Study of a Convenient Method for the Preparation of Hydrosoluble Fluorescent Triazatruxene Derivatives

被引：40

作者：

Franceschin, Marco ^{[1
]}

Ginnari-Satriani, Luca ^{[1
]}

Alvino, Antonello ^{[1
]}

Ortaggi, Giancarlo ^{[1
]}

Bianco, Armandodoriano ^{[1
]}

机构：

[1] Univ Roma La Sapienza, Dipartimento Chim, I-00185 Rome, Italy

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2010年 / 2010卷 / 01期

关键词：

Fused-ring systems; Nitrogen heterocycles; Hydrosolubility; Cyclotrimerization; Fluorescence spectroscopy; QUADRUPLEX DNA STRUCTURES; PERYLENE DERIVATIVES; SIDE-CHAINS; SERIES;

D O I：

10.1002/ejoc.200900869

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Triazatruxene derivatives find many applications as lipophilic compounds, but few examples of hydrosoluble derivatives have been reported so far. In this paper, we compare different synthetic routes for the preparation of hydrophilic triazatruxene derivatives and define the most versatile path-way. The synthesized compounds are fluorescent not only in organic solvents, as reported for other lipophilic derivatives, but also in water, making them particularly suitable for biological applications.

引用

页码：134 / 141

页数：8

共 24 条

[1] Synthesis and spectroscopic properties of highly water-soluble perylene derivatives [J].

Alvino, Antonello ;

Franceschin, Marco ;

Cefaro, Chiara ;

Borioni, Silvia ;

Ortaggi, Giancarlo ;

Bianco, Armandodoriano .

TETRAHEDRON, 2007, 63 (33) :7858-7865

[2] SYNTHESIS AND CHARACTERIZATION OF NEW INDOLE TRIMERS AND TETRAMERS [J].

BOCCHI, V ;

PALLA, G .

TETRAHEDRON, 1986, 42 (18) :5019-5024

[3] AMINOALKYLINDOLES - STRUCTURE-ACTIVITY-RELATIONSHIPS OF NOVEL CANNABINOID MIMETICS [J].

EISSENSTAT, MA ;

BELL, MR ;

DAMBRA, TE ;

ALEXANDER, EJ ;

DAUM, SJ ;

ACKERMAN, JH ;

GRUETT, MD ;

KUMAR, V ;

ESTEP, KG ;

OLEFIROWICZ, EM ;

WETZEL, JR ;

ALEXANDER, MD ;

WEAVER, JD ;

HAYCOCK, DA ;

LUTTINGER, DA ;

CASIANO, FM ;

CHIPPARI, SM ;

KUSTER, JE ;

STEVENSON, JI ;

WARD, SJ .

JOURNAL OF MEDICINAL CHEMISTRY, 1995, 38 (16) :3094-3105

[4] SCHMIDT REACTION WITH AROMATIC KETONES [J].

EVANS, D ;

LOCKHART, IM .

JOURNAL OF THE CHEMICAL SOCIETY, 1965, (SEP) :4806-&

[5] Synthesis of novel star-shaped carbazole-functionalized triazatruxenes [J].

Feng, Guo-Liang ;

Lai, Wen-Yong ;

Ji, Shun-Jun ;

Huang, Wei .

TETRAHEDRON LETTERS, 2006, 47 (39) :7089-7092

[6] The number and distances of positive charges of polyamine side chains in a series of perylene diimides significantly influence their ability to induce G-quadruplex structures and inhibit human telomerase [J].

Franceschin, Marco. ;

Lombardo, Caterina Maria ;

Pascucci, Emanuela ;

D'Ambrosio, Danilo ;

Micheli, Emanuela ;

Bianco, Armandodoriano ;

Ortaggi, Giancarlo ;

Savino, Maria .

BIOORGANIC & MEDICINAL CHEMISTRY, 2008, 16 (05) :2292-2304

[7] New highly hydrosoluble and not self-aggregated perylene derivatives with three and four polar side-chains as G-quadruplex telomere targeting agents and telomerase inhibitors [J].

Franceschin, Marco ;

Pascucci, Emanuela ;

Alvino, Antonello ;

D'Ambrosio, Danilo ;

Bianco, Armandodoriano ;

Ortaggi, Giancarlo ;

Savino, Maria .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2007, 17 (09) :2515-2522

[8] Specific interactions with intra- and intermolecular G-quadruplex DNA structures by hydrosoluble coronene derivatives: A new class of telomerase inhibitors [J].

Franceschin, Marco ;

Alvino, Antonello ;

Casagrande, Valentina ;

Mauriello, Clementina ;

Pascucci, Emanuela ;

Savino, Maria ;

Ortaggi, Giancarlo ;

Bianco, Armandodoriano .

BIOORGANIC & MEDICINAL CHEMISTRY, 2007, 15 (04) :1848-1858

[9] G-Quadruplex DNA Structures and Organic Chemistry: More Than One Connection [J].

Franceschin, Marco .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2009, 2009 (14) :2225-2238

[10] Synthesis and Preferred All-syn Conformation of C3-Symmetrical N-(Hetero)arylmethyl Triindoles [J].

Garcia-Frutos, Eva M. ;

Gomez-Lor, Berta ;

Monge, Angeles ;

Gutierrez-Puebla, Enrique ;

Alkorta, Ibon ;

Elguero, Jose .

CHEMISTRY-A EUROPEAN JOURNAL, 2008, 14 (28) :8555-8561

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