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Journal articles on the topic 'Pyrrolidine carboxamides'

Author: Grafiati

Published: 4 June 2021

Last updated: 17 February 2022

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1

Slobodyanyuk, Evgeniy Y., Oleksiy S. Artamonov, Irene B. Kulik, Eduard Rusanov, Dmitriy M. Volochnyuk, and Oleksandr O. Grygorenko. "A bio-inspired approach to proline-derived 2,4-disubstituted oxazoles." Heterocyclic Communications 24, no. 1 (February 23, 2018): 11–17. http://dx.doi.org/10.1515/hc-2017-0235.

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Abstract A convenient four-step approach to the synthesis of (S)-4-alkyl-2-(pyrrolidin-2-yl)oxazoles starting from l-Boc-proline inspired by naturally occurring oxazole-containing peptidomimetics is described. The key step is the cyclization of 1-Boc-N-(1-oxoalkan-2-yl)pyrrolidine-2-carboxamides – aldehyde intermediates which demonstrate low to moderate stability – under Appel reaction conditions. This method furnishes the target compounds with more than 98% ee and in a 17–51% overall yield and has been used at up to a 45-g scale.

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2

Young, Jonathan R., Ronsar Eid, Cherilyn Turner, Robert J. DeVita, Marc M. Kurtz, Kwei-Lan C. Tsao, Gary G. Chicchi, Alan Wheeldon, Emma Carlson, and Sander G. Mills. "Pyrrolidine-carboxamides and oxadiazoles as potent hNK1 antagonists." Bioorganic & Medicinal Chemistry Letters 17, no. 19 (October 2007): 5310–15. http://dx.doi.org/10.1016/j.bmcl.2007.08.028.

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3

Smolobochkin, Andrey, Almir Gazizov, Marina Sazykina, Nurgali Akylbekov, Elena Chugunova, Ivan Sazykin, Anastasiya Gildebrant, et al. "Synthesis of Novel 2-(Het)arylpyrrolidine Derivatives and Evaluation of Their Anticancer and Anti-Biofilm Activity." Molecules 24, no. 17 (August 25, 2019): 3086. http://dx.doi.org/10.3390/molecules24173086.

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A library of novel 2-(het)arylpyrrolidine-1-carboxamides were obtained via a modular approach based on the intramolecular cyclization/Mannich-type reaction of N-(4,4-diethoxybutyl)ureas. Their anti-cancer activities both in vitro and in vivo were tested. The in vitro activity of some compounds towards M-Hela tumor cell lines was twice that of the reference drug tamoxifen, whereas cytotoxicity towards normal Chang liver cell did not exceed the tamoxifen toxicity. In vivo studies showed that the number of surviving animals on day 60 of observation was up to 83% and increased life span (ILS) was up to 447%. Additionally, some pyrrolidine-1-carboxamides possessing a benzofuroxan moiety obtained were found to effectively suppress bacterial biofilm growth. Thus, these compounds are promising candidates for further development both as anti-cancer and anti-bacterial agents.

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4

Valenta, Vladimír, Karel Dobrovský, Ivan Krejčí, and Zdeněk Polívka. "Potential Antagonists of Excitatory Amino Acids and Anticonvulsants: Some Heterocyclic (±)-Pyrrolidine-2-carboxamides." Collection of Czechoslovak Chemical Communications 61, no. 7 (1996): 1077–84. http://dx.doi.org/10.1135/cccc19961077.

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The benzylpyrrolidine amides 1a-1d, 3a-3e, 5a, and 5b were prepared from N-benzyl-L-proline methyl ester with corresponding diamines. Compounds 2a-2d, 4b, and 4e have similarly been synthesized from L-proline methyl ester and the corresponding diamines in refluxing methanol. In both cases, the reactions were accompanied by racemization. Prepared amides were transformed to salts, suitable for pharmacological testing (hydrogen maleates, hydrogen oxalates and hydrochlorides). The products were tested by selected methods of biochemical and behavioural pharmacology.

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5

Sonia, George, and Thengungal Kochupappy Ravi. "Oxadiazolo pyrrolidine carboxamides as enoyl-ACP reductase inhibitors: design, synthesis and antitubercular activity screening." Medicinal Chemistry Research 22, no. 7 (November 23, 2012): 3428–33. http://dx.doi.org/10.1007/s00044-012-0340-3.

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6

VALENTA, V., K. DOBROVSKY, I. KREJCI, and Z. POLIVKA. "ChemInform Abstract: Potential Antagonists of Excitatory Amino Acids and Anticonvulsants: Some Heterocyclic (.+-.)-Pyrrolidine-2-carboxamides." ChemInform 27, no. 46 (August 4, 2010): no. http://dx.doi.org/10.1002/chin.199646215.

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7

Hari, Swetha, Toreshettahally R. Swaroop, Habbanakuppe D. Preetham, Chakrabhavi D. Mohan, Umashakara Muddegowda, Salundi Basappa, Israel Vlodavsky, Gautam Sethi, and Kanchugarakoppal S. Rangappa. "Synthesis, Cytotoxic and Heparanase Inhibition Studies of 5-oxo-1-arylpyrrolidine-3- carboxamides of Hydrazides and 4-amino-5-aryl-4H-1,2,4-triazole-3-thiol." Current Organic Synthesis 17, no. 3 (June 9, 2020): 243–50. http://dx.doi.org/10.2174/1570179417666200225123329.

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Design of chemically novel, biologically potent small heterocyclic molecules with anticancer activities, which targets the enzyme heparanase has gained prominent clinical interest. We have synthesized a novel class of carboxamide derivatives by coupling various substituted aromatic acid hydrazides and triazoleamine with pyrrolidine carboxylic acid by using coupling agents. The synthesized compounds are characterized by spectroscopic techniques such as FT-IR, HRMS and NMR. These compounds are investigated for cytotoxicity on different cancer cell lines and heparanase inhibitory activity. Most of them showed moderate heparanase inhibitory activity and good cytotoxicity.

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8

He, Xin, Akram Alian, Robert Stroud, and Paul R. Ortiz de Montellano. "Pyrrolidine Carboxamides as a Novel Class of Inhibitors of Enoyl Acyl Carrier Protein Reductase fromMycobacterium tuberculosis." Journal of Medicinal Chemistry 49, no. 21 (October 2006): 6308–23. http://dx.doi.org/10.1021/jm060715y.

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9

Gazizov, А. S., А. V. Smolobochkin, J. K. Voronina, А. R. Burilov, and М. А. Pudovik. "Acid-catalyzed ring opening in 2-(2-hydroxynaphthalene-1-yl)-pyrrolidine-1-carboxamides: formation of dibenzoxanthenes, diarylmethanes, and calixarenes." Tetrahedron 71, no. 3 (January 2015): 445–50. http://dx.doi.org/10.1016/j.tet.2014.12.011.

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10

Smolobochkin, A. V., R. A. Turmanov, A. S. Gazizov, N. O. Appazov, A. R. Burilov, and M. A. Pudovik. "Synthesis of 2-(Diphenylphosphoryl)pyrrolidine-1-carboxamides Based on the Reaction of 1-(4,4-Diethoxybutyl)ureas with Diphenyl Chlorophosphine." Russian Journal of General Chemistry 89, no. 10 (October 2019): 2143–46. http://dx.doi.org/10.1134/s1070363219100244.

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11

Yu, Shuling, Jintao Yuan, Jiahua Shi, Xiaojiao Ruan, Ting Zhang, Yanli Wang, and Yu Du. "HQSAR and topomer CoMFA for predicting melanocortin-4 receptor binding affinities of trans-4-(4-chlorophenyl) pyrrolidine-3-carboxamides." Chemometrics and Intelligent Laboratory Systems 146 (August 2015): 34–41. http://dx.doi.org/10.1016/j.chemolab.2015.04.017.

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12

Kumar, Ashutosh, and Mohammad Imran Siddiqi. "CoMFA based de novo design of Pyrrolidine Carboxamides as Inhibitors of Enoyl Acyl Carrier Protein Reductase from Mycobacterium tuberculosis." Journal of Molecular Modeling 14, no. 10 (July 15, 2008): 923–35. http://dx.doi.org/10.1007/s00894-008-0326-8.

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13

Chen, Caroline W., Joe A. Tran, Beth A. Fleck, Fabio C. Tucci, Wanlong Jiang, and Chen Chen. "Synthesis and characterization of trans-4-(4-chlorophenyl)pyrrolidine-3-carboxamides of piperazinecyclohexanes as ligands for the melanocortin-4 receptor." Bioorganic & Medicinal Chemistry Letters 17, no. 24 (December 2007): 6825–31. http://dx.doi.org/10.1016/j.bmcl.2007.10.032.

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14

Kolbe, Adelheid, Robert Kramell, Andrea Porzel, Jürgen Schmidt, Gernot Schneider, and Günter Adam. "Syntheses of Dexamethasone Conjugates of the Phytohormones Gibberellin A3 and 24-Epicastasterone." Collection of Czechoslovak Chemical Communications 67, no. 1 (2002): 103–14. http://dx.doi.org/10.1135/cccc20020103.

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The syntheses of N-[10-(9α-fluoro-11β,17α-dihydroxy-16α-methyl-3-oxoandrosta-1,4-diene-17β-carboxamido)decyl]gibberellamide (7) and 6-[({N-[10-(9α-fluoro-11β,17α-dihydroxy- 16α-methyl-3-oxoandrosta-1,4-diene-17β-carboxamido)decyl]carbamoyl}methoxy)imino]-24-epicastasterone (10) are described. [(Benzotriazol-1-yl)oxy]bis(pyrrolidin-1-yl)methylium hexafluorophosphate (HBPyU) was used as the coupling agent for the reaction of gibberellic acid as well as of 24-epicastasterone-O-(carboxymethyl)oxime with N-(10-aminodecyl)- 9α-fluoro-11β,17α-dihydroxy-16α-methyl-3-oxoandrosta-1,4-diene-17β-carboxamide (4). The gibberellic acid conjugate 7 was also synthesised by the coupling of succinimidyl gibberellate 6 with amine 4.

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15

Odusami, Jocelyn A., Monisola I. Ikhile, Josephat U. Izunobi, Idris A. Olasupo, Foluso O. Osunsanmi, Andrew R. Opoku, Marthe C. D. Fotsing, Olayinka T. Asekun, Oluwole B. Familoni, and Derek T. Ndinteh. "Synthesis of substituted N-(2′-nitrophenyl)pyrrolidine-2-carboxamides towards the design of proline-rich antimicrobial peptide mimics to eliminate bacterial resistance to antibiotics." Bioorganic Chemistry 105 (December 2020): 104340. http://dx.doi.org/10.1016/j.bioorg.2020.104340.

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16

Ovonramwen, Oluwaseyi B., Bodunde J. Owolabi, and Abiodun Falodun. "Synthesis and Antimicrobial Activities of 1-((5-Chloro-1-ethyl-2-methyl-1H-imidazol-4-yl)sulfonyl)-N-ethylpyrrolidine-2-carboxamide." Tanzania Journal of Science 47, no. 3 (August 31, 2021): 1296–302. http://dx.doi.org/10.4314/tjs.v47i3.36.

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A new 1-((5-chloro-1-ethyl-2-methyl-1H-imidazol-4-yl)sulfonyl)-N-ethylpyrrolidine-2-carboxamide was synthesized from methyl-1-[(5-chloro-1-ethyl-2-methyl-1H-imidazol-4-yl)sulfonyl]pyrrolidine-2-carboxylate and ethylamine. The compound methyl-1-[(5-chloro-1-ethyl-2-methyl-1H-imidazol-4-yl)sulfonyl]pyrrolidine-2-carboxylate was synthesized from methyl pyrrolidine-2-carboxylate and 5-chloro-4-chlorosulfonyl-1-ethyl-2-methyl-imidazole. The compounds were characterized based on FTIR, 1H, 13C NMR, and DEPT 135 analysis. Antimicrobial activities of the 1-((5-chloro-1-ethyl-2-methyl-1H-imidazol-4-yl)sulfonyl)-N-ethylpyrrolidine-2-carboxamide against Gram-positive (methicillin-susceptible Staphylococcus aureus, methicillin-resistant Staphylococcus aureus, and Bacillus subtilis), Gram-negative (Pseudomonas aeruginosa, Escherichia coli, Klebsiella pneumoniae), and Candida albicans were carried out using the standard microbiological method. The newly synthesized 1-((5-chloro-1-ethyl-2-methyl-1H-imidazol-4-yl)sulfonyl)-N-ethylpyrrolidine-2-carboxamide had no activities against the tested organisms. Keywords: 1-((5-chloro-1-ethyl-2-methyl-1H-imidazol-4-yl)sulfonyl)-N-ethylpyrrolidine-2-carboxamide; methyl-1-[(5-chloro-1-ethyl-2-methyl-1H-imidazol-4-yl)sulfonyl]pyrrolidine-2-carboxylate; L-proline; ethylamine.

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17

Habibi, Azizollah, Leyla Mousavifar, Mohammad R. Yazdanbakhsh, and Issa Yavari. "Synthesis of 1‐(2,6‐Dimethylphenyl)‐N‐hydroxy‐4,4‐dialkyl‐2,5‐dioxo‐N‐aryl‐3‐pyrrolidine‐carboxamides from Reaction of 2,6‐Dimethylphenyl Isocyanide, Alkylidene Meldrum's Acids, and Arylhydroxylamines." Synthetic Communications 38, no. 6 (February 1, 2008): 873–80. http://dx.doi.org/10.1080/00397910701845365.

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18

Gomes, Ligia R., John Nicolson Low, Fernando Cagide, Alexandra Gaspar, and Fernanda Borges. "A comparison of the structures of some 2- and 3-substituted chromone derivatives: a structural study on the importance of the secondary carboxamide backbone for the inhibitory activity of MAO-B." Acta Crystallographica Section E Crystallographic Communications 71, no. 11 (October 3, 2015): 1270–77. http://dx.doi.org/10.1107/s2056989015017958.

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The crystal structures of the 3-substituted tertiary chromone carboxamide derivative, C17H13NO3,N-methyl-4-oxo-N-phenyl-4H-chromene-3-carboxamide (1), and the chromone carbonyl pyrrolidine derivatives, C14H13NO3, 3-(pyrrolidine-1-carbonyl)-4H-chromen-4-one (3) and 2-(pyrrolidine-1-carbonyl)-4H-chromen-4-one (4) have been determined. Their structural features are discussed and compared with similar compounds namely with respect to their MAO-B inhibitory activities. The chromone carboxamide presents a –synconformation with the aromatic rings twisted with respect to each other [the dihedral angle between the mean planes of the chromone system and the exocyclic phenyl ring is 58.48 (8)°]. The pyrrolidine derivatives also display a significant twist: the dihedral angles between the chromone system and the best plane formed by the pyrrolidine atoms are 48.9 (2) and 23.97 (12)° in (3) and (4), respectively. Compound (3) shows a short C—H...O intramolecular contact forming anS(7) ring. The supramolecular structures for each compound are defined by weak C—H...O hydrogen bonds, which link the molecules into chains and sheets. The Cambridge Structural Database gave 45 hits for compounds with a pyrrolidinecarbonyl group. A simple statistical analysis of their geometric parameters is made in order to compare them with those of the molecules determined in the present work.

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19

Pei, Shuchen, Jie Li, Boyi Qu, Li Hai, and Yong Wu. "N-(2,3,4-Trifluorophenyl)pyrrolidine-1-carboxamide." Acta Crystallographica Section E Structure Reports Online 68, no. 1 (December 3, 2011): o12. http://dx.doi.org/10.1107/s1600536811051385.

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20

Liu, Wei, Yan-Ling Guo, Cong Han, and Shao-Ling Cheng. "1-(4-Nitrophenyl)pyrrolidine-2-carboxamide." Acta Crystallographica Section E Structure Reports Online 63, no. 5 (April 30, 2007): o2778—o2779. http://dx.doi.org/10.1107/s1600536807020120.

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21

Li, Yu-Feng. "N-(4-Chlorophenyl)pyrrolidine-1-carboxamide." Acta Crystallographica Section E Structure Reports Online 67, no. 7 (June 25, 2011): o1792. http://dx.doi.org/10.1107/s1600536811024111.

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22

Kamal, Ahmed, Manda Sathish, Vunnam Srinivasulu, Jadala Chetna, Kunta Chandra Shekar, Shalini Nekkanti, Yellaiah Tangella, and Nagula Shankaraiah. "Asymmetric Michael addition of ketones to nitroolefins: pyrrolidinyl-oxazole-carboxamides as new efficient organocatalysts." Org. Biomol. Chem. 12, no. 40 (2014): 8008–18. http://dx.doi.org/10.1039/c4ob01223b.

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New pyrrolidinyl-oxazole-carboxamides were synthesized and utilized as efficient organocatalysts for asymmetric Michael addition reaction. In addition, computational mechanistic studies were performed.

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23

Mao, Zhuo-Ya, Xiao-Di Nie, Yi-Man Feng, Chang-Mei Si, Bang-Guo Wei, and Guo-Qiang Lin. "Cu(OTf)2 catalyzed Ugi-type reaction of N,O-acetals with isocyanides for the synthesis of pyrrolidinyl and piperidinyl 2-carboxamides." Chemical Communications 57, no. 73 (2021): 9248–51. http://dx.doi.org/10.1039/d1cc03113a.

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24

Loesche, Anne, Michael Kahnt, Immo Serbian, Wolfgang Brandt, and René Csuk. "Triterpene-Based Carboxamides Act as Good Inhibitors of Butyrylcholinesterase." Molecules 24, no. 5 (March 7, 2019): 948. http://dx.doi.org/10.3390/molecules24050948.

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A set of overall 40 carboxamides was prepared from five different natural occurring triterpenoids including oleanolic, ursolic, maslinic, betulinic, and platanic acid. All of which were derived from ethylene diamine holding an additional substituent connected to the ethylene diamine group. These derivatives were evaluated regarding their inhibitory activity of the enzymes acetylcholinesterase (AChE) and butyrylcholinesterase (BChE) employing Ellman’s assay. We further determined the type of inhibition and inhibition constants. Carboxamides derived from platanic acid have been shown to be potent and selective BChE inhibitors. Especially the mixed-type inhibitor (3β)-N-(2-pyrrolidin-1-ylethyl)-3-acetyloxy-20-oxo-30-norlupan-28-amide (35) showed a remarkably low Ki of 0.07 ± 0.01 µM (Ki′ = 2.38 ± 0.48 µM) for the inhibition of BChE.

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25

Burdzhiev, Nikola T., and Elena R. Stanoeva. "Synthesis of New Polysubstituted Pyrrolidinones with Potential Biological Activity." Zeitschrift für Naturforschung B 63, no. 3 (March 1, 2008): 313–20. http://dx.doi.org/10.1515/znb-2008-0315.

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The reaction of succinic anhydride and N-benzylidene-benzylamine gave rise to the corresponding substituted trans-5-oxopyrrolidine-3-carboxylic acid, which was transformed stereoselectively into two series of compounds. The first one consists of carboxamides, and the second one includes aminomethyl derivatives. The compounds prepared incorporate both a pyrrolidinone part and other nitrogen containing heterocyclic fragments of pharmacological interest.

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26

Han, Xiao-Dan, Chuan-Qing Ren, Jian-Ping Fu, Wei Xiong, Hui-Bin Wang, Xiao-Na Dong, Jian-Wei Ji, and Ju-Wu Hu. "An Intramolecular Cycloaddition Approach to Construct Polysubstituted Pyrrolidones from Alkynyl Carboxamides and PTSA." Synthesis 49, no. 20 (July 25, 2017): 4703–10. http://dx.doi.org/10.1055/s-0036-1588500.

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An efficient synthetic route to highly substituted pyrrolidone derivatives has been developed from an easily available alkynyl carboxamide and 4-methylbenzenesulfonic acid (PTSA). In the reaction, PTSA is not only used as acid catalyst but also as a reactant to provide a source for OTs group. A mechanism is proposed to involve the protonation of the alcohol substrate/cyclopropylcarbinol-homoallylic rearrangement/intramolecular N-nucleophilic cyclization reactions.

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27

Jang, Miyoung, Youri Oh, Hyunwook Cho, Songyi Yang, Hyungwoo Moon, Daseul Im, and Jung-Mi Hah. "Discovery of 1-Pyrimidinyl-2-Aryl-4,6-Dihydropyrrolo [3,4-d]Imidazole-5(1H)-Carboxamide as a Novel JNK Inhibitor." International Journal of Molecular Sciences 21, no. 5 (March 2, 2020): 1698. http://dx.doi.org/10.3390/ijms21051698.

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We designed and synthesized 1-pyrimidinyl-2-aryl-4, 6-dihydropyrrolo [3,4-d] imidazole-5(1H)-carboxamide derivatives as selective inhibitors of c-Jun-N-terminal Kinase 3 (JNK3), a target for the treatment of neurodegenerative diseases. Based on the compounds found in previous studies, a novel scaffold was designed to improve pharmacokinetic characters and activity, and compound 18a, (R)-1-(2-((1-(cyclopropanecarbonyl)pyrrolidin-3-yl)amino)pyrimidin-4-yl)-2-(3,4-dichlorophenyl)-4,6-dihydro pyrrolo [3,4-d]imidazole-5(1H)-carboxamide, showed the highest IC50 value of 2.69 nM. Kinase profiling results also showed high selectivity for JNK3 among 38 kinases, having mild activity against JNK2, RIPK3, and GSK3β, which also known to involve in neuronal apoptosis.

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28

Zheng, Ji-Fu, Suo-Qin Zhang, Li Wang, Song-Tao Yang, and Yao-Xian Li. "(S)-N-(1H-Tetrazol-5-ylmethyl)pyrrolidine-2-carboxamide dihydrate." Acta Crystallographica Section E Structure Reports Online 62, no. 12 (November 30, 2006): o5927—o5928. http://dx.doi.org/10.1107/s1600536806050380.

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29

Cheng, Hengmiao, Jacqui Hoffman, Phuong Le, Sajiv K. Nair, Stephan Cripps, Jean Matthews, Christopher Smith, et al. "The development and SAR of pyrrolidine carboxamide 11β-HSD1 inhibitors." Bioorganic & Medicinal Chemistry Letters 20, no. 9 (May 2010): 2897–902. http://dx.doi.org/10.1016/j.bmcl.2010.03.032.

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30

Keskin, Elif, Cigdem Yolacan, and Feray Aydogan. "Synthesis of New Di- and Triamides as Potential Organocatalysts for Asymmetric Aldol Reaction in Water." Acta Chimica Slovenica 67, no. 4 (December 15, 2020): 1014–23. http://dx.doi.org/10.17344/acsi.2018.4748.

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New di- or triamide organocatalysts derived from (L)-proline were synthesized and successfully used in the direct asymmetric aldol reaction of aliphatic ketones and aromatic aldehydes in water at 0 °C in the presence of benzoic acid as co-catalyst. (S)-methyl-2-((S)-3-hydroxy-2-((S)-3-pyrrolidine-2-carboxamido)propanamido)-3-phenylpropanoate (7c) as organocatalyst showed best results under these reaction conditions, and good diastereoselectivities (up to 99%), enantioselectivities (up to 98%) and yields (up to 91%) were observed.

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31

Gelbrich, Thomas, Volker Kahlenberg, Christoph Langes, and Ulrich J. Griesser. "Telaprevir: helical chains based on three-point hydrogen-bond connections." Acta Crystallographica Section C Crystal Structure Communications 69, no. 2 (January 16, 2013): 179–82. http://dx.doi.org/10.1107/s0108270113000954.

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The crystal structure of the title compound [systematic name: (1S,3aR,6aS)-2-((2S)-2-{[(2S)-2-cyclohexyl-2-(pyrazine-2-carbonylamino)acetyl]amino}-3,3-dimethylbutanoyl)-N-[(3S)-1-(cyclopropylamino)-1,2-dioxohexan-3-yl]-3,3a,4,5,6,6a-hexahydro-1H-cyclopenta[c]pyrrole-1-carboxamide], C36H53N7O6, contains two independent molecules, which possess distinct conformations and a disordered cyclopenta[c]pyrrolidine unit. In the crystal, molecules are linked into helical chainsviathree-point N—H...O hydrogen-bond connections in which three NH and three carbonyl groups per molecule are utilized. The chiralities of the six stereocentres per molecule inferred from this study are in agreement with the synthetic procedure.

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32

Chen, Gang, Ying Tang, Qun-Zheng Zhang, Mei Meng, and Xiao-Jiang Hao. "Crystal and Molecular Structure of (S)-N-(2-Hydroxyphenyl)pyrrolidine-2-carboxamide." Journal of Chemical Crystallography 41, no. 2 (December 25, 2010): 251–54. http://dx.doi.org/10.1007/s10870-010-9935-z.

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33

Görbitz, Carl Henrik, and Vitthal N. Yadav. "A water wire inL-prolyl-L-serine monohydrate." Acta Crystallographica Section C Crystal Structure Communications 69, no. 5 (April 18, 2013): 556–59. http://dx.doi.org/10.1107/s0108270113010299.

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Despite the extra functional group in the serine side chain, the crystal packing arrangement of the title compound {systematic name: (S)-3-hydroxy-2-[(S)-pyrrolidine-2-carboxamido]propanoic acid monohydrate}, C8H14N2O4·H2O, is essentially the same as observed for a series of L-Pro-L-Nop peptide hydrates, where Nop is a strictly nonpolar residue. This is rendered possible by a monoclinicP21packing arrangement withZ′ = 2 that deviates from orthorhombicP212121symmetry only for the seryl hydroxy groups, which form infinite O—H...O—H hydrogen-bonded chains along the 5.3 Åaaxis. At the same time, cocrystallized water molecules form parallel water wires.

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34

Tumosienė, Ingrida, Kristina Kantminienė, Ilona Jonuškienė, Artūras Peleckis, Sergey Belyakov, and Vytautas Mickevičius. "Synthesis of 1-(5-Chloro-2-hydroxyphenyl)-5-oxopyrrolidine-3-carboxylic Acid Derivatives and Their Antioxidant Activity." Molecules 24, no. 5 (March 9, 2019): 971. http://dx.doi.org/10.3390/molecules24050971.

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A series of novel 1-(5-chloro-2-hydroxyphenyl)-5-oxopyrrolidine-3-carboxylic acid derivatives containing chloro, hydroxyl, isopropyl, nitro, nitroso, and amino substituents at benzene ring and 1-(5-chloro-2-hydroxyphenyl)-5-oxopyrrolidine-3-carbohydrazide derivatives bearing heterocyclic moieties were synthesized. Antioxidant activity of the synthesized compounds was screened by DPPH radical scavenging method and reducing power assay. A number of compounds were identified as potent antioxidants. Antioxidant activity of 1-(5-chloro-2-hydroxyphenyl)-4-(5-thioxo-4,5-dihydro-1,3,4-oxadiazol-2-yl)pyrrolidin-2-one has been tested to be 1.5 times higher than that of a well-known antioxidant ascorbic acid. 1-(5-Chloro-2-hydroxyphenyl)-4-(4-methyl-5-thioxo-4,5-dihydro-1H-1,2,4-triazol-3-yl)pyrrolidin-2-one has shown 1.35 times higher antioxidant activity than that of vitamin C by DPPH radical scavenging method and optical density value of 1.149 in reducing power assay. The structure of 1-(5-chloro-2-hydroxyphenyl)-N-(1,3-dioxoisoindolin-2-yl)-5-oxopyrrolidine-3-carboxamide was unambiguously assigned by means of X-ray diffraction analysis data.

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35

Darehkordi, Ali, and Mahin Ramezani. "One-pot synthesis of novel (2R,4S)-N-aryl-4-hydroxy-1-(2,2,2-trifluoroacetyl) pyrrolidine-2-carboxamides via $$\hbox {TiO}_{2}$$ TiO 2 -NPs and $$\hbox {Pd}(\hbox {PPh}_{3})_{2}\hbox {Cl}_{2}$$ Pd ( PPh 3 ) 2 Cl 2 catalysts and investigation of their biological activities." Molecular Diversity 21, no. 2 (February 11, 2017): 305–15. http://dx.doi.org/10.1007/s11030-017-9726-y.

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36

Banerjee, S., A. K. Mukherjee, D. Goswami, A. U. De, and M. Helliwell. "Structure and Conformation of Solvated 1-(4-methoxybenzenesulfonyl)-5-oxo-pyrrolidine-2-carboxamide." Crystal Research and Technology 37, no. 2-3 (February 2002): 309–17. http://dx.doi.org/10.1002/1521-4079(200202)37:2/3<309::aid-crat309>3.0.co;2-9.

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37

Narkhede, Yogesh, Benjamin Merget, Steffen Wagner, and Christoph Sotriffer. "Activity-based classification circumvents affinity prediction problems for pyrrolidine carboxamide inhibitors of InhA." Journal of Molecular Graphics and Modelling 80 (March 2018): 76–84. http://dx.doi.org/10.1016/j.jmgm.2017.12.012.

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38

Li, Xinyong, Jiarong Chen, Xianggao Meng, and Wenjing Xiao. "(1R,2R,2′S)-2-(4-Methylphenylsulfonamido)-1-(pyrrolidine-2′-carboxamido)cyclohexane." Acta Crystallographica Section E Structure Reports Online 61, no. 8 (July 30, 2005): o2730—o2732. http://dx.doi.org/10.1107/s1600536805023718.

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39

Zhong, Desong, Pravin Kotian, Christopher D. Wyrick, Herbert H. Seltzman, John A. Kepler, Michael J. Kuhar, John W. Boja, and F. Ivy Carroll. "Synthesis of 3β-(4-[125I]iodophenyl)tropane-2-β-pyrrolidine carboxamide ([125I]RTI-229)." Journal of Labelled Compounds and Radiopharmaceuticals 42, no. 3 (March 1999): 281–86. http://dx.doi.org/10.1002/(sici)1099-1344(199903)42:3<281::aid-jlcr188>3.0.co;2-x.

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40

TAHARA, Tetsuya, Kiyoharu HAYANO, Shu MURAKAMI, Takemi FUKUDA, Michihide SETOGUCHI, Kuniki IKEDA, and Nobuhiro MARUBAYASHI. "Potential neuroleptic agents, N-((2-pyrrolidinyl)methyl)-2,3-dihydrobenzofuran-7-carboxamide derivatives." CHEMICAL & PHARMACEUTICAL BULLETIN 38, no. 6 (1990): 1609–15. http://dx.doi.org/10.1248/cpb.38.1609.

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41

Li, Xiang. "4-[2-(3-Ethyl-4-methyl-2-oxo-3-pyrrolidine-1-carboxamido)ethyl]benzenesulfonamide." Acta Crystallographica Section E Structure Reports Online 62, no. 7 (June 28, 2006): o3019—o3020. http://dx.doi.org/10.1107/s1600536806021660.

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In the title molecular structure, C16H21N3O4S, the dihedral angle between the essentially planar 2,5-dihydro-1H-pyrrole and benzene rings is 20.8 (2)°. In the crystal structure, molecules are linked by N—H...O hydrogen bonds [H...O = 2.07 (3)–2.57 (3) Å] to form a two-dimensional network.

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42

Habibi, Azizollah, and Leyla Mousavifar. "Structure of 1-(2,6-dimethylphenyl)-N-hydroxy-4,4-dimethyl-2,5-dioxo-N-phenyl-3-pyrrolidine carboxamide." Crystallography Reports 55, no. 7 (November 30, 2010): 1214–16. http://dx.doi.org/10.1134/s1063774510070205.

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43

Fujio, Masakazu, Yoshifumi Togo, Hideo Tomozane, Takanobu Kuroita, Yasunori Morio, Jiro Katayama, and Yasuhiro Matsumoto. "N-{[1-(2-Phenylethyl)pyrrolidin-2-yl]methyl}cyclohexane-carboxamides as selective 5-HT1A receptor agonists." Bioorganic & Medicinal Chemistry Letters 10, no. 5 (March 2000): 509–12. http://dx.doi.org/10.1016/s0960-894x(00)00030-5.

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44

Omar, Hany A., Dana M. Zaher, Vunnam Srinivasulu, Fatema Hersi, Hamadeh Tarazi, and Taleb H. Al-Tel. "Design, synthesis and biological evaluation of new pyrrolidine carboxamide analogues as potential chemotherapeutic agents for hepatocellular carcinoma." European Journal of Medicinal Chemistry 139 (October 2017): 804–14. http://dx.doi.org/10.1016/j.ejmech.2017.08.054.

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45

Ueda, I., N. Marubayashi, S. Hayano, S. Murakami, and T. Tahara. "N-[(1-Butyl-2-pyrrolidinyl)methyl]-2-methyl-5-sulfamoyl-2,3-dihydrobenzofuran-7-carboxamide." Acta Crystallographica Section C Crystal Structure Communications 47, no. 8 (August 15, 1991): 1697–700. http://dx.doi.org/10.1107/s0108270190014123.

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46

Kamal, Ahmed, Manda Sathish, Vunnam Srinivasulu, Jadala Chetna, Kunta Chandra Shekar, Shalini Nekkanti, Yellaiah Tangella, and Nagula Shankaraiah. "ChemInform Abstract: Asymmetric Michael Addition of Ketones to Nitroolefins: Pyrrolidinyl-oxazole-carboxamides as New Efficient Organocatalysts." ChemInform 46, no. 12 (March 2015): no. http://dx.doi.org/10.1002/chin.201512034.

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47

Maxson, Tucker, Jeffery A. Bertke, Danielle L. Gray, and Douglas A. Mitchell. "Crystal structure and absolute configuration of (3S,4aS,8aS)-N-tert-butyl-2-[(S)-3-(2-chloro-4-nitrobenzamido)-2-hydroxypropyl]decahydroisoquinoline-3-carboxamide and (3S,4aS,8aS)-N-tert-butyl-2-{(S)-2-[(S)-1-(2-chloro-4-nitrobenzoyl)pyrrolidin-2-yl]-2-hydroxyethyl}decahydroisoquinoline-3-carboxamide." Acta Crystallographica Section E Crystallographic Communications 71, no. 11 (October 31, 2015): 1401–7. http://dx.doi.org/10.1107/s2056989015020046.

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The crystal structure and absolute configuration of the two new title nelfinavir analogs, C24H35ClN4O5, (I), and C27H39ClN4O5, (II), have been determined. Each of these molecules exhibits a number of disordered moieties. There are intramolecular N—H...O hydrogen bonds in both (I) and (II). In (I) it involves the two carboxamide groups, while in (II) it involves theN-tert-butyl carboxamide group and the 2-hydroxyl O atom. The intermolecular hydrogen bonding in (I) (O—H...O and N—H...O) leads to two-dimensional sheets that extend parallel to theacplane. The intermolecular hydrogen bonding in (II) (O—H...O) leads to chains that extend parallel to theaaxis.

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48

Wakenhut, Florian, Paul V. Fish, M. Jonathan Fray, Ian Gurrell, James E. Mills, Alan Stobie, and Gavin A. Whitlock. "N-Benzyl-N-(pyrrolidin-3-yl)carboxamides as a new class of selective dual serotonin/noradrenaline reuptake inhibitors." Bioorganic & Medicinal Chemistry Letters 18, no. 15 (August 2008): 4308–11. http://dx.doi.org/10.1016/j.bmcl.2008.06.078.

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Senwar, Kishna Ram, Pankaj Sharma, Shalini Nekkanti, Manda Sathish, Ahmed Kamal, B. Sridhar, and Nagula Shankaraiah. "A one-pot ‘click’ reaction from spiro-epoxides catalyzed by Cu(i)-pyrrolidinyl-oxazole-carboxamide." New Journal of Chemistry 39, no. 5 (2015): 3973–81. http://dx.doi.org/10.1039/c4nj02131b.

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Catalano, Alessia, Alessia Carocci, Antonia Di Mola, Claudio Bruno, Patrick M. L. Vanderheyden, and Carlo Franchini. "1-Pentanoyl-N-{[2'-(1H-tetrazol-5-yl)biphenyl-4-yl]methyl}-pyrrolidine-2-carboxamide: Investigation of Structural Variations." Archiv der Pharmazie 344, no. 9 (June 28, 2011): 617–26. http://dx.doi.org/10.1002/ardp.201000296.

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