Matrix Metallo‐Proteinase (MMP‐2) Organoboronate Inhibitors

Abstract

Novel organoboronate derivatives consisting of BB, BC(R(1)R(2))B, BCCB, CBC, Department of Medicinal RBC=CBB, and RBC=CBP structures were synthesized and have been investigated in vitro as MMP-2 inhibitors. We discovered that most of the boronate derivatives (those not containing phosphorus) showed significant activity against MMP-2. The trisboronate 14 proved to be a potent MMP-2 inhibitor at 5 and 10 microM. Structure activity relationships (SARs) data for the compounds were investigated and are discussed.

Copper‐Catalyzed Triboration of Terminal Alkynes Using B2pin2: Efficient Synthesis of 1,1,2‐Triborylalkenes

“…These methods suffer from major or minor drawbacks, such as weak functional group tolerance, tedious procedures, or expensive catalysts. On the other hand, 1,1,2‐triborylalkenes ( 2 a and 2 r ) have been shown to be potent matrix metalloproteinase (MMP‐2) inhibitors . Therefore, the development of efficient and versatile chemical transformations for the synthesis of diverse multiborylated alkenes from easily available starting materials is highly desirable.…”

“…On the other hand, 1,1,2triborylalkenes (2 a and 2 r) have been shown to be potent matrix metalloproteinase (MMP-2) inhibitors. [26] Therefore, the development of efficient and versatile chemical transformations for the synthesis of diverse multiborylated alkenes from easily available starting materials is highly desirable. Herein, we report a novel and straightforward coppercatalyzed synthesis of 1,1,2-triborylalkenes from terminal alkynes.…”

Kupfer‐katalysierte Triborierung terminaler Alkine mit B2pin2: Effiziente Synthese von 1,1,2‐Triborylalkenen

“…Jedoch weisen all diese Methoden Nachteile wie eine schwache Toleranz gegenüber funktionellen Gruppen, langwierige Verfahren oder die Verwendung teurer Katalysatoren auf. Wiederum haben sich 1,1,2‐Triborylalkene ( 2 a und 2 r ) als wirksame Inhibitoren der Matrix‐Metallo‐Proteinase (MMP‐2) erwiesen, was eine effiziente und vielfältige Synthese dieser Verbindungsklasse aus einfach zugänglichen Ausgangsmaterialien erstrebenswert macht.…”

Copper‐Catalyzed Preparation of Alkenylboronates and Arylboronates

“…[11][12][13] Currently, alkenyl-and arylboronates and their derivatives are extensively used as building blocks in synthesis, particularly in the Suzuki-Miyaura coupling that is now considered a "Gold standard" for the construction of conjugated aromatic compounds. [8][9][10] They are important building blocks in the fields of bioactive compounds (Figure 2) [14][15][16][17] and material sciences. [18,19] They have also found applications, as catalysts, [20][21][22] protecting group of diols, [23] molecular recognition sensors, [24] separation tools, [25] and cell-penetrating carriers for peptide delivery.…”

“…Alkenylboronates and their derivatives are versatile reagents and building blocks in synthesis especially in the Suzuki-Miyaura coupling reactions, and are widely employed in academia and the pharmaceutical industry. [8][9][10]76] Their CÀ B bonds can be readily transformed into a series of functional groups having CÀ C, CÀ O, CÀ N, CÀ F, CÀ Br, and CÀ I bonds by transition metal-catalyzed coupling reactions, [12][13][14]77] and by methods that do not use transition metals. [78,79] Development in copper-catalyzed borylation methods to access alkenylboronates is described in the following sections.…”