2443-68-7Relevant articles and documents
Synthesis and docking studies of N-(5-(alkylthio)-1,3,4-oxadiazol-2-yl)methyl)benzamide analogues as potential alkaline phosphatase inhibitors
Iqbal, Zafar,Iqbal, Ambreen,Ashraf, Zaman,Latif, Muhammad,Hassan, Mubashir,Nadeem, Humaira
, p. 646 - 654 (2019/05/08)
A series of N-(5-(alkylthio)-1,3,4-oxadiazol-2-yl)methyl)benzamides 6a–i were synthesized as alkaline phosphatase inhibitors. The intermediate 5-substituted 1,3,4-oxadiazole-2-thione 4 was synthesized starting with hippuric acid. Hippuric acid in the first step was converted into corresponding methyl ester 2 which upon reaction with hydrazine hydrate furnished the formation of hydrazide 3. The hippuric acid hydrazide was then cyclized into 5-substituted 1,3,4-oxadiazole-2-thione 4. The intermediate 4 was then reacted with alkyl or aryl halides 5a–5i to afford the title compounds N-(5-(methylthio)-1,3,4-oxadiazol-2-yl)methyl)benzamides 6a–i. The bioassay results showed that compounds 6a–i exhibited good to excellent alkaline phosphatase inhibitory activity. The most potent activity was exhibited by the compound 6i having IC50 value 0.420 μM, whereas IC50 value of standard (KH2PO4) was 2.80 μM. Molecular docking studies was performed against alkaline phosphatase enzyme (PDBID 1EW2) to check binding affinity of the synthesized compounds 6a–i against target protein. The docking results showed that three compounds 6c, 6e, and 6i have maximum binding interactions with binding energy values of ?8 kcal/mol. The compound 6i displayed the interactions of oxadiazole ring nitrogen with amino acid His265 having a binding distance 2.13 ?. It was concluded from our results that synthesized compounds, especially compound 6i may serve as lead structure to design more potent inhibitors of human alkaline phosphatase.
Synthesis of Hydrazones from Amino Acids and their Antimicrobial and Cytotoxic Activities
Abid, Obaid-Ur-Rahman,Khatoon, Ghamama,Arfan, Muhammad,Sajid, Imran,Langer, Peter,Rehman, Wajid,Rahim, Fazal,Yasir, Muhammad,Waqar, Muhammad,Haleem, Kashif Syed
, p. 1079 - 1087 (2017/09/26)
Hydrazones 6a–6n were synthesized from different amino acids with various aldehydes under reflux in methanol/ethanol. The structures of synthesized compounds were ascertained by elemental analysis and spectroscopic techniques. A comparative study of the antimicrobial activity and cytotoxicity was carried out of the N-protected amino acids, their esters, hydrazides, and the respective hydrazones, providing good results in cytotoxicity studies.
2-azetidinone derivatives: Synthesis, antimicrobial, anticancer evaluation and QSAR studies
Deep, Aakash,Kumar, Pradeep,Narasimhan, Balasubramanian,Lim, Siong Meng,Ramasamy, Kalavathy,Mishra, Rakesh Kumar,Mani, Vasudevan
, p. 65 - 78 (2016/03/19)
A series of 2-azetidinone derivatives was synthesized from hippuric acid and evaluated for its in vitro antimicrobial and anticancer activities. Antimicrobial properties of the title compounds were investigated against Gram positive and Gram negative bact
