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Journal articles on the topic 'N-acyl'

Author: Grafiati

Published: 5 June 2025

Last updated: 1 August 2025

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1

Cerrini, Silvio, Walter Fedeli, Gino Lucente, Fernando Mazza, Francesco Pinnen, and GIancarlo Zanotti. "N-acyl-diketopiperazines." International Journal of Peptide and Protein Research 23, no. 3 (2009): 223–29. http://dx.doi.org/10.1111/j.1399-3011.1984.tb02713.x.

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2

MAZZA, FERNANDO, GIORGIO POCHETTI, DOMENICO ROSSI, and GINO LUCENTE. "N-Acyl-diketopiperazines." International Journal of Peptide and Protein Research 26, no. 2 (2009): 166–73. http://dx.doi.org/10.1111/j.1399-3011.1985.tb03193.x.

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3

Zhao, Huanxia, Chengxuan He, Yawen Zhou, Jian Yang, Cong Luo, and Baocai Xu. "Study on foaming properties of N-acyl amino acid surfactants: Sodium N-acyl glycinate and sodium N-acyl phenylalaninate." Colloids and Surfaces A: Physicochemical and Engineering Aspects 567 (April 2019): 240–48. http://dx.doi.org/10.1016/j.colsurfa.2019.01.073.

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4

Tørring, Thomas, Stephanie R. Shames, Wooyoung Cho, Craig R. Roy, and Jason M. Crawford. "Acyl Histidines: New N-Acyl Amides fromLegionella pneumophila." ChemBioChem 18, no. 7 (2017): 638–46. http://dx.doi.org/10.1002/cbic.201600618.

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5

Esker, John L., and Martin Newcomb. "Multiple Reaction Channels of (N-Acyl-N-alkylcarbamoyl)oxyl Radicals from N-Acyl PTOC Carbamates." Journal of Organic Chemistry 59, no. 10 (1994): 2779–86. http://dx.doi.org/10.1021/jo00089a023.

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6

Paik, S. "N-acyl-N-nitrosoamino acids and peptides." Tetrahedron Letters 35, no. 41 (1994): 7731–34. http://dx.doi.org/10.1016/s0040-4039(00)77358-8.

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7

Paik, Seunguk, and Emil H. White. "N-acyl-N-nitrosoamino acids and peptides." Tetrahedron Letters 35, no. 42 (1994): 7731–34. http://dx.doi.org/10.1016/0040-4039(94)80104-5.

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8

Van Overloop, Helena, Gerd Van der Hoeven, and Paul P. Van Veldhoven. "N-Acyl migration in ceramides." Journal of Lipid Research 46, no. 4 (2005): 812–16. http://dx.doi.org/10.1194/jlr.d400034-jlr200.

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9

Damon, R. E., and G. M. Coppola. "Cleavage of N-acyl oxazolidones." Tetrahedron Letters 31, no. 20 (1990): 2849–52. http://dx.doi.org/10.1016/0040-4039(90)80164-h.

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10

Beyer, Lothar, Eberhard Hoyer, Jürgen Liebscher, and Horst Hartmann. "Komplexbildung mit N-Acyl-thioharnstoffen." Zeitschrift für Chemie 21, no. 3 (2010): 81–91. http://dx.doi.org/10.1002/zfch.19810210302.

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11

BERDYSHEV, Evgueni V., Patricia C. SCHMID, Zigang DONG, and Harald H. O. SCHMID. "Stress-induced generation of N-acylethanolamines in mouse epidermal JB6 P+ cells." Biochemical Journal 346, no. 2 (2000): 369–74. http://dx.doi.org/10.1042/bj3460369.

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It has long been known that N-acylethanolamine phospholipids [N-acylphosphatidylethanolamine (N-acyl PE)] and N-acylethanolamines (NAEs) accumulate in mammalian tissues undergoing degenerative membrane changes associated with necrosis. Here we studied the effects of stress factors (UVB irradiation and serum deprivation) on the endogenous levels of N-acyl PE and NAE in mouse epidermal JB6 P+ cells. We found that 16:0, 18:0, 18:1,n-9 and 18:1,n-7 are the predominant amide-linked fatty acids in both N-acyl PE and NAE in these cells. UVB irradiation and serum deprivation resulted in significantly

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12

Koval?, I. V., and T. G. Oleinik. "N-arylsulfanyl-N-arylsulfonyl(acyl)-N?-phenylthiourea sodium salts." Russian Journal of Organic Chemistry 40, no. 10 (2004): 1483–86. http://dx.doi.org/10.1007/s11178-005-0045-x.

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13

ESKER, J. L., and M. NEWCOMB. "ChemInform Abstract: Multiple Reaction Channels of (N-Acyl-N-alkylcarbamoyl)oxyl Radicals from N-Acyl PTOC Carbamates." ChemInform 25, no. 49 (2010): no. http://dx.doi.org/10.1002/chin.199449093.

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14

Jo, Dong Geun, Changeun Kim, Sinjae Lee, Sooyeon Yun, and Seewon Joung. "Synthesis of Cyclic N-Acyl Amidines by [3 + 2] Cycloaddition of N-Silyl Enamines and Activated Acyl Azides." Molecules 27, no. 5 (2022): 1696. http://dx.doi.org/10.3390/molecules27051696.

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In this study, we describe the synthesis of cyclic N-acyl amidines from readily available N-heteroarenes. The synthetic methodology utilized the versatile N-silyl enamine intermediates from the hydrosilylation of N-heteroarenes for the [3 + 2] cycloaddition reaction step. We evaluated various acyl azides and selected an electronically activated acyl azide, thereby achieving a reasonable yield of cyclic N-acyl amidines. We analyzed the relationship between the reactivity of each step and the electronic nature of substrates using in situ nuclear magnetic resonance spectroscopy. In addition, we d

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15

Wallach, J., F. Peypoux, O. Lapr�vote, and M. Pagadoy. "N -Acyl derivatives of Asn, new bacterial N -acyl D -amino acids with surfactant activity." Amino Acids 26, no. 2 (2004): 209–14. http://dx.doi.org/10.1007/s00726-003-0056-2.

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16

Dwivedi, Atma P., Shailesh Kumar, Vandana Varshney, Amar B. Singh, Arvind K. Srivastava, and Devi P. Sahu. "Synthesis and antihyperglycemic activity of novel N-acyl-2-arylethylamines and N-acyl-3-coumarylamines." Bioorganic & Medicinal Chemistry Letters 18, no. 7 (2008): 2301–5. http://dx.doi.org/10.1016/j.bmcl.2008.03.003.

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17

CARAMELO, Julio J., Jorge FLORIN-CHRISTENSEN, and José M. DELFINO. "Phospholipase activity on N-acyl phosphatidylethanolamines is critically dependent on the N-acyl chain length." Biochemical Journal 374, no. 1 (2003): 109–15. http://dx.doi.org/10.1042/bj20021840.

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We have recently shown that an endogenous phospholipase A2 from bovine erythrocytes does not hydrolyse NAPEs (N-acyl l-α-phosphatidylethanolamines), which accumulate remarkably in this system [Florin-Christensen, Suarez, Florin-Christensen, Wainszelbaum, Brown, McElwain and Palmer (2001) Proc. Natl. Acad. Sci. U.S.A. 98, 7736–7741]. Here we investigate the causes underlying this resistance. N-acylation of PE (l-α-phosphatidylethanolamine) results in alteration of charge, head-group volume and conformation, the last two features depending on the N-acyl chain length. To evaluate each effect sepa

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18

REKATAS, G. V., V. J. DEMOPOULOS, and P. N. KOUROUNAKIS. "ChemInform Abstract: Synthesis of N-Acyl-2-pyrrolidinones from the Corresponding N-Acyl- GABA Derivatives." ChemInform 27, no. 50 (2010): no. http://dx.doi.org/10.1002/chin.199650102.

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19

Lin, Peishan, and A. Ganesan. "Solid-phase synthesis of N-acyl-N′-carbamoylguanidines." Tetrahedron Letters 39, no. 52 (1998): 9789–92. http://dx.doi.org/10.1016/s0040-4039(98)02174-1.

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20

Hansen, Harald S., Lotte Lauritzen, Birthe Moesgaard, Anne Mette Strand, and Henrik H. Hansen. "Formation of N-Acyl-phosphatidylethanolamines and N-Acylethanolamines." Biochemical Pharmacology 55, no. 6 (1998): 719–25. http://dx.doi.org/10.1016/s0006-2952(97)00396-1.

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21

Yung Wang, Ching, Elfriede M. Linsmaier-Bednar, Mei-Sie Lee, and Charles M. King. "Mutagenicities of N-acyl-N-arylhydroxylamines for Salmonella." Chemico-Biological Interactions 67, no. 3-4 (1988): 215–23. http://dx.doi.org/10.1016/0009-2797(88)90059-2.

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22

Ma, Xiao-Yan, Fu-Qiang Shao, Xinjun Hu, and Xingyong Liu. "Progress in the Synthesis of N-Acyl-N,O-acetals." Synthesis 54, no. 05 (2021): 1203–16. http://dx.doi.org/10.1055/a-1684-0772.

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Abstract N-Acyl-N,O-acetals are key components in a variety of bioactive natural products. Furthermore, they are synthetic equivalents of unstable N-acylimines and building blocks in organic synthesis. Tremendous efforts have been made in the synthesis of such acetals, these methods can be broadly classified into two categories: electrochemical oxidation and chemical methods. Herein, we will summarize progress in the preparation of these subunits, which may aid the development of new synthetic methods for N-acyl-N,O-acetals.1 Introduction2 Synthetic Methods for Preparing N-Acyl-N,O-acetals2.1

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23

Marsh, Derek, and Musti J. Swamy. "Derivatised lipids in membranes. Physico-chemical aspects of N-biotinyl phosphatidylethanolamines, N-acyl phosphatidylethanolamines and N-acyl ethanolamines." Chemistry and Physics of Lipids 105, no. 1 (2000): 43–69. http://dx.doi.org/10.1016/s0009-3084(99)00132-2.

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24

Shamsabadi, André, Jack Ren, and Vijay Chudasama. "Enabling the facile conversion of acyl hydrazides into N-acyl carbamates via metal-free ionic-based rupture of the N–N linkage." RSC Advances 7, no. 44 (2017): 27608–11. http://dx.doi.org/10.1039/c7ra04178k.

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25

Katritzky, Alan, Nader Abo- Dya, Srinivasa Tala, Ebrahim Ghazvini-Zadeh, Kiran Bajaj, and Said El-Feky. "Efficient and Selective Syntheses of S-Acyl and N-Acyl Glutathiones." Synlett 2010, no. 09 (2010): 1337–40. http://dx.doi.org/10.1055/s-0029-1219837.

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26

Bulman Page, Philip C., M. Thomas Gareh, and A. Porter. "N-acyl imidazoles: Excellent acyl electrophiles for 1,3-dithiane oxide anions." Tetrahedron Letters 34, no. 32 (1993): 5159–62. http://dx.doi.org/10.1016/s0040-4039(00)60702-5.

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27

Dang, Chi-Hien, Cong-Hao Nguyen, Thanh-Danh Nguyen, and Chan Im. "Synthesis and characterization of N-acyl-tetra-O-acyl glucosamine derivatives." RSC Advances 4, no. 12 (2014): 6239. http://dx.doi.org/10.1039/c3ra46007j.

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28

Malassa, Irene, та Dieter Matthies. "N-Acyl-α-iminosäure-Derivate, III. Synthese vonN-Acyl-α-oxoaldiminen". Liebigs Annalen der Chemie 1986, № 7 (1986): 1133–39. http://dx.doi.org/10.1002/jlac.198619860701.

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29

SUN, Yong-Xin, Kazuhito TSUBOI, Yasuo OKAMOTO, et al. "Biosynthesis of anandamide and N-palmitoylethanolamine by sequential actions of phospholipase A2 and lysophospholipase D." Biochemical Journal 380, no. 3 (2004): 749–56. http://dx.doi.org/10.1042/bj20040031.

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Anandamide (an endocannabinoid) and other bioactive long-chain NAEs (N-acylethanolamines) are formed by direct release from N-acyl-PE (N-acyl-phosphatidylethanolamine) by a PLD (phospholipase D). However, the possible presence of a two-step pathway from N-acyl-PE has also been suggested previously, which comprises (1) the hydrolysis of N-acyl-PE to N-acyl-lysoPE by PLA1/PLA2 enzyme(s) and (2) the release of NAEs from N-acyllysoPE by lysoPLD (lysophospholipase D) enzyme(s). In the present study we report for the first time the characterization of enzymes responsible for this pathway. The PLA1/P

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30

Li, Dan, Wei Gao, and Xiaochao Chen. "Asymmetric Synthesis of C1-Chiral THIQs with Imines in Isoquinoline Rings." Synthesis 52, no. 22 (2020): 3337–55. http://dx.doi.org/10.1055/s-0040-1707206.

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Tetrahydroisoquinoline (THIQ) scaffolds are important structural units that widely exist in a variety of natural alkaloids and synthetic analogues. Asymmetric synthesis of C1-chiral THIQ is of particular importance due to its significant pharmaceutical, agrochemical, and other biological activities, and the usually distinct bioactivities exhibited by the two enantiomers. In this review, we highlight the significant advances achieved in this field, present recent asymmetric synthesis with imines in isoquinoline rings ordered according to the sequence of various substrate types. New strategies c

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31

Dunkelmann, Daniel L., Yuki Hirata, Kyle A. Totaro, et al. "Amide-forming chemical ligation via O-acyl hydroxamic acids." Proceedings of the National Academy of Sciences 115, no. 15 (2018): 3752–57. http://dx.doi.org/10.1073/pnas.1718356115.

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The facile rearrangement of “S-acyl isopeptides” to native peptide bonds via S,N-acyl shift is central to the success of native chemical ligation, the widely used approach for protein total synthesis. Proximity-driven amide bond formation via acyl transfer reactions in other contexts has proven generally less effective. Here, we show that under neutral aqueous conditions, “O-acyl isopeptides” derived from hydroxy-asparagine [aspartic acid-β-hydroxamic acid; Asp(β-HA)] rearrange to form native peptide bonds via an O,N-acyl shift. This process constitutes a rare example of an O,N-acyl shift that

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32

Negrete, George R., and Joseph P. Konopelski. "Asymmetric alkylations of n-acyl dihydropyrimidinones." Tetrahedron: Asymmetry 2, no. 2 (1991): 105–8. http://dx.doi.org/10.1016/s0957-4166(00)80528-5.

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33

Romanov, V. E., E. E. Shul’ts, M. M. Shakirov, and G. A. Tolstikov. "New acyl derivatives of N-deacetyllappaconitine." Chemistry of Natural Compounds 44, no. 3 (2008): 346–51. http://dx.doi.org/10.1007/s10600-008-9058-3.

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34

Hirano, Shigehiro, Yasuhiro Yamaguchi, and Mitsutomo Kamiya. "Water-SolubleN-(n-Fatty acyl)chitosans." Macromolecular Bioscience 3, no. 10 (2003): 629–31. http://dx.doi.org/10.1002/mabi.200350029.

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35

Hoffmann, Siegfried, Klaus-Jürgen Hartung, Nguyen Thi Hanh, Reinhard Mewes, and Wenelin Baluzow. "Synthesen vinyloger N-Acyl-azole (Vinazolide)." Zeitschrift für Chemie 26, no. 3 (2010): 105–6. http://dx.doi.org/10.1002/zfch.19860260314.

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36

Kolbe, Adelheid, and Horst-Robert Schütte. "Synthese von Acyl-N-ethyl-glycinen." Zeitschrift für Chemie 27, no. 6 (2010): 215–16. http://dx.doi.org/10.1002/zfch.19870270609.

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37

Voronkov, M. G., I. P. Tsyrendorzhieva, and V. I. Rakhlin. "Acyl Iodides in Organic Synthesis. Reaction of Acyl Iodides with N,N-Dimethyl Carboxylic Acid Amides." Russian Journal of Organic Chemistry 46, no. 10 (2010): 1476–78. http://dx.doi.org/10.1134/s1070428010100064.

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38

Murase, Hironobu, Akihiko Nagao, and Junji Terao. "Antioxidant and emulsifying activity of N-(long-chain-acyl)histidine and N-(long-chain-acyl)carnosine." Journal of Agricultural and Food Chemistry 41, no. 10 (1993): 1601–4. http://dx.doi.org/10.1021/jf00034a014.

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39

Connor, Mark, Chris W. Vaughan, and Robert J. Vandenberg. "N-Acyl amino acids and N-acyl neurotransmitter conjugates: neuromodulators and probes for new drug targets." British Journal of Pharmacology 160, no. 8 (2010): 1857–71. http://dx.doi.org/10.1111/j.1476-5381.2010.00862.x.

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40

Wood, Mark E., Victoria M. Annis, and Clifford D. Jones. "Unusual reactivity of N-acyl imides: N-aroyl-1,2,4-dithiazolidine-3,5-diones as acyl isocyanate equivalents." Organic & Biomolecular Chemistry 6, no. 22 (2008): 4099. http://dx.doi.org/10.1039/b814677b.

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41

Izawa, Kunisuke, Seiichi Nishi та Shoichi Asada. "Synthesis of N-acyl-α-amino esters via cobalt-catalyzed carbonylation of N-acyl-α-alkoxyamines". Journal of Molecular Catalysis 41, № 1-2 (1987): 135–46. http://dx.doi.org/10.1016/0304-5102(87)80024-x.

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42

Vincent, Guillaume, Hussein Abou-Hamdan, and Cyrille Kouklovsky. "Dearomatization Reactions of Indoles to Access 3D Indoline Structures." Synlett 31, no. 18 (2020): 1775–88. http://dx.doi.org/10.1055/s-0040-1707152.

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This Account summarizes our involvement in the development of dearomatization reactions of indoles that has for origin a total synthesis problematic. We present the effort from our group to obtain 3D-indolines scaffold from the umpolung of N-acyl indoles via activation with FeCl3 to the oxidative spirocyclizations of N-EWG indoles and via the use of electrochemistry.1 Introduction2 Activation of N-Acyl Indoles with FeCl3 2.1 Hydroarylation of N-Acyl Indoles2.2 Difunctionalization of N-Acyl Indoles3 Radical-Mediated Dearomatization of Indoles for the Synthesis of Spirocyclic Indolines4 Electroc

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43

van Vliet, Kaj M., Lara H. Polak, Maxime A. Siegler, Jarl Ivar van der Vlugt, Célia Fonseca Guerra, and Bas de Bruin. "Efficient Copper-Catalyzed Multicomponent Synthesis of N-Acyl Amidines via Acyl Nitrenes." Journal of the American Chemical Society 141, no. 38 (2019): 15240–49. http://dx.doi.org/10.1021/jacs.9b07140.

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44

Rekatas, George V., Vassilis J. Demopoulos, and Panos N. Kourounakis. "Synthesis ofN-acyl-2-pyrrolidinones from the corresponding N-acyl-GABA derivatives." Journal of Heterocyclic Chemistry 33, no. 3 (1996): 989–90. http://dx.doi.org/10.1002/jhet.5570330372.

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45

Taylor, James E., Matthew D. Jones, Jonathan M. J. Williams, and Steven D. Bull. "N-Acyl DBN Tetraphenylborate Salts as N-Acylating Agents." Journal of Organic Chemistry 77, no. 6 (2012): 2808–18. http://dx.doi.org/10.1021/jo202647f.

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46

Sinitsa, A. D., N. V. Kolotylo, E. A. Suvalova, and P. P. Onys'ko. "N-Acyl-and N-Phosphorylpolyhalogenoalkyl-Imidolylphosphonates: Synthesis and Reactions." Phosphorus, Sulfur, and Silicon and the Related Elements 147, no. 1 (1999): 381. http://dx.doi.org/10.1080/10426509908053670.

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47

Lynch, V. M., C. Hulme, P. Magnus та B. E. Davis. "Novel N-Acyl α-Azidopyrrolidines (N-Acyliminium-Ion Precursors)". Acta Crystallographica Section C Crystal Structure Communications 51, № 2 (1995): 262–65. http://dx.doi.org/10.1107/s0108270194005676.

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48

Mazgarova, G. G., and R. R. Gataullin. "Synthesis of N-allyl- and N-acyl-2-vinylindoline." Russian Journal of General Chemistry 84, no. 4 (2014): 672–75. http://dx.doi.org/10.1134/s1070363214040112.

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49

Zosimo-Landolfo, Guido, Jean M. J. Tronchet, and Ford Habashi. "N- and O-acyl derivatives of Deoxy-N-hydroxyaminosugars." Journal f�r Praktische Chemie/Chemiker-Zeitung 336, no. 3 (1994): 273–76. http://dx.doi.org/10.1002/prac.19943360318.

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50

Enright, Robert N., Jeffrey L. Grinde, Lincoln I. Wurtz, et al. "Synthesis of N,O-acetals by net amide C N bond insertion of aldehydes into N-acyl phthalimides and N-acyl azoles." Tetrahedron 72, no. 41 (2016): 6397–408. http://dx.doi.org/10.1016/j.tet.2016.08.041.

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