Literature DB >> 17048824

Efficient microwave-assisted synthesis of amine-substituted tetrakis(pentafluorophenyl)porphyrin.

Diana Samaroo1, Clifford E Soll, Louis J Todaro, Charles M Drain.   

Abstract

We report an efficient and rapid means for the synthesis of tetrakis(pentafluorophenyl)porphyrin (TPPF(20)) derivatives by microwave irradiation in an environmentally acceptable solvent. The selective displacement of the para-fluorine groups in TPPF(20) by primary amines occurs in yields between 70 and 95%. This method demonstrates that TPPF(20) is an ideal platform for the rapid formation of porphyrin conjugates for therapeutic, catalytic, and other applications. [reaction: see text]

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Year:  2006        PMID: 17048824      PMCID: PMC2631550          DOI: 10.1021/ol060946z

Source DB:  PubMed          Journal:  Org Lett        ISSN: 1523-7052            Impact factor:   6.005


  7 in total

1.  Microwave-assisted synthesis utilizing supported reagents: a rapid and efficient acylation procedure.

Authors:  Daryl R Sauer; Douglas Kalvin; Kathleen M Phelan
Journal:  Org Lett       Date:  2003-11-27       Impact factor: 6.005

2.  Synthesis and biological evaluation of thioglycosylated porphyrins for an application in photodynamic therapy.

Authors:  I Sylvain; R Zerrouki; R Granet; Y M Huang; J-F Lagorce; M Guilloton; J-C Blais; P Krausz
Journal:  Bioorg Med Chem       Date:  2002-01       Impact factor: 3.641

3.  Pegylation of a chlorin(e6) polymer conjugate increases tumor targeting of photosensitizer.

Authors:  M R Hamblin; J L Miller; I Rizvi; B Ortel; E V Maytin; T Hasan
Journal:  Cancer Res       Date:  2001-10-01       Impact factor: 12.701

4.  Efficient synthesis of 4-aminoquinazoline and thieno[3,2-d]pyrimidin-4-ylamine derivatives by microwave irradiation.

Authors:  David S Yoon; Ying Han; Todd M Stark; James C Haber; Brian T Gregg; Sara B Stankovich
Journal:  Org Lett       Date:  2004-12-09       Impact factor: 6.005

5.  Efficient synthesis and photodynamic activity of porphyrin-saccharide conjugates: targeting and incapacitating cancer cells.

Authors:  Xin Chen; Li Hui; David A Foster; Charles Michael Drain
Journal:  Biochemistry       Date:  2004-08-31       Impact factor: 3.162

6.  Poly(ethylene glycol)-supported tetrahydroxyphenyl porphyrin: a convenient, recyclable catalyst for photooxidation reactions.

Authors:  Maurizio Benaglia; Tamara Danelli; Fabrizio Fabris; Davide Sperandio; Gianluca Pozzi
Journal:  Org Lett       Date:  2002-11-28       Impact factor: 6.005

Review 7.  Pegylation: engineering improved biopharmaceuticals for oncology.

Authors:  Graham Molineux
Journal:  Pharmacotherapy       Date:  2003-08       Impact factor: 4.705

  7 in total
  17 in total

1.  Synthesis and cell phototoxicity of a triply bridged fused diporphyrin appended with six thioglucose units.

Authors:  Sunaina Singh; Amit Aggarwal; N V S Dinesh K Bhupathiraju; Brandon Newton; Ahmad Nafees; Ruomei Gao; Charles Michael Drain
Journal:  Tetrahedron Lett       Date:  2014-09-28       Impact factor: 2.415

Review 2.  Glycosylated Porphyrins, Phthalocyanines, and Other Porphyrinoids for Diagnostics and Therapeutics.

Authors:  Sunaina Singh; Amit Aggarwal; N V S Dinesh K Bhupathiraju; Gianluca Arianna; Kirran Tiwari; Charles Michael Drain
Journal:  Chem Rev       Date:  2015-08-28       Impact factor: 60.622

3.  Carbon-1 versus Carbon-3 Linkage of d-Galactose to Porphyrins: Synthesis, Uptake, and Photodynamic Efficiency.

Authors:  Patrícia M R Pereira; Waqar Rizvi; N V S Dinesh K Bhupathiraju; Naxhije Berisha; Rosa Fernandes; João P C Tomé; Charles Michael Drain
Journal:  Bioconjug Chem       Date:  2018-01-26       Impact factor: 4.774

Review 4.  Self-organized porphyrinic materials.

Authors:  Charles Michael Drain; Alessandro Varotto; Ivana Radivojevic
Journal:  Chem Rev       Date:  2009-05       Impact factor: 60.622

Review 5.  Controlled microwave heating in modern organic synthesis: highlights from the 2004-2008 literature.

Authors:  C Oliver Kappe; Doris Dallinger
Journal:  Mol Divers       Date:  2009-04-21       Impact factor: 2.943

6.  A New Crosslinkable Oxygen Sensor Covalently Bonded into Poly(2-hydroxyethyl methacrylate)-CO-Polyacrylamide Thin Film for Dissolved Oxygen Sensing.

Authors:  Yanqing Tian; Bradley R Shumway; Deirdre R Meldrum
Journal:  Chem Mater       Date:  2010-03-23       Impact factor: 9.811

Review 7.  Fluorinated porphyrinoids as efficient platforms for new photonic materials, sensors, and therapeutics.

Authors:  N V S Dinesh K Bhupathiraju; Waqar Rizvi; James D Batteas; Charles Michael Drain
Journal:  Org Biomol Chem       Date:  2016-01-14       Impact factor: 3.876

8.  Synthesis and photophysical properties of thioglycosylated chlorins, isobacteriochlorins, and bacteriochlorins for bioimaging and diagnostics.

Authors:  Sunaina Singh; Amit Aggarwal; Sebastian Thompson; João P C Tomé; Xianchun Zhu; Diana Samaroo; Mikki Vinodu; Ruomei Gao; Charles Michael Drain
Journal:  Bioconjug Chem       Date:  2010-10-21       Impact factor: 4.774

9.  meso-Tetra(pentafluorophenyl)porphyrin as an efficient platform for combinatorial synthesis and the selection of new photodynamic therapeutics using a cancer cell line.

Authors:  Diana Samaroo; Mikki Vinodu; Xin Chen; Charles Michael Drain
Journal:  J Comb Chem       Date:  2007-09-15

10.  Synthesis and cellular studies of polyamine conjugates of a mercaptomethyl-carboranylporphyrin.

Authors:  N V S Dinesh K Bhupathiraju; M Graça H Vicente
Journal:  Bioorg Med Chem       Date:  2012-11-17       Impact factor: 3.641

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