Novel 1-(2-pyrimidin-2-yl)piperazine derivatives as selective monoamine oxidase (MAO)-A inhibitors

References

• Blackwell B. Adverse effects of antidepressant drugs. Part 1: monoamine oxidase inhibitors and tricyclics. Drugs 1981;21:201–19.
   PubMed Web of Science ®Google Scholar
• Khattab SN, Abdel-Moneim SAH, Bekhit AA, et al. Exploring new selective 3-benzylquinoxaline-based MAO-A inhibitors: design, synthesis, biological evaluation and docking studies. Eur J Med Chem 2015;93:308–20.
   PubMed Web of Science ®Google Scholar
• Avram S, Buiu C, Duda-Seiman D, et al. Evaluation of the pharmacological descriptors related to the induction of antidepressant activity and its prediction by QSAR/QRAR methods. Mini Rev Med Chem 2012;12:467–76.
   PubMed Web of Science ®Google Scholar
• Shelton RC. Classification of antidepressants and their clinical implications. Prim Care Companion J Clin Psychiatry 2003;5:27–32.
   Google Scholar
• Chancellor D. The depression market. Nat Rev Drug Discov 2011;10:809–10.
   PubMed Web of Science ®Google Scholar
• Micó JA, Ardid D, Berrocoso E, et al. Antidepressants and pain. Trends Pharmacol Sci 2006;27:348–54.
   PubMed Web of Science ®Google Scholar
• Millan MJ. The role of monoamines in the actions of established and “novel” antidepressant agents: a critical review. Eur J Pharmacol 2004;500:371–84.
   PubMed Web of Science ®Google Scholar
• Fishback JA, Robson MJ, Xu YT, et al. Sigma receptors: potential targets for a new class of antidepressant drug. Pharmacol Ther 2010;127:271–82.
   PubMed Web of Science ®Google Scholar
• Elmer LW, Bertoni JM. The increasing role of monoamine oxidase type B inhibitors in Parkinson’s disease therapy. Expert Opin Pharmacother 2008;9:2759–72.
   PubMed Web of Science ®Google Scholar
• Westlund KN, Denney RM, Rose RM, et al. Localization of distinct monoamine oxidase A and monoamine oxidase B cell populations in human brainstem. Neuroscience 1988;25:439–56.
   PubMed Web of Science ®Google Scholar
• Hall DWR, Logan BW, Parsons GH. Further studies on the inhibition of monoamine oxidase by M & B 9302 (clorgyline), I. Substrate specificity in various mammalian species. Biochem Pharmacol 1969;18:1447–54.
   PubMed Web of Science ®Google Scholar
• Roth JA, Feor K. Deamination of dopamine and its 3-O-methylated derivative by human brain monoamine oxidase. Biochem Pharmacol 1978;27:l606–8.
   Web of Science ®Google Scholar
• Youdim MB, Finberg JP. New directions in monoamine oxidase A and B selective inhibitors and substrates. Biochem Pharmacol 1991;41:155–62.
   PubMed Web of Science ®Google Scholar
• Youdim MB, Edmondson D, Tipton KF. The therapeutic potential of monoamine oxidase inhibitors. Nat Rev Neurosci 2006;7:295–309.
   PubMed Web of Science ®Google Scholar
• Finberg JPM. Update on the pharmacology of selective inhibitors of MAO-A and MAO-B: focus on modulation of CNS monoamine neurotransmitter release. Pharmacol Ther 2014;143:133–52.
   PubMed Web of Science ®Google Scholar
• Pecknold JC. Serotonin 5-HT1A agonists: a comparative review. CNS Drugs 1994;2:234–51.
   Web of Science ®Google Scholar
• Bronowska A, Leś A, Mazgajska M, et al. Conformational analysis and pharmacophore design for selected 1-(2-pyrimidinyl)piperazine derivatives with sedative-hypnotic activity. Acta Pol Pharm 2001;58:79–86.
   PubMedGoogle Scholar
• Goldberg HL, Finnerty RJ. The comparative efficacy of buspirone and diazepam in the treatment of anxiety. Am J Psychiatry 1979;136:1184–7.
   PubMed Web of Science ®Google Scholar
• Levy AD, Van de Kar LD. Endocrine and receptor pharmacology of serotonergic anxiolytics, antipsychotics and antidepressants. Life Sci 1992;51:83–94.
   PubMed Web of Science ®Google Scholar
• Taylor DP, Moon SL. Buspirone and related compounds as alternative anxiolytics. Neuropeptides 1991;19:15–19.
   PubMed Web of Science ®Google Scholar
• Seidel WF, Cohen SA, Bliwise NG, et al. Buspirone: an anxiolytic without sedative effect. Psychopharmacology (Berl) 1985;87:371–3.
   PubMed Web of Science ®Google Scholar
• Yevich JP, New JS, Lobeck WG, et al. Synthesis and biological characterization of α-(4-fluorophenyl)-4-(5-fluoro-2-pyrimidinyl)-1-piperazinebutanol and analogs as potential atypical antipsychotic agents. J Med Chem 1992;35:4516–25.
   PubMed Web of Science ®Google Scholar
• Chojnacka-Wójcik E, Kłodzińska A, Drabczyńska A, et al. A new putative 5-HT1A receptor antagonist of the 1-arylpiperazine class of ligands. Eur J Med Chem 1995;30:587–92.
   Web of Science ®Google Scholar
• Ishizumi K, Kojima A, Antoku F. Synthesis and anxiolytic activity of N-substituted cyclic imides (1R*,2S*,3R*,4S*)-N-[4-[4-(2-pyrimidinyl)-1-piperazinyl]butyl]-2,3-bicyclo[2.2.1]heptanedicarboximide (tandospirone) and related compounds. Chem Pharm Bull 1991;39:2288–300.
   PubMed Web of Science ®Google Scholar
• Abou-Gharbia M, Patel UR, Moyer JA, et al. Psychotropic agents: synthesis and antipsychotic activity of substituted beta-carbolines. J Med Chem 1987;30:1100–5.
   PubMed Web of Science ®Google Scholar
• Abou-Gharbia M, Moyer JA, Patel U, et al. Synthesis and structure-activity relationship of substituted tetrahydro- and hexahydro-1,2-benzisothiazol-3-one 1,1-dioxides and thiadiazinones: potential anxiolytic agents. J Med Chem 1989;32:1024–33.
   PubMed Web of Science ®Google Scholar
• Taylor DI, Hyslop DK, Riblet LA. Trazodone, a new nontricyclic antidepressant without anticholinergic activity. Biochem Pharmacol 1980;29:2149–50.
   PubMed Web of Science ®Google Scholar
• Becker I. Preparation of derivatives of 1-(2-pyrimidinyl)piperazine as potential antianxiety, antidepressant, and antipsychotic agents. J Heterocyclic Chem 2008;45:1005–22.
   Web of Science ®Google Scholar
• Prashanth MK, Revanasiddappa HD, Lokanatha Rai KM, et al. Synthesis, characterization, antidepressant and antioxidant activity of novel piperamides bearing piperidine and piperazine analogues. Bioorg Med Chem Lett 2012;22:7065–70.
   PubMed Web of Science ®Google Scholar
• Gomółka A, Ciesielska A, Wróbel MZ, et al. Novel 4-aryl-pyrido[1,2-c]pyrimidines with dual SSRI and 5-HT1A activity. Part 5. Eur J Med Chem 2015;98:221–36.
   PubMed Web of Science ®Google Scholar
• Matsumoto T, Suzuki O, Furuta T, et al. A sensitive fluorometric assay for serum monoamine oxidase with kynuramine as substrate. Clin Biochem 1985;18:126–9.
   PubMed Web of Science ®Google Scholar
• Küçükgüzel SG, Küçükgüzel İ, Tatar E, et al. Synthesis of some novel heterocyclic compounds derived from diflunisal hydrazide as potential anti-infective and anti-inflammatory agents. Eur J Med Chem 2007;42:893–901.
   PubMed Web of Science ®Google Scholar
• http://www.molinspiration.com/cgi-bin/properties [last accessed 25 Oct 2016].
   Google Scholar
• http://molsoft.com/mprop/Last [last accessed 25 Oct 2016].
   Google Scholar
• Zhao Y, Abraham MH, Lee J, et al. Rate-limited steps of human oral absorption and QSAR studies. Pharm Res 2002;19:1446–57.
   PubMed Web of Science ®Google Scholar
• Bakht MA, Yar MS, Abdel-Hamid SG, et al. Molecular properties prediction, synthesis and antimicrobial activity of some newer oxadiazole derivatives. Eur J Med Chem 2010;45:5862–9.
   PubMed Web of Science ®Google Scholar
• Lipinski CA, Lombardo F, Dominy BW, et al. Experimental and computational approaches to estimate solubility and permeability in drug discovery and development settings. Adv Drug Deliv Rev 1997;23:3–25.
   Web of Science ®Google Scholar
• Kaya B, Sağlık BN, Levent S, et al. Synthesis of some novel 2-substituted benzothiazole derivatives containing benzylamine moiety as monoamine oxidase inhibitory agents. J Enzym Inhib Med Chem, Article in press.
   Web of Science ®Google Scholar
• Trott O, Olson AJ. AutoDock Vina: improving the speed and accuracy of docking with a new scoring function, efficient optimization, and multithreading. J Comput Chem 2010;31:455–61.
   PubMed Web of Science ®Google Scholar
• Sanner MF. Python: a programming language for software integration and development. J Mol Graph Model 1999;17:57–61.
   PubMed Web of Science ®Google Scholar
• The PyMOL Molecular Graphics System, Version 1.8, Schrödinger, LLC.
   Google Scholar
• Abdelhafez OM, Amin KM, Ali HI, et al. Monoamine oxidase A and B inhibiting effect and molecular modeling of some synthesized coumarin derivatives. Neurochem Int 2013;62:198–209.
   PubMed Web of Science ®Google Scholar
• Yurttaş L, Özkay Y, Duran M, et al. Synthesis and antimicrobial activity evaluation of new dithiocarbamate derivatives bearing thiazole/benzothiazole rings. Phosphorus Sulfur Silicon Relat Elem 2016;191:1166–73.
   Web of Science ®Google Scholar