Synthesis and Antimycobacterial Activity of Novel Thiadiazolylhydrazones of 1‐Substituted Indole‐3‐carboxaldehydes |
| |
| Authors: | Kamaleddin Haj Mohammad Ebrahim Tehrani Vida Mashayekhi Parisa Azerang Soroush Sardari Farzad Kobarfard Kobra Rostamizadeh |
| |
| Affiliation: | 1. Department of Medicinal Chemistry, School of Pharmacy, Zanjan University of Medical Sciences, , Gavazang Road, Zanjan 45139‐56184, Iran;2. Drug Design and Bioinformatics Unit, Department of Medical Biotechnology, Biotechnology Research Center, Pasteur Institute, , Tehran 13164, Iran;3. Department of Medicinal Chemistry, School of Pharmacy, Shahid Beheshti University of Medical Sciences, Vali Asr Ave. Niayesh Junction, , Tehran 14155‐6153, Iran;4. Phytochemistry Research Center, Shahid Beheshti University of Medical Sciences, , Vali Asr Ave. Niayesh Junction, Tehran 14155‐6153, Iran;5. Pharmaceutical Nanotechnology Research Center, Zanjan University of Medical Sciences, , Gavazang Road, Zanjan 45139‐56184, Iran |
| |
| Abstract: | A series of novel thiocarbohydrazones of substituted indoles and their corresponding thiadiazole derivatives were prepared, and their structures were confirmed by different analytical and spectroscopic methods. The derivatives were prepared by a sequential synthetic strategy including substitution at N‐1 position of indole ring by various aliphatic and benzylic substituents, followed by condensation with thiocarbohydrazide, and finally cyclization by triethyl orthoformate. The derivatives were tested for their antimycobacterial activity against Mycobacterium bovis BCG, and the results revealed that among the synthesized compounds, thiadiazole derivatives 4e , 4f , 4n , 4p , 4q , and 4t exhibited the highest activity with IC50 value of 3.91 μg/mL. The results indicate that the thiadiazole moiety plays a vital role in exerting antimycobacterial activity. |
| |
| Keywords: | antimycobacterial indole structure– activity relationship thiadiazolylhydrazone thiosemicarbazones |
|
|
