European Journal of Chemistry 2017, 8(4), 344-348 | doi: https://doi.org/10.5155/eurjchem.8.4.344-348.1630 | Get rights and content






  OPEN ACCESS | PEER-REVIEWED | RESEARCH ARTICLE | DOWNLOAD PDF | VIEW FULL-TEXT PDF | TOTAL VIEWS

Synthesis and antioxidant study of new hydrazones derived from bisdemethoxycurcumin pyrazole


Tahseen Abdul Qader Alsalim (1,*) , Hussain Ali Mzban (2) , Einas Nasir Abood (3)

(1) Chemistry Department, College of Education for Pure Sciences, University of Basrah, Basrah, 16001, Iraq
(2) Chemistry Department, College of Education for Pure Sciences, University of Basrah, Basrah, 16001, Iraq
(3) Center of Polymer Research, University of Basrah, Basrah, 16001, Iraq
(*) Corresponding Author

Received: 14 Jul 2017 | Accepted: 10 Sep 2017 | Published: 31 Dec 2017 | Issue Date: December 2017

Abstract


The antioxidant activity of new hydrazones derived from bisdemethoxycurcumin pyrazole was investigated. The study was divided into two main parts: The first one includes the synthesis and characterization of the target compounds from bisdemethoxycurcumin (BDMC), while the second step is devoted to the investigation of their antioxidant activities. In the first step of synthesis, the curcumin-pyrazole (2) was synthesized by the reaction of BDMC with hydrazine hydrate. Later, the obtained product treated with ethyl 2-chloroacetate to produce curcumine ester (3), then the product was converted to hydrazide (4) by the reaction of curcumin ester (3) with hydrazine hydrate. Finally, curcumine hydrazones (5a-f) were synthesized from the reaction of hydrazide (4) with substituted aromatic aldehydes. All compounds were characterized with the aid of suitable spectroscopic techniques. The antioxidant activity of the prepared compounds was studied against the stable radical α,α-diphenyl-β-picrylhydrazyl. The study showed that only the phenolic OH-containing compounds (2, 5b and 5f) have antioxidant activity.


Keywords


Pyrazole; Hydrazone; Curcuminoids; Antioxidant activity; Bisdemethoxycurcumin; α,α-Diphenyl-β-picrylhydrazyl

Full Text:

PDF /    /


DOI: 10.5155/eurjchem.8.4.344-348.1630

Links for Article


| | | | | | |

| | | | | | |

Related Articles




Article Metrics

This Abstract was viewed 743 times | PDF Article downloaded 233 times

Funding information


Chemistry Department, College of Education for Pure Sciences, University of Basrah, Basrah, 16001, Iraq

References

[1]. Ravindran, P. N.; NirmalBabu, K.; Sivaraman, K. Turmeric: The genus Curcuma, Vol. 45, CRC Press the Taylor & Francis Group, 2007.

[2]. Ramawat, K. G., Herbal Drugs: Ethnomedicine to Modern Medicine, 1st addition, Springer-Verlag, Berlin, Heidelberg, 2002.

[3]. Shim, J. S; Kim, D. H; Jung, H. J.; Kim, J. H.; Lim, D.; Lee, S. K.; Kim, K. W.; Ahn, J. W.; Yoo, J. S.; Rho, J. R.; kwon, H. J. Bioorg. Med. Chem. 2002, 10, 2439-2444.

[4]. Goel, A.; Kunnumakkara, B; AggarwaL, B. Biochem. Pharmacol. 2008, 75, 787-809.
https://doi.org/10.1016/j.bcp.2007.08.016

[5]. Abdeldaiem, M. H. Am. J. Food Sci. Tech. 2014, 2, 36-47.

[6]. Wichitnithad, W.; Nimmannit, U.; Wacharasindhu, S.; Rojsitthisak, P. Molecules 2011, 16, 1888-1900.
https://doi.org/10.3390/molecules16021888

[7]. Masuda, T.; Hidakd, K.; Shinohara, A.; Maekawa, T.; Takeda, Y.; Yamaguchi, H. J. Agric. Food Chem. 1999, 47, 71-77.
https://doi.org/10.1021/jf9805348

[8]. Weber, W. M.; Hussaker, L. A.; Abcouwer, S. F.; Deck, L. M.; Vanderjagt, D. L. J. Bioorg. Med. Chem. 2005, 13, 3811-3820.
https://doi.org/10.1016/j.bmc.2005.03.035

[9]. Priyadarsini, K. I.; Maity, D. K.; Naik, G. H.; Kumar, M. S.; Unnikrishnan, M. K.; Satav, J. H.; Mohan, H. Free Radical Bio. Med. 2003, 35, 475-784.
https://doi.org/10.1016/S0891-5849(03)00325-3

[10]. Gupta, P.; Garg, P.; Roy N. Mol Divers. 2011, 15, 733-750.
https://doi.org/10.1007/s11030-011-9304-7

[11]. Rai, D.; Singh, J. K.; Roy, N.; Panda, D. Biochem. J. 2008, 410, 147-155.
https://doi.org/10.1042/BJ20070891

[12]. Hasimun, B.; Sukander, E. Y.; Adnyana, I. K.; Tjahjono, D. Int. J. Pharmacol. 2011, 7, 268-272.
https://doi.org/10.3923/ijp.2011.268.272

[13]. Ahmed, T.; Gilani, A. H. Pharmcol. Biochem. Behav. 2009, 91, 554-559.
https://doi.org/10.1016/j.pbb.2008.09.010

[14]. Naama, J. H.; Al-Temimi, A. A.; Al-Amiery, A. H. Afr. J. Pure Appl. Chem. 2010, 4, 68-73.

[15]. Ohtsu, H.; Xiao, Z.; Ishida, J.; Nagai, M.; Wang, H. K.; Itokawa, H.; Su, C. Y.; Shih, C.; Chiang, T.; Chang, E.; Tasi, M. Y.; Chang, C.; Lee, K. H. J. Med. Chem. 2002, 45, 5037-5042.
https://doi.org/10.1021/jm020200g

[16]. Epelbaum, R.; Schaffer, M.; Vizel B.; Badmeav V.; Bar-Sela, G. Nutr. Cancer, 2010, 62, 1137-1141.
https://doi.org/10.1080/01635581.2010.513802

[17]. Wilken, R.; Veena, M. S.; Wang, M. B.; Srivatsan, E. S. Mol. Cancer. 2011, 10, 1-19.
https://doi.org/10.1186/1476-4598-10-12

[18]. Ooko, E.; Alsalim T. A; Saeed, B.; M.; Saeed, E. M.; Kadioglu, O.; Abbo, H. S. Titinchi, S. J. J.; Efferth, T. Toxicol. Appl. Pharmacol, 2016, 305, 216-233.
https://doi.org/10.1016/j.taap.2016.06.002

[19]. Alsalim, T. A.; Saeed, B. A.; Elias, R. S.; Abbo, H. S.; Titinchi, S. J. Eur. J. Chem. 2013, 4(1), 70‐73.
https://doi.org/10.5155/eurjchem.4.1.70-73.728

[20]. Anand, P.; Thomas, S. G.; Kunnumakkara, A. B.; Sundaram, C.; Harikumar, K. B.; Sung. B.; Tharakan, S. T.; Misra, K.; Priyadarsini, I. K.; Rajasekharan, K. N.; Aggarwal, B. B. Biochem. Pharmacol. 2008, 76, 1590-1611.
https://doi.org/10.1016/j.bcp.2008.08.008

[21]. Bayomi, S. M.; El-Kashef, H. A.; El-Ashmawy, M. B.; Nasr M. N.; El-Sherbeny, M. A.; Badria, F. A.; Abou-zeid, L. A.; Ghaly, M. A.; Abdel-Aziz, N. I. MedChem. Res. 2013, 22, 1147-1162.
https://doi.org/10.1007/s00044-012-0116-9

[22]. NurAlam, M. D.; Bristi, N. J.; Rafiquzzaman, M. D. Saudi Pharmacol. J. 2013, 21, 143-152.

[23]. Narlawar, R.; Pickhardt, M.; Leuchtenberger, S.; Baumann, K.; Krause, S.; Dyrks, T.; Weggen, S.; Mandelkow, E.; Schmidt, B. Chem. Med. Chem. 2008, 3, 165-172.
https://doi.org/10.1002/cmdc.200700218

[24]. Bade, T. S.; Ebrahimi, H. P.; Alsalim, T. A.; Titinchi, S. J. J.; Abbo, H. S.; Bolandnazar, Z.; Ebrahimi, A. J. Mol. Struct. 2017, 1138, 136-148.
https://doi.org/10.1016/j.molstruc.2017.03.005

How to cite


Alsalim, T.; Mzban, H.; Abood, E. Eur. J. Chem. 2017, 8(4), 344-348. doi:10.5155/eurjchem.8.4.344-348.1630
Alsalim, T.; Mzban, H.; Abood, E. Synthesis and antioxidant study of new hydrazones derived from bisdemethoxycurcumin pyrazole. Eur. J. Chem. 2017, 8(4), 344-348. doi:10.5155/eurjchem.8.4.344-348.1630
Alsalim, T., Mzban, H., & Abood, E. (2017). Synthesis and antioxidant study of new hydrazones derived from bisdemethoxycurcumin pyrazole. European Journal of Chemistry, 8(4), 344-348. doi:10.5155/eurjchem.8.4.344-348.1630
Alsalim, Tahseen, Hussain Ali Mzban, & Einas Nasir Abood. "Synthesis and antioxidant study of new hydrazones derived from bisdemethoxycurcumin pyrazole." European Journal of Chemistry [Online], 8.4 (2017): 344-348. Web. 27 May. 2020
Alsalim, Tahseen, Mzban, Hussain, AND Abood, Einas. "Synthesis and antioxidant study of new hydrazones derived from bisdemethoxycurcumin pyrazole" European Journal of Chemistry [Online], Volume 8 Number 4 (31 December 2017)

The other citation formats (EndNote | Reference Manager | ProCite | BibTeX | RefWorks) for this article can be found online at: How to cite item


DOI Link: https://doi.org/10.5155/eurjchem.8.4.344-348.1630

| | | | | | |

| | | | | |

Save to Zotero Save to Mendeley



European Journal of Chemistry 2017, 8(4), 344-348 | doi: https://doi.org/10.5155/eurjchem.8.4.344-348.1630 | Get rights and content

Refbacks

  • There are currently no refbacks.




Copyright (c)




© Copyright 2010 - 2020  Atlanta Publishing House LLC All Right Reserved.

The opinions expressed in all articles published in European Journal of Chemistry are those of the specific author(s), and do not necessarily reflect the views of Atlanta Publishing House LLC, or European Journal of Chemistry, or any of its employees.

Copyright 2010-2020 Atlanta Publishing House LLC. All rights reserved. This site is owned and operated by Atlanta Publishing House LLC whose registered office is 2850 Smith Ridge Trce Peachtree Cor GA 30071-2636, USA. Registered in USA.

hatay escort hatay escort corlu escort corum escort burgaz escort giresun escort aydin escort ordu escort erzincan escort hatay escort sivas escort rize escort edirne escort aksaray escort kibris escort isparta escort erzurum escort tekirdag escort usak escort urfa escort kastamonu escort kibris escort manisa escort giresun escort urfa escort nevsehir escort sivas escort yalova escort ordu escort hatay escort yalova escort amasya escort kayseri escort ordu escort maras escort canakkale escort yalova escort balikesir escort manisa escort urfa escort mugla escort trabzon escort bolu escort corlu escort diyarbakir escort isparta escort kutahya escort elazig escort erzurum escort sakarya escort afyon escort kutahya escort konya escort agri escort cesme escort sinop escort sivas escort konya escort kibris escort adapazari escort luleburgaz escort adana escort kibris escort rize escort sakarya escort alanya escort isparta escort burdur escort konya escort bitlis escort canakkale escort sivas escort amasya escort mus escort aydin escort van escort yalova escort kastamonu escort mardin escort bolu escort afyon escort sakarya escort isparta escort tokat escort trakya escort bayburt escort urfa escort mardin escort