Diels–Alder Reactions of Heterocyclic Azadienes: Development of a Strategy for the Total Synthesis of Streptonigrin, Lavendamycin, and Synthetic Quinoline-5, 8-Quinones
“… 2 It is plausible that streptonigrin 1) causes chromosomal damage when added to cultures of human leukocytes, 2) inhibits DNA synthesis in tissue culture cells as well as in bacteria, and 3) inhibits partial RNA and protein synthesis. 2 However, the investigation into determining the best pathways for the synthesis for streptonigrin did not stop there and was continued by Boger, 3 who successfully modified its structure by implementing an inverse electron demand Diels–Alder reaction of electron-deficient heterocyclic azadienes. Figure 1 Role of streptonigrin in the management of various diseases.…”
Streptonigrin is an aminoquinone alkaloid isolated from
Streptomyces flocculus
and is gaining attention as a drug molecule owing to its potential antitumor and antibiotic effects. It was previously used as an anticancer drug but has been discontinued because of its toxic effects. However, according to the most recent studies, the toxicity of streptonigrin and its structurally modified derivatives has been reduced while maintaining their potential pharmacological action at lower concentrations. To date, many investigations have been conducted on this molecule and its derivatives to determine the most effective molecule with low toxicity to enable new drug discovery. Therefore, the main objective of this study is to provide a comprehensive review and to discuss the prospects for streptonigrin and its derived compounds, which may boost the molecule as a highly interesting target molecule for new drug design, development and therapy. To complete this review, relevant literature was collected from several scientific databases, including Google Scholar, PubMed, Scopus and ScienceDirect. Following a complete screening, the obtained information is summarized in the present review to provide a good reference and accelerate the development and utilization of streptonigrin and its derivatives as pharmaceuticals.
“… 2 It is plausible that streptonigrin 1) causes chromosomal damage when added to cultures of human leukocytes, 2) inhibits DNA synthesis in tissue culture cells as well as in bacteria, and 3) inhibits partial RNA and protein synthesis. 2 However, the investigation into determining the best pathways for the synthesis for streptonigrin did not stop there and was continued by Boger, 3 who successfully modified its structure by implementing an inverse electron demand Diels–Alder reaction of electron-deficient heterocyclic azadienes. Figure 1 Role of streptonigrin in the management of various diseases.…”
Streptonigrin is an aminoquinone alkaloid isolated from
Streptomyces flocculus
and is gaining attention as a drug molecule owing to its potential antitumor and antibiotic effects. It was previously used as an anticancer drug but has been discontinued because of its toxic effects. However, according to the most recent studies, the toxicity of streptonigrin and its structurally modified derivatives has been reduced while maintaining their potential pharmacological action at lower concentrations. To date, many investigations have been conducted on this molecule and its derivatives to determine the most effective molecule with low toxicity to enable new drug discovery. Therefore, the main objective of this study is to provide a comprehensive review and to discuss the prospects for streptonigrin and its derived compounds, which may boost the molecule as a highly interesting target molecule for new drug design, development and therapy. To complete this review, relevant literature was collected from several scientific databases, including Google Scholar, PubMed, Scopus and ScienceDirect. Following a complete screening, the obtained information is summarized in the present review to provide a good reference and accelerate the development and utilization of streptonigrin and its derivatives as pharmaceuticals.
A study on interaction between N‐(4‐pyridinyliden)anilines 1‐4 and 2,2‐dimethoxypropane under Kametani reaction conditions was realized. According to the GC‐MS analysis of crude reaction, besides the needed 4‐methyl‐2‐(4‐pyridinyl)quinolines 5‐8, three collateral products: secondary amines 9‐12, 4‐(2‐methylprop‐1‐enyl)quinolines 13‐16 and 4‐(2‐methoxy‐2‐methylpropyl)quinolines 17‐20 were formed. Unexpected quinolines 13‐16 as well the desired quinolines 5‐8 were isolated and fully characterized. In contrast, a condensation of N‐benzylidenaniline 21 with 2,2‐dimethoxypropane afforded a set of different quinoline products.
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