Synthesis and Antiplatelet, Antiinflammatory and Antiallergic Activities of 2,3-Disubstituted 1,4-Naphthoquinones.

Abstract

Modification of 2-acetamido-3-chloro-1,4-naphthoquinone, which has potent antiplatelet, antiallergic and antiinflammatory activities, led to a series of 2,3-disubstituted 1,4-naphthoquinones. Some of these compounds showed significant antiplatelet, antiallergic and antiinflammatory activities. Among them, 2-methoxy-3-chloro-1,4-naphthoquinone (15) and 2-ethoxy-3-chloro-1,4-naphthoquinone (17) exhibited potent inhibitory effects on neutrophil and mast cell degranulation. 2-Methoxy-1,4-naphthoquinone (20) and 2-ethoxy-1,4-naphthoquinone (21) exhibited potent inhibitory effect on neutrophil superoxide formation. These four compounds were thus selected for further evaluation.

In Vitro Activity of 2‐methoxy‐1,4‐naphthoquinone and Stigmasta‐7,22‐diene‐3β‐ol from Impatiens balsamina L. against Multiple Antibiotic‐Resistant Helicobacter pylori

“…The plant Swertia calycina (Gentianaceae) was also found to contain this compound [11]. Some bioactivities were demonstrated in MeONQ including antipruritic [12], antiinflammatory, antiallergic [13] and anticancer [14] activities. Furthermore, reducing oral lesion recurrence in human immunodeficiency virus patients was also reported for this compound [15].…”

Bioactivity-guided isolation and structural characterization of the antifungal compound, plumbagin, fromNepenthes gracilis

“…Plumbagin is a secondary metabolite belonging to the naphthoquinone group which is produced by many plants belonging to the Caryophyllales order (Richer et al, 2002) such as Droseraceae (Budzianowski, 2000), Plumbaginaceae (Bothiraja et al, 2011), Ebenaceae (Evans et al, 1999), and Nepenthaceae (Aung et al, 2002). A wide range of biological properties of plumbagin such as anticancer (Kawiak et al, 2007), antiviral (Perez-Sacau et al, 2003), anti-inflammatory, antiplatelet, antiallergic (Lien et al, 1996), antimalarial (Biot et al, 2004), and antibacterial (Cai et al, 2000) have been reported. Dzoyem et al (2007) reported the antifungal activity of plumbagin isolated from the stem bark of Diospyros crassiflora.…”

2,3-Disubstituted-1,4-naphthoquinones, 12H-benzo[b]phenothiazine-6,11-diones and related compounds: Synthesis and Biological evaluation as potential antiproliferative and antifungal agents

“…The clinical importance of this class of compounds has led to the development of new agents in which retaining the core 1,4-naphthoquinone moiety could exhibit variety of biological effects including cytotoxic [8e11], antiviral [12], molluscidal [13], anti-inflammatory, antiplatelet, antiallergic [14,15], antimalarial [16], antileishmanial [17], antibacterial, antifungal [18e27] and antiproliferative activities [28].…”