2021
DOI: 10.1007/s11172-021-3119-1
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Synthesis of cholesterol derivatives based on closo- and nido-carboranes

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Cited by 16 publications
(4 citation statements)
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“…The reaction of the trimethylammonium salt of 1-mercapto-ortho-carborane with 2bromomethyl pyridine followed by the deboronation of the resulting pyridine-containing ortho-carborane 1- (4) was used to prepare the nido-carborane derivative with a longer spacer between the carborane cage and the pendant pyridyl group Cs[7-(NC 5 H 4 -2 -CH 2 S)-7,8-C 2 B 9 H 11 ] (Cs [5]) (Scheme 3). Previously, this approach was used for the synthesis of various alkylsulfenyl derivatives of orthoand nido-carboranes including those containing various functional groups [75][76][77][78][79]. The obtained carboranes were characterized using methods of 1 H, 13 C, and 11 B NMR and IR spectroscopy and mass spectrometry (See Supplementary Materials).…”
Section: Scheme 1 Synthesis Of Csmentioning
confidence: 99%
“…The reaction of the trimethylammonium salt of 1-mercapto-ortho-carborane with 2bromomethyl pyridine followed by the deboronation of the resulting pyridine-containing ortho-carborane 1- (4) was used to prepare the nido-carborane derivative with a longer spacer between the carborane cage and the pendant pyridyl group Cs[7-(NC 5 H 4 -2 -CH 2 S)-7,8-C 2 B 9 H 11 ] (Cs [5]) (Scheme 3). Previously, this approach was used for the synthesis of various alkylsulfenyl derivatives of orthoand nido-carboranes including those containing various functional groups [75][76][77][78][79]. The obtained carboranes were characterized using methods of 1 H, 13 C, and 11 B NMR and IR spectroscopy and mass spectrometry (See Supplementary Materials).…”
Section: Scheme 1 Synthesis Of Csmentioning
confidence: 99%
“…which was obtained during the drying of the solution of parent potassium salt in diethyl ether over Na 2 SO 4 , was determined by X-ray analysis [79] (Figure 3). The obtained azides can be used for medical application due to the possibility of their conjugation with biomolecules by standard methods of bioorganic chemistry such as, for example, Cu(I)-catalyzed reaction of 1,3-dipolar [3 + 2] -cycloaddition of terminal azido group with alkynes ("click" reaction) [44,[82][83][84][85][86]. Thus, several conjugates with nucleosides were prepared by Cu(I)-catalyzed click reaction of 10-N 3 CH 2 CH 2 OCH 2 CH 2 O-7,8-C 2 B 9 H 11 with modified derivatives of 2 -deoxyadenosine [80], uridine and thymidine [81], containing terminal alkyne group (Scheme 13).…”
Section: Properties Of Oxonium Derivatives Of Nido-carborane Reaction...mentioning
confidence: 99%
“…Among the methods for obtaining bioconjugates, the Cu(I)-catalyzed 1,3-dipolar [3 + 2] cycloaddition reaction of alkynes to azides is widely used, leading to the formation of 1,2,3 triazoles, termed as the "click"-reaction" [44][45][46]. Earlier, the "click"-reaction was successfully used to obtain a wide range of conjugates of polyhedral boron hydrides with various biologically active molecules, such as nucleosides [47] and chlorine e 6 [48], as well as derivatives of cholesterol based on cobalt/iron bis(dicarbollide) [49][50][51][52], closo-dodecaborate dianion [53] and nido-carborane [54][55][56]. Such reactions must proceed rapidly under ambient conditions, resulting in a high yield of desired 1,2,3-triazole.…”
Section: Synthesis Of the Conjugates Of Curcumin With Closo-dodecabor...mentioning
confidence: 99%