Boron analogs of amino acids. Synthesis and biological activity of boron analogs of betaine

Spielvogel, Bernard F.; Wojnowich, L.; Das, Mrinal K.; McPhail, Andrew T.; Hargrave, Karl D.

doi:10.1021/ja00434a053

Cited by 90 publications

(44 citation statements)

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“…The synthesis of (55) was performed by the reaction of sodium cyanoborohydride with trimethylammonium hydrochloride to give (52). Since direct hydrolysis of the nitrile group could not be achieved, its conversion to a carboxylic acid was performed in two steps comprising the a reaction with Meerweins reagent, followed by alkaline hydrolysis of the intermediate nitrilium salt [49][50][51]. The metal-complexing capabilities and basicity of this betaine (54) have been described [52].…”

Section: Synthesis Of Glycine A-aminoboronic Acidsmentioning

confidence: 99%

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Chemistry of α‐Aminoboronic Acids and their Derivatives

Dembitsky

Srebnik

2009

Amino Acids, Peptides and Proteins in Organic Chemistry

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Section: Synthesis Of Glycine A-aminoboronic Acidsmentioning

confidence: 99%

“…Compound (51) can be obtained in varying yields upon reaction of (62) with chloroformates in the presence of triethylamine and 4-dimethyl-aminopyridine (DMAP). These conditions were found to be more advantageous than using [55].…”

Section: Synthesis Of Glycine A-aminoboronic Acidsmentioning

confidence: 99%

Chemistry of α‐Aminoboronic Acids and their Derivatives

Dembitsky

Srebnik

2009

Amino Acids, Peptides and Proteins in Organic Chemistry

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“…When a 10 B atom is bombarded with low kinetic energy thermal neutrons of approximately 0.025 eV, it splits into 7 Li and Another important rationale for the use of boron is that in tetrahedral borane complexes, the boron atom is isosteric to a tetrahedral carbon, but is more lipophilic. This pharmacological property enhances their lipid solubility and facilitates their crossing biological membranes [10,15].…”

Section: Introductionmentioning

confidence: 99%

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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“…Amine and phosphine cyanoboranes are an intriguing group of compounds that have inspired extensive biological screening. The promising early results led to the synthesis of a large number derivatives, some of which have been shown in model studies to have potent antitumor [10][11][12][13][14][15], anti-inflammatory [16][17][18], hypolipidemic [11,19], anti-hyperlipidemic [20], anti-ostoeoporotic [21], anti-neoplastic [22][23][24], BNCT [25], and other promising biological activities [26,27]. In the present study, the diborane (4) derivatives of the corresponding amine cyanoborane were synthesized as their 2LiBr complexes from of the monobromo derivative of the corresponding amine cyanoborane, followed by B-B coupling using elemental sodium or n-BuLi.…”

Section: Introductionmentioning

confidence: 99%