Self-Immolative System for Disclosure of Reactive Electrophilic Alkylating Agents: Understanding the Role of the Reporter Group.
Journal
The Journal of organic chemistry
ISSN: 1520-6904
Titre abrégé: J Org Chem
Pays: United States
ID NLM: 2985193R
Informations de publication
Date de publication:
06 08 2021
06 08 2021
Historique:
pubmed:
23
7
2021
medline:
6
10
2021
entrez:
22
7
2021
Statut:
ppublish
Résumé
The development of stable, efficient chemoselective self-immolative systems, for use in applications such as sensors, requires the optimization of the reactivity and degradation characteristics of the self-immolative unit. In this paper, we describe the effect that the structure of the reporter group has upon the self-immolative efficacy of a prototype system designed for the disclosure of electrophilic alkylating agents. The amine of the reporter group (a nitroaniline unit) was a constituent part of a carbamate that functioned as the self-immolative unit. The number and position of substituents on the nitroaniline unit were found to play a key role in the rate of self-immolative degradation and release of the reporter group. The position of the nitro substituent (
Identifiants
pubmed: 34292742
doi: 10.1021/acs.joc.1c00996
pmc: PMC8389931
doi:
Substances chimiques
Alkylating Agents
0
Carbamates
0
Types de publication
Journal Article
Research Support, Non-U.S. Gov't
Langues
eng
Sous-ensembles de citation
IM
Pagination
10263-10279Références
Chem Commun (Camb). 2019 May 8;55(36):5219-5222
pubmed: 30945702
Angew Chem Int Ed Engl. 2011 May 23;50(22):5197-9
pubmed: 21520372
J Am Chem Soc. 2009 Dec 30;131(51):18327-34
pubmed: 19950931
J Org Chem. 2008 Feb 15;73(4):1546-52
pubmed: 18205386
J Am Chem Soc. 2010 Jul 14;132(27):9234-5
pubmed: 20565108
ChemMedChem. 2015 Feb;10(2):253-65
pubmed: 25504894
Angew Chem Int Ed Engl. 2015 Jun 22;54(26):7492-509
pubmed: 26053475
Chem Rev. 2016 Feb 10;116(3):1309-52
pubmed: 26355446
J Med Chem. 1981 May;24(5):479-80
pubmed: 7241503
Acc Chem Res. 2014 Oct 21;47(10):2970-84
pubmed: 25181456
J Am Chem Soc. 1972 Feb 23;94(4):1323-34
pubmed: 5060276
Org Biomol Chem. 2015 Aug 28;13(32):8703-7
pubmed: 26179935
Angew Chem Int Ed Engl. 2012 Mar 12;51(11):2763-6
pubmed: 22302600
Anticancer Agents Med Chem. 2008 Aug;8(6):618-37
pubmed: 18690826
Chem Commun (Camb). 2019 Jul 18;55(59):8655-8658
pubmed: 31287112
ChemMedChem. 2008 Jan;3(1):20-53
pubmed: 17963208
Nature. 1958 Aug 16;182(4633):421-2
pubmed: 13577867
Chembiochem. 2007 Mar 26;8(5):560-6
pubmed: 17300128
Chem Commun (Camb). 2014 Feb 21;50(15):1836-8
pubmed: 24402325
J Am Chem Soc. 2009 Jul 29;131(29):9934-6
pubmed: 19569684
J Am Chem Soc. 2010 Jul 21;132(28):9602-3
pubmed: 20583793
Org Biomol Chem. 2008 Aug 7;6(15):2669-72
pubmed: 18633521
J Am Chem Soc. 2010 Aug 4;132(30):10266-8
pubmed: 20662509
J Org Chem. 2005 Feb 4;70(3):1019-28
pubmed: 15675863
Org Biomol Chem. 2009 Dec 7;7(23):4825-8
pubmed: 19907770
Bioorg Med Chem Lett. 2009 Jul 15;19(14):3959-62
pubmed: 19303773
Bioorg Med Chem. 2007 Jun 1;15(11):3720-7
pubmed: 17416532
Chem Sci. 2020 Mar 3;11(14):3713-3718
pubmed: 34094059
J Org Chem. 2012 May 4;77(9):4363-74
pubmed: 22494313
Angew Chem Int Ed Engl. 2015 May 18;54(21):6200-5
pubmed: 25824123
Org Biomol Chem. 2007 Apr 7;5(7):1062-80
pubmed: 17377660