17444-22-3Relevant academic research and scientific papers
Straightforward synthesis of radioiodinated Cc-substituted o-carboranes: Towards a versatile platform to enable the in vivo assessment of BNCT drug candidates
Gona,Thota,Baz,Gómez-Vallejo,Llop
, p. 9915 - 9920 (2015)
Due to their high boron content and rich chemistry, dicarba-closo-dodecaboranes (carboranes) are promising building blocks for the development of drug candidates with application in Boron Neutron Capture Therapy. However, the non-invasive determination of their pharmacokinetic properties to predict therapeutic efficacy is still a challenge. Herein, we have reported the unprecedented preparation of mono-[125I] iodinated decaborane via a catalyst-assisted isotopic exchange. Subsequent reactions of the radiolabelled species with acetylenes in acetonitrile under microwave heating yield the corresponding 125I-labelled, Cc-substituted o-carboranes with good overall radiochemical yields in short reaction times. The same synthetic strategy was successfully applied to the preparation of 131I-labelled analogues, and further extension to other radioisotopes of iodine such as 124I (positron emitter) or 123I (gamma emitter) can be envisaged. Hence, the general strategy reported here is suitable for the preparation of a wide range of radiolabelled Cc-substituted o-carborane derivatives. The labelled compounds might be subsequently investigated in vivo by using nuclear imaging techniques such as Single Photon Emission Computerized Tomography or Positron Emission Tomography.
Practical Synthesis of B(9)-Halogenated Carboranes with N-Haloamides in Hexafluoroisopropanol
Guo, Wenjing,Guo, Chenyang,Ma, Yan-Na,Chen, Xuenian
, p. 5326 - 5334 (2022/04/07)
The B(9)-H halogenation of o-carborane and m-carborane was achieved with excellent selectivities in hexafluoroisopropanol (HFIP) under simple reaction conditions: single reagent [trichloroisocyanuric acid (TCCA), tribromoisocyanuric acid (TBCA) or N-iodosuccinimide (NIS)], catalyst-free, air-/moisture-tolerant, and convenient work-up. With this method, a variety of 9-halogenated o-carboranes and m-carboranes were obtained in good to excellent yields with broad tolerance of functional groups.
Poly-iodinated closo 1,2-C2B10 and nido [7,8-C2B9]- carborane frameworks: Synthesis and consequences
Lupu, Marius,Zaulet, Adnana,Teixidor, Francesc,Sillanp??, Reijo,Vi?as, Clara
, p. 171 - 181 (2015/12/18)
The preparation of Cc-monosubstituted closo and nido carborane derivatives, mono-, di and tetraiodinated is reported. Some of these mono-to poly-iodinated nido carboranes are studied in terms of the acidity of the open face bridging proton, the
Practical synthesis of 1,12-difunctionalized o-carborane for the investigation of polar liquid crystals
Jankowiak, Aleksandra,Kaszynski, Piotr
, p. 8762 - 8769 (2014/10/16)
Two isomerically pure 1,12-difunctionalized derivatives of o-carborane, 12-iodo-1-vinyl (1b) and 12-iodo-1-phenyl (1c), are conveniently obtained on a practical scale in yields of 22% and 32%, respectively, by monoiodination of the corresponding o-carborane derivatives (4b and 4c) followed by separation of the regioisomers by crystallization (1b) and chromatography (1c). Subsequent functional group transformations gave access to other derivatives, including two liquid-crystalline compounds, in which o-carborane is a linear structural element. Regioselectivity of substitution on the carborane cage and on the benzene ring correlates with the inductive effect parameter of the substituent. The preparation of analogous derivatives of m-carborane was also investigated.
