1,3-Benzothiazoles as Antimicrobial Agents

Abstract

Starting from 2‐amino‐1,3‐mercaptobenzothiazoles recently reported (1a, 1b, 1c, 1d, 1e, 1f, 1g, 1h), a series of the corresponding 2‐mercapto‐1,3‐benzothiazole isosters (2a, 2b, 2c, 2d, 2e, 2f, 2g, 2h) were screened for their in vitro antibacterial and antifungal activities. Results underline that the presence of the mercapto moiety at the 2‐position of the heterocyclic nucleus is crucial for activity against bacteria. The biological screening against Candida spp. identified commercial 2f as the most promising compound as antifungal against Candida albicans and tropicalis. Molecular modeling studies supported these results. Then, to enlarge structure‐activity relationship (SAR) studies on series 1, newly synthesized compounds (1k, 1l, 1m, 1n, 1o, 1p) were reported. All the compounds belonging to this series and bearing a bulky substituent at the 6‐position of the aryl moiety showed high antifungal activity.

Importance of Fluorine in Benzazole Compounds

“…Moreover, the benzothiazole core is a widespread scaffold that has been extensively studied [ 54 , 55 , 56 , 57 , 58 , 59 ] and many derivatives are found to be antimicrobial [ 49 , 60 , 61 , 62 , 63 , 64 , 65 , 66 , 67 , 68 , 69 , 70 , 71 , 72 , 73 , 74 ], anticancer [ 75 , 76 , 77 , 78 , 79 , 80 , 81 , 82 , 83 , 84 , 85 , 86 , 87 , 88 , 89 , 90 , 91 ], anti-Alzheimer’s [ 92 , 93 ], anti-inflammatory [ 94 , 95 , 96 ], anti-HIV [ 97 , 98 , 99 ] anticonvulsant [ 100 , 101 , 102 ], antioxidant [ 39 , 103 ], anti-tuberculosis [ 104 ...…”

Modern Approaches to the Synthesis and Transformations of Practically Valuable Benzothiazole Derivatives

“…2-Aminobenzothiazoles demonstrate high antiviral activity [ 6 , 7 , 8 , 9 , 10 , 11 , 12 , 13 , 14 ], which is especially important in this period of global COVID-19 pandemic. They also possess antimicrobial [ 14 , 15 , 16 , 17 , 18 , 19 , 20 ], antioxidant [ 20 ], anti-inflammatory [ 21 , 22 , 23 , 24 ], analgesic [ 24 ], antidepressant [ 25 , 26 ], anticonvulsant [ 27 , 28 , 29 ], anti-diabetic [ 21 , 30 ], antitumor [ 31 , 32 , 33 , 34 , 35 ], antituberculosis [ 14 , 36 ] activity. Their derivatives show also antimalarial [ 37 , 38 ], insecticide [ 39 ] and herbicide effect [ 40 ].…”

Metal-free C–H mercaptalization of benzothiazoles and benzoxazoles using 1,3-propanedithiol as thiol source

“…2-Mercapto-5-nitro-1,3-benzoxazole and its derivatives shows strong anthelmintic activity [7]. 2-Mercapto-5-chloro-1,3-benzothiazoles possess antifungal activity against Candida albicans and Candida tropicalis [8] and 2-mercapto-1,3-benzothiol and its derivatives exhibit inhibitory effects against thyroid peroxidase [9].…”