3-Carbomethoxy Fentanyl: Synthesis, Pharmacology and Conformational Analysis

Μίćονίć, I.V.; Ivanović, Milan; Vučković, Sonja; Jovanović-Mićić, D; Beleslin, D.B.; Došen‐Mićović, Lj.; Kiricojević, Vesna D.

doi:10.1515/hc.1998.4.2.171

Cited by 5 publications

(3 citation statements)

References 9 publications

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“…As a synthon for a four methylene linker, 4-chlorobutyryl chloride was selected. 23 Acylation of N-aryl piperazine hydrochloride 12a-c with 4-chlorobutyryl chloride under standard acylation conditions 24 successfully provided carboxamides 7a-c in almost quantitative yields (Scheme 3B). The required anilinopiperidine 6, was prepared according to Scheme 3A using a known protocol.…”

Section: Resultsmentioning

confidence: 99%

Synthetic route towards potential bivalent ligands possessing opioid and D2/D3 pharmacophores

Jevtić

Penjisevic

Ivanović

et al. 2019

JSCS

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A scalable, cost-efficient and simple synthetic pathway towards potential bivalent opioid/dopamine receptor ligands was developed and optimized. Three novel compounds that contain both opioid and dopamine pharmacophores linked by the four methylene group chain were synthesized in 33, 35 and 39 % overall yield after a four-step synthetic route starting from three commercially available N-aryl piperazines. The anilino piperidine precursor was easily prepared in three steps, as previously published, starting from 4piperidone. The synthesis presented in this paper could be of interest for heterocyclic and general organic chemistry. The newly designed compounds possessing two pharmacophores, opioid and D 2 /D 3 , are potentially useful pharmacological probes. Of particular interest would be the simultaneous binding to both opioid and D 2 /D 3 receptors, and the resulting pharmacological responses may be useful for the further understanding of tolerance and dependence phenomena in opioid clinical use and/or abuse.

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Section: Resultsmentioning

confidence: 99%

Synthetic route towards potential bivalent ligands possessing opioid and D2/D3 pharmacophores

Jevtić

Penjisevic

Ivanović

et al. 2019

JSCS

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“…Among various types of analgesic compounds, anilidopiperidines including Fentanyl(50‐100 × Morphine), Carfentanil (7000‐8000× Morphine), Lofentanil (5000‐6000 × Morphine), and others, 5 which belong to the synthetic opioids class, provide the most potential as analgesics. Anilidopiperidines, due to the fast onset and short duration of action, act in the central nervous system to decrease pain and are extensively used in surgical anesthesia as the citrate salt at doses ranging from 2 to 50 μg/kg.…”

Section: Introductionmentioning

confidence: 99%

“…Fentanyl and its derivatives are used in various medical conditions such as observant patients, managing postoperative pains, in obstetrics and also in various orthopedic interventions. Fentanyl transdermal patches are useful in controlling chronic cancer pain, 7 due to the slow and controlled release of the drug over several days, Many fentanyl analogues have been synthesized 5,8–14 as potential candidates for novel drugs, to establish the structure‐activity relationship and to investigate the opioid receptors. Lots of works have been performed on the synthesis of fentanyl and its derivatives 15,16 .…”

Section: Introductionmentioning

confidence: 99%

Improved method for the total synthesis of thiofentanyl

Taghizadeh

Hosseini

Moosavi

et al. 2020

Journal of Heterocyclic Chem

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Thiofentanyl is a potent analgesic and anesthetic drug that belongs to the microreceptor agonist group and is mainly used in animal's anesthesia. We present an optimized synthesis route for synthesis of thiofentanyl using nanocatalysts such as MCM-41-SO 3 H and SBA-15-Ph-PrSO 3 H as green, heterogeneous and recyclable catalysts according to the strategy. The intermediate 2-(thiophen-2-yl) ethyl methanesulfonate (1) easily obtained after conversion of the alcohol functional group into the mesylate leaving group using methanesulfonyl chloride (97% yield). The alkylation of commercially available 4-piperidone monohydrate hydrochloride with 2-(thiophen-2-yl) ethyl methanesulfonate in the presence of phase transfer catalyst was then carried out giving N-[2-(2-thienyl) ethyl]-4-piperidone (2) with 90% yield. N-[2-(2-thienyl)ethyl]-4-piperidone was then reacted with aniline in the presence of MCM-41-SO 3 H catalyst giving the imine derivative which reduced with sodium triacetoxyborohydride to N-phenyl-1-(2-(thiophen-2-yl)ethyl) piperidine-4-amine (ANTP) (4) with 80% yield. ANTP was finally acylated using propionyl chloride to achieve thiofentanyl (5) with 90% yield. High yields, mild reaction conditions, decreased reaction times, and convenient workup were the advantages of this method compared to the previous work.

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