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Synthesis, SAR study, and biological evaluation of a series of piperazine ureas as fatty acid amide hydrolase (FAAH) inhibitors.

Kono M, Matsumoto T, Kawamura T, Nishimura A, Kiyota Y, Oki H, Miyazaki J, Igaki S, Behnke CA, Shimojo M, Kori M
Bioorg Med Chem 21 28-41 (2013)
Cited: 15 times
EuropePMC logo PMID: 23218778

Abstract

A series of piperazine ureas was designed, synthesized, and evaluated for their potential as novel orally available fatty acid amide hydrolase (FAAH) inhibitors that are therapeutically effective against pain. We carried out an optimization study of the lead compound 3 to improve its DMPK profile as well as in vitro potency. We identified the thiazole compound 60j with potent inhibitory activity, high brain permeability, and good bioavailability. Compound 60j showed a potent and dose-dependent anti-nociceptive effect in the acetic acid-induced writhing test in mice.

Reviews - 4hbp mentioned but not cited (1)

  1. Stability and Removal of Benzophenone-Type UV Filters from Water Matrices by Advanced Oxidation Processes. Imamović B, Trebše P, Omeragić E, Bečić E, Pečet A, Dedić M. Molecules 27 1874 (2022)

Articles - 4hbp mentioned but not cited (1)

  1. Maternal Benzophenone Exposure Impairs Hippocampus Development and Cognitive Function in Mouse Offspring. Cui F, Pan Q, Wang S, Zhao F, Wang R, Zhang T, Song Y, He J, Zhang H, Weng Q, Jin Y, Xia W, Li Y, Yang GY, De Vos WH, Timmermans JP, Xu S, Tang Y, Sheng X. Adv Sci (Weinh) 8 e2102686 (2021)


Articles citing this publication (13)

  1. Synthesis, in vitro anticancer and antimycobacterial evaluation of new 5-(2,5-dimethoxyphenyl)-1,3,4-thiadiazole-2-amino derivatives. Polkam N, Rayam P, Anireddy JS, Yennam S, Anantaraju HS, Dharmarajan S, Perumal Y, Kotapalli SS, Ummanni R, Balasubramanian S. Bioorg Med Chem Lett 25 1398-1402 (2015)
  2. Piperazine and piperidine carboxamides and carbamates as inhibitors of fatty acid amide hydrolase (FAAH) and monoacylglycerol lipase (MAGL). Korhonen J, Kuusisto A, van Bruchem J, Patel JZ, Laitinen T, Navia-Paldanius D, Laitinen JT, Savinainen JR, Parkkari T, Nevalainen TJ. Bioorg Med Chem 22 6694-6705 (2014)
  3. Design and Potency of Dual Soluble Epoxide Hydrolase/Fatty Acid Amide Hydrolase Inhibitors. Kodani SD, Wan D, Wagner KM, Hwang SH, Morisseau C, Hammock BD. ACS Omega 3 14076-14086 (2018)
  4. Design, synthesis, and characterization of α-ketoheterocycles that additionally target the cytosolic port Cys269 of fatty acid amide hydrolase. Otrubova K, Cravatt BF, Boger DL. J Med Chem 57 1079-1089 (2014)
  5. Piperidinyl thiazole isoxazolines: A new series of highly potent, slowly reversible FAAH inhibitors with analgesic properties. Pember SO, Mejia GL, Price TJ, Pasteris RJ. Bioorg Med Chem Lett 26 2965-2973 (2016)
  6. Synthesis and Biological Investigation of some Novel Sulfonamide and Amide Derivatives Containing Coumarin Moieties. Saeedi M, Goli F, Mahdavi M, Dehghan G, Faramarzi MA, Foroumadi A, Shafiee A. Iran J Pharm Res 13 881-892 (2014)
  7. Design, synthesis, and biological evaluation of a series of piperazine ureas as fatty acid amide hydrolase inhibitors. Kono M, Matsumoto T, Imaeda T, Kawamura T, Fujimoto S, Kosugi Y, Odani T, Shimizu Y, Matsui H, Shimojo M, Kori M. Bioorg Med Chem 22 1468-1478 (2014)
  8. Discovery libraries targeting the major enzyme classes: the serine hydrolases. Otrubova K, Srinivasan V, Boger DL. Bioorg Med Chem Lett 24 3807-3813 (2014)
  9. Three-Dimensional Quantitative Structure-Activity Relationships (3D-QSAR) on a Series of Piperazine-Carboxamides Fatty Acid Amide Hydrolase (FAAH) Inhibitors as a Useful Tool for the Design of New Cannabinoid Ligands. Lorca M, Valdes Y, Chung H, Romero-Parra J, Pessoa-Mahana CD, Mella J. Int J Mol Sci 20 E2510 (2019)
  10. Synthesis of new pyrazolo[3,4-d]pyrimidine derivatives and evaluation of their anti-inflammatory and anticancer activities. Abd El Razik HA, Mroueh M, Faour WH, Shebaby WN, Daher CF, Ashour HMA, Ragab HM. Chem Biol Drug Des 90 83-96 (2017)
  11. α-Ketoheterocycle inhibitors of fatty acid amide hydrolase: exploration of conformational constraints in the acyl side chain. Duncan KK, Otrubova K, Boger DL. Bioorg Med Chem 22 2763-2770 (2014)
  12. Design and Optimization of Thioglycosyl-naphthalimides as Efficient Inhibitors Against Human O-GlcNAcase. Shen S, Dong L, Chen W, Wu R, Lu H, Yang Q, Zhang J. Front Chem 7 533 (2019)
  13. External oxidant-free and transition metal-free synthesis of 5-amino-1,2,4-thiadiazoles as promising antibacterials against ESKAPE pathogen strains. Shetnev A, Tarasenko M, Kotlyarova V, Baykov S, Geyl K, Kasatkina S, Sibinčić N, Sharoyko V, Rogacheva EV, Kraeva LA. Mol Divers 27 651-666 (2023)


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