A Mini Library of Novel Triazolothiadiazepinylindole Analogues: Synthesis, Antioxidant and Antimicrobial Evaluations

Abstract

A new series of novel triazolothiadiazepinylindole analogues were synthesized with an aim to examine possible antioxidant and antimicrobial activities. The titled compounds (3a–z) were obtained in good yield by reacting 5-(5-substituted-3-phenyl-1H-indol-2-yl)-4-amino-4H-1,2,4-triazole-3-thiols 1a–c with 3-(2,5-disubstituted-1H-indol-3-yl)-1(4-substituted phenyl)prop-2-en-1-ones 2a–i. All the newly synthesized compounds were characterized by IR, 1H NMR, mass spectroscopic and analytical data. The synthesized analogues were tested for antioxidant and antimicrobial potency. Among the tested compounds 3a–c and 3j–l have shown very promising free radical scavenging activity and total antioxidant capacity. Compounds 3d–f, 3m–o, and 3s–z have shown excellent ferric reducing antioxidant activity. An outstanding antimicrobial activity is observed with compounds 3a–c and 3j–l.

Antibacterial and antitubercular evaluation of dihydronaphthalenone‐indole hybrid analogs

“…On other hand, structurally diverse indole appended analogs have been claimed to exhibit various biological activities, including antimicrobial, antiviral, anti‐inflammatory, analgesic, and CNS depressant properties . Noteworthily, previous research in our laboratory led to the discovery of a series of novel indole analogs possessing excellent antimicrobial, antioxidant, and anticancer activities . Most interestingly, more recent literature survey has revealed that the incorporation of a thiophene moiety can significantly enhance the antimicrobial activity of candidate compounds …”

Design, synthesis, and characterization of novel pyrimidines bearing indole as antimicrobial agents

“…According to the previously mentioned benefits, the combination of indole and pyrimidine moieties will greatly enhance the biological activity of the compounds they present. As reviewed from earlier literature reports, such compounds containing indole and pyrimidine were found to be potent as antitumor, antimicrobial, and antioxidant agents . Based on these previous facts and in continuation of our work in the field of synthesis of organic compounds with high biological activity, here, we described a method for introducing pyrimidine moiety in two positions of indole, hopefully improving the potency of the synthesized compounds.…”

Synthesis, crystal structure investigation, DFT studies and DPPH radical scavenging activity of 1-(furan-2-ylmethyl)-2,4,5-triphenyl- 1H -imidazole derivatives

“…Imidazole ring structure display a range of pharmaceutical actions [1][2][3] and play a significant role in biochemical processes. Imidazole derivatives have diverse biological activities such as anti-inflammatory [4], anti-allergic [5], analgesic [6], antibacterial [7], anti-oxidant [8], antitumor [9], Heme oxygenase-1 (HO-1) and Heme oxygenase-2 (HO-2) inhibitors and their cytotoxic activity [10], FAK inhibitors with anticancer activity [11], light-sensitive materials in photography are known as inhibitors, fungicides and herbicides [12], inhibitors of p38 MAP kinase [13], A recent report indicates that imidazoles are potent inhibitors of protein-protein interactions [14], plant growth regulators and therapeutic agents [15], The imidazole ring's biocompatibility provides a scaffold for biomimetic applications [16], DNA sequence targets for alkylating DNA and suppressing gene expression [17], Inhibit enzymes and kill fungal pathogens, inhibition of post-translational farnesylation, which is a key step for Ras proteins that influence cancer proliferation, a naturally occurring imidazole in the body is involved with everyday functions: sleeping, eating, drinking, and cognitive processes, antagonists for histamine may provide treatments for Alzheimer's disease and depression [18], Physicochemical behavior [19], dye super sensitized star cells (DSSCs) [20][21], nonlinear optics (NLO) [22][23][24][25] and organic light emitting diodes (OLED) [26][27][28][29]. Vibrational spectroscopy is a valuable tool for the elucidation of molecular structure and gives a dynamical image of the molecule.…”