Three-component synthesis of (E)-α,β-unsaturated amides of the piperine family

Schobert, Rainer; Siegfried, Sven; Gordon, G. J.

doi:10.1039/b105745f

Cited by 35 publications

(22 citation statements)

References 17 publications

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“…): 259(57), 175(73), 148(30), 145(100), 138(17), 117(33), 89(66), 84(86) and 63(31). NMR data are in agreement with published data (Schobert et al, 2001).…”

Section: Extraction and Isolationsupporting

confidence: 92%

“…This is a new compound and was not reported by Tuntiwachwuttikul et al (2006) in their paper on P. sarmentosum. The structures of the other eight alkaloids were determined by comparisons of spectral data with that of published data -pellitorine (2) (Rosario et al, 1996) (3) (Schobert et al, 2001), 2,4-tetradecadienoic acid isobutyl amide (4) (Greger et al, 1981), piperine (5) (Parmar et al, 1998), sylvamide (6) (Banerjit et al, 2002), cepharadione A (7) (Akasu et al, 1990), piperolactam D (8) (Sanjay et al, 1974) and paprazine (9) (Ikuo et al, 1991).…”

Section: Resultsmentioning

confidence: 99%

“…74-76 C (Lit. 83 C (Schobert, Siegfried, & Gordon, 2001)). UV (CHCl 3 ) max nm (log "): 325(2.46), 235(0.82), 397(0.01) and 251(0.60).…”

Section: Extraction and Isolationmentioning

confidence: 94%

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Alkaloids from Piper sarmentosum and Piper nigrum

Lim

et al. 2009

Natural Product Research

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Detailed chemical studies on the roots of Piper sarmentosum and Piper nigrum have resulted in several alkaloids. The roots of P. sarmentosum gave a new aromatic compound, 1-nitrosoimino-2,4,5-trimethoxybenzene (1). Piper nigrum roots gave pellitorine (2), (E)-1-[3',4'-(methylenedioxy)cinnamoyl]piperidine (3), 2,4-tetradecadienoic acid isobutyl amide (4), piperine (5), sylvamide (6), cepharadione A (7), piperolactam D (8) and paprazine (9). Structural elucidation of these compounds was achieved through NMR and MS techniques. Cytotoxic activity screening of the plant extracts indicated some activity.

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“…): 259(57), 175(73), 148(30), 145(100), 138(17), 117(33), 89(66), 84(86) and 63(31). NMR data are in agreement with published data (Schobert et al, 2001).…”

Section: Extraction and Isolationsupporting

confidence: 92%

Section: Resultsmentioning

confidence: 99%

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Alkaloids from Piper sarmentosum and Piper nigrum

Lim

et al. 2009

Natural Product Research

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“…A more recent preparation of piperine analogues is given by Schobert which utilizes intermolecular three component reaction between aldehydes (alkyl or aryl), amines (1° or 2°) and ketenylidenetriphenylphospharane (Fig. 6) [34]. Apart from this, various amide analogues of piperine were synthesized by using substituted aromatic aldehydes [35] which generally undergoes alkaline hydrolysis in presence of ethanol and provides the basic units such as piperidine, pyrollidine or isobutyl amine and their corresponding acids such as piperic acid or piperylinic acid or guineensic acid, depending on the nature of the carbon chain of the respective amide [36,37].…”

Section: Chemical Synthesis Of Piperine and Related Compoundsmentioning

confidence: 99%

Piperine and Its Various Physicochemical and Biological Aspects: A Review

Chopra¹,

Dhingra²,

Kapoor³

et al. 2016

CHEM

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Abstract:Piper nigrum L. is examined as the king of species worldwide by virtue of its principle piperine. In Ayurveda, since from the ancient times, it is known as "Yogvahi". It is one of the important alkaloids of Pepper fruits (Family Piperaceae) and has been found to have numerous medicinal properties such as antioxidant, antiplatelet, anti-inflammatory, antihypertensive, hepatoprotective, antithyroid, antitumor, antiasthmatic activity and also have significant role as fertility enhancer. The present review discusses the biosynthetic pathway, extraction process, chemistry and various analytical methods of piperine. It also describes the structural modification of piperine and its various effects on biological system. The utility of piperine as a bioenhancer for certain antibacterialantibiotics and a potent inhibitor of drug metabolism are also discussed. Thus, review provides knowledgeable erudition on the piperine which paves way for further work.

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“…27 As shown in Table 1, prolonged reaction time (2-3 d) was required for the reaction achievement, and the expected bicyclic tetramic acids 7a-h were isolated. However, only low to good yields ranging from 24% up to 77% were obtained (see Table 1, entries 1-8).…”

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confidence: 99%

Constrained Tetramic Acids, Homostreptopyrrolidine, and their Analogues Based on Unusual Intramolecular Wittig Olefination with Phosphorus Ylides

Ïuriš¹,

Daı̈ch²,

Berkeš³

2011

Synlett

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The synthesis of bicyclic tetramic acids based on the 'nonclassical' intramolecular Wittig reaction catalyzed by the corresponding phosphonium salt was developed. We have found that such applications proceed smoothly with high yield with N-substituted aminobutanolides when catalyzed with hydrochloride salt of the starting aminolactones. In addition, a convenient multigram synthesis of optically pure 4-hydroxy-5-substituted pyrrolidinones, including homostreptopyrrolidine as methylene homologues of naturally occurring streptopyrrolidine, via two consecutive reduction is also developed.

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Three-component synthesis of (E)-α,β-unsaturated amides of the piperine family

Cited by 35 publications

References 17 publications

Alkaloids from Piper sarmentosum and Piper nigrum

Alkaloids from Piper sarmentosum and Piper nigrum

Piperine and Its Various Physicochemical and Biological Aspects: A Review

Constrained Tetramic Acids, Homostreptopyrrolidine, and their Analogues Based on Unusual Intramolecular Wittig Olefination with Phosphorus Ylides

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