, COJ, C(O)OK, C(O)NJ 2 , C(O)N(J)(H), C(NJ)J, C(S)NH 2 , C(S)NJ 2 and C(S)N(J)(H);
A 2 is selected from H, Me, Et, Pr, Bu, F, Br, I, OH, OJ, OC(O)J, CF 3 , CCl 3 , CN, SO 3 H, C(O)OH, CHO, C(O)OJ, COJ, C(O)OK, C(O)NJ 2 , C(O)N(J)(H), C(NJ)J, C(S)NH 2 , C(S)NJ 2 and C(S)N(J)(H);
E 1 is selected from H, Me, Et, Pr, Bu, F, Br, I, OH, OL, OC(O)L, CF 3 , CCl 3 , CN, SO 3 H, C(O)OH, CHO, CH 2 OH, C(O)OL, COL, C(O)OK, C(O)NL 2 , C(O)N(L)(H), C═NL, C(NL)L, C(S)NH 2 , C(S)NL 2 and C(S)N(L)(H);
E 2 is selected from H, Me, Et, Pr, Bu, F, Br, I, OH, OL, OC(O)L, CF 3 , CCl 3 , CN, SO 3 H, C(O)OH, CHO, CH 2 OH, C(O)OL, COL, C(O)OK, C(O)NL 2 , C(O)N(L)(H), C═NL, C(NL)L, C(S)NH 2 , C(S)NL 2 and C(S)N(L)(H);
D is selected from H, Et, n-Pr, c-Pr, Bu, Cl, Br, I, OT b , OC(O)T b , NO 2 , CF 3 , CCl 3 , CN, SO 3 H, C(O)OH, CHO, C(O)OT a , COT b , C(O)OK, C(O)NT b 2 , C(O)N(T b )(H), C(NT b )T b , C(S)NH 2 , C(S)NT b 2 and C(S)N(T b )(H);
G 1 is selected from H, Et, Pr, Bu, F, Cl, Br, I, OH, OM a , OC(O)M a , NO 2 , CF 3 , CCl 3 , CN, SO 3 H, C(O)OH, CHO, C(O)OM a , COM a , C(O)OK, C(O)NM a 2 , C(O)N(M a )(H), C(NM a )M a , C(S)NH 2 , C(S)NM a 2 and C(S)N(M a )(H);
G 2 is selected from H, Et, Pr, Bu, F, Cl, Br, I, OH, OM a , OC(O)M a , NO 2 , CF 3 , CCl 3 , CN, SO 3 H, C(O)OH, CHO, C(O)OM a , COM a , C(O)OK, C(O)NM a 2 , C(O)N(M a )(H), C(NM a )M a , C(S)NH 2 , C(S)NM a 2 and C(S)N(M a )(H);
Q 1 is selected from H, Et, Pr, Bu, Br, I, OH, OM b , OC(O)M b , NO 2 , CCl 3 , SO 3 H, C(O)OH, CHO, C(O)OM b , COM b , C(O)OK, C(O)NM c 2 , C(O)N(M d )(H), and C(NM b )M b ;
Q 2 is selected from H, Et, Pr, Bu, Br, I, OH, OM b , OC(O)M b , NO 2 , CCl 3 , SO 3 H, C(O)OH, CHO, C(O)OM b , COM b , C(O)OK, C(O)NM c 2 , C(O)N(M d )(H), and C(NM b )M b ;
provided that at least one of A 1 , A 2 , E 1 , E 2 , D, G 1 , G 2 , Q 1 and Q 2 is other than H;
J is independently selected from a 1-20 carbon alkyl, 1-20 carbon aryl or 1-20 carbon alkenyl group, optionally substituted with one or more of: ═O, ═S, OH, SH, NH 2 , I, Br, Cl, F, CN, C(O)OH, CHO, C(O)NH 2 , C(O)SH, NO 2 , or SO 3 H;
K is potassium;
L is independently selected from a 1-20 carbon alkyl, 1-20 carbon aryl or 1-20 carbon alkenyl group, optionally substituted with one or more of: ═O, ═S, OH, SH, NH 2 , I, Br, Cl, F, CN, C(O)OH, CHO, C(O)NH 2 , C(O)SH, NO 2 , or SO 3 H;
T a is independently selected from a 1, or 3-20 carbon alkyl, 1-20 carbon aryl or 1-20 carbon alkenyl group, optionally substituted with one or more of: ═O, ═S, OH, SH, NH 2 , I, Br, Cl, F, CN, C(O)OH, CHO, C(O)NH 2 , COSH, NO 2 , or SO 3 H;
T b is independently selected from a 1-20 carbon alkyl, 1-20 carbon aryl or 1-20 carbon alkenyl group, optionally substituted with one or more of: ═O, ═S, OH, SH, NH 2 , I, Br, Cl, F, CN, C(O)OH, CHO, C(O)NH 2 , C(O)SH, NO 2 , or SO 3 H;
M a is independently selected from a 1-20 carbon alkyl, 1-20 carbon aryl or 1-20 carbon alkenyl group, optionally substituted with one or more of: ═O, ═S, OH, SH, NH 2 , I, Br, Cl, F, CN, C(O)OH, CHO, C(O)NH 2 , C(O)SH, NO 2 , or SO 3 H;
M b may be independently selected from a 1-20 carbon alkyl, 1-20 carbon aryl or 1-20 carbon alkenyl group, optionally substituted with one or more of: ═O, ═S, OH, SH, NH 2 , I, Br, Cl, F, CN, C(O)OH, CHO, C(O)NH 2 , C(O)SH, NO 2 , or SO 3 H;
M c is independently selected from a 1-20 carbon alkyl, 1-20 carbon aryl or 1-20 carbon alkenyl group, optionally substituted with one or more of: ═O, ═S, OH, SH, NH 2 , I, Br, Cl, F, CN, C(O)OH, CHO, C(O)NH 2 , C(O)SH, NO 2 , or SO 3 H; and
M d may be independently selected from a 2-20 carbon alkyl, 1-20 carbon aryl or 1-20 carbon alkenyl group, optionally substituted with one or more of: ═O, ═S, OH, SH, NH 2 , I, Br, Cl, F, CN, C(O)OH, CHO, C(O)NH 2 , C(O)SH, NO 2 , or SO 3 H.

2. The compound of claim 1 , wherein
A 1 is selected from H, Me, Et, Pr, Bu, F, Br, I, OJ, OC(O)J, CF 3 , CCl 3 , CN, SO 3 H, C(O)OH, CHO, C(O)OJ, COJ, C(O)OK, C(O)NJ 2 , C(O)N(J)(H), C(NJ)J, C(S)NH 2 , C(S)NJ 2 and C(S)N(J)(H);
A 2 is selected from H, Me, Et, Pr, Bu, F, Br, I, OJ, OC(O)J, CF 3 , CCl 3 , CN, SO 3 H, C(O)OH, CHO, C(O)OJ, COJ, C(O)OK, C(O)NJ 2 , C(O)N(J)(H), C(NJ)J, C(S)NH 2 , C(S)NJ 2 and C(S)N(J)(H);
E 1 is selected from H, F, Br, I, OC(O)L, CF 3 , CCl 3 , CN, SO 3 H, C(O)OH, CHO, CH 2 OH, C(O)OL, COL, C(O)OK, C(O)NL 2 , C(O)N(L)(H), C═NL, C(NL)L, C(S)NH 2 , C(S)NL 2 and C(S)N(L)(H);
E 2 is selected from H, F, Br, I, OC(O)L, CF 3 , CCl 3 , CN, SO 3 H, C(O)OH, CHO, CH 2 OH, C(O)OL, COL, C(O)OK, C(O)NL 2 , C(O)N(L)(H), C═NL, C(NL)L, C(S)NH 2 , C(S)NL 2 and C(S)N(L)(H);
D is selected from H, Cl, Br, I, OC(O)T b , NO 2 , CF 3 , CCl 3 , CN, SO 3 H, C(O)OH, CHO, C(O)OT a , COT b , C(O)OK, C(O)NT b 2 , C(O)N(T b )(H), C(NT b )T b , C(S)NH 2 , C(S)NT b 2 and C(S)N(T b )(H);
G 1 is selected from H, F, Cl, Br, I, NO 2 , CF 3 , CCl 3 , CN, SO 3 H, C(O)OH, CHO, OC(O)M a , C(O)OM a , COM a , C(O)OK, C(O)NM a 2 , C(O)N(M a )(H), C(NM a )M a , C(S)NH 2 , C(S)NM a 2 and C(S)N(M a )(H);
G 2 is selected from H, Et, Pr, Bu, F, Cl, Br, I, OH, NO 2 , CF 3 , CCl 3 , CN, SO 3 H, C(O)OH, CHO, OC(O)M a , C(O)OM a , COM a , C(O)OK, C(O)NM a 2 , C(O)N(M a )(H), C(NM a )M a , C(S)NH 2 , C(S)NM a 2 and C(S)N(M a )(H);
Q 1 is selected from H, Et, Pr, Bu, Br, I, OH, OM b NO 2 ;
Q 2 is selected from H, Et, Pr, Bu, Br, I, OH, OM b and NO 2 ;
J is independently selected from a 1-20 carbon alkyl, 1-20 carbon aryl or 1-20 carbon alkenyl group, optionally substituted with one or more of: ═O, ═S, OH, SH, NH 2 , CN, C(O)OH, CHO, C(O)NH 2 , C(O)SH or SO 3 H;
L is independently selected from a 1-20 carbon alkyl, 1-20 carbon aryl or 1-20 carbon alkenyl group, optionally substituted with one or more of: ═O, ═S, OH, SH, NH 2 , CN, C(O)OH, CHO, C(O)NH 2 , C(O)SH or SO 3 H;
T a is independently selected from a 1, or 3-20 carbon alkyl, 1-20 carbon aryl or 1-20 carbon alkenyl group, optionally substituted with one or more of: ═O, ═S, OH, SH, NH 2 , CN, C(O)OH, CHO, C(O)NH 2 , COSH or SO 3 H;
T b is independently selected from a 1-20 carbon alkyl, 1-20 carbon aryl or 1-20 carbon alkenyl group, optionally substituted with one or more of: ═O, ═S, OH, SH, NH 2 , CN, C(O)OH, CHO, C(O)NH 2 , C(O)SH or SO 3 H;
M a is independently selected from a 1-20 carbon alkyl, 1-20 carbon aryl or 1-20 carbon alkenyl group, optionally substituted with one or more of: ═O, ═S, OH, SH, NH 2 , CN, C(O)OH, CHO, C(O)NH 2 , C(O)SH or SO 3 H;
M b may be independently selected from a 1-20 carbon alkyl, 1-20 carbon aryl or 1-20 carbon alkenyl group, optionally substituted with one or more of: ═O, ═S, OH, SH, NH 2 , CN, C(O)OH, CHO, C(O)NH 2 , C(O)SH or SO 3 H;
M c is independently selected from a 1-20 carbon alkyl, 1-20 carbon aryl or 1-20 carbon alkenyl group, optionally substituted with one or more of: ═O, ═S, OH, SH, NH 2 , CN, C(O)OH, CHO, C(O)NH 2 , C(O)SH or SO 3 H; and
M d may be independently selected from a 2-20 carbon alkyl, 1-20 carbon aryl or 1-20 carbon alkenyl group, optionally substituted with one or more of: ═O, ═S, OH, SH, NH 2 , CN, C(O)OH, CHO, C(O)NH 2 , C(O)SH or SO 3 H.

3. The compound of claim 1 , wherein
A 1 is selected from H, Me, Et, Pr, Bu, F, Br, I, OJ, OC(O)J, CF 3 , CCl 3 , CN, SO 3 H, C(O)OH, CHO, C(O)OJ, COJ, C(O)OK, C(O)NJ 2 , C(O)N(J)(H) and C(NJ)J;
A 2 is selected from H, Me, Et, Pr, Bu, F, Br, I, OJ, OC(O)J, CF 3 , CCl 3 , CN, SO 3 H, C(O)OH,

Assignees

• Univ British Columbia

Inventors

• Love Jennifer Ann
• Provencher Philip Andrew

Classifications

• C07F7/1804

  Compounds having Si-O-C linkages (Si-O-acyl linkages C07F7/1896) · CPC title

• C07D213/55

  Acids; Esters · CPC title

• G01N33/52 Primary

  Use of compounds or compositions for colorimetric, spectrophotometric or fluorometric investigation, e.g. use of reagent paper {and including single- and multilayer analytical elements (immunological elements G01N33/54386; involving labelled immunochemicals G01N33/58; for haemoglobin or occult blood G01N33/72)} · CPC title

• C07D213/53

  Nitrogen atoms · CPC title

• C07D213/56

  Amides · CPC title