The Rise of Boron-Containing Compounds: Advancements in Synthesis, Medicinal Chemistry, and Emerging Pharmacology

Grams, R. Justin; Santos, Webster L.; Scorei, Ion Romulus; Abad-García, Antonio; Rosenblum, Carol Ann; Bita, Andrei; Cerecetto, Hugo; Viñas, Clara; Soriano-Ursúa, Marvin A.

doi:10.1021/acs.chemrev.3c00663

Cited by 25 publications

(12 citation statements)

References 830 publications

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“…Further, multiple chemical reactions deal with the formation, breaking, and/or transformation of such bonds. In particular, relevant reviews [1,2] (see also the references therein) describe the role of boron in organic synthesis, along with an explosive growth of its applications in materials and pharmaceutical science [3,4]. For instance, some protease inhibitors containing boron are approved medications for dealing with viral infections such as HIV/AIDS, hepatitis C, and COVID-19.…”

Section: Introductionmentioning

confidence: 99%

Metalloid–Organic Intermolecular Complexes with Charge State-Controlled Conformations

Naumkin

2024

Molecules

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Shape alterations of molecular systems, induced by their (electric) charging/discharging, could facilitate useful electronic and/or mechanical functions in molecular-scale devices and machines. The present study reports structures, stabilities, charge distributions, and IR spectra for a group of complexes of a main-group metalloid (boron) atom with hydrocarbon molecules. The considered systems include the smallest species demonstrating the basic principle of operation, as well as their size-extended analogues, generalizing it to larger counterparts based on such units. The system geometries vary considerably between neutral and ionic counterparts and exhibit two–three typical conformations related to twisting by up to about 90 degrees. The predicted structures correlate with specific infrared spectra, which can enable their experimental identification and transformation tracking. The above-mentioned characteristics suggest the potential utility of such systems for intermolecular switches, with the possible spectral monitoring of their functioning.

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Section: Introductionmentioning

confidence: 99%

Metalloid–Organic Intermolecular Complexes with Charge State-Controlled Conformations

Naumkin

2024

Molecules

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“…Boron-containing compounds (BCCs) are interesting molecules in pharmacological sciences because many of them are bioactive compounds, thus being attractive for study as potential drugs [ 1 ]. In particular, some boronic acids can easily form diester bonds with molecules with hydroxyls, yielding stable boron-containing adducts [ 2 ].…”

Section: Introductionmentioning

confidence: 99%

“…In nature, some BCCs have similar characteristics to those reported herein, such as fructoborate (bis[β- d -fructofuranosato(2-)-κ 2 O 2 ,O 3 ]borate), formed by the reaction of two fructose molecules and a boron atom, which is synthesized by plants [ 3 ]. Some properties are conferred to that molecule, for example, protective activity against metabolic and inflammatory disorders in humans [ 1 ]. This is a fact that supports the notion that structurally related compounds can be studied as potential drugs [ 3 ].…”

Section: Introductionmentioning

confidence: 99%

One-Step Synthesis, Crystallography, and Acute Toxicity of Two Boron–Carbohydrate Adducts That Induce Sedation in Mice

Cordova-Chávez,

Trujillo-Ferrara,

Padilla-Martínez

et al. 2024

Pharmaceuticals

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Boronic acids form diester bonds with cis-hydroxyl groups in carbohydrates. The formation of these adducts could impair the physical and chemical properties of precursors, even their biological activity. Two carbohydrate derivatives from d-fructose and d-arabinose and phenylboronic acid were synthesized in a straightforward one-step procedure and chemically characterized via spectroscopy and X-ray diffraction crystallography. Additionally, an acute toxicity test was performed to determine their lethal dose 50 (LD50) values by using Lorke’s method. Analytical chemistry assays confirmed the formation of adducts by the generation of diester bonds with the β-d-pyranose of carbohydrates, including signals corresponding to the formation of new bonds, such as the stretching of B–O bonds. NMR spectra yielded information about the stereoselectivity in the synthesis reaction: Just one signal was found in the range for the anomeric carbon in the 13C NMR spectra of both adducts. The acute toxicity tests showed that the LD50 value for both compounds was 1265 mg/kg, while the effective dose 50 (ED50) for sedation was 531 mg/kg. However, differences were found in the onset and lapse of sedation. For example, the arabinose derivative induced sedation for more than 48 h at 600 mg/kg, while the fructose derivative induced sedation for less than 6 h at the same dose without the death of the mice. Thus, we report for the first time two boron-containing carbohydrate derivatives inducing sedation after intraperitoneal administration. They are bioactive and highly safe agents. Further biological evaluation is desirable to explore their medical applications.

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“…We inquire whether the asymmetric decarboxylative C(sp 3 )-C(sp 3 ) cross-coupling reactions could employ moderate organometallic reagents to install versatile chiral alkylboron derivatives，which possess a diverse reactivity profile crucial for drug discovery and material sciences [30][31][32][33] . Considerable effort has been devoted to exploring synthetic methodologies for the preparation of these scaffolds [34][35][36][37][38] .…”

Section: Introductionmentioning

confidence: 99%

Enantioselective Decarboxylative C(sp3)-C(sp3) Cross-Coupling of Aliphatic Acids with gem-Borazirconocene Alkanes

Wang,

Bai,

Yang

et al. 2024

Preprint

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Asymmetric decarboxylative cross-couplings of carboxylic acids represent a powerful tool to synthesize chiral building blocks for medicinal chemistry and material science. However, synthesis of versatile chiral alkylboron derivatives via asymmetric decarboxylative C(sp3)-C(sp3) cross-coupling from readily available primary aliphatic acids and mild organometallic reagents is still challenging. In this study, we report a visible-light-induced, Ni-catalyzed enantioconvergent C(sp3)-C(sp3) cross-coupling of unactivated primary aliphatic acids with gem-borazirconocene alkanes, furnishing a diverse array of valuable chiral alkylboron building blocks. The broad substrate scope, high functional group tolerance, and the late-stage modification of complex drug molecules and natural products with high enantioselectivity demonstrate the synthetic potential of the method. Mechanistic investigations suggest an enantioconvergent radical-radical cross-coupling pathway, wherein the primary radical from carboxylic acids is generated through single-electron reduction with ZrIII species, representing an unprecedented example of enantioselective radical C(sp3)-C(sp3) cross coupling in the absence of photocatalysts.

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The Rise of Boron-Containing Compounds: Advancements in Synthesis, Medicinal Chemistry, and Emerging Pharmacology

Cited by 25 publications

References 830 publications

Metalloid–Organic Intermolecular Complexes with Charge State-Controlled Conformations

Metalloid–Organic Intermolecular Complexes with Charge State-Controlled Conformations

One-Step Synthesis, Crystallography, and Acute Toxicity of Two Boron–Carbohydrate Adducts That Induce Sedation in Mice

Enantioselective Decarboxylative C(sp3)-C(sp3) Cross-Coupling of Aliphatic Acids with gem-Borazirconocene Alkanes

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