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

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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

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DOI: 10.5155/eurjchem.5.3.488-496.1073

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Funding information


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

Citations

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[2]. Hatem A. Abuelizz, Rabab El Dib, Mohamed Marzouk, El-Hassane Anouar, Yousreya A. Maklad, Hanan N. Attia, Rashad Al-Salahi
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[3]. Biao Li, Xinju Zhu, Yuan Guo, Ya-Ping Ren, Zhao-Dong Jia, Jing-Na Wei, Dong-Xia Fu, Yan Xu, Xin-Qi Hao
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/

[4]. Zhaodong Jia, Jingna Wei, Yaping Ren, Ning Zhang, Xin-Qi Hao, Xinju Zhu, Yan Xu
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/

[5]. Walaa Hamada Abd-Allah, Mona Elsayed Aboutabl, Mohamed Nabil Aboul-Enein, Aida Abdel Sattar El-Azzouny
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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. 18 Jan. 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)

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