European Journal of Chemistry 2014, 5(3), 488-496 | doi: https://doi.org/10.5155/eurjchem.5.3.488-496.1073 | Get rights and content

Issue cover





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

Design, synthesis, and biological profile of novel N-(5-aryl-1,3,4-thiadiazol-2-yl) hydrazinecarboxamides


Mohammed Farrag El-Behairy (1) , Mohamed Nabil Aboul-Enein (2,*) , Aida Abdel-Sattar El-Azzouny (3) , Ola Ahmed Saleh (4) , Yousreya Aly Maklad (5) , Mona Elsayed Aboutabl (6) , Amany Sayed Maghraby (7)

(1) Medicinal and Pharmaceutical Chemistry Department, Pharmaceutical and Drug Industries Research Division, National Research Centre, Dokki, 12311, Cairo, Egypt
(2) Medicinal and Pharmaceutical Chemistry Department, Pharmaceutical and Drug Industries Research Division, National Research Centre, Dokki, 12311, Cairo, Egypt
(3) Medicinal and Pharmaceutical Chemistry Department, Pharmaceutical and Drug Industries Research Division, National Research Centre, Dokki, 12311, Cairo, Egypt
(4) Medicinal and Pharmaceutical Chemistry Department, Pharmaceutical and Drug Industries Research Division, National Research Centre, Dokki, 12311, Cairo, Egypt
(5) Medicinal and Pharmaceutical Chemistry Department, Pharmaceutical and Drug Industries Research Division, National Research Centre, Dokki, 12311, Cairo, Egypt
(6) Medicinal and Pharmaceutical Chemistry Department, Pharmaceutical and Drug Industries Research Division, National Research Centre, Dokki, 12311, Cairo, Egypt
(7) Therapeutic Chemistry Department, Pharmaceutical and Drug Industries Research Division, Immunology and Infectious Diseases Laboratory, Centre of Excellence for Advanced Sciences, National Research Centre, Dokki, 12311, Cairo, Egypt
(*) Corresponding Author

Received: 10 Apr 2014 | Revised: 29 Apr 2014 | Accepted: 29 Apr 2014 | Published: 30 Sep 2014 | Issue Date: September 2014

Abstract


New series of arylthiadiazole hydrazinecarboxamides (5a-e) have been synthesized by hydrazinolysis of carbamates (4a-e) and spectrally characterized. The new candidates have been screened for their anticonvulsant and immunomodulatory activities. Compound 5e was the most potent anticonvulsant candidate as it showed 100% protection against both maximal electroshock seizure (MES) and subcutaneous pentylenetetrazole (scPTZ) screens without neurotoxicity at 100 mg/kg (0.318 mmol/kg). With respect to immunomodulation, compounds 5a and 5d revealed immunostimulatory activity while compounds 5b, 5c, and 5e had immunosuppressive responses based on ELISA detection of IgM and IgG levels, counting the total mesenteric lymph nodes lymphocytes, and histo-pathological examinations.


Keywords


ELISA; Thiadiazoles; Arylthiadiazole; Anticonvulsants; Immunomodulatory; Hydrazinecarboxamides

Full Text:

PDF
PDF    Open Access

DOI: 10.5155/eurjchem.5.3.488-496.1073

Links for Article


| | | | | | |

| | | | | | |

| | | |

Related Articles




Article Metrics

icon graph This Abstract was viewed 2989 times | icon graph PDF Article downloaded 505 times

Funding information


National Research Centre (Project No: 10010302), Dokki, Cairo, Egypt

Citations

/


[1]. Hazem A. Ghabbour, Adnan A. Kadi, Kamal E. H. ElTahir, Rihab F. Angawi, Hussein I. El-Subbagh
Synthesis, biological evaluation and molecular docking studies of thiazole-based pyrrolidinones and isoindolinediones as anticonvulsant agents
Medicinal Chemistry Research  24(8), 3194, 2015
DOI: 10.1007/s00044-015-1371-3
/

[2]. Hatem A. Abuelizz, Rabab El Dib, Mohamed Marzouk, El-Hassane Anouar, Yousreya A. Maklad, Hanan N. Attia, Rashad Al-Salahi
Molecular Docking and Anticonvulsant Activity of Newly Synthesized Quinazoline Derivatives
Molecules  22(7), 1094, 2017
DOI: 10.3390/molecules22071094
/

[3]. Biao Li, Xinju Zhu, Yuan Guo, Ya-Ping Ren, Zhao-Dong Jia, Jing-Na Wei, Dong-Xia Fu, Yan Xu, Xin-Qi Hao
Synthesis and properties of m -ferrocenylbenzoylthiadiazole derivatives
Applied Organometallic Chemistry  32(4), e4265, 2018
DOI: 10.1002/aoc.4265
/

[4]. Zhaodong Jia, Jingna Wei, Yaping Ren, Ning Zhang, Xin-Qi Hao, Xinju Zhu, Yan Xu
A new colorimetric and fluorescent chemosensor based on thiazolyl-hydrazone for sensitive detection of copper ions
Journal of the Iranian Chemical Society  17(3), 609, 2020
DOI: 10.1007/s13738-019-01802-3
/

[5]. Walaa Hamada Abd-Allah, Mona Elsayed Aboutabl, Mohamed Nabil Aboul-Enein, Aida Abdel Sattar El-Azzouny
Synthesis, molecular modeling studies and anticonvulsant activity of certain (1-(benzyl (aryl) amino) cyclohexyl) methyl esters
Bioorganic Chemistry  71, 135, 2017
DOI: 10.1016/j.bioorg.2017.01.021
/

References


[1]. Masihi, K. N. Immunotherapy of Infections, 1st edition, New York: Marcel Dekker, 1994.

[2]. Masihi, K. N. Int. J. Immunopharmacol. 1997, 19, 463-617.
http://dx.doi.org/10.1016/S0192-0561(97)00056-8

[3]. Foroumadi, A.; Jazayeri, S.; Moshafi, M. H.; Firoozpour, L.; Emami, S.; Rajabalian, S.; Haddad, M.; Pahlavanzadeh, F.; Esnaashari, M.; Shafiee, A. Eur. J. Med. Chem. 2009, 44, 1205-1209.
http://dx.doi.org/10.1016/j.ejmech.2008.09.012

[4]. Goksen, U. S.; Kelekci, N. G.; Goktas, O.; Koysal, Y.; Kilic, E.; Isik, S.; Aktay, G.; Ozalp, M. Bioorg. Med. Chem. 2007, 15, 5738-5751.
http://dx.doi.org/10.1016/j.bmc.2007.06.006

[5]. Mavrova, A. T.; Wesselinova, D.; Tsenov, Y. A.; Denkova, P. Eur. J. Med. Chem. 2009, 44, 63-69.
http://dx.doi.org/10.1016/j.ejmech.2008.03.006

[6]. Pattanayak, P.; Sharma, R.; Sahoo, P. K. Med. Chem. Res. 2009, 18, 351-361.
http://dx.doi.org/10.1007/s00044-008-9132-1

[7]. Kus, C.; Kilcigil, G. A.; Ozbey, S.; Kaynak, F. B.; Kaya, M.; Coban, T.; Eke, B. C. Bioorg. Med. Chem. 2008, 16, 4294-4303.
http://dx.doi.org/10.1016/j.bmc.2008.02.077

[8]. Behrouzi-Fardmoghadam, M.; Poorrajab, F.; Ardestani, S. K.; Emami, S.; Shafieea, A.; Foroumadi, A. Bioorg. Med. Chem. 2008, 16, 4509-4515.
http://dx.doi.org/10.1016/j.bmc.2008.02.052

[9]. Bhuva, H.; Sahu, D.; Shaha, B.; Modia, D.; Patel, M. Pharmacology Online 2011, 1, 528-543.

[10]. Takezawa, R.; Cheng, H.; Beck, A.; Ishikawa, J.; Launay, P.; Kubota, H.; Kinet, J. P.; Fleig, A.; Yamada, T.; Penner, R. Mol. Pharmacol. 2006, 69, 1413-1420.
http://dx.doi.org/10.1124/mol.105.021154

[11]. Yoshino, T.; Ishikawa, J.; Ohga, K.; Morokata, T.; Takezawa, R.; Morio, H.; Okada, Y.; Honda, K.; Yamada, T. Eur. J. Pharm. 2007, 560, 225-233.
http://dx.doi.org/10.1016/j.ejphar.2007.01.012

[12]. Vo, N. H.; Chen, S.; Che, S. US patent US 2007/0254925 A1, 2007.

[13]. Jingwu, D.; Bin, J. WO 2007/073503 A2, 2007.

[14]. Beraldo, H.; Gambinob, D. Mini Rev. Med. Chem. 2004, 4, 31-39.
http://dx.doi.org/10.2174/1389557043487484

[15]. Rajak, H. R.; Avantika, A.; Poonam, P.; Singh, T. B.; Ravichandran, V.; Chander, S. P.; Dhar, K. M. Bioorg. Med. Chem. Lett. 2011, 21, 5735-5738.
http://dx.doi.org/10.1016/j.bmcl.2011.08.022

[16]. Tu, G. G.; Huang, H. H.; Li, G.; Xiong, F.; Mai, X.; Zhu, H. W.; Kuang, B. H.; Xu, W. H. Bioorg. Med. Chem. 2008, 16, 6663-6668.
http://dx.doi.org/10.1016/j.bmc.2008.05.081

[17]. Rango, R. V.; Srinivasan, V. R. Indian J. Chem. 1970, 8, 509-513.

[18]. Pryde, D. C.; Maw, G. N.; Planken, S.; Platts, M. Y.; Sanderson, V.; Corless, M.; Stobie, A.; Barber, C. G.; Russell, R.; Foster, L.; Barker, L.; Wayman, C.; Van der Graaf, P.; Stacey, P.; Morren, D.; Kohl, C.; Beaumount, K.; Coggon, S.; Tute, M. J. Med. Chem. 2006, 49, 4409-4424.
http://dx.doi.org/10.1021/jm060133g

[19]. Doyle, K. M.; Kurzer, F. Tetrahedron 1976, 32, 2347-2352.
http://dx.doi.org/10.1016/0040-4020(76)88013-1

[20]. Fariello, R. G.; McArthur, R. A.; Bonsignori, A.; Cervini, M. A.; Maj, R.; Marrari, P.; Pevarello, P.; Wolf, H. H.; Woodhead, J. W.; White, H. S.; Varasi, M.; Salvati, P.; Post, C. J. Pharm. Exp. Therap. 1998, 285, 397-403.

[21]. Alam, O.; Mullick, P.; Verma, S. P.; Gilani, S. J.; Khan, S. A.; Siddiqui, N.; Ahsan, W. Eur. J. Med. Chem. 2010, 45, 2467-2472.
http://dx.doi.org/10.1016/j.ejmech.2010.02.031

[22]. Krall, R. L.; Penry, J. K.; White, B. G.; Kupferberg, H. J.; Swinyard, E. A. Epilepsia 1978, 19, 409-428.
http://dx.doi.org/10.1111/j.1528-1157.1978.tb04507.x

[23]. Luszczki, J. J.; Czuczwar, M.; Gawlik, P.; Sawiniec-Pozniak, G.; Czuczwar, K.; Czuczwar, S. J. J. Neural. Transm. 2006, 113, 1157-1168.
http://dx.doi.org/10.1007/s00702-005-0417-y

[24]. Dunham, N. W.; Miya, T. S. Amer. Pharm. Assoc. 1957, 46, 208-209.
http://dx.doi.org/10.1002/jps.3030460322

[25]. Maghraby, A.; Bahgat, M. Arzneimittel-Forschung, 2004, 54, 545-550.

[26]. Maghraby, A., M. Sc. Thesis submitted to the faculty of science, Cairo University, Egypt, 1989, p. 43-46.

[27]. Augustine, J. K.; Vairaperumal, V.; Narasimhan, S.; Alagarsamy, P.; Radhakrishnan, A. Tetrahedron 2009, 65, 9989-9996.
http://dx.doi.org/10.1016/j.tet.2009.09.114

[28]. Yadav, J. S.; Reddy, G. S.; Reddy, M. M.; Meshram, H. M. Tetrahedron Lett. 1998, 39, 3259-3262.
http://dx.doi.org/10.1016/S0040-4039(98)00464-X

[29]. Balack, D. A.; Arndtsen, B. A. Org. Lett. 2006, 8, 1991-1993.
http://dx.doi.org/10.1021/ol060277p

[30]. Elghamry, I. Synthetic Commun. 2009, 39, 3010-3015.
http://dx.doi.org/10.1080/00397910802564741

[31]. Lebel, H.; Leogane, O. Org. Lett. 2006, 8, 5717-5720.
http://dx.doi.org/10.1021/ol0622920

[32]. Lebel, H.; Leogane, O. Org. Lett. 2005, 7, 4107-4110.
http://dx.doi.org/10.1021/ol051428b

[33]. Han, C.; Porco, J. A. Jr. Org. Lett. 2007, 9, 1517-1520.
http://dx.doi.org/10.1021/ol0702728

[34]. Curini, M.; Epifano, F.; Maltese, F.; Rosati, O. Tetrahedron Lett. 2002, 43, 4895-4897.
http://dx.doi.org/10.1016/S0040-4039(02)00965-6

[35]. Caddick, S.; Judd, D. B.; Lewis, K.; Reich, M. T.; Williams, M. R. V. Tetrahedron 2003, 59, 5417-5423.
http://dx.doi.org/10.1016/S0040-4020(03)00858-5

[36]. Sun, C.; Weinreb, S. Synthesis 2006, 3585-3588.

[37]. White, H. S. Epilepsia 2003, 44, 2-8.
http://dx.doi.org/10.1046/j.1528-1157.44.s7.10.x

[38]. Porter, R. J.; Cereghino, J. J.; Gladding, G. D.; Hessie, B. J.; Kupferberg, H. J.; Scoville, B.; White, B. G. Cleveland Clin. Q. 1984, 51, 293-305.
http://dx.doi.org/10.3949/ccjm.51.2.293

[39]. Amir, M.; Kumar, H.; Javed, S. A. Eur. J. Med. Chem. 2008, 43, 2056-2066.
http://dx.doi.org/10.1016/j.ejmech.2007.09.025


How to cite


El-Behairy, M.; Aboul-Enein, M.; El-Azzouny, A.; Saleh, O.; Maklad, Y.; Aboutabl, M.; Maghraby, A. Eur. J. Chem. 2014, 5(3), 488-496. doi:10.5155/eurjchem.5.3.488-496.1073
El-Behairy, M.; Aboul-Enein, M.; El-Azzouny, A.; Saleh, O.; Maklad, Y.; Aboutabl, M.; Maghraby, A. Design, synthesis, and biological profile of novel N-(5-aryl-1,3,4-thiadiazol-2-yl) hydrazinecarboxamides. Eur. J. Chem. 2014, 5(3), 488-496. doi:10.5155/eurjchem.5.3.488-496.1073
El-Behairy, M., Aboul-Enein, M., El-Azzouny, A., Saleh, O., Maklad, Y., Aboutabl, M., & Maghraby, A. (2014). Design, synthesis, and biological profile of novel N-(5-aryl-1,3,4-thiadiazol-2-yl) hydrazinecarboxamides. European Journal of Chemistry, 5(3), 488-496. doi:10.5155/eurjchem.5.3.488-496.1073
El-Behairy, Mohammed, Mohamed Nabil Aboul-Enein, Aida Abdel-Sattar El-Azzouny, Ola Ahmed Saleh, Yousreya Aly Maklad, Mona Elsayed Aboutabl, & Amany Sayed Maghraby. "Design, synthesis, and biological profile of novel N-(5-aryl-1,3,4-thiadiazol-2-yl) hydrazinecarboxamides." European Journal of Chemistry [Online], 5.3 (2014): 488-496. Web. 1 Dec. 2021
El-Behairy, Mohammed, Aboul-Enein, Mohamed, El-Azzouny, Aida, Saleh, Ola, Maklad, Yousreya, Aboutabl, Mona, AND Maghraby, Amany. "Design, synthesis, and biological profile of novel N-(5-aryl-1,3,4-thiadiazol-2-yl) hydrazinecarboxamides" European Journal of Chemistry [Online], Volume 5 Number 3 (30 September 2014)

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.5.3.488-496.1073

CrossRef | Scilit | GrowKudos | Researchgate | Publons | Microsoft | scibey | Scite | Lens | OUCI

WorldCat Paperbuzz | LibKey Citeas | Dimensions | Semanticscholar | Plumx | Kopernio | Zotero | Mendeley

ZoteroSave to Zotero MendeleySave to Mendeley



European Journal of Chemistry 2014, 5(3), 488-496 | doi: https://doi.org/10.5155/eurjchem.5.3.488-496.1073 | Get rights and content

Refbacks

  • There are currently no refbacks.


Bookmark and Share


Copyright (c)




© Copyright 2010 - 2021 • 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 2010-2021 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.