S-substituted derivatives of 1,2,4-triazol-3-thiol as new drug candidates for type II diabetes

Öz The therapeutic applications of 1,2,4-triazoles motivated us to synthesize some new derivatives. Two series of $S$-substituted derivatives (8a-8j, 12a-12i) of 5-$\{$1-[(4-chlorophenyl)sulfonyl]-3-piperidinyl$\}$-4-phenyl-4$H$-1,2,4-triazol-3-thiol (6) have been synthesized and evaluated for their biological potential. Using 4-chlorobenzene sulfonyl chloride (1) and ethyl piperidine-3-carboxylate (2), ethyl 1-[(4-chlorophenyl)sulfonyl]piperidine-3-carboxylate (3) was synthesized and converted into 3,4,5-trisubstituted 1,2,4-triazole (6) through formation of the corresponding carbohydrazide (4) and hydrazinecarbothioamide (5). Compound 6 was transformed into 8a-8j by alkyl halides (7a-7j) and into 12a-12i by $N$-aralkyl/aryl-2-bromoacetamides (11a-11i) in an aprotic solvent. The electrophiles, 11a-11i, were synthesized by gearing up $N$-substituted aralkyl/aryl amines (10a-10i) with 2-bromoacetyl bromide (9) under dynamic pH control by aqueous sodium carbonate. Structures were elucidated through the spectral techniques of IR, EIMS, $^{1}$H NMR, and $^{13}$C NMR. Most of the synthesized derivatives were found to be potent inhibitors of $\alpha $-glucosidase enzyme and even better than acarbose. Acarbose is a reference standard and is a commercially available $\alpha $-glucosidase inhibitor to treat patients with type II diabetes. The low hemolytic activity also emphasized the potential of the synthesized compounds as new drug candidates.

Kaynak Göster

Bibtex @araştırma makalesi { tbtkchem572683, journal = {Turkish Journal of Chemistry}, issn = {1300-0527}, eissn = {1303-6130}, address = {}, publisher = {TÜBİTAK}, year = {2018}, volume = {42}, pages = {652 - 671}, doi = {}, title = {S-substituted derivatives of 1,2,4-triazol-3-thiol as new drug candidates for type II diabetes}, key = {cite}, author = {Rehman, Aziz Ur and Nafeesa, Khadija and Abbası, Muhammad Athar and Saddıquı, Sabahat Zahra and Rasool, Shahid and Shah, Syed Adnan Ali and Ashraf, Muhammad and Lodhı, Muhammad Arif and Khan, Farman Ali and Jahan, Bakht} }
APA Rehman, A , Nafeesa, K , Abbası, M , Saddıquı, S , Rasool, S , Shah, S , Ashraf, M , Lodhı, M , Khan, F , Jahan, B . (2018). S-substituted derivatives of 1,2,4-triazol-3-thiol as new drug candidates for type II diabetes . Turkish Journal of Chemistry , 42 (3) , 652-671 .
MLA Rehman, A , Nafeesa, K , Abbası, M , Saddıquı, S , Rasool, S , Shah, S , Ashraf, M , Lodhı, M , Khan, F , Jahan, B . "S-substituted derivatives of 1,2,4-triazol-3-thiol as new drug candidates for type II diabetes" . Turkish Journal of Chemistry 42 (2018 ): 652-671 <
Chicago Rehman, A , Nafeesa, K , Abbası, M , Saddıquı, S , Rasool, S , Shah, S , Ashraf, M , Lodhı, M , Khan, F , Jahan, B . "S-substituted derivatives of 1,2,4-triazol-3-thiol as new drug candidates for type II diabetes". Turkish Journal of Chemistry 42 (2018 ): 652-671
RIS TY - JOUR T1 - S-substituted derivatives of 1,2,4-triazol-3-thiol as new drug candidates for type II diabetes AU - Aziz Ur Rehman , Khadija Nafeesa , Muhammad Athar Abbası , Sabahat Zahra Saddıquı , Shahid Rasool , Syed Adnan Ali Shah , Muhammad Ashraf , Muhammad Arif Lodhı , Farman Ali Khan , Bakht Jahan Y1 - 2018 PY - 2018 N1 - DO - T2 - Turkish Journal of Chemistry JF - Journal JO - JOR SP - 652 EP - 671 VL - 42 IS - 3 SN - 1300-0527-1303-6130 M3 - UR - Y2 - 2021 ER -
EndNote %0 Turkish Journal of Chemistry S-substituted derivatives of 1,2,4-triazol-3-thiol as new drug candidates for type II diabetes %A Aziz Ur Rehman , Khadija Nafeesa , Muhammad Athar Abbası , Sabahat Zahra Saddıquı , Shahid Rasool , Syed Adnan Ali Shah , Muhammad Ashraf , Muhammad Arif Lodhı , Farman Ali Khan , Bakht Jahan %T S-substituted derivatives of 1,2,4-triazol-3-thiol as new drug candidates for type II diabetes %D 2018 %J Turkish Journal of Chemistry %P 1300-0527-1303-6130 %V 42 %N 3 %R %U
ISNAD Rehman, Aziz Ur , Nafeesa, Khadija , Abbası, Muhammad Athar , Saddıquı, Sabahat Zahra , Rasool, Shahid , Shah, Syed Adnan Ali , Ashraf, Muhammad , Lodhı, Muhammad Arif , Khan, Farman Ali , Jahan, Bakht . "S-substituted derivatives of 1,2,4-triazol-3-thiol as new drug candidates for type II diabetes". Turkish Journal of Chemistry 42 / 3 (Haziran 2018): 652-671 .
AMA Rehman A , Nafeesa K , Abbası M , Saddıquı S , Rasool S , Shah S , Ashraf M , Lodhı M , Khan F , Jahan B . S-substituted derivatives of 1,2,4-triazol-3-thiol as new drug candidates for type II diabetes. Turk J Chem. 2018; 42(3): 652-671.
Vancouver Rehman A , Nafeesa K , Abbası M , Saddıquı S , Rasool S , Shah S , Ashraf M , Lodhı M , Khan F , Jahan B . S-substituted derivatives of 1,2,4-triazol-3-thiol as new drug candidates for type II diabetes. Turkish Journal of Chemistry. 2018; 42(3): 652-671.
IEEE A. Rehman , K. Nafeesa , M. Abbası , S. Saddıquı , S. Rasool , S. Shah , M. Ashraf , M. Lodhı , F. Khan ve B. Jahan , "S-substituted derivatives of 1,2,4-triazol-3-thiol as new drug candidates for type II diabetes", Turkish Journal of Chemistry, c. 42, sayı. 3, ss. 652-671, Haz. 2018
  • ISSN: 1300-0527
  • Yayın Aralığı: Yılda 6 Sayı
  • Yayıncı: TÜBİTAK

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