Functional organo-boron compounds

Zimmer, H.; Sill, A. D.; Andrews, Edwin R.

doi:10.1007/bf00631386

Cited by 13 publications

(15 citation statements)

References 3 publications

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“…The [B 9 H 13 (SMe 2 )] cluster is obtained from decaborane (14) and, thus, can be obtained in boron-10-enriched form if desired. As we were primarily interested whether the synthesis of purine derivatives is possible, we used the natural isotope distribution of boron.…”

Section: Resultsmentioning

confidence: 99%

“…Modified nucleosides and nucleic acid bases have been the subject of many studies due to their potential activity as enzyme inhibitors resulting in antitumor [8] and antiviral activity [9]. Early work focused on the development and synthesis of boron containing purine and pyrimidine bases [10][11][12][13][14][15][16][17]. In some cases, the boron atom was placed within the purine or pyrimidine ring flanked by two nitrogen atoms [13].…”

Section: Introductionmentioning

confidence: 99%

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Synthesis and characterization of azanonaborane-containing purine derivatives for boron neutron capture therapy

2008

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Derivatives of purine, adenine, guanine, and 2,6-diaminopurine linked to the azanonaborane (B 8 N cluster) have been prepared, for possible use as powerful agents for boron neutron capture therapy (BNCT). The synthesis was carried out via a ligand exchange reaction. The exo-NH 2 R group of the azanonaborane of the type [(RH 2 N)B 8 H 11 NHR] can be exchanged by one hetero-nitrogen atom of the pyrimidine ring, and except for guanine, also by an N atom of the imidazole ring. The identity of the products was confirmed by NMR, elemental analysis, IR, and mass spectrometry. No reaction was found to occur with caffeine and theophylline under the same reaction conditions.© Versita Warsaw and Springer-Verlag Berlin Heidelberg.

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Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Synthesis and characterization of azanonaborane-containing purine derivatives for boron neutron capture therapy

2008

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“…The mixture was dissolved in 15 mL of acetic anhydride and 60 mL of pyridine and stirred at room temperature for 12 h. The solution was evaporated to dryness, and the remaining mixture of the acetylated isomers was separated by column chromatography (dichloromethane/acetone 8:2). 2a: yield 3.7 g (50%) of a clear glass-like compound; R/0.45 (dichloromethane/acetone 8:2); MS (FAB+, 3-NBA) 367 ( + H)+; -NMR (CDC13) 2.14 (s, 3 H, Ac), 2.16 (s, 3 H, Ac), 2.44 (t, 1 H, CH2C=Ctf, Jli3propynvi = 2.3), 4.29-4.43 (m, 6 H, H2-5', CH2C=CH, H-4', H-2'), 5.08 (t [dd], 1 , H-3', J2,3, = 5.4, «/3.4-= 5.4), 5.94 (d, 1 H, H-V, JV21 = 4.6), 7.49 (d, 1 ,' H-6), 8.76 (br s, 1 H, H-3); -NMR (CD3OD) 5.22 (dd, 1 , H-3', Jz3. = 5.6, =/3-4-= 4.0), 4.49 (t [dd], 1 , H-2', Jv21 = J2S¡ = 5.6), 5.92 (d, 1 H, H-V, Jr?…”

Section: Methodsmentioning

confidence: 99%

Synthesis and in vitro evaluation of boronated uridine and glucose derivatives for boron neutron capture therapy.

Tjarks

Anisuzzaman²,

Liu³

et al. 1992

J. Med. Chem.

117

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The following boron-containing nucleoside and glucose derivatives have been synthesized as potential boron delivery agents for boron neutron capture therapy (BNCT): 2'-O-(o-carboran-1-ylmethyl)uridine (4a), 3'-O-(o-carboran-1-ylmethyl)uridine (4b), sodium 7-(uridin-2'-ylmethyl)dodecahydro-7,8-dicarba-++ +nido-undecaborate (5), 5'-O-(o-carboran-1-ylmethyl)uridine (9), and 3'-O-(o-carboran-1-ylmethyl)-D-glucose (13). In vitro cellular uptake studies were performed with F98 rat glioma cells. Following 16 h incubation, cellular boron concentrations were determined by direct current plasma atomic emission spectroscopy (DCP-AES). Boron concentrations ranged from 65 to 103 micrograms/g of cells for the neutral closo structures compared with 1.5 micrograms/g of cells for the charged nido species. Cellular uptake of sodium mercaptoundecahydro-closo-dodecaborate (BSH), the compound currently being used in Japan for the treatment of malignant brain tumors by BNCT, was 2 micrograms/g of cells.

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“…Zimmer et al [71] reported that 8-phenyl-8-borapurine (see Fig. (15)) demonstrated anti-inflammatory activity in a hind limb edema test and in a PMN infiltration assay.…”

Section: Heteroboranesmentioning

confidence: 97%

Synthesis and Pharmacological Activities of Amine-Boranes

Burnham¹

2005

CMC

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A number of amine-boranes and related derivatives possess a wide range of biological activities including antineoplastic, antiviral, hypolipidemic, anti-inflammatory activities, anti-osteoporotic and dopamine receptor antagonist activities. The compounds include borane complexes of alpha-amino acids, aromatic, aliphatic and heterocyclic amines, and nucleosides. The syntheses of amine-borane derivatives are generally carried out by first preparing a tertiary amine- or phosphine-cyano- or carboxyborane to serve as a borane donor for a subsequent Lewis acid exchange reaction. Borane adducts of simple aliphatic amines, heterocyclic amines and nucleic acids demonstrated potent cytotoxic activity in vitro and in vivo against murine and human tumor models. These boron-containing compounds were shown to inhibit DNA synthesis; such inhibition was caused primarily by reducing de novo purine biosynthesis via inhibition of PRPP amidotransferase, IMP dehydrogenase and dihydrofolate reductase activities. Aliphatic, heterocyclic and nucleoside amine-boranes have also been shown to possess hypolipidemic activity in mice and rats. Many boron derivatives from different chemical classes demonstrated both cytotoxic and hypolipidemic activities. They decreased low-density lipoprotein (LDL) cholesterol while increasing high-density lipoprotein (HDL) cholesterol levels. The mode of action of these compounds in the 50-100 microM concentration range appeared to be by increasing lipid excretion from the body and by inhibiting rate-limiting enzyme activities for the de novo synthesis of lipids and cholesterol (e.g., phosphatidylate phosphohydrolase, ATP-dependent citrate lyase, cytoplasmic acetyl coenzyme A [CoA] synthetase, HMG CoA reductase, and acetyl CoA carboxylase). Selected amine-boranes (e.g., trimethylamine-cyanoborane, N-methylmorpholine-cyanoborane, and the base-boronated 2'-deoxynucleosides) have anti-inflammatory, analgesic, anti-arthritic and anti-osteoporotic activities.

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Functional organo-boron compounds

Cited by 13 publications

References 3 publications

Synthesis and characterization of azanonaborane-containing purine derivatives for boron neutron capture therapy

Synthesis and characterization of azanonaborane-containing purine derivatives for boron neutron capture therapy

Synthesis and in vitro evaluation of boronated uridine and glucose derivatives for boron neutron capture therapy.

Synthesis and Pharmacological Activities of Amine-Boranes

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