108354-78-5Relevant articles and documents
Design and synthesis of thiourea derivatives with sulfur-containing heterocyclic scaffolds as potential tyrosinase inhibitors
Liu, Pingping,Shu, Chen,Liu, Lujie,Huang, Qingchun,Peng, Yanqing
, p. 1866 - 1871 (2016)
Tyrosinase is a key enzyme during the production of melanins in plants and animals. A class of novel N-aryl-N′-substituted phenylthiourea derivatives (3a-i, 6a-k) were designed, synthesized and their inhibitory effects on the diphenolase activity of mushroom tyrosinase were evaluated. The results showed some 4,5,6,7-tetrahydro-2-[[(phenylamino)thioxomethyl]amino]-benzo[b]thiophene-3-carboxylic acid derivatives (3a-i) exhibited moderate inhibitory potency on diphenolase activity of tyrosinase. When the scaffold of 4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxylic acid was replaced with 2-(1,3,4-thiadiazol-2-yl)thio acetic acid, the inhibitory activity of compounds (6a-k) against tyrosinase was improved obviously; especially, the inhibitory activity of compound 6h (IC50 = 6.13 μM) is significantly higher than kojic acid (IC50 = 33.3 μM). Moreover, the analysis on inhibition mechanism revealed that compound 6h might plays the role as a noncompetitive inhibitor.
Physicochemical properties of novel methyl 2-{(E)-[(2-hydroxynaphthalen-1-yl)methylidene] amino}-4,5,6,7-tetrahydro-1-benzothiophene-3-carboxylate as turn-off fluorometric chemosensor for detection Fe3 + ion
Khan, Salman A.,Asiri, Abdullah M.
, p. 85 - 90 (2017)
Schiff base (HATC) was synthesized by the reaction of 2-hydroxy-1-naphthaldehyde with methyl 2-amino-4,5,6,7-tetrahydro-1-benzothiophene-3-carboxylate. Structure of HATC was confirmed by the EI-MA, IR, 1H NMR, 13C NMR and elemental analysis. Photophysical and physicochemical studies of the HATC such as oscillator strength, extinction coefficient, transition dipole moment, fluorescence quantum yield and stokes shift was investigated in different solvents on the basis of polarities. The observed bathochromic absorbance, emission band and different parameter's on changing the polarity of the solvents. HATC interact with the various metal ions were also studied by spectrofluorophotometer. Schiff base used as on- off type fluorescent chemosensor for sensitive and selective detection of Fe3 + ion. Complexation stoichiometry and mechanism of quenching were determined from Benesi–Hildebrand and Stern-Volmer plot.
Microwave-assisted synthesis of 2-aminothiophene derivatives via improved gewald reactions
Ruan, Bankang,Zhang, Zhiyan,Huang, Lei,Xu, Chao,Li, Luolan
, p. 2007 - 2018 (2021/09/29)
In this paper, a new and efficient method was developed to prepare 2-aminothiophene derivatives through improved Gewald reaction. Thirty-one final products were synthesized under microwave radiation for 30 min with 57%-95% isolated yields. All the product
Room temperature synthesis and characterization of novel Bi(III) complex with 2-amino-3-carbomethoxy-4,5,6,7-tetrahydrobenzo[b]thiophene as potential antimicrobial agent
Djeukoua, Sorel Kamal Dimo,Doungmo, Giscard,Ekom, Steve Endeguele,Fondjo, Emmanuel Sopbué,Kuiate, Jules Roger,Siéwé, Désire André,Simon, Peter F. W.,Tamokou, Jean-de-Dieu,Tsopmo, Appolinnaire,Walters, Mallory E.
, p. 203 - 211 (2020/03/30)
A novel bismuth(III) complex with 2-amino-3-carbomethoxy-4,5,6,7-tetrahydrobenzo[b]thiophene (ACTT) as a ligand have been synthesized. The novel complex was characterized on the basis of its IR, NMR, elemental analysis and MS spectral data. It was found that the ligand behaves as a monodentate chelating agent and bonds to the metal ion through the nitrogen atom of the amino group to form the [BiIII(ACTT)6]Cl3 complex. The new complex compound displayed significant antimicrobial activity (MIC = 8-32 μg/mL) against Bacillus subtilis, Staphylococcus aureus, Escherichia coli, Pseudomonas aeruginosa, Shigella flexneri, Candida albicans, Candida tropicalis and Cryptococcus neoformans.
In vitro and in vivo evaluation of the antimalarial MMV665831 and structural analogs
Carlier, Paul R.,Ding, Sha,Fike, Katherine R.,Klemba, Michael
supporting information, (2020/07/03)
Antimalarial candidates possessing novel mechanisms of action are needed to control drug resistant Plasmodium falciparum. We were drawn to Malaria Box compound 1 (MMV665831) by virtue of its excellent in vitro potency, and twelve analogs were prepared to probe its structure–activity relationship. Modulation of the diethyl amino group was fruitful, producing compound 25, which was twice as potent as 1 against cultured parasites. Efforts were made to modify the phenolic Mannich base functionality of 1, to prevent formation of a reactive quinone methide. Homologated analog 28 had reduced potency relative to 1, but still inhibited growth with EC50 ≤ 200 nM. Thus, the antimalarial activity of 1 does not derive from quinone methide formation. Chemical stability studies on dimethyl analog 2 showed remarkable hydrolytic stability of both the phenolic Mannich base and ethyl ester moieties, and 1 was evaluated for in vivo efficacy in P. berghei-infected mice (40 mg/kg, oral). Unfortunately, no reduction in parasitemia was seen relative to control. These results are discussed in the context of measured plasma and hepatocyte stabilities, with reference to structurally-related, orally-efficacious antimalarials.
