Synthesis of new tetrahydropyridinylidene ammonium salts and their antiprotozoal potency

Seebacher, Werner; Faist, Johanna; Belaj, Ferdinand; Saf, Robert; Kaiser, Marcel; Brun, Reto; Weis, Robert

doi:10.1007/s00706-015-1503-y

Cited by 13 publications

(8 citation statements)

References 19 publications

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“…Starting compounds were the bases 1a-1d of 6-unsubstituted tetrahydropyridin-4-ylidene ammonium salts (THPS) which were prepared from their 6-methylsulfanyl analogues via selective reduction with deactivated Raney nickel [19]. During the reaction of compounds 1a-1d with alkane-or arenesulfonyl chlorides a ring cleavage occurred.…”

Section: Resultsmentioning

confidence: 99%

Unexpected ring-opening of 2,3-dihydropyridines

et al. 2021

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The reaction of 2,3-dihydropyridines with sulfonyl halides surprisingly yielded open chain dienes with sulfonylimine structure. The products were specific out of several possible isomers and, therefore, a separation of isomers was not necessary. All new compounds were characterized using FT-IR spectroscopy, HRMS, and NMR spectroscopy. A bicyclic by-product from the reaction of a 2,3-dihydropyridine with mesyl chloride was isolated and its structure elucidated using a single X-ray crystal analysis. Some biological activities, like antimicrobial and cytotoxic properties were investigated. Graphic abstract

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Section: Resultsmentioning

confidence: 99%

Unexpected ring-opening of 2,3-dihydropyridines

et al. 2021

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“…The preparation of the base 1f started from the 6-sulfanylidenpiperidin-4-one 8 [11] which reacted with tryptamine to the corresponding 4-amino derivative 9 in a similar procedure as reported [8]. The sulfanylidene group was methylated.…”

Section: Resultsmentioning

confidence: 99%

“…We already reported the antiprotozoal activities of tetrahydropyridin-4-ylidene ammoniumsalts [8]. Since, 1-benzyl substitution significantly enhanced the antiprotozoal activities, we initially focused our efforts on the optimization of these benzyl moieties [9,10].…”

Section: Introductionmentioning

confidence: 99%

Modifications and hybrids of 1,2,3,4-tetrahydropyridinium salts and their antiprotozoal potencies

et al. 2021

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The antiprotozoal activity of 1-benzyltetrahydropyridin-4-yliden iminium salts is reported. This paper describes the preparation of a series of analogs from dihydropyridines or dihydrothiopyrans as educts. The new compounds were investigated for their activity against Plasmodium falciparum NF54, a causative organism of Malaria tropica and Trypanosoma brucei rhodesiense, the causative organism of Human African Trypanosomiasis (sleeping sickness). Several structure–activity relationships were detected. Both the substituents in ring positions 1 and 4 of the tetrahydropyridinium moiety had a strong impact on the antiprotozoal activities as well as on the cytotoxicity of compounds against L-6 cells (rat skeletal myoblasts). All new compounds were characterized using FT-IR spectroscopy, HRMS, and NMR spectroscopy. Graphic abstract

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“…The different 4-dialkylaminotetrahydropyridinylidene salts 1a-1d used as starting products were prepared as described earlier [1]. They were exposed for several days to aromatic aldehydes or aliphatic aldehydes in an alkaline medium at room temperature.…”

Section: Chemistrymentioning

confidence: 99%

“…Recently, we described the synthesis and antiprotozoal potency of 4-aminotetrahydropyridinylidene salts [1] and of 1-benzyl derivatives of these salts with enhanced antiprotozoal activities [2,3]. The insertion of an additional benzyl group in ring position 3 via alkylation under basic conditions yielded 1,3-disubstituted compounds with increased antiplasmodial activity [4].…”

Section: Introductionmentioning

confidence: 99%

Formation of 5-Aminomethyl-2,3-dihydropyridine-4(1H)-ones from 4-Amino-tetrahydropyridinylidene Salts

Seebacher,

Hoffelner,

Belaj

et al. 2023

Molecules

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Various 4-aminotetrahydropyridinylidene salts were treated with aldehydes in an alkaline medium. Their conversion to 5-substituted β-hydroxyketones in a one-step reaction succeeded only with an aliphatic aldehyde. Instead, aromatic aldehydes gave 5-substituted β-aminoketones or a single δ-diketone. The new compounds were characterized using spectroscopic methods and a single crystal structure analysis. Some of them showed anticancer and antibacterial properties.

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Synthesis of new tetrahydropyridinylidene ammonium salts and their antiprotozoal potency

Cited by 13 publications

References 19 publications

Unexpected ring-opening of 2,3-dihydropyridines

Unexpected ring-opening of 2,3-dihydropyridines

Modifications and hybrids of 1,2,3,4-tetrahydropyridinium salts and their antiprotozoal potencies

Formation of 5-Aminomethyl-2,3-dihydropyridine-4(1H)-ones from 4-Amino-tetrahydropyridinylidene Salts

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