Synthesis of chloroquinocin, a pyranonaphthoquinone antibiotic against Gram-positive bacteria

Laccase‐Catalyzed CS and CC Coupling for a One‐Pot Synthesis of 1,4‐Naphthoquinone Sulfides and 1,4‐Naphthoquinone Sulfide Dimers

“…[9][10][11][12][13][14][15][16] Natural and synthetic 1,4-naphthoquinone derivatives have been recognized for their biological activities, and thus, enormous interest has been stimulated in this class of com-pounds. [17][18][19][20][21][22][23] There have also been reports on naphthoquinone sulfides demonstrating anticancer and antifungal activities. [24][25][26][27][28][29][30] The goal of our research was to use biocatalysis to access novel compounds that can have potential pharmaceutical value in addition to developing green methods of synthesis.…”

Fundamental and Applied Aspects of the Chemistry of Acetylenylquinones

“…Similarly the synthesis of acetylenylquinones was also possible via hydrolysis of the corresponding dimethoxynaphthalene analogs containing a C≡C TB as a part of their structure ( Figure 6) [12]. Selective hydrolysis resulted in acetylenylnaphthoquinone in a 71 % yield and was accomplished through the action of DDQ (2,3-dichloro-5,6dicyano-1,4-benzoquinone) at room temperature.…”

“…Indeed, both molecular docking and cell cytotoxicity assays revealed that 2 was a more effective anticarcinogen when compared with 1 and 3 as it was capable of binding to DNA strands and triggering apoptosis [29]. Of particular interest was the antimicrobial agent Chloroquinocin 1, which was shown to be active against Gram-positive bacteria, such as methicillin-resistant Staphylococcus aureus (MRSA) [12]. Details on the synthesis of analogs of Chloroquinocin 1 were reported in Section 2 ( Figure 27) [12].…”

“…Of particular interest was the antimicrobial agent Chloroquinocin 1, which was shown to be active against Gram-positive bacteria, such as methicillin-resistant Staphylococcus aureus (MRSA) [12]. Details on the synthesis of analogs of Chloroquinocin 1 were reported in Section 2 ( Figure 27) [12]. The route of synthesis for chloroquinone and its analogs was shown to be very effective as it provided the basis for the creation of a new series of this in-demand class of compounds.…”

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

“…EtOH (50 mL) gave the product 3 in 90e95% yield after crystallization with suitable solvent. Sodium azide (30 mmol) was added to a stirred solution of 2-chloro-3-arylsulfanyl- [1,4]naphthoquinones (2) in DMF (15 mL) and H 2 O (1.5 mL). The reaction mixture was stirred for 4 h at 100 C. The resulting solution was poured onto crushed ice (50 g) and the solid precipitate was filtered, dried and subjected to column chromatography on silica gel using EtOAc/hexane (1:15) and the product was crystallized with suitable solvent to give 6e9 in 67e85% yield.…”