Synthesis and Antimicrobial Activity of Polyfunctionally Substituted Heterocyclic Compounds Derived from 5‐Cinnamoylamino‐2‐Cyanomethyl‐1,3,4‐Thiadiazole

Abstract

in Wiley Online Library (wileyonlinelibrary.com).Cinnamoyl isothiocyanate 1 was reacted with 2-cyanoethanoic acid hydrazide 2 to afford 1-cyanoacetyl-4-substituted thiosemicarbazide 3, which on treatment with a mixture of glacial acetic acid and acetic anhydride gave the desired 5-cinnamoylamino-2-cyanomethyl-1,3,4-thiadiazole 4. Compound 4 was subjected to react with aromatic aldehydes, phenylisothiocyanate, carbon disulphide, and arylidene malononitrile to give coumarin 5, thiazolidines 8,9, and 1,3,4-thiadiazolo[3,2-a]pyridine 13 derivatives. The structures of all synthesized compounds were ascertained by spectral and analytical data. Antimicrobial activity of some of prepared compounds was investigated, and compounds 7, 8 were found to exhibit the highest strength.Scheme 3. Synthesis of the 1,3,4-thiadiazole derivatives 7 and 8.Scheme 2. Synthesis of 2-(2-Oxo-2H-chromen-3-yl)-5-cinnamoylamino-1,3,4-thiadiazole.

Combined 3D-QSAR and Molecular Docking Analysis of Thienopyrimidine Derivatives as Staphylococcus aureus Inhibitors

“…The inhibitors molecules induce cell death by trapping the gyrase DNA complex, inducing oxidative damage, and preventing DNA replication. 4 Thienopyrimidines represent important chemical class in drug discovery due to vast range of pharmacological properties including antiallergic, 5 antiviral, [6][7] anti-in-flammatory, [8][9][10][11][12] analgesic, [13][14] antispasmodic, antibacterial, [14][15] antifungal, 16 antimicrobial, [17][18][19][20][21] antidiabetic, 22 antioxidant, 23 antitumor, [24][25][26][27][28][29] antipsychotic 30 etc. This useful activity of thienopyrimidine generates our interest in developing a tool for screening novel thienopyrimidine analogs are promise antibacterial agent.…”

Coumarin‐containing hybrids and their antibacterial activities

“…The coumarin–thiadiazole hybrid 29 (inhibition zone: 15.2–17.1 mm), which was also less potent than the references ampicillin (inhibition zone: 23.8–27.4 mm) and ciprofloxacin (inhibition zone: 20.6–23.0 mm), still needs to be modified. [ 73 ]…”

Design, Spectroscopy, and Assessment of Cholinesterase Inhibition and Antimicrobial Activities of Novel Coumarin–Thiadiazole Hybrids

“…Therefore, in this work we report the isolation and structural characterization of another series of coumarin and 1,3,4-thiadiazole conjugates, wherein the link between coumarin and thiadiazole moieties is established at the C3 and C15 positions, respectively ( Figure 1 ). A literature search revealed the previous isolation of only a limited number of similar hybrids with only a thiadiazole hybrid, derived from an unsubstituted coumarin 3-carboxylic acid, was reported to possess antimicrobial [ 34 ], analgesic, and antiprotolytic activities [ 35 ] and a structurally similar thiol-substituted derivative of that compound was reported to possess antitumor activity [ 36 ]. Regardless of the structural similarities, the synthetic protocols applied therein were notably different to those established by our group.…”