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Автор: Grafiati

Опубліковано: 18 травня 2024

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1

Tsang, Wing Y., Naveed Ahmed, Karl Hemming та Michael I. Page. "Competitive endo- and exo-cyclic CN fission in the hydrolysis of N-aroyl β-lactams". Canadian Journal of Chemistry 83, № 9 (1 вересня 2005): 1432–39. http://dx.doi.org/10.1139/v05-153.

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The balance between endo- and exo-cyclic CN fission in the hydrolysis of N-aroyl β-lactams shows that the difference in reactivity between strained β-lactams and their acyclic analogues is minimal. Attack of hydroxide ion occurs preferentially at the exocyclic acyl centre rather than that of the β-lactam during the hydrolysis of N-p-nitrobenzoyl β-lactam. In general, both endo- and exo-cyclic CN bond fission occurs in the alkaline hydrolysis of N-aroyl β-lactams, the ratio of which varies with the aryl substituent. Hence, the Brønsted β-values differ for the two processes: 0.55 for the ring-opening reaction and 1.54 for the exocyclic CN bond fission reaction. For the pH-independent and acid-catalysed hydrolysis of N-benzoyl β-lactam, less than 3% of products are derived from exocyclic CN bond fission. Key words: β-lactams, hydrolysis, linear free energy relationships, strain.

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2

Barba, Victor, Cecilia Hernández, Susana Rojas-Lima, Norberto Farfán та Rosa Santillan. "Preparation of N-aryl-substituted spiro-β-lactams via Staudinger cycloaddition". Canadian Journal of Chemistry 77, № 12 (5 грудня 1999): 2025–32. http://dx.doi.org/10.1139/v99-212.

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The interest in the study of β-lactams continues due to their therapeutic importance as antibiotics. In this work, six spiro-β-lactams (7a-7c, 8a-8c) have been prepared using the [2+2] cycloaddition of isomaleimides to acid chlorides. The heterobicyclic structures obtained have been characterized by mass spectrometry, IR, NMR spectroscopy, and for compounds 7a, 7b, and 8b the X-ray crystallographic study showed a nearly planar arrangement for the β-lactam ring.Key words: β-lactams, azetidinone, isomaleimides, ketenes, X-ray crystallography.

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3

Möhrle, H., and M. Jeandrée. "Chinazolinderivate durch Cyclodehydrierung von N-(2-substituierten Aryl)-Piperidinen / Quinazoline Derivatives by Cyclodehydrogenation of N-(2-Substituted Aryl)-Piperidines." Zeitschrift für Naturforschung B 54, no. 12 (December 1, 1999): 1577–88. http://dx.doi.org/10.1515/znb-1999-1217.

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Dehydrogenation of the N-[2-(aminocarbonyl)phenyl]piperidines 1 -5 using Hg(II)-EDTA, generated the quinazolinones 6 -9 . Increasing size of the 4-substituent in the piperidine decreased the oxidation rate and the product yield.N-[2-(Hydroxyiminomethyl)phenyl]piperidines 18-22 showed a different behaviour. While 18 with H g(II)-EDTA in water produced the oxime lactam 24 in quantitative yield, the 4- substituted piperidines 19-21 caused not only a lower reaction rate but also an altered product pattern. The double dehydrogenation to lactams was reduced and the cyclic nitrones, formed by two electron withdrawal, became dominant. From the spiro compounds 21 and 22, solely the quinazoline-N-oxides 29 and 30 resulted. The mechanism of the reactions is discussed.

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4

Fang, Zeguo, Lin Xie, Liang Wang, Qian Zhang та Dong Li. "Silver-catalyzed cascade cyclization and functionalization of N-aryl-4-pentenamides: an efficient route to γ-lactam-substituted quinone derivatives". RSC Advances 12, № 41 (2022): 26776–80. http://dx.doi.org/10.1039/d2ra05283k.

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The synthesis of γ-lactam and related 2-oxazolidinone substituted quinone derivatives through a Ag2O-catalyzed cascade cyclization and functionalization of N-ary-4-pentenamides and N-aryl allyl carbamates has been developed.

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5

Saliu, Francesco, Marco Orlandi, and Maurizio Bruschi. "N-Aryl Lactams by Regioselective Ozonation of N-Aryl Cyclic Amines." ISRN Organic Chemistry 2012 (October 15, 2012): 1–5. http://dx.doi.org/10.5402/2012/281642.

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Ozonation of N-aryl-cyclic amines in organic solvents gave N-aryl-lactams regioselectively. In particular, 4-(4-aminophenyl)-morpolin-3-one, a key intermediate in the preparation of factor Xa inhibitors, was obtained in fair yields. The method represents an alternative approach for the lactamization of tertiary N-arylic substrates and is based on a “metal-free” introduction of the carbonyl function into the heterocyclic ring.

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6

Haldar, Pranab, та Jayanta K. Ray. "CAN mediated decarboxylative hydroxylation/alkoxylation of N-aryl-γ-lactam-carboxylic acids at room temperature: an easy access to N-aryl-α-hydroxy/alkoxy-γ-lactams". Tetrahedron Letters 49, № 22 (травень 2008): 3659–62. http://dx.doi.org/10.1016/j.tetlet.2008.03.147.

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7

Yurino, Taiga, Takeshi Ohkuma, Hamdiye Ece, and Yuji Tange. "Silyl Cyanopalladate-Catalyzed Friedel–Crafts-Type Cyclization Affording 3-Aryloxindole Derivatives." Synlett 32, no. 09 (January 26, 2021): 935–39. http://dx.doi.org/10.1055/a-1373-7017.

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Abstract3-Aryloxindole derivatives were synthesized through a Friedel–Crafts-type cyclization. The reaction was catalyzed by a trimethylsilyl tricyanopalladate complex generated in situ from trimethylsilyl cyanide and Pd(OAc)2. Wide varieties of diethyl phosphates derived from N-arylmandelamides were converted almost quantitatively into oxindoles. When N,N-dibenzylamide was used instead of an anilide substrate, a benzo-fused δ-lactam was obtained. An oxindole product was subjected to substitution reactions to afford 3,3-diaryloxindoles with two different aryl groups.

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8

Patra, Prasanta, Gandhi K. Kar, Aparna Sarkar, Jayanta K. Ray, Tista Dasgupta, Mahua Ghosh та Sugata Bhattacharya. "N-Aryl Modification in γ-Lactam: Design and Synthesis of Novel Monocyclic γ-Lactam Derivatives as Inhibitor for Bacterial Propagation". Synthetic Communications 42, № 20 (21 червня 2012): 3031–41. http://dx.doi.org/10.1080/00397911.2011.574807.

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9

Dorbec, Matthieu, Jean-Claude Florent, Claude Monneret, Marie-Noëlle Rager та Emmanuel Bertounesque. "1-Aryltetralin privileged structure-based libraries: parallel synthesis of N-aryl and N-biaryl γ-lactam lignans". Tetrahedron 62, № 50 (грудень 2006): 11766–81. http://dx.doi.org/10.1016/j.tet.2006.09.026.

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10

Patra, Prasanta, Gandhi K. Kar, Aparna Sarkar, Jayanta K. Ray, Tista Dasgupta, Mahua Ghosh та Sugata Bhattacharya. "ChemInform Abstract: N-Aryl Modification in γ-Lactam: Design and Synthesis of Novel Monocyclic γ-Lactam Derivatives as Inhibitor for Bacterial Propagation." ChemInform 44, № 1 (1 січня 2013): no. http://dx.doi.org/10.1002/chin.201301160.

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11

Browning, R. Greg, Vivek Badarinarayana, Hossen Mahmud, and Carl J. Lovely. "Palladium-catalyzed aryl-amidation. Synthesis of non-racemic N-aryl lactams." Tetrahedron 60, no. 2 (January 2004): 359–65. http://dx.doi.org/10.1016/j.tet.2003.11.008.

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12

Zhang, Bo, Peng Feng, Li-Hui Sun, Yuxin Cui, Song Ye та Ning Jiao. "N-Heterocyclic Carbene-Catalyzed Homoenolate Additions with N-Aryl Ketimines as Electrophiles: Efficient Synthesis of Spirocyclic γ-Lactam Oxindoles". Chemistry - A European Journal 18, № 30 (26 червня 2012): 9198–203. http://dx.doi.org/10.1002/chem.201201375.

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13

de Oliveira, Arnaldo G., Martí F. Wang, Rafaela C. Carmona, Danilo M. Lustosa, Sergei A. Gorbatov та Carlos R. D. Correia. "Enantioselective synthesis of β-aryl-γ-lactam derivatives via Heck–Matsuda desymmetrization of N-protected 2,5-dihydro-1H-pyrroles". Beilstein Journal of Organic Chemistry 20 (29 квітня 2024): 940–49. http://dx.doi.org/10.3762/bjoc.20.84.

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We report herein an enantioselective palladium-catalyzed Heck–Matsuda reaction for the desymmetrization of N-protected 2,5-dihydro-1H-pyrroles with aryldiazonium salts, using the chiral N,N-ligand (S)-PyraBox. This strategy has allowed straightforward access to a diversity of 4-aryl-γ-lactams via Heck arylation followed by a sequential Jones oxidation. The overall method displays a broad scope and good enantioselectivity, favoring the (R) enantiomer. The applicability of the protocol is highlighted by the efficient enantioselective syntheses of the selective phosphodiesterase-4-inhibitor rolipram and the commercial drug baclofen as hydrochloride.

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14

Jha, Amitabh, Ting-Yi Chou, Zainab ALJaroudi, Bobby D. Ellis, and T. Stanley Cameron. "Aza-Diels–Alder reaction between N-aryl-1-oxo-1H-isoindolium ions and tert-enamides: Steric effects on reaction outcome." Beilstein Journal of Organic Chemistry 10 (April 14, 2014): 848–57. http://dx.doi.org/10.3762/bjoc.10.81.

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The synthesis of 5-substituted 6,6a-dihydroisoindolo[2,1-a]quinolin-11(5H)-ones via [4 + 2] imino-Diels–Alder cyclization from N-aryl-3-hydroxyisoindolinones and N-vinyl lactams under Lewis acid-catalysed anhydrous conditions is reported. Reactions of N-(2-substituted-aryl)-3-hydroxyisoindolinones with N-vinylpyrrolidone under identical conditions resulted in the formation of 2-(2-substitued-aryl)-3-(2-(2-oxopyrrolidin-1-yl)vinyl)isoindolin-1-one analogues indicating steric hinderance as the cause of deviation. The probable mechanism of the reaction based on the results from X-ray crystallography and molecular modelling is discussed.

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15

Xi, Ning, Stephen Arvedson, Shawn Eisenberg, Nianhe Han, Michael Handley, Liang Huang, Qi Huang та ін. "N-Aryl-γ-lactams as integrin αvβ3 antagonists". Bioorganic & Medicinal Chemistry Letters 14, № 11 (червень 2004): 2905–9. http://dx.doi.org/10.1016/j.bmcl.2004.03.033.

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16

Ray, Jayanta, та Gopa Barman. "NaIO4-Mediated Decarboxylative Oxidation of γ-Lactam Carboxylic Acids: A Simple Approach towards N-Aryl Maleimide Derivatives". Synlett 2009, № 20 (18 листопада 2009): 3333–35. http://dx.doi.org/10.1055/s-0029-1218379.

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17

Zhang, Bo, Peng Feng, Li-Hui Sun, Yuxin Cui, Song Ye та Ning Jiao. "ChemInform Abstract: N-Heterocyclic Carbene-Catalyzed Homoenolate Additions with N-Aryl Ketimines as Electrophiles: Efficient Synthesis of Spirocyclic γ-Lactam Oxindoles." ChemInform 43, № 52 (18 грудня 2012): no. http://dx.doi.org/10.1002/chin.201252095.

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18

Durán, Rocío, César Barrales-Martínez, Fabián Santana-Romo, Diego F. Rodríguez, Flavia C. Zacconi, and Barbara Herrera. "Substitution Effects in Aryl Halides and Amides into the Reaction Mechanism of Ullmann-Type Coupling Reactions." Molecules 29, no. 8 (April 13, 2024): 1770. http://dx.doi.org/10.3390/molecules29081770.

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In this article, we present a comprehensive computational investigation into the reaction mechanism of N-arylation of substituted aryl halides through Ullmann-type coupling reactions. Our computational findings, obtained through DFT ωB97X-D/6-311G(d,p) and ωB97X-D/LanL2DZ calculations, reveal a direct relation between the previously reported experimental reaction yields and the activation energy of haloarene activation, which constitutes the rate-limiting step in the overall coupling process. A detailed analysis of the reaction mechanism employing the Activation Strain Model indicates that the strain in the substituted iodoanilines is the primary contributor to the energy barrier, representing an average of 80% of the total strain energy. Additional analysis based on conceptual Density Functional Theory (DFT) suggests that the nucleophilicity of the nitrogen in the lactam is directly linked to the activation energies. These results provide valuable insights into the factors influencing energetic barriers and, consequently, reaction yields. These insights enable the rational modification of reactants to optimize the N-arylation process.

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19

W. Joachim Demnitz, F., Esther Aebischer, Edmond Bacher, Thomas H. Keller, Miriam Kurzmeyer, Marta L. Ortiz, Esteban Pombo-Villar, and Hans-Peter Weber. "Synthesis of N-Arylrolipram Derivatives - Potent and Selective Phosphodiesterase-IV Inhibitors - by Copper Catalyzed Lactam-Aryl Halide Coupling." HETEROCYCLES 48, no. 11 (1998): 2225. http://dx.doi.org/10.3987/com-98-8322.

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20

Kirillov, N. F., E. A. Nikiforova, D. V. Baibarodskikh, T. A. Zakharova та L. S. Govorushkin. "Synthesis of New Bis(spiro-β-lactams) via Interaction of Methyl 1-Bromocycloalcanecarboxylates with Zinc and N,N′-Bis(arylmethylidene)benzidines". Journal of Chemistry 2019 (3 лютого 2019): 1–7. http://dx.doi.org/10.1155/2019/7496512.

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Interaction of the Reformatsky reagents, prepared from methyl 1-bromocyclopentane-1-carboxylate or methyl 1-bromocyclohexane-1-carboxylate, with N,N′-bis(arylmethylidene)benzidines has given rise to a set of intermediates as a result of nucleophilic addition to the C=N group of a substrate. Further intramolecular attack of the amide nitrogen atom onto the ester carbonyl group is responsible for the ring closure, which affords two series of spirocompounds: 2,2′-([1,1′-biphenyl]-4,4′-diyl)bis(3-aryl-2-azaspiro[3.4]octan-1-one) or 2,2′-([1,1′-biphenyl]-4,4′-diyl)bis(3-aryl-2-azaspiro[3.5]nonan-1-ones).

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21

More, Devidas A., Ganesh H. Shinde, Aslam C. Shaikh, and M. Muthukrishnan. "Oxone promoted dehydrogenative Povarov cyclization of N-aryl glycine derivatives: an approach towards quinoline fused lactones and lactams." RSC Advances 9, no. 52 (2019): 30277–91. http://dx.doi.org/10.1039/c9ra06212b.

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Oxone promoted intramolecular dehydrogenative imino Diels–Alder reaction (Povarov cyclization) of alkyne tethered N-aryl glycine esters and amides has been explored, thus affording biologically significant quinoline fused lactones and lactams.

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22

Barman, Gopa, та Jayanta K. Ray. "A novel access to bisformylated pyrroles via decarboxylation of N-aryl-γ-lactam-carboxylic acids under Vilsmeier reaction conditions". Tetrahedron Letters 51, № 2 (січень 2010): 297–300. http://dx.doi.org/10.1016/j.tetlet.2009.11.005.

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23

Barman, Gopa. "A facile synthesis of diformylated pyrroles by dehydroxylation of N-aryl-5-hydroxy-γ-lactam derivatives under Vilsmeier reaction conditions". Chemistry of Heterocyclic Compounds 51, № 10 (жовтень 2015): 869–71. http://dx.doi.org/10.1007/s10593-015-1789-z.

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24

Aebischer, Esther, Edmond Bacher, F. W. Joachim Demnitz, Thomas H. Keller, Miriam Kurzmeyer, Marta L. Ortiz, Esteban Pombo-Villar, and Hans-Peter Weber. "ChemInform Abstract: Synthesis of N-Arylrolipram Derivatives - Potent and Selective Phosphodiesterase-IV Inhibitors - by Copper-Catalyzed Lactam-Aryl Halide Coupling." ChemInform 30, no. 9 (June 17, 2010): no. http://dx.doi.org/10.1002/chin.199909132.

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25

Koleoso, Olusesan K., Mark R. J. Elsegood, Simon J. Teat та Marc C. Kimber. "Photoredox Approach to N-Acyl-N′-aryl-N,N′-aminals Using Enamides and Their Conversion to γ-Lactams". Organic Letters 20, № 4 (26 січня 2018): 1003–6. http://dx.doi.org/10.1021/acs.orglett.7b03946.

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26

Wang, Eng-Chi, Keng-Shiang Huang, Gwo-Woei Lin, Jia-Ruei Lin та Ming-Kun Hsu. "A New Route toN-Aryl 2-Alkenamides,N-AllylN-Aryl 2-Alkenamides, andN-Aryl α,β-Unsaturated γ-Lactams fromN-Aryl 3-(Phenylsulfonyl)propanamides". Journal of the Chinese Chemical Society 48, № 1 (лютий 2001): 83–90. http://dx.doi.org/10.1002/jccs.200100016.

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27

Bentabed-Ababsa, Ghenia, Ekhlass Nassar, Ziad Fajloun, Florence Mongin, Rim Amara, Madani Hedidi, Joseph Khoury та ін. "Synthesis of N-Aryl and N-Heteroaryl γ-, δ-, and ε-Lactams Using Deprotometalation–Iodination and N-Arylation, and Properties Thereof". Synthesis 28, № 19 (19 липня 2017): 4500–4516. http://dx.doi.org/10.1055/s-0036-1590798.

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Xanthone, thioxanthone, fluorenone, benzophenone, 2-benzoylpyridine, dibenzofuran, and dibenzothiophene were deprotonated using a base prepared in situ from MCl2·TMEDA (M = Zn or Cd; TMEDA = N,N,N′,N′-tetramethylethylenediamine) and lithium 2,2,6,6-tetramethylpiperidide in a 1:3 ratio, as demonstrated by subsequent iodolysis. The different aryl halides were involved as partners in the N-arylation of pyrrolidin-2-one. In the presence of copper(I) iodide and tripotassium phosphate, and using dimethyl sulfoxide as solvent, the reactions could be performed in yields ranging from 40 to 70%. Most of the products were tested for their antimicrobial, antifungal, antioxidant, and cytotoxic (MCF-7) activity.

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28

Long, Timothy E., Edward Turos, Monika I. Konaklieva, Allison L. Blum, Amal Amry, Ejae A. Baker, Lita S. Suwandi та ін. "Effect of Aryl Ring Fluorination on the Antibacterial Properties of C4 Aryl-Substituted N-Methylthio β-Lactams". Bioorganic & Medicinal Chemistry 11, № 8 (квітень 2003): 1859–63. http://dx.doi.org/10.1016/s0968-0896(03)00037-3.

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29

Kolkenbrock, Stephan, Katja Parschat, Bernd Beermann, Hans-Jürgen Hinz та Susanne Fetzner. "N-Acetylanthranilate Amidase from Arthrobacter nitroguajacolicus Rü61a, an α/β-Hydrolase-Fold Protein Active towards Aryl-Acylamides and -Esters, and Properties of Its Cysteine-Deficient Variant". Journal of Bacteriology 188, № 24 (13 жовтня 2006): 8430–40. http://dx.doi.org/10.1128/jb.01085-06.

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ABSTRACT N-acetylanthranilate amidase (Amq), a 32.8-kDa monomeric amide hydrolase, is involved in quinaldine degradation by Arthrobacter nitroguajacolicus Rü61a. Sequence analysis and secondary structure predictions indicated that Amq is related to carboxylesterases and belongs to the α/β-hydrolase-fold superfamily of enzymes; inactivation of (His6-tagged) Amq by phenylmethanesulfonyl fluoride and diethyl pyrocarbonate and replacement of conserved residues suggested a catalytic triad consisting of S155, E235, and H266. Amq is most active towards aryl-acetylamides and aryl-acetylesters. Remarkably, its preference for ring-substituted analogues was different for amides and esters. Among the esters tested, phenylacetate was hydrolyzed with highest catalytic efficiency (k cat/Km = 208 mM−1 s−1), while among the aryl-acetylamides, o-carboxy- or o-nitro-substituted analogues were preferred over p-substituted or unsubstituted compounds. Hydrolysis by His6Amq of primary amides, lactams, N-acetylated amino acids, azocoll, tributyrin, and the acylanilide and urethane pesticides propachlor, propham, carbaryl, and isocarb was not observed; propanil was hydrolyzed with 1% N-acetylanthranilate amidase activity. The catalytic properties of the cysteine-deficient variant His6AmqC22A/C63A markedly differed from those of His6Amq. The replacements effected some changes in Km s of the enzyme and increased k cats for most aryl-acetylesters and some aryl-acetylamides by factors of about three to eight while decreasing k cat for the formyl analogue N-formylanthranilate by several orders of magnitude. Circular dichroism studies indicated that the cysteine-to-alanine replacements resulted in significant change of the overall fold, especially an increase in α-helicity of the cysteine-deficient protein. The conformational changes may also affect the active site and may account for the observed changes in kinetic properties.

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30

Chaturvedi, Devdutt, Amit Chaturvedi, Nisha Mishra, and Virendra Mishra. "Efficient, One-Pot, BF3·OEt2-Mediated Synthesis of Substituted N-Aryl Lactams." Synlett 23, no. 18 (October 18, 2012): 2627–30. http://dx.doi.org/10.1055/s-0032-1317326.

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31

Haldar, Pranab, Joyram Guin та Jayanta K. Ray. "Sodium borohydride–iodine mediated reduction of γ-lactam carboxylic acids followed by DDQ mediated oxidative aromatisation: a facile entry to N-aryl-formylpyrroles". Tetrahedron Letters 46, № 7 (лютий 2005): 1071–74. http://dx.doi.org/10.1016/j.tetlet.2004.12.107.

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32

Filatov, Vadim E., Dmitrii A. Iuzabchuk, Viktor A. Tafeenko, Yuri K. Grishin, Vitaly A. Roznyatovsky, Dmitrii A. Lukianov, Yulia A. Fedotova та ін. "Dispirooxindole-β-Lactams: Synthesis via Staudinger Ketene-Imine Cycloaddition and Biological Evaluation". International Journal of Molecular Sciences 23, № 12 (15 червня 2022): 6666. http://dx.doi.org/10.3390/ijms23126666.

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In this work, we present the first synthesis of dispirooxindole-β-lactams employing optimized methodology of one-pot Staudinger ketene-imine cycloaddition with N-aryl-2-oxo-pyrrolidine-3-carboxylic acids as the ketene source. Spiroconjugation of indoline-2-one with β-lactams ring is considered to be able to provide stabilization and wide scope of functionalization to resulting scaffolds. The dispipooxindoles obtained demonstrated medium cytotoxicity in the MTT test on A549, MCF7, HEK293, and VA13 cell lines, and one of the compounds demonstrated antibacterial activity against E. coli strain LPTD.

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33

Chaturvedi, Devdutt, Amit K. Chaturvedi, Nisha Mishra, and Virendra Mishra. "An efficient and novel approach for the synthesis of substituted N-aryl lactams." Organic & Biomolecular Chemistry 10, no. 46 (2012): 9148. http://dx.doi.org/10.1039/c2ob26230d.

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34

Barba, Victor, Cecilia Hernandez, Susana Rojas-Lima, Norberto Farfan та Rosa Santillan. "ChemInform Abstract: Preparation of N-Aryl-Substituted Spiro-β-lactams via Staudinger Cycloaddition." ChemInform 31, № 23 (8 червня 2010): no. http://dx.doi.org/10.1002/chin.200023109.

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35

He, Zhi-Tao, Ya-Bing Wei, Hong-Jie Yu, Cai-Yun Sun, Chen-Guo Feng, Ping Tian та Guo-Qiang Lin. "Rhodium/diene-catalyzed asymmetric arylation of N-Boc-protected α,β-unsaturated δ-lactam with arylboronic acids: enantioselective synthesis of 4-aryl-2-piperidinones". Tetrahedron 68, № 45 (листопад 2012): 9186–91. http://dx.doi.org/10.1016/j.tet.2012.09.001.

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36

Lavoie, Christopher M., Preston M. MacQueen, and Mark Stradiotto. "Nickel-Catalyzed N-Arylation of Primary Amides and Lactams with Activated (Hetero)aryl Electrophiles." Chemistry - A European Journal 22, no. 52 (November 16, 2016): 18752–55. http://dx.doi.org/10.1002/chem.201605095.

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Chaturvedi, Devdutt, Amit K. Chaturvedi, Nisha Mishra, and Virendra Mishra. "ChemInform Abstract: Efficient, One-Pot, BF3·OEt2-Mediated Synthesis of Substituted N-Aryl Lactams." ChemInform 44, no. 13 (March 18, 2013): no. http://dx.doi.org/10.1002/chin.201313088.

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38

Hu, Yinqiao, Xiaolan Fu, Badru-Deen Barry, Xihe Bi та Dewen Dong. "Regiospecific β-lactam ring-opening/recyclization reactions of N-aryl-3-spirocyclic-β-lactams catalyzed by a Lewis–Brønsted acids combined superacid catalyst system: a new entry to 3-spirocyclicquinolin-4(1H)-ones". Chem. Commun. 48, № 5 (2012): 690–92. http://dx.doi.org/10.1039/c1cc15881c.

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Patra, Prasanta, та Gandhi K. Kar. "Studies on the Suzuki reaction on methyl 1-(2-bromoaryl)-5-oxo-3-aryl/heteroaryl-pyrrolidin-2-carboxylate derivatives: synthesis of N-aryl modified monocyclic γ-lactam derivatives in search for newer antibacterial agents". Tetrahedron Letters 55, № 2 (січень 2014): 326–28. http://dx.doi.org/10.1016/j.tetlet.2013.11.009.

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Chaturvedi, Devdutt, Amit K. Chaturvedi, Nisha Mishra, and Virendra Mishra. "ChemInform Abstract: An Efficient and Novel Approach for the Synthesis of Substituted N-Aryl Lactams." ChemInform 44, no. 19 (April 18, 2013): no. http://dx.doi.org/10.1002/chin.201319192.

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41

He, Zhi-Tao, Ya-Bing Wei, Hong-Jie Yu, Cai-Yun Sun, Chen-Guo Feng, Ping Tian та Guo-Qiang Lin. "ChemInform Abstract: Rhodium/Diene-Catalyzed Asymmetric Arylation of N-Boc-Protected α,β-Unsaturated δ-Lactam with Arylboronic Acids: Enantioselective Synthesis of 4-Aryl-2-piperidinones." ChemInform 44, № 11 (8 березня 2013): no. http://dx.doi.org/10.1002/chin.201311149.

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42

Wang, Shi-Meng, Chen Li, Jing Leng, Syed Nasir Abbas Bukhari та Hua-Li Qin. "Rhodium(iii)-catalyzed Oxidative Coupling of N-Methoxybenzamides and Ethenesulfonyl fluoride: a C–H Bond Activation Strategy for the Preparation of 2-Aryl ethenesulfonyl fluorides and Sulfonyl fluoride Substituted γ-Lactams". Organic Chemistry Frontiers 5, № 9 (2018): 1411–15. http://dx.doi.org/10.1039/c7qo01128h.

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43

Patra, Prasanta, та Gandhi K. Kar. "ChemInform Abstract: Studies on the Suzuki Reaction on Methyl 1-(2-Bromoaryl)-5-oxo-3-aryl/heteroaryl-pyrrolidin-2-carboxylate Derivatives: Synthesis of N-Aryl Modified Monocyclic γ-Lactam Derivatives in Search for Newer Antibacterial Agents." ChemInform 45, № 25 (5 червня 2014): no. http://dx.doi.org/10.1002/chin.201425115.

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44

Haldar, Pranab, Gopa Barman та Jayanta K. Ray. "Sodium borohydride–iodine mediated reduction of γ-lactam carboxylic acids followed by DDQ mediated oxidative aromatisation: a simple approach towards N-aryl-formylpyrroles and 1,3-diaryl-formylpyrroles". Tetrahedron 63, № 14 (квітень 2007): 3049–56. http://dx.doi.org/10.1016/j.tet.2007.01.058.

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45

Haldar, Pranab, and Jayanta K. Ray. "Chemoselective reduction of a lactam carbonyl group in the presence of a gem-dicarboxylate by sodium borohydride and iodine: a facile entry to N-aryl trisubstituted pyrroles." Tetrahedron Letters 44, no. 45 (November 2003): 8229–31. http://dx.doi.org/10.1016/j.tetlet.2003.09.085.

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46

Hu, Yinqiao, Xiaolan Fu, Badru-Deen Barry, Xihe Bi та Dewen Dong. "ChemInform Abstract: Regiospecific β-Lactam Ring-Opening/Recyclization Reactions of N-Aryl-3-spirocyclic-β-lactams Catalyzed by a Lewis-Broensted Acids Combined Superacid Catalyst System: A New Entry to 3-Spirocyclicquinolin-4(1H)-ones." ChemInform 43, № 20 (23 квітня 2012): no. http://dx.doi.org/10.1002/chin.201220149.

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47

D'hooghe, Matthias, Stijn Dekeukeleire та Norbert De Kimpe. "Reactivity of N-(ω-haloalkyl)-β-lactams with regard to lithium aluminium hydride: novel synthesis of 1-(1-aryl-3-hydroxypropyl)aziridines and 3-aryl-3-(N-propylamino)propan-1-ols". Organic & Biomolecular Chemistry 6, № 7 (2008): 1190. http://dx.doi.org/10.1039/b719686e.

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48

Erbay, Tuğçe G., Daniel P. Dempe, Bhaskar Godugu, Peng Liu та Kay M. Brummond. "Thiol Reactivity of N-Aryl α-Methylene-γ-lactams: A Reactive Group for Targeted Covalent Inhibitor Design". Journal of Organic Chemistry 86, № 17 (11 серпня 2021): 11926–36. http://dx.doi.org/10.1021/acs.joc.1c01335.

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Wei, Cui, Jie‐Feng Zhu, Jin‐Qi Zhang, Qi Deng та Dong‐Liang Mo. "Synthesis of Spirofluorenyl‐ β ‐Lactams through Cycloaddition and Ring Contraction from N ‐Aryl Fluorenone Nitrones and Methylenecyclopropanes". Advanced Synthesis & Catalysis 361, № 17 (16 липня 2019): 3965–73. http://dx.doi.org/10.1002/adsc.201900523.

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Makhmudov, R. R., E. A. Nikiforova, D. P. Zverev, L. A. Balyukina, and A. Р. Skachkov. "Synthesis and antinociceptive activity of 2,2’-(1,4-phenylene)bis[3-aryl-2-azaspiro[3.5]nonan-1-ones]." Proceedings of Universities. Applied Chemistry and Biotechnology 13, no. 4 (December 26, 2023): 476–82. http://dx.doi.org/10.21285/2227-2925-2023-13-4-476-482.

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Анотація:

Over the years, azetidin-2-ones, or β-lactams, have received a lot of attention from scientists as potential drug candidates due to their diverse biological activity. Spiro-β-lactams also exhibit biological activity; therefore, it is of interest to synthesize and study the properties of new compounds belonging to this class. The study aims to examine the antinociceptive activity of several synthesized bis(spirolactams), specifically 2,2’-(1,4-phenylene)bis[3-aryl-2azaspiro[3.5]nonan-1-ones]. These bis(spiroazetidine-2-ones) were obtained in the interaction of a twofold excess of the Reformatsky reagent, derived from methyl 1-bromocyclohexane carboxylate and zinc, with N,N-(1,4-phenyle- ne)bis(1-arylmethanimines) by means of boiling them in a 10:1 mixture of toluene and hexamethylphosphorictriamide for four hours. Bis(spiro-β-lactams) on the basis of diimines derived from p-phenylenediamine, 2-methoxybenzaldehyde, p-tolualdehyde, and 3-bromobenzoic aldehyde were synthesized for the first time. The composition and structure of the previously undescribed products were established using IR, [1]H, and 13C NMR spectroscopy and elemental analysis. The antinociceptive activity of the obtained compounds was studied on outbred white mice of both sexes via the hot plate test with an intraperitoneal injection. The effect was estimated two hours after administration. Several synthesized compounds were found to exhibit antinociceptive activity at or above the level of the comparator product – metamizole sodium. Nerve endings can be considered the target of the antinociceptive activity of examined substances since under the effect of these substances, no signs of central action are observed in the behavior of animals. Thus, the conducted studies showed the promise of further search for biologically active substances among the compounds of this series.

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