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Design, Synthesis, and Fungicidal Activity of Novel Thiosemicarbazide Derivatives Containing Piperidine Fragments

Xuebo Zhang, Peng Lei, Tengda Sun, Xiaoyu Jin, Xinling Yang, Yun Ling

Molecules. 2017 Dec; 22(12): 2085. Published online 2017 Dec 11. doi: 10.3390/molecules22122085

PMCID:: PMC6149837

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Synthesis of Aminoethyl‐Substituted Piperidine Derivatives as σ₁ Receptor Ligands with Antiproliferative Properties

Dr. Catharina Holtschulte, Dr. Frederik Börgel, Stefanie Westphälinger, Dr. Dirk Schepmann, Dr. Gianluca Civenni, Prof. Dr. Erik Laurini, Domenico Marson, Prof. Dr. Carlo V. Catapano, Prof. Dr. Sabrina Pricl, Prof. Dr. Bernhard Wünsch

ChemMedChem. 2022 Apr 5; 17(7): e202100735. Published online 2022 Feb 9. doi: 10.1002/cmdc.202100735

PMCID:: PMC9303367

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Development of coumarine derivatives as potent anti-filovirus entry inhibitors targeting viral glycoprotein

Yinyi Gao, Han Cheng, Sameer Khan, Gaokeng Xiao, Lijun Rong, Chuan Bai

Eur J Med Chem. Author manuscript; available in PMC 2021 Oct 15.

Published in final edited form as: Eur J Med Chem. 2020 Oct 15; 204: 112595. Published online 2020 Jul 12. doi: 10.1016/j.ejmech.2020.112595

PMCID:: PMC7529935

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Synthesis and Antimalarial Activity of 1,4-Disubstituted Piperidine Derivatives

Rokhyatou Seck, Abdoulaye Gassama, Sandrine Cojean, Christian Cavé

Molecules. 2020 Jan; 25(2): 299. Published online 2020 Jan 11. doi: 10.3390/molecules25020299

PMCID:: PMC7024169

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Discovery of Spiro-Piperidine Inhibitors and Their Modulation of the Dynamics of the M2 Proton Channel from Influenza A Virus

Jun Wang, Sarah D. Cady, Victoria Balannik, Lawrence H. Pinto, William F. DeGrado, Mei Hong

J Am Chem Soc. Author manuscript; available in PMC 2013 Oct 25.

Published in final edited form as: J Am Chem Soc. 2009 Jun 17; 131(23): 10.1021/ja900063s. doi: 10.1021/ja900063s

PMCID:: PMC3807247

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Piperidine scaffold as the novel P2-ligands in cyclopropyl-containing HIV-1 protease inhibitors: Structure-based design, synthesis, biological evaluation and docking study

Huiyu Zhou, Mei Zhu, Ling Ma, Jinming Zhou, Biao Dong, Guoning Zhang, Shan Cen, Yucheng Wang, Juxian Wang

PLoS One. 2020; 15(7): e0235483. Published online 2020 Jul 22. doi: 10.1371/journal.pone.0235483

PMCID:: PMC7375528

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Spirocyclic Nitroxides as Versatile Tools in Modern Natural Sciences: From Synthesis to Applications. Part I. Old and New Synthetic Approaches to Spirocyclic Nitroxyl Radicals

Elena V. Zaytseva, Dmitrii G. Mazhukin

Molecules. 2021 Feb; 26(3): 677. Published online 2021 Jan 28. doi: 10.3390/molecules26030677

PMCID:: PMC7865516

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Discovery and SAR study of piperidine-based derivatives as novel influenza virus inhibitors

Guoxin Wang, Longjian Chen, Tongmei Xian, Yujie Liang, Xintao Zhang, Zhen Yang, Ming Luo

Org Biomol Chem. Author manuscript; available in PMC 2015 Oct 28.

Published in final edited form as: Org Biomol Chem. 2014 Oct 28; 12(40): 8048–8060. doi: 10.1039/c4ob01079e

PMCID:: PMC4177008

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Synthesis, Antimicrobial, and Anti-Proliferative Activities of Novel 4-(Adamantan-1-yl)-1-arylidene-3-thiosemicarbazides, 4-Arylmethyl N′-(Adamantan-1-yl)piperidine-1-carbothioimidates, and Related Derivatives

Aamal A. Al-Mutairi, Monirah A. Al-Alshaikh, Fatmah A. M. Al-Omary, Hanan M. Hassan, Areej M. El-Mahdy, Ali A. El-Emam

Molecules. 2019 Dec; 24(23): 4308. Published online 2019 Nov 26. doi: 10.3390/molecules24234308

PMCID:: PMC6930481

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Bisubstrate inhibitors of 6-hydroxymethyl-7,8-dihydropterin pyrophosphokinase: Transition state analogs for high affinity binding

Genbin Shi, Gary X. Shaw, Fengxia Zhu, Sergey G. Tarasov, Xinhua Ji

Bioorg Med Chem. Author manuscript; available in PMC 2022 Jan 1.

Published in final edited form as: Bioorg Med Chem. 2021 Jan 1; 29: 115847. Published online 2020 Nov 9. doi: 10.1016/j.bmc.2020.115847

PMCID:: PMC7855645

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Design, Synthesis, and Preclinical Efficacy of Novel Nonretinoid Antagonists of Retinol-Binding Protein 4 in the Mouse Model of Hepatic Steatosis

Christopher L. Cioffi, Boglarka Racz, Andras Varadi, Emily E. Freeman, Michael P. Conlon, Ping Chen, Lei Zhu, Douglas B. Kitchen, Keith D. Barnes, William H. Martin, Paul G. Pearson, Graham Johnson, William S. Blaner, Konstantin Petrukhin

J Med Chem. Author manuscript; available in PMC 2019 Sep 11.

Published in final edited form as: J Med Chem. 2019 Jun 13; 62(11): 5470–5500. Published online 2019 May 28. doi: 10.1021/acs.jmedchem.9b00352

PMCID:: PMC6737539

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A microiontophoretic study of the actions of the putative sleep factor, piperidine, in the rat brainstem.

R. C. Horton, S. D. Logan, J. H. Wolstencroft

Br J Pharmacol. 1985 May; 85(1): 37–44. doi: 10.1111/j.1476-5381.1985.tb08828.x

PMCID:: PMC1916750

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Structure-guided design of potent and permeable inhibitors of MERS coronavirus 3CL protease that utilize a piperidine moiety as a novel design element

Anushka C. Galasiti Kankanamalage, Yunjeong Kim, Vishnu C. Damalanka, Athri D. Rathnayake, Anthony R. Fehr, Nurjahan Mehzabeen, Kevin P. Battaile, Scott Lovell, Gerald H. Lushington, Stanley Perlman, Kyeong-Ok Chang, William C. Groutas

Eur J Med Chem. 2018 Apr 25; 150: 334–346. Published online 2018 Mar 6. doi: 10.1016/j.ejmech.2018.03.004

PMCID:: PMC5891363

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Synthesis and SAR of Analogues of the M1 allosteric agonist TBPB. Part II. Amides, sulfonamides and ureas: the effect of capping the distal basic piperidine nitrogen

Nicole R. Miller, R. Nathan Daniels, Thomas M. Bridges, Ashley E. Brady, P. Jeffrey Conn, Craig W. Lindsley

Bioorg Med Chem Lett. Author manuscript; available in PMC 2011 Sep 21.

Published in final edited form as: Bioorg Med Chem Lett. 2008 Oct 15; 18(20): 5443–5447. Published online 2008 Sep 11. doi: 10.1016/j.bmcl.2008.09.032

PMCID:: PMC3177607

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Syntheses and Reactions of Pyrroline, Piperidine Nitroxide Phosphonates

Mostafa Isbera, Balázs Bognár, József Jekő, Cecilia Sár, Kálmán Hideg, Tamás Kálai

Molecules. 2020 May; 25(10): 2430. Published online 2020 May 22. doi: 10.3390/molecules25102430

PMCID:: PMC7287729

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Select item 417500016.

Development of a Highly Potent, Novel M₅ Positive Allosteric Modulator (PAM) Demonstrating CNS Exposure: 1-((1H-Indazol-5-yl)sulfoneyl)-N-ethyl-N-(2-(trifluoromethyl)benzyl)piperidine-4-carboxamide (ML380)

Patrick R. Gentry, Masaya Kokubo, Thomas M. Bridges, Meredith J. Noetzel, Hyekyung P. Cho, Atin Lamsal, Emery Smith, Peter Chase, Peter S. Hodder, Colleen M. Niswender, J. Scott Daniels, P. Jeffrey Conn, Craig W. Lindsley, Michael R. Wood

J Med Chem. 2014 Sep 25; 57(18): 7804–7810. Published online 2014 Aug 22. doi: 10.1021/jm500995y

PMCID:: PMC4175000

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Select item 473026417.

Enzymatic Kinetic Resolution of 2-Piperidineethanol for the Enantioselective Targeted and Diversity Oriented Synthesis

Dario Perdicchia, Michael S. Christodoulou, Gaia Fumagalli, Francesco Calogero, Cristina Marucci, Daniele Passarella

Int J Mol Sci. 2016 Jan; 17(1): 17. Published online 2015 Dec 24. doi: 10.3390/ijms17010017

PMCID:: PMC4730264

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A Piperidine Chiron for the Veratrum Alkaloids

Douglass F. Taber, Peter W. DeMatteo

J Org Chem. Author manuscript; available in PMC 2014 Nov 10.

Published in final edited form as: J Org Chem. 2012 May 4; 77(9): 4235–4241. Published online 2012 Apr 13. doi: 10.1021/jo2026228

PMCID:: PMC4226469

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Select item 746455219.

Structural Basis of Beneficial Design for Effective Nicotinamide Phosphoribosyltransferase Inhibitors

Sei-ichi Tanuma, Kiyotaka Katsuragi, Takahiro Oyama, Atsushi Yoshimori, Yuri Shibasaki, Yasunobu Asawa, Hiroaki Yamazaki, Kosho Makino, Miwa Okazawa, Yoko Ogino, Yoshimi Sakamoto, Miyuki Nomura, Akira Sato, Hideaki Abe, Hiroyuki Nakamura, Hideyo Takahashi, Nobuhiro Tanuma, Fumiaki Uchiumi

Molecules. 2020 Aug; 25(16): 3633. Published online 2020 Aug 10. doi: 10.3390/molecules25163633

PMCID:: PMC7464552

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Select item 614733820.

Fluorescence Studies of Selected 2-Alkylaminopyrimidines

Z. Abdullah, N. Mohd Tahir, M. R Abas, Z. Aiyub, B.K Low

Molecules. 2004 Jul; 9(7): 520–526. Published online 2004 Jun 30. doi: 10.3390/90700520

PMCID:: PMC6147338

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PMC Images search for ethyl piperidine

Scheme 1

Synthesis of the imidazopyranotacrines 1–13. Reagents and conditions: (a) Malononitrile, piperidine, ethanol, rt (93%); (b) ethyl 3-oxobutanoate, piperidine, ethanol, rt (92%); (c) cyclopentanone (n = 0), cyclohexanone (n = 1), cycloheptanone (n = 2), AlCl₃, 1,2-dichloroethane, reflux; (d) pentane-2,4-dione, piperidine, ethanol, rt (90%); (e) 5,5-dimethylcyclohexane-1,3-dione, piperidine, ethanol, rt (69%); (f) 2-naphthol, piperidine, ethanol, rt (72%); (g) 1-naphthol, piperidine, ethanol, rt (75%); (h) 8-hydroxyquinoline, piperidine, ethanol, rt (47%).

Imidazopyranotacrines as Non-Hepatotoxic, Selective Acetylcholinesterase Inhibitors, and Antioxidant Agents for Alzheimer′s Disease Therapy

Molecules. 2016 Apr;21(4):400.
Figure 2

The chemical reactions involved in the synthesis of ethyl piperidine substituted nickel(II) salphen complex: (a) Chemical reaction between 1,2-diamino-benzene and 2,4-dihydroxybenzaldehyde to form the salphen ligand followed by reaction with Ni(OAc)₂•4H₂O to form the nickel(II) salphen complex; (b) The nickel(II) salphen complex further reacted with 1-(2-chloroethyl) piperidine hydrochloride in the presence of potassium carbonate to obtained the desired piperidine side chain functionalized nickel(II) salphen complex.

Optical DNA Biosensor Based on Square-Planar Ethyl Piperidine Substituted Nickel(II) Salphen Complex for Dengue Virus Detection

Sensors (Basel). 2018 Apr;18(4):1173.
Figure 4

Dengue virus DNA biosensor reflectance spectra before (a) and after (b) hybridization with 1 × 10⁻⁷ µM target containing 1 mM ethyl piperidine substituted nickel(II) salphen complex at pH 7.0.

Optical DNA Biosensor Based on Square-Planar Ethyl Piperidine Substituted Nickel(II) Salphen Complex for Dengue Virus Detection

Sensors (Basel). 2018 Apr;18(4):1173.
Figure 6

Synthetic route employed to obtain coumarins A1–A6 from eugenol: (i) hexamine, glacial acetic acid, 140 °C, followed by hydrolysis with aqueous HCl; (ii) malonic acid, piperidine, ethanol, 80 °C; (iii) ethyl acetoacetate, piperidine, ethanol, 80 °C; (iv) ethyl benzoylcetate, piperidine, ethanol, 80 °C; (v) ethyl 4-nitrobenzoylcetate, piperidine, ethanol, 80 °C; (vi) tin chloride, ethanol, reflux; (vii) succinic anhydride, pyridine, 80 °C. The coumarin chemical names are as follows: Coumarin A1: 8-methoxy-2-oxo-6-(prop-2-en-1-yl)-2H-chromene-3-carboxylic acid; Coumarin A2: 3-acetyl-8-methoxy-6-(prop-2-en-1-yl)-2H-chromen-2-one; Coumarin A3: 3-benzoyl-8-methoxy-6-(prop-2-en-1-yl)-2H-chromen-2-one; Coumarin A4: 8-methoxy-3-(4-nitrobenzoyl)-6-(prop-2-en-1-yl)-2H-chromen-2-one; Coumarin A5: 3-(4-aminobenzoyl)-8-methoxy-6-(prop-2-en-1-yl)-2H-chromen-2-one; Coumarin A6: 4-((4-(8-methoxy-6-(prop-2-en-1-yl)-2H-chromen-3-carbonyl)phenyl)amino)-4-oxobutanoic acid.

Allelochemical Activity of Eugenol-Derived Coumarins on Lactuca sativa L.

Plants (Basel). 2020 Apr;9(4):533.