Linked Life Data

16872176

Source:http://linkedlifedata.com/resource/pubmed/id/16872176

Statements in which the resource exists as a subject.
PredicateObject
rdf:type
lifeskim:mentions
pubmed:issue
16
pubmed:dateCreated
2006-7-28
pubmed:abstractText
A novel approach toward "locked" chlorins with increased stability has been studied in detail. The chlorin skeleton is assembled in a convergent fashion from two fragments via a porphyrin forming reaction, followed by 1,3-dipolar cycloaddition of azomethine ylides, which are formed in situ. Central to the success of the process is the presence of two electron-withdrawing groups in vicinal positions at the perimeter of the porphyrin. As a result, the 1,3-dipolar cycloaddition took place regioselectively, on the bond activated by two electron-withdrawing groups. Moreover, the chlorins formed are locked and hence more stable because of the presence of two quaternary carbon atoms. Overall, in just six steps locked chlorins were constructed from easily available materials. The large array of functionalities tolerated in this approach validates it for a broad use in more advanced studies. The correlation between the results of the 1,3-dipolar cycloaddition and dipolarophile (porphyrin) LUMO energy was extensively studied. There was a definite correlation between the reaction time and the LUMO energy level, and a partial correlation between the reaction yield and the distribution of the LUMO. Additionally, various approaches toward crucial building blocks, namely 3,4-disubstituted-2,5-diformylpyrroles, were investigated.
pubmed:language
eng
pubmed:journal
pubmed:citationSubset
IM
pubmed:chemical
pubmed:status
MEDLINE
pubmed:month
Aug
pubmed:issn
0022-3263
pubmed:author
pubmed:issnType
Print
pubmed:day
4
pubmed:volume
71
pubmed:owner
NLM
pubmed:authorsComplete
Y
pubmed:pagination
5942-50
pubmed:meshHeading
pubmed:year
2006
pubmed:articleTitle
Synthesis of locked meso-beta-substituted chlorins via 1,3-dipolar cycloaddition.
pubmed:affiliation
Institute of Organic Chemistry of the Polish Academy of Sciences, Warsaw, Poland.
pubmed:publicationType
Journal Article, Research Support, Non-U.S. Gov't