7410-53-9Relevant academic research and scientific papers
Ruthenium(II) mediated C-H activation of substituted acetophenone thiosemicarbazones: Synthesis, structural characterization, luminescence and electrochemical properties
Prabhu, Rupesh Narayana,Pandiarajan, Devaraj,Ramesh, Rengan
, p. 4170 - 4177 (2009)
Treatment of [RuHCl(CO)(AsPh3)3] with 4′-substituted acetophenone thiosemicarbazone derivatives in methanol under reflux afford a series of air stable new ruthenium(II) cyclometalated complexes containing thiosemicarbazone of general
Microwave-assisted synthesis and biological evaluation of new thiazolylhydrazone derivatives as tyrosinase inhibitors and antioxidants
Fu, Xi,Liu, Jinbing,Yan, Yangting,Zhang, Yu
, (2020/02/04)
In this work, we have synthesized a series of 2-thiazolylhydrazone derivatives (1–27) and investigated their biological activities as tyrosinase inhibitors and antioxidants. Some compounds showed potent tyrosinase inhibitory activities and 4-(2-(2-(1-(4-Aminophenyl)ethylidene)-hydrazinyl)thiazol-4-yl) phenol (26) showed more potent inhibitory effect than the standard tyrosinase inhibitor kojic acid (IC50: 9.8 μM vs. 23.6 μM). Compounds 2, 14, and 26 exhibited high antioxidant activities in 2,2-diphenyl-1-picrylhydrazyl (DPPH) and 2,2′-azinobis (3-ethylbenzothiazoline-6-sulfonic acid) (ABTS) assays. The structure–activity relationship (SAR) indicated that the substitutions of bromine, hydroxyl group, and amino groups cause great effect to the inhibition effect against tyrosinase. The mechanism and kinetic studies demonstrated that the inhibitory effect of compound 26 on the tyrosinase by acting as the reversible and uncompetitive inhibitor. Docking studies suggests that compound 26 interacts strongly with mushroom tyrosinase via hydrogen bonding.
Structure-based modification of 3-/4-aminoacetophenones giving a profound change of activity on tyrosinase: From potent activators to highly efficient inhibitors
You, Ao,Zhou, Jie,Song, Senchuan,Zhu, Guoxun,Song, Huacan,Yi, Wei
, p. 255 - 262 (2015/03/04)
In this study, we developed 3-/4-aminoacetophenones and their structure-based 3-/4-aminophenylethylidenethiosemicarbazide derivatives, respectively, as novel tyrosinase activators and inhibitors. Notably, all the obtained thiosemicarbazones displayed more potent tyrosinase inhibitory activities than kojic acid. Especially, compound 7k was found to be the most active tyrosinase inhibitor with IC50 value of 0.291 1/4M. The structure-activity relationships (SARs) analysis showed that: (1) the amine group was absolutely necessarily for determining the tyrosinase activation activity; (2) the introduction of thiosemicarbazide group played a very vital role in transforming tyrosinase activators into tyrosinase inhibitors; (3) the phenylethylenethiosemicarbazide moiety was crucial for determining the tyrosinase inhibitory activity; (4) the type of acyl group had no obvious effect on the inhibitory activity; (5) the position of amide substituent on the phenyl ring influenced the tyrosinase inhibitory potency. Moreover, the inhibition mechanism and inhibition kinetics study revealed that compound 7k was reversible and non-competitive inhibitor, and compound 8h was reversible and competitive-uncompetitive mixed-II type inhibitor.
Design, synthesis and biological evaluation of new aryl thiosemicarbazone as antichagasic candidates
Blau, Lorena,Menegon, Renato Farina,Trossini, Gustavo H. G.,Molino, Jo?o Vitor Dutra,Vital, Drielli Gomes,Cicarelli, Regina Maria Barretto,Passerini, Gabriela Duó,Bosquesi, Priscila Longhin,Chin, Chung Man
, p. 142 - 151 (2013/10/01)
The present work reports on the synthesis, biological assaying and docking studies of a series of 12 aryl thiosemicarbazones, which were planned to act over two main enzymes, cruzain and trypanothione reductase. These enzymes are used as targets of trypanocidal activity in Chagas disease control with a minimal mutagenic profile. Three p-nitroaromatic thiosemicarbazones showed high activity against Trypanosoma cruzi in in vitro assays (IC50 57 μM), and no mutagenic profile was observed in micronucleous tests. Although the in vitro inhibition test showed that 10-μM doses of eight compounds inhibited cruzain activity, no correlation was found between cruzain inhibition and trypanocidal activity.
A new type of synthesis of 1,2,3- Thiadiazole and 1,2,3-diazaphosphole derivatives via-hurd-mori cyclization
Hosny, Mona A.,El-Sayed, Taghreed H.,El-Sawi, Emtithal A.
experimental part, p. 1276 - 1287 (2012/06/01)
We present a short and efficient synthesis of the title compounds starting with cheap and readily available camphor and derivatives of acetophenone. The optimized sequence allows the large-scale preparation of this new type of synthesis in a few steps. Ne
Evaluation of semicarbazones for anticonvulsant and sedative-hypnotic properties
Pandeya,Aggarwal,Jain
, p. 300 - 302 (2007/10/03)
A series of semicarbazones and thiosemicarbazones were synthesized and evaluated for anti-convulsant activity. Some compounds provided significant protection against Maximal Electroshock (MES) and subcutaneous strychnine induced seizures. Compound 1 was the most active in the series with activity in a dose of 30 mg/kg in the strychnine seizure pattern test and an ED50 of 10 mg/kg in the MES test. Hence it could serve as a prototype molecule for future development. Also compounds with a p-nitrophenyl substitution in place of the amino hydrogen of semicarbazone moiety showed activity in a dose of 30 mg/kg and an ED50 of 83 mg/kg in the MES test.
