Design, synthesis, and biological evaluation of 1-(5-(benzylthio)-1,3,4-thiadiazol-2-yl)-3-phenylurea derivatives as anticancer agents

Synthesis of novel 2‐acetamide‐5‐phenylthio‐1,3,4‐thiadiazole‐containing phenyl urea derivatives as potential VEGFR‐2 inhibitors

“…The lead compounds N‐(5‐{[4‐(3‐phenylureido)phenyl]thio}‐1,3,4‐thiadiazol‐2‐yl)acetamide ( 9a–j ) were prepared through the synthetic route presented in Scheme 1. The intermediate compound 3 was synthesized [ 21 ] by the condensation reaction of thiosemicarbazide 1 and carbon disulfide 2 and converted to the N‐(5‐mercapto‐1,3,4‐thiadiazole‐2‐yl)acetamide 4 in the presence of acetic anhydride. The yield was 90%.…”

“…The intermediate compound 3 was synthesized through the reported previous method. [ 21 ] A mixture of thiosemicarbazide 1 (1 g), sodium carbonate (0.96 g), and carbon disulfide 2 (2 ml) in absolute ethanol (7 ml) was heated under reflux for 8 h. After solvent evaporation, the crude was dissolved in HCl (6 M), the resulting solid was filtered and washed with water.…”

The Different Facets of Triclocarban: A Review

“…In this review, we will focus our attention on TCC, a small molecule also named 3,4,4′-trichlorocarbanilide that belongs to the class of diarylures or bis-arylureas. This interesting class of compounds has been recently reviewed by our research group as anticancer agents [ 6 ], and then, due to their multiple actions [ 7 , 8 , 9 , 10 , 11 ], they were also suggested for repositioning to antimicrobial agents and/or potential treatment for new pandemics, as COVID-19 [ 12 , 13 ]. TCC is a common ingredient in personal care products, especially dermal cleaning products such as antibacterial bar/Liquid soaps, body lotions, deodorants, detergents, medical disinfectants, aftershave soaps, hand sanitizers, toothpaste, handwash and mouthwash, body washes, cleansing lotions, baby teethers and wipes for its sanitizing properties and detergents [ 14 , 15 , 16 , 17 ].…”

“…In this review, we will focus our attention on TCC, a small molecule also named 3,4,4trichlorocarbanilide that belongs to the class of diarylures or bis-arylureas. This interesting class of compounds has been recently reviewed by our research group as anticancer agents [6], and then, due to their multiple actions [7][8][9][10][11], they were also suggested for Since its advent in 1957 [22], TCC has been produced and used on a large scale, and its consumption from personal care products in the United States reached 500,000-1,000,000 pounds per year [23]. The 2013-2014 National Health and Nutrition Examination Survey showed that 36.9% of the urine samples in the United States (U.S.) contained TCC [24].…”

Design, Synthesis and Anticancer Activity of a New Series of N-aryl-N′-[4-(pyridin-2-ylmethoxy)benzyl]urea Derivatives

“…Among the currently clinically used multi-target kinase inhibitors, sorafenib and its derivative regorafenib with a diaryl urea structure were the prime representatives, because they had excellent inhibitory effects on a variety of solid tumors [14,15]. In sorafenib, the rigidity of the diaryl urea structure causes the molecular rotation to not happen freely, thus the poor solubility of sorafenib results in low bioavailability [16,17]. This study is based on the structure of sorafenib and the retention of the urea scaffold, in which, in order to enhance the molecular flexibility, a carbon atom was inserted into the diaryl urea structure, and the basic urea scaffold was changed to an N-aryl-N'-benzylurea scaffold.…”