

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







(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
Full Text:
PDF

DOI: 10.5155/eurjchem.5.3.488-496.1073
Links for Article
| | | | | | |
| | | | | | |
| | |
Related Articles
Article Metrics


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
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

















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.
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.