Skip to main content
SpringerLink
Log in

Synthesis and antidepressant-like action of N-(2-hydroxyethyl) cinnamamide derivatives in mice

  • Original Research
  • Published:
Medicinal Chemistry Research Aims and scope Submit manuscript

Abstract

This study described the chemical synthesis and pharmacological evaluation of a series of N-(2-hydroxyethyl) cinnamamide derivatives. The structures of them were characterized by IR, 1H-NMR, MS and elemental analysis. Their antidepressant activities were evaluated by the forced swimming test (FST) and tail suspension test (TST). Pharmacological results of these compounds showed that some of them, given orally, significantly reduced the immobility time in the FST and TST, indicating the antidepressant-like action. Among them, compounds N-(2-hydroxyethyl)cinnamamide (1g), (E)-3-(4-hydroxy-3-methoxyphenyl)-N-(2-hydroxyethyl)acrylamide (1i) and (E)-N-(2-hydroxyethyl)-3-(3-hydroxyphenyl)acrylamide (1n), active in the two models, were considered as the most promising compounds in this study.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Fig. 1
Scheme 1
Fig. 2
Fig. 3

Similar content being viewed by others

References

  • Balsamo A, Barili PL, Crotti P, Macchia B, Macchia F, Pecchia A, Cuttica A, Passerini N (1975) Structure-activity relations in cinnamamides. 1. Synthesis and pharmacological evaluation of some (E)- and (Z)-N-alkyl-alpha,beta-dimethylcinnamamides. J Med Chem 18:842–846

    Article  PubMed  CAS  Google Scholar 

  • Balsamo A, Crotti P, Lapucci A, Macchia B, Macchia F, Cuttica A, Passerini N (1981) Structure-activity relationship in cinnamamides. 3. Synthesis and anticonvulsant activity evaluation of some derivatives of (E)- and (Z)-m-(trifluoromethyl)cinnamamide. J Med Chem 24:525–532

    Article  PubMed  CAS  Google Scholar 

  • Bourin M, Chenu F, Ripoll N, David DJ (2005) A proposal of decision tree to screen putative antidepressants using forced swim and tail suspension tests. Behav Brain Res 164:266–269

    Article  PubMed  CAS  Google Scholar 

  • Bruce Moffett R (1964) Central nervous system depressants. VI. Polymethoxyphenyl esters and amides. J Med Chem 7:319–325

    Article  Google Scholar 

  • Cryan JF, Markou A, Lucki I (2002) Assessing antidepressant activity in rodents: recent developments and future needs. Trends Pharmacol Sci 23:238–245

    Article  PubMed  CAS  Google Scholar 

  • Cryan JF, Valentino RJ, Lucki I (2005) Assessing substrates underlying the behavioral effects of antidepressants using the modified rat forced swimming test. Neurosci Biobehav Rev 29:547–569

    Article  PubMed  CAS  Google Scholar 

  • Guan LP, Su X, Deng XQ, Zhao, DH, Qu, YL, Quan, ZS (2010) N-palmitoylethanolamide derivatives: synthesis and studies on anticonvulsant and antidepressant activities. Med Chem Res. doi10.1007/s00044-010-9357-7

  • Hirschfeld RM (1999) Efficacy of SSRIs and newer antidepressants in severe depression : comparison with TCAs. J Clin Psychiatry 60:326–335

    Article  PubMed  CAS  Google Scholar 

  • Lopez AD, Murray CC (1998) The global burden of disease, 1990–2020. Nat Med 4:1241–1243

    Article  PubMed  CAS  Google Scholar 

  • Meyer C (2004) Depressive disorders were the fourth leading cause of global disease burden in the year 2000. Evid Based Ment Health 7:123–127

    Article  PubMed  Google Scholar 

  • Petit-Demouliere B, Chenu F, Bourin M (2005) Forced swimming test in mice: a review of antidepressant activity. Psychopharmacology (Berl) 177:245–255

    Article  CAS  Google Scholar 

  • Porsolt RD, Bertin A, Jalfre M (1977) Behavioural despair in mice: a primary screening test for antidepressants. Arch Int Pharmacodyn Ther 229:327–336

    PubMed  CAS  Google Scholar 

  • Steru L, Chermat R, Thierry B, Simon P (1985) The tail suspension test: a new method for screening antidepressants in mice. Psychopharmacology 85:367–370

    Article  PubMed  CAS  Google Scholar 

  • Thase ME (2003) Evaluating antidepressant therapies: remission as the optimal outcome. J Clin Psychiatry 64(Suppl 13):18–25

    PubMed  CAS  Google Scholar 

  • Thase ME, Corya SA, Osuntokun O, Case M, Henley DB, Sanger TM et al (2007) A randomized, double-blind comparison of olanzapine/fluoxetine combination, olanzapine, and fluoxetine in treatment-resistant major depressive disorder. J Clin Psychiatry 68:224–236

    Article  PubMed  CAS  Google Scholar 

  • Van Heyningen E, Brown CN, Jose′ F, Henderson JK, Stark P (1966) N-monoalkyl-β-alkylcinnamamides as sedatives. J Med Chem 9:675–681

    Article  PubMed  Google Scholar 

Download references

Acknowledgment

This work was supported by the National Natural Science Foundation of China (No. 30860340).

Author information

Authors and Affiliations

  1. College of Pharmacy, Yanbian University, No. 977, Park road, Yanji, 133002, Jilin, China

    Xian-Qing Deng, Di Wu, Cheng-Xi Wei & Zhe-Shan Quan

Authors
  1. Xian-Qing Deng
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Di Wu
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Cheng-Xi Wei
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Zhe-Shan Quan
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Zhe-Shan Quan.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Deng, XQ., Wu, D., Wei, CX. et al. Synthesis and antidepressant-like action of N-(2-hydroxyethyl) cinnamamide derivatives in mice. Med Chem Res 20, 1273–1279 (2011). https://doi.org/10.1007/s00044-010-9470-7

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s00044-010-9470-7

Keywords

Search

Navigation