295325-87-0Relevant articles and documents
1-Acyl-7-nitroindoline derivatives, their preparation and their use as photocleavable precursors
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Page column 15, (2010/02/07)
Photoreleasable compounds comprising a caging moiety linked to an effector moiety represented by structural formula (I) wherein R1is hydrogen; C1-10alkyl or substituted alkyl; O(CH2)n—Y; N(COZ)(CH2)mY; or N[(CH2)mY′[(CH2)NY]; R2and R3are independently selected from: hydrogen; C1-10alkyl or substituted alkyl; or R2and R3together are cycloalkyl; R4is hydrogen; C1-10alkyl or substituted alkyl; phenyl or substituted phenyl; (CH2)nY; or (CH2)mO(CH2)nY; wherein m and n are independently between 1 and 10; Y and Y′ are independently selected from hydrogen, CO2H or salts thereof or OPO32?, Z is hydrogen or C1-10alkyl or substituted alkyl; and, X is an effector moiety or a group capable of being coupled or converted to an effector moiety, which are capable of releasing the effector moiety on irradiation, typically by flash irradiation with UV light. The photoreleasable compounds can therefor be used to deliver biologically active effector moieties such as neuroactive amino acids or metal chelators to sites where their activity is required.
Effects of aromatic substituents on the photocleavage of 1-acyl-7-nitroindolines
Papageorgiou, George,Corrie, John E.T
, p. 8197 - 8205 (2007/10/03)
Photolysis of 1-acyl-7-nitroindolines in aqueous solution gives a carboxylic acid and a 7-nitrosoindole. These compounds are useful as photolabile precursors of carboxylic acids, particularly neuroactive amino acids. The effect of electron-donating substituents at the 4-position has been explored for its effect on photolysis efficiency. 4-Methoxy substitution improved the photolysis efficiency >2-fold but the 4-dimethylamino analogue was essentially inert. A 5-alkyl substituent, that blocks unwanted nitration at this position, reduced the beneficial effect of the 4-methoxy group. (C) 2000 Elsevier Science Ltd.
