Unconventional [2 + 3] Cyclization Involving [1,4]-Sulfonyl Transfer to Construct Polysubstituted Fluorazones as Inhibitors of Indoleamine 2,3-Dioxygenase 1.
Org Lett
; 22(20): 7909-7914, 2020 10 16.
Article
in En
| MEDLINE
| ID: mdl-32991179
ABSTRACT
An unconventional [2 + 3] cyclization of pyridinium ylides with 2-ylideneoxindoles has been developed for the facile construction of pharmacologically interesting polysubstituted 9H-pyrrolo[1,2-a]indol-9-ones (fluorazones). Mechanistic studies revealed that the reaction, which has a broad substrate scope, proceeds via intermolecular [1,4]-sulfonyl transfer. Moreover, biological evaluation showed that polysubstituted fluorazone 3ak potently inhibits indoleamine 2,3-dioxygenase 1, kynurenine production, and immunotolerance in tumors.
Full text:
1
Collection:
01-internacional
Database:
MEDLINE
Main subject:
Indoleamine-Pyrrole 2,3,-Dioxygenase
/
Kynurenine
/
Antineoplastic Agents
Limits:
Humans
Language:
En
Journal:
Org Lett
Journal subject:
BIOQUIMICA
Year:
2020
Document type:
Article