Organoboron Compounds: Effective Antibacterial and Antiparasitic Agents

Abstract

The unique electron deficiency and coordination property of boron led to a wide range of applications in chemistry, energy research, materials science and the life sciences. The use of boron-containing compounds as pharmaceutical agents has a long history, and recent developments have produced encouraging strides. Boron agents have been used for both radiotherapy and chemotherapy. In radiotherapy, boron neutron capture therapy (BNCT) has been investigated to treat various types of tumors, such as glioblastoma multiforme (GBM) of brain, head and neck tumors, etc. Boron agents playing essential roles in such treatments and other well-established areas have been discussed elsewhere. Organoboron compounds used to treat various diseases besides tumor treatments through BNCT technology have also marked an important milestone. Following the clinical introduction of bortezomib as an anti-cancer agent, benzoxaborole drugs, tavaborole and crisaborole, have been approved for clinical use in the treatments of onychomycosis and atopic dermatitis. Some heterocyclic organoboron compounds represent potentially promising candidates for anti-infective drugs. This review highlights the clinical applications and perspectives of organoboron compounds with the natural boron atoms in disease treatments without neutron irradiation. The main topic focuses on the therapeutic applications of organoboron compounds in the diseases of tuberculosis and antifungal activity, malaria, neglected tropical diseases and cryptosporidiosis and toxoplasmosis.

2-Bromo-3-((1-(7-chloroquinolin-4-yl)-1H-1,2,3-triazol-4-yl)-methoxy)-benzaldehyde

“…The other cycloaddition partner, acetylenic intermediate 4, was generated by O-alkylation of 2-bromo-3-hydroxybenzaldehyde 3 with propargyl bromide (1.5 equiv.) and Clinically approved quinoline (red) and 1,2,3-triazole (blue) containing drugs (some structures of quinolone-and triazole-based hybrids reported in the literature (a-f) [9][10][11][12][13][14]); and the structure of the compound (cyan, 5) reported in this paper. Square: synthesis of 1,2,3-triazoles using click chemistry.…”

“…Figure 1. Clinically approved quinoline (red) and 1,2,3-triazole (blue) containing drugs (some structures of quinolone-and triazole-based hybrids reported in the literature (a-g) [9][10][11][12][13][14]); and the structure of the compound (cyan, 5) reported in this paper. Square: synthesis of 1,2,3-triazoles using click chemistry.…”

“…Previously, we reported the synthesis of a novel 4-amino-7-chloroquinoline-based 1,2,3-triazole hybrid g by Cu(I)-catalyzed azide-alkyne cycloaddition (click chemistry) [12]. Recently, a library of 1,2,3-triazoles 4-aminoquinoline-benzoxaborole derivatives was synthesized [13], and our recent interest in boron derivatives [14] advanced further studies on similar derivatives.…”

New Insights into Boron Essentiality in Humans and Animals

“…These bacteria need B for the biosynthesis of AI-2B, and the MoA that we proposed for NOB complexes could explain why these complexes ensure absorption of neutrons and gamma-radiation when they reach the colon [ 138 , 168 , 169 ]. Additionally, in areas where the natural radiation of the soil is increased, the concentration of B in the blood of animals and humans is very low because B in the body is consumed by natural radiation from the environment and transformed into lithium and helium, but only the 10 B isotope conducts the reaction [ 174 , 175 , 176 ]. In these areas, people have very advanced OA (over 70%) [ 177 , 178 , 179 , 180 ].…”

Merging Electron Deficient Boronic Centers with Electron-Withdrawing Fluorine Substituents Results in Unique Properties of Fluorinated Phenylboronic Compounds

“… Benzoxaboroles, cyclic hemiesters of phenylboronic acids, have been known since 1957 [ 8 ] and received moderate interest until it was found that these compounds bind sugars at a physiological pH [ 9 ]. This allowed not only development of a group of receptors of new type but also for the application of these compounds as biologically active substances with antibacterial, antiprotozoal and antifungal activity [ 10 , 11 , 12 ]. The most famous representative of benzoxaboroles contains a fluorine atom and is used as powerful drug against onychomycosis—Kerydin (Tavaborole) [ 13 ] ( Figure 2 ).…”