Efficient preparation of photolabile agent mni-glu by regioselective nitration of 4-methoxyindoline derivative

Synthetic Communications

Volumn 39, Issue 22, 2009, Pages 4030-4038

  Wang, Xiaowei ^a   Gao, Yu ^a   Xu, Yang ^a   Li, Li ^a   Zhang, Zhili ^a   Liu, Junyi ^a,b  

^a PEKING UNIVERSITY HEALTH SCIENCE CENTER   (China)

^b PEKING UNIVERSITY   (China)

Author keywords

Aromatic nitration; Caged L glutamate; Claypop; Nitroindolines; Photorelease agent

Indexed keywords

1 [(4 AMINO 4 CARBOXYBUTANOYL)] 4 METHOXY 7 NITROINDOLINE; 1 GLUTAMINE 4 METHYLOXY 7 NITROINDOLINE; 4 METHOXYINDOLINE DERIVATIVE; AMINE; GLUTAMIC ACID DERIVATIVE; INDOLE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; NITRATION; SYNTHESIS;

EID: 70350662763     PISSN: 00397911     EISSN: 15322432     Source Type: Journal    
DOI: 10.1080/00397910902883645     Document Type: Article

References (8)

1. Papageorgiou, G.; Ogden, D. C.; Barth, A.; Corrie, J. E. T. Photorelease of carboxylic acids from 1-acyl-7-nitroindolines in aqueous solution: Rapid and efficient photorelease of L-glutamate. J. Am. Chem. Soc. 1999, 121, 6503-6504.
2. Papageorgiou, G.; Corrie, J. E. T. Effects of aromatic substituents on the photocleavage of 1-acyl-7-nitroindolines. Tetrahedron 2000, 56 (41), 8197-8205.
3. Fedoryak, O. D.; Sul, J. Y.; Haydon, P. G.; Ellis-Davies, G. C. R. Synthesis of a caged glutamate for efficient one-and two-photon photorelease on living cells. Chem. Commun. 2005, 29, 3664-3666.
4. Papageorgiou, G.; Corrie, J. E. T. Regioselective nitration of 1-acyl-4-methoxyindolines leads to efficient synthesis of a photolabile L-glutamate precursor. Synth. Commun. 2002, 32 (10), 1571-1577.
5. Papageorgiou, G.; Corrie, J. E. T. Optimised synthesis and photochemistry of antenna-sensitised 1-acyl-7-nitroindolines. Tetrahedron 2005, 61, 609-616.
6. Emil, H. W.; Daniel, W. G. The preparation and decomposition of certain N-nitroamides and N-nitrocarbamates. J. Am. Chem. Soc. 1961, 83, 1191.
7. Papageorgiou, G.; Ogden, D.; Corrie, J. E. T. An antenna-sensitized nitroin-doline precursor to enable photorelease of L-glutamate in high concentrations. J. Org. Chem. 2004, 69, 7228-7233.
8. Laszlo, P.; Cornelis, A. ''Claycop,'' a user-friendly oxidizing and nitrating reagent. Aldrichim. Acta 1988, 21 (4), 97.