Synthesis and Antimicrobial Activity of New 2,5‐Disubstituted 1,3,4‐Oxadiazoles and 1,2,4‐Triazoles and Their Sugar Derivatives

Abstract

A series of new 2,5-disubstituted-1,3,4-oxadiazole and 1,2,4-triazole derivatives were synthesized by heterocyclization of acid hydrazide 1 and thiosemicarbazide derivative 2. Furthermore, the acyclic C-nucleoside analogs were prepared by cyclization of their corresponding sugar hydrazones by reaction with acetic anhydride. The antimicrobial activity of the prepared compounds was evaluated and some of the synthesized compounds revealed good activities against fungi.

Synthetic Approaches and Pharmacological Activity of 1,3,4-Oxadiazoles: A Review of the Literature from 2000–2012

“…Another interesting approach to the synthesis of 5-substituted-2-amino-1,3,4-oxadiazoles is the cyclization reaction of acylthiosemicarbazides using iodine as the oxidizing agent. El-Sayed and co-workers [ 13 ] reported the synthesis of 5-((naphthalen-2-yloxy)methyl)- N -phenyl-1,3,4-oxadiazol-2-amine ( 24 ) in 62% yield, by heating compound 23 in ethanol in the presence of sodium hydroxide and iodine in potassium iodide ( Scheme 5 ).…”

“…Compounds 112 and 113 were twice as potent as fluconazole against C. albicans [ 69 ] ( Figure 5 ). Other oxadiazole compounds with antibacterial activity are: 114 [ 70 ], 115 [ 71 ], 116 [ 72 ], 117 [ 13 ], 118 [ 73 ], 119 [ 24 ], 120 [ 74 ], 121 [ 75 ] and 122 [ 76 ] ( Figure 5 ).…”

Synthesis, characterization and antibacterial evaluation of 1,3,4-oxadiazole derivatives

“…FT-IR spectrum of OXD (Mashraqui et al, 2003;El-Sayed et al, 2012;Arora et al, 2013;Oliveira et al, 2012;Fuloria et al, 2009;Kashaw et al, 2010;Zarghi et al, 2005) The IR spectra for all OXD performed by the KBr disc method. FT-IR spectra for all studied compounds were measured as KBr disks using FT-IR 8400S SHIMADZU (Japan), in the technique Laboratory of Pharmaceutical Chemistry Department / College of Pharmacy / Basra University.…”

Synthesis and biological evaluation of a series of 1,4-disubstituted 1,2,3-triazole derivatives as possible antimicrobial agents

“…Recently, piperazine bearing 1,2,3-triaozles are reported as potential anticancer, antiproliferative agents [16,17]. On the other hand, 1,3,4-oxadiazole is also a significant heterocycle that exhibit activities such as antimicrobial [18][19][20][21][22][23], anti-inflammatory, analgesic [24,25], antitubercular [26][27][28], anticonvulsant [29], antidiabetic [30] and anticancer [31]. In view of these findings and in continuation of our earlier attempts for the design and synthesis of novel azole containing heterocycles as possible antimicrobial and anti-inflammatory agents [32,33], we report herein the synthesis and antimicrobial evaluation of a series of piperazine carboxamide and 1,3,4-oxadiazole derivatives of 1-(2,6-difluorobenzyl)-1H-1,2,3-triazole-4-carboxylic acid as possible antimicrobial agents.…”