Synthesis and Analgesic Activity of Some Deaza Derivatives of Anpirtoline

Rádl, S.; Hezky, Petr; Proška, Jan; Krejcí, I

doi:10.1002/(sici)1521-4184(19991)332:1<13::aid-ardp13>3.0.co;2-l

Cited by 10 publications

(4 citation statements)

References 5 publications

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“…Derivatives of phenothiazines, a large class of drugs with antipsychotic properties, can be synthesized using nitrobenzene or halonitrobenzenes (54,170). Chloronitrobenzenes are feedstocks used to create new derivatives of anpirtoline, a nonopioid analgesic (155). Synthesis of lidocaine (a local anesthetic) is a classic organic chemistry laboratory exercise that starts with the reduction of 2,6-dimethylnitrobenzene to 2,6-xylidine.…”

Section: Synthetic Nitroaromatic Compoundsmentioning

confidence: 98%

Nitroaromatic Compounds, from Synthesis to Biodegradation

Parales

2010

Microbiol Mol Biol Rev

770

470

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SUMMARY Nitroaromatic compounds are relatively rare in nature and have been introduced into the environment mainly by human activities. This important class of industrial chemicals is widely used in the synthesis of many diverse products, including dyes, polymers, pesticides, and explosives. Unfortunately, their extensive use has led to environmental contamination of soil and groundwater. The nitro group, which provides chemical and functional diversity in these molecules, also contributes to the recalcitrance of these compounds to biodegradation. The electron-withdrawing nature of the nitro group, in concert with the stability of the benzene ring, makes nitroaromatic compounds resistant to oxidative degradation. Recalcitrance is further compounded by their acute toxicity, mutagenicity, and easy reduction into carcinogenic aromatic amines. Nitroaromatic compounds are hazardous to human health and are registered on the U.S. Environmental Protection Agency's list of priority pollutants for environmental remediation. Although the majority of these compounds are synthetic in nature, microorganisms in contaminated environments have rapidly adapted to their presence by evolving new biodegradation pathways that take advantage of them as sources of carbon, nitrogen, and energy. This review provides an overview of the synthesis of both man-made and biogenic nitroaromatic compounds, the bacteria that have been identified to grow on and completely mineralize nitroaromatic compounds, and the pathways that are present in these strains. The possible evolutionary origins of the newly evolved pathways are also discussed.

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Section: Synthetic Nitroaromatic Compoundsmentioning

confidence: 98%

Nitroaromatic Compounds, from Synthesis to Biodegradation

Parales

2010

Microbiol Mol Biol Rev

770

470

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“…Antipsychotic drugs such as phenothiazine derivatives can be generated from halonitrobenzenes (Gritsenko, A.N., Ermakova, Z.I. & Zhuravlev, 1970), while chloronitrobenzene is useful in the synthesis of the analgesic anpirtolin (Rádl et al, 1999). Two over-the-counter drugs, paracetamol and lidocaine, use pnitrophenol and 2,6-dimethylnitrobenzene in their synthesis (Bhattacharya et al, 2006).…”

Section: Introductionmentioning

confidence: 99%

N-oxygenation of amino compounds: Early stages in its application to the biocatalyzed preparation of bioactive compounds

Nóbile

Stricker

Marchesano

et al. 2021

Biotechnology Advances

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“…We have modified the anpirtoline structure in several possible ways. The initial biological evaluation of deazaanpirtoline (1b) and several of its derivatives, including homologues 2, showed these compounds to have weaker analgesic and binding properties than anpirtoline [6,7] . These findings inspired us to prepare a series of similar pyrrolidine and piperidine derivatives 3, containing 6-chloropyridin-2-yl or 3-chlorophenyl group as an aromatic part and a pyrrolidine or piperidine ring as a cyclic amino group connected to the aromatic part by a methylsulfanyl bridge.…”

Section: Introductionmentioning

confidence: 99%