315239-25-9Relevant academic research and scientific papers
Three-Component Synthesis of 2-Substituted Thiobenzoazoles Using Tetramethyl Thiuram Monosulfide (TMTM) as Thiocarbonyl Surrogate
Wang, Xi,Wu, Chun-Yan,Li, Yue-Sheng,Dong, Zhi-Bing
, p. 6770 - 6775 (2020/11/23)
A metal-free synthesis of 2-benzyl/allyl-substituted thiobenzoazoles was developed starting from tetramethyl thiuram monosulfide (TMTM) which served as thiocarbonyl surrogate. By using 2-aminophenols (or 2-aminothiophenols, or 1,2-phenylenediamines) and TMTM as starting materials, 2-mercaptobenzoazoles could be synthesized efficiently. The subsequent C–S bond formation with benzyl/allyl halides gave the final products (2-benzyl/allyl-substituted thiobenzoazoles) with good to excellent yields. The metal-free conditions, inexpensive and easily available starting materials, and broad substrate scope are the advantageous features of this protocol.
One-Pot Synthesis of 2-Benzyl/2-Allyl-Substituted Thiobenzoazoles Using Transition-Metal-Free Conditions in Water
Zhang, Shi-Bo,Liu, Xing,Gao, Ming-Yuan,Dong, Zhi-Bing
, p. 14933 - 14941 (2019/01/04)
A transition-metal-free protocol for the one-pot synthesis of 2-benzyl/2-allyl-substituted thiobenzoazoles in water was developed. The cyclization of 2-aminothiophenols, 2-aminophenols, and 1,2-phenylenediamines with tetramethylthiuram disulfide (TMTD) gave mercapto benzoheterocycles, and the subsequent C-S coupling with benzyl or allyl halides furnished the desired products in good to excellent yields. This method features transition-metal-free conditions with water as a solvent, an easy performance, mild reaction conditions, a wide substrate scope, and good to excellent yields, thus paving an efficient and useful way to establish a library of potentially active drug molecules.
Acylhydrazone derivatives as potential anticancer agents: Synthesis, bio-evaluation and mechanism of action
Yu, Xifang,Shi, Liqiao,Ke, Shaoyong
, p. 5772 - 5776 (2015/11/24)
A series of novel acylhydrazone derivatives were designed, synthesized and evaluated for their potential cytotoxic effects against human cancer cell lines. The preliminary results indicated that some of the obtained compounds (such as 8b, 13c) exhibited good to moderate cytotoxic activities against human HepG2, Huh-7, and BCG-823 cell lines. Especially, compounds 8c and 8e presented obviously selective cytotoxic activities against Huh-7 in vitro (8c, IC50 = 7.74 ± 2.18 μg/mL; 8e, IC50 = 4.46 ± 1.05 μg/mL) compared to 5-FU (IC50 = 10.41 ± 3.41 μg/mL). The highly potential compounds to induce apoptosis in HepG2 cells were analyzed by flow cytometry, and the apoptotic effects of compounds 8b and 13c were further evaluated using Annexin V-FITC/propidium iodide dual staining assay.
4-(Heteroarylaminomethyl)-N-(2-aminophenyl)-benzamides and their analogs as a novel class of histone deacetylase inhibitors
Frechette, Sylvie,Leit, Silvana,Woo, Soon Hyung,Lapointe, Guillaume,Jeannotte, Guillaume,Moradei, Oscar,Paquin, Isabelle,Bouchain, Giliane,Raeppel, Stephane,Gaudette, Frederic,Zhou, Nancy,Vaisburg, Arkadii,Fournel, Marielle,Yan, Pu Theresa,Trachy-Bourget, Marie-Claude,Kalita, Ann,Robert, Marie-France,Lu, Aihua,Rahil, Jubrail,Robert MacLeod,Besterman, Jeffrey M.,Li, Zuomei,Delorme, Daniel
, p. 1502 - 1506 (2008/09/19)
The synthesis and biological evaluation of a variety of 4-(heteroarylaminomethyl)-N-(2-aminophenyl)-benzamides and their analogs is described. Some of these compounds were shown to inhibit HDAC1 with IC50 values below the micromolar range, indu
