New developments in the medicinal chemistry of carboranes

Satapathy, Rashmirekha; Dash, Barsha; Maguire, John A.; Hosmane, Narayan S.

doi:10.1135/cccc2010050

Cited by 41 publications

(17 citation statements)

References 156 publications

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“…[5] These properties have made them suitable for potential application in the fields of catalysis, [6] material science such as heat-stable polymer or hybrid materials, [7] and especially in medicine. [8] Due to the versatility of o-carboranes to be chemically modified, [1c, 9] they have been an ideal group for the preparation of stable, agile, and suitable building blocks that can be subsequently attached to a molecule, such as star-shaped systems; [10] dendrons and dendrimers; [11,12] or porphyrins. [13] In addition, it is also possible to achieve the partial degradation of the closo clusters to obtain the corresponding nido-carborane derivatives, thereby transforming neutral molecules into anionic systems.…”

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confidence: 99%

Synthesis and Characterization of New Fluorescent Styrene‐Containing Carborane Derivatives: The Singular Quenching Role of a Phenyl Substituent

Ferrer‐Ugalde

Juárez-Pérez

Teixidor

et al. 2011

Chemistry A European J

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A set of neutral and anionic carborane derivatives in which the styrenyl fragment is introduced as a fluorophore group has been successfully synthesized and characterized. The reaction of the monolithium salts of 1-Ph-1,2-C(2)B(10)H(11), 1-Me-1,2-C(2)B(10)H(11) and 1,2-C(2)B(10)H(12) with one equivalent of 4-vinylbenzyl chloride leads to the formation of compounds 1-3, whereas the reaction of the dilithium salt of 1,2-C(2)B(10)H(12) with two equivalents of 4-vinylbenzyl chloride gives disubstituted compound 4. The closo clusters were degraded using the classical method, KOH in EtOH, to afford the corresponding nido species, which were isolated as tetramethylammonium salts. The crystal structure of the four closo compounds 1-4 were analyzed by X-ray diffraction. All compounds, except 1, display emission properties, with quantum yields dependent on the nature of the cluster (closo or nido) and the substituent on the second C(cluster) atom. In general, closo compounds 2-4 exhibit high fluorescence emission, whereas the presence of a nido cluster produces a decrease of the emission intensity. The presence of a phenyl group bonded to the C(cluster) results in an excellent electron-acceptor unit that produces a quenching of the fluorescence. DFT calculations have confirmed the charge-separation state in 1 to explain the quenching of the fluorescence and the key role of the carboranyl fragment in this luminescent process.

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confidence: 99%

Synthesis and Characterization of New Fluorescent Styrene‐Containing Carborane Derivatives: The Singular Quenching Role of a Phenyl Substituent

Ferrer‐Ugalde

Juárez-Pérez

Teixidor

et al. 2011

Chemistry A European J

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“…After the first hour, there was formation of a beige precipitate; but the stirring was maintained for another 4 h. The resulting suspension was filtered through a frit, the solid washed with pentane, and dried under vacuum for 8 h. The product was finally crystallized from CH 2 Cl 2 /hexane to give 230 mg of 6 (62%). 11 [9,9,9,(H)(PPh 3 ) 2 -arachno-9,6-IrSB 8 H 10 ] (7)…”

Section: General Proceduresmentioning

confidence: 99%

Synthesis and characterization of new 10- and 12-vertex CO-ligated metallathiaboranes

Luaces

Bould

Macı́as

et al. 2012

Journal of Organometallic Chemistry

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Dedicated to Professor Thomas P. Fehlner on his 75th birthday. He has been a superb mentor of many scientists around the world working on "inorganometallic chemistry". Keywords:The reaction between [arachno-6-SB 9 H 12 ] À and [IrCl(CO)(PMe 3 ) 2 ] affords the previously reported 11-vertex cluster, [8,8,(PMe 3 ) 2 -arachno-8,7-IrSB 9 H 10 ] (4), and small amounts of the new 10-vertex iridathiaborane [9,9,9,(H)(PMe 3 ) 2 -arachno-9,6-IrSB 8 H 10 ] (5). Alternatively, a rational synthesis of iridathiadecaboranes is effected from the reaction of the 9-vertex anion [arachno-4-SB 8 H 11 ] À with [MCl(CO)(PPh 3 ) 2 ], to afford new CO-ligated 10-vertex metallathiaboranes of formulation, [9,9,9,(H)(PPh 3 ) 2 -arachno-9,6-MSB 8 H 10 ], where M ¼ Rh (6) and Ir (7), in useful yields of 61% and 60% respectively. Treatment of the 11-vertex rhodathiaborane, [8,8-(PPh 3 ) 2 -8,7-nido-RhSB 9 H 10 ] (1) with nBuLi, followed by addition of [IrCl(CO)(PMe 3 ) 2 ] affords the 12-vertex iridarhodathiaborane, [1,2-(m-CO)-1,1,2-(PMe 3 ) 3 -2-(PPh 3 )-closo-1,2-IrRhSB 9 H 9 ] (8) in low yield (0.7%). The 10-vertex metallathiaboranes, 5, 6 and 7, and the bimetallic 12-vertex cluster, 8, have been characterized by multinuclear NMR spectroscopy. In addition, the molecular structures of compounds 5, 6, and 8 have been studied by X-ray diffraction.

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“…Both topics have been mentioned in several recent reviews on the medicinal chemistry of carboranes, 60,65,66 or enzyme inhibition 67 and the latter is also treated in much detail in a book chapter. 64 The best established role of boron-based compounds in medicine is as agents for the boron neutron capture therapy (BNCT) of cancer.…”

Section: F2) Second-order Nonlinear Optical (Nlo) Coefficient Calcmentioning

confidence: 99%

“…64 The best established role of boron-based compounds in medicine is as agents for the boron neutron capture therapy (BNCT) of cancer. 66 Although this area has been reserved mainly to substituted 12-vertex boranes, several metallacarborane derivativescobaltabisdicarbollide conjugates with nucleosides-have also been tested and shown to accumulate in the cells and to be nontoxic. 65 Furthemore, conjugates of metallacarboranes with porphyrins hold promise to be useful in the dual photodynamic therapy (PDT)/BNCT of cancer.…”

Section: F2) Second-order Nonlinear Optical (Nlo) Coefficient Calcmentioning

confidence: 99%

Metallacarboranes and their interactions: theoretical insights and their applicability

et al. 2012

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New developments in the medicinal chemistry of carboranes

Cited by 41 publications

References 156 publications

Synthesis and Characterization of New Fluorescent Styrene‐Containing Carborane Derivatives: The Singular Quenching Role of a Phenyl Substituent

Synthesis and Characterization of New Fluorescent Styrene‐Containing Carborane Derivatives: The Singular Quenching Role of a Phenyl Substituent

Synthesis and characterization of new 10- and 12-vertex CO-ligated metallathiaboranes

Metallacarboranes and their interactions: theoretical insights and their applicability

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