Document Detail


Regioselective 15-bromination and functionalization of a stable synthetic bacteriochlorin.
MedLine Citation:
PMID:  17567079     Owner:  NLM     Status:  MEDLINE    
Abstract/OtherAbstract:
5-Methoxy-8,8,18,18-tetramethyl-2,12-di-p-tolylbacteriochlorin (MeO-BC) undergoes regioselective electrophilic bromination with NBS to give the 15-bromo analogue (MeO-BC-Br15) in 85% yield. By contrast, the bacteriochlorin lacking the 5-methoxy group (8,8,18,18-tetramethyl-2,12-di-p-tolylbacteriochlorin, H-BC) gives a mixture of two monobromo- and two dibromobacteriochlorins. Deuterium exchange of both bacteriochlorins (H-BC and MeO-BC) in acidic media (TFA-d) occurs preferentially at the beta-pyrrole positions (3, 13) > unhindered meso-positions (5, 15 for H-BC; 15 for MeO-BC) > hindered meso-positions (10, 20). The 15-bromo-5-methoxybacteriochlorin MeO-BC-Br15 was subjected to three types of Pd-mediated coupling reactions (Suzuki, Sonogashira, Hartwig-Buchwald) to give six bacteriochlorins bearing functional groups at the 15-position (49% to 85% yield). The groups include 4-(tert-butoxycarbonylmethoxy)phenyl, 4-pyridyl, 3,5-diformylphenyl, phenylethynyl, TIPS-ethynyl, and N-benzamido. The presence of the 15-ethynyl moiety shifts the position of the long-wavelength Qy band from 732 nm to approximately 753 nm. The ability to introduce a range of groups at a specific site enables synthetic bacteriochlorins to be tailored for a variety of applications.
Authors:
Dazhong Fan; Masahiko Taniguchi; Jonathan S Lindsey
Related Documents :
23049399 - Comparison of cytokine levels and metabolic parameters of stored platelet concentrates ...
8116929 - Altered platelet indices in dogs with hypothyroidism and cats with hyperthyroidism.
23518829 - Reactive thrombocytosis accompanying subclinical hypothyroidism due to hashimoto's thyr...
8173019 - Platelet membrane fluidity and plasma malondialdehyde levels in alzheimer's demented pa...
7146619 - Structural features of platelet activating factor (1-alkyl-2-acetyl-sn-glycero-3-phosph...
7161779 - Platelet activation, fibrinolytic activity and circulating immune complexes in raynaud'...
12893689 - Mechanisms involved in adenosine triphosphate--induced platelet aggregation in whole bl...
17452929 - Evaluation of tris-hydroxymethylaminomethane on reversing coagulation abnormalities cau...
12046059 - Influencing factors of pancreatic microcirculatory impairment in acute panceatitis.
Publication Detail:
Type:  Journal Article; Research Support, N.I.H., Extramural; Research Support, Non-U.S. Gov't; Research Support, U.S. Gov't, Non-P.H.S.     Date:  2007-06-13
Journal Detail:
Title:  The Journal of organic chemistry     Volume:  72     ISSN:  0022-3263     ISO Abbreviation:  J. Org. Chem.     Publication Date:  2007 Jul 
Date Detail:
Created Date:  2007-06-29     Completed Date:  2007-08-13     Revised Date:  2013-06-06    
Medline Journal Info:
Nlm Unique ID:  2985193R     Medline TA:  J Org Chem     Country:  United States    
Other Details:
Languages:  eng     Pagination:  5350-7     Citation Subset:  IM    
Affiliation:
Department of Chemistry, North Carolina State University, Raleigh, North Carolina 27695-8204, USA.
Export Citation:
APA/MLA Format     Download EndNote     Download BibTex
MeSH Terms
Descriptor/Qualifier:
Bromine / chemistry*
Deuterium Exchange Measurement
Magnetic Resonance Spectroscopy
Molecular Structure
Palladium / chemistry
Porphyrins / chemical synthesis*,  chemistry
Spectrophotometry
Stereoisomerism
Grant Support
ID/Acronym/Agency:
GM36238/GM/NIGMS NIH HHS; R01 GM036238-19/GM/NIGMS NIH HHS; R01 GM036238-20/GM/NIGMS NIH HHS
Chemical
Reg. No./Substance:
0/Porphyrins; 0/bacteriochlorin; 7440-05-3/Palladium; 7726-95-6/Bromine
Comments/Corrections

From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine


Previous Document:  Conformationally locked bridged bicyclic diselenides: synthesis, structure, Se...O interaction, and ...
Next Document:  Survey of the diversity space coverage of reported combinatorial libraries.