2,7,12,17‐Tetra(<i>p</i>‐butylphenyl)‐3,6,13,16‐tetraazaporphycene: The First Example of a Straightforward Synthetic Approach to a New Class of Photosensitizing Macrocycles

Nonell, Santi; Borrell, José I.; Borrós, Salvador; Colominas, Carles; Rey, Oscar; Rubio, Noemí; Sánchez‐García, David; Teixidó, Jordi

doi:10.1002/ejoc.200200684

Cited by 27 publications

(31 citation statements)

References 30 publications

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“…5). Indeed, the first compound synthesized, 2,7,12,17-tetrakis(4-butylphenyl)-3,6,13,16-tetraazaporphycene (TAPo), showed a bathochromic shift in toluene solution of 101 nm relative to 2,7,12,17-tetraphenylporphycene, actually 20 nm larger than predicted [110,121]. 20%) as a result of the sequential inter-and intramolecular McMurry couplings.…”

Section: The Ideal Pdt Sensitizermentioning

confidence: 98%

“…4) more rapidly than standard ab initio methods. This methodology usually starts with a standard DFT ground state structure optimization [108] followed by a TDDFT energy calculation of excited states [109], UV/Vis prediction [110,111], etc.…”

Section: The Ideal Pdt Sensitizermentioning

confidence: 99%

“…Finally, red shifts can also be induced by introduction of heteroatoms in the porphycene core [92,110,[115][116][117][118][119][120]. The batho-and hyperchromic effects brought about by aza substitution in porphyrins encouraged exploration of whether such effects would also occur in porphycenes.…”

Section: The Ideal Pdt Sensitizermentioning

confidence: 99%

“…Reduction of (38) with DIBAL-H (diisobutylaluminium hydride) in tetrahydrofuran (THF) at reflux to diol (39) followed by oxidation with DDQ afforded dialdehyde (40), which was converted to 3,6,13,16-tetraazaporphycene (41) upon oxidation of the corresponding [20]annulene with DDQ [120]. Almost simultaneously, a general methodology for the synthesis of 2,7,12,17-tetraaryl-substituted 3,6,13,16-tetraazaporphycenes (46) (Scheme 4), that avoids the development of a de novo synthesis whenever a new peripheral substituent is desired, was described [110]. Such procedure, easily amenable to a combinatorial approach, starts with bromination of the di-SEM ([2-(trimethylsilyl)ethoxy]methyl) protected 2,2'-biimidazole (42) to give the tetrabromo derivative (43) [152].…”

Section: Peripheral Functionalization 233 Modification Of the Corementioning

confidence: 99%

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Porphycenes: Facts and Prospects in Photodynamic Therapy of Cancer

Stockert¹,

Cañete²,

Juarranz³

et al. 2007

CMC

177

130

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The photodynamic process induces cell damage and death by the combined effect of a photosensitizer (PS), visible light, and molecular oxygen, which generate singlet oxygen ((1)O(2)) and other reactive oxygen species that are responsible for cytotoxicity. The most important application of this process with increasing biomedical interest is the photodynamic therapy (PDT) of cancer. In addition to hematoporphyrin-based drugs, 2nd generation PSs with better photochemical properties are now studied using cell cultures, experimental tumors and clinical trials. Porphycene is a structural isomer of porphyrin and constitutes an interesting new class of PS. Porphycene derivatives show higher absorption than porphyrins in the red spectral region (lambda > 600 nm, epsilon > 50000 M-(1)cm(-1)) owing to the lower molecular symmetry. Photophysical and photobiological properties of porphycenes make them excellent candidates as PSs, showing fast uptake and diverse subcellular localizations (mainly membranous organelles). Several tetraalkylporphycenes and the tetraphenyl derivative (TPPo) induce photodamage and cell death in vitro. Photodynamic treatments of cultured tumor cells with TPPo and its palladium(II) complex induce cytoskeletal changes, mitotic blockage, and dose-dependent apoptotic or necrotic cell death. Some pharmacokinetic and phototherapeutic studies on experimental tumors after intravenous or topical application of lipophilic alkyl-substituted porphycene derivatives are known. Taking into account all these features, porphycene PSs should be very useful for PDT of cancer and other biomedical applications.

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Section: The Ideal Pdt Sensitizermentioning

confidence: 98%

Section: The Ideal Pdt Sensitizermentioning

confidence: 99%

Section: The Ideal Pdt Sensitizermentioning

confidence: 99%

Section: Peripheral Functionalization 233 Modification Of the Corementioning

confidence: 99%

See 2 more Smart Citations

Porphycenes: Facts and Prospects in Photodynamic Therapy of Cancer

Stockert¹,

Cañete²,

Juarranz³

et al. 2007

CMC

177

130

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“…In addition to iodides, bromides can serve as leaving groups. A double cross-coupling reaction in the 4-position was accomplished on biimidazole 75 to give 76 in 55% yield (Scheme 23) [31].…”

Section: Scheme 20: Synthesis Of Coumarin Derivatives5-and 8-methoxypmentioning

confidence: 99%

Metal Catalyzed Suzuki-Miyaura Cross-Coupling– Efficient Methodology for Synthesis the Natural and non-Natural biological active Molecules

israr¹,

Kaousar²,

Rasool³

et al. 2017

Preprint

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New class of biologically active and non-active compounds can be synthesized via transition metal mediated Suzuki cross coupling reaction that has a great impact on the advancement of organic chemistry. These resulted products can lend a helping hand in pharmaceutical and polymer chemistry for the betterment of mankind. Suzuki-Miyaura cross coupling reaction is one of the best tools through which many natural and non-natural compounds can be synthesized.

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The McMurry Coupling and Related Reactions

Takeda

Tsubouchi

2013

Organic Reactions

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The McMurry coupling reaction has been recognized as one of the most efficient methods for the synthesis of alkenes from carbonyl compounds. This reaction can be applied to the preparation of various alkenes that are otherwise difficult to prepare. For example, sterically congested tetrasubstituted alkenes as well as medium to large membered rings involving natural products may be accessed via this process. This coupling utilizes various low‐valent titanium reagents generated by the reduction of titanium (III or IV) chloride with K, Zn, LiAlH 4 , C 8 K, amongst others. Furthermore, a variety of low‐valent metal species other than titanium, including aluminum, zirconium, niobium, molybdenum, indium, tungsten, and samarium, have also been found to promote the reductive coupling of carbonyl compounds. The scope and limitations of these reagent systems are reviewed in this chapter, together with the stereochemistry and reaction mechanism. This reaction is categorized into four coupling modes: i) homocoupling giving symmetrical alkenes, ii) mixed coupling giving unsymmetrical alkenes, iii) intramolecular coupling giving cycloalkenes, and iv) tandem coupling giving cyclic polyenes. Characteristics of these reaction modes are described briefly. A selection of synthetic applications are reviewed, including examples of the preparation of sterically congested and strained alkenes, medium to large‐ring compounds, biologically active targets, as well as substrates applicable in material science. Experimental conditions used for this versatile process are summarized to assist the choice of suitable conditions.

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2,7,12,17‐Tetra(p‐butylphenyl)‐3,6,13,16‐tetraazaporphycene: The First Example of a Straightforward Synthetic Approach to a New Class of Photosensitizing Macrocycles

Cited by 27 publications

References 30 publications

Porphycenes: Facts and Prospects in Photodynamic Therapy of Cancer

Porphycenes: Facts and Prospects in Photodynamic Therapy of Cancer

Metal Catalyzed Suzuki-Miyaura Cross-Coupling– Efficient Methodology for Synthesis the Natural and non-Natural biological active Molecules

The McMurry Coupling and Related Reactions

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2,7,12,17‐Tetra(p‐butylphenyl)‐3,6,13,16‐tetraazaporphycene: The First Example of a Straightforward Synthetic Approach to a New Class of Photosensitizing Macrocycles

Cited by 27 publications

References 30 publications

Porphycenes: Facts and Prospects in Photodynamic Therapy of Cancer

Porphycenes: Facts and Prospects in Photodynamic Therapy of Cancer

Metal Catalyzed Suzuki-Miyaura Cross-Coupling&ndash; Efficient Methodology for Synthesis the Natural and non-Natural biological active Molecules

The McMurry Coupling and Related Reactions

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Product

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Metal Catalyzed Suzuki-Miyaura Cross-Coupling– Efficient Methodology for Synthesis the Natural and non-Natural biological active Molecules