14152-97-7Relevant articles and documents
Synthesis and Antimicrobial Activities of 1,2,4-Thiadiazolidin-3-thione Hydrochlorides
Mangte, Anvita D.,Nayak, Riddhi A.
, p. 77 - 83 (2022/03/27)
Synthesis of N-glucosyl/lactosyl/maltosyl-1,2,4-thiadizolidin-3-thione hydrochlorides by the reaction of N-phenyl-S-chloroisothiocarbamoyl chloride and N-glucosyl/lactosyl/maltosyl thiocarbamides is reported. The simple isolation method with good yields under mild condition is applicable for the present protocol. All the newly synthesized thiadiazolidin-3-thiones exhibit moderate to good antimicrobial activities against a variety of pathogen
Matrix metalloproteinase-12 inhibitors: synthesis, structure-activity relationships and intestinal absorption of novel sugar-based biphenylsulfonamide carboxylates
Cuffaro, Doretta,Camodeca, Caterina,D'Andrea, Felicia,Piragine, Eugenia,Testai, Lara,Calderone, Vincenzo,Orlandini, Elisabetta,Nuti, Elisa,Rossello, Armando
, p. 5804 - 5815 (2018/11/23)
MMP-12 is a validated target in pulmonary and cardiovascular diseases. The principal obstacles to clinical development of MMP-12 inhibitors are an inadequate selectivity for the target enzyme and a poor water solubility, with consequent poor oral bioavailability. We recently reported a new class of sugar-based arylsulfonamide carboxylates with a nanomolar activity for MMP-12, a good selectivity and an improved water solubility. In this study, we designed and synthesized new derivatives to characterize the structure-activity relationship (SAR) within this class of glycoconjugate inhibitors. All the new derivatives were tested on human recombinant MMP-12 and MMP-9 in order to evaluate their affinity and the selectivity for the target enzyme. Among them, the four most promising compounds were selected to assess their intestinal permeability using an ex vivo everted gut sac model. Given the high polarity and structural similarity to glucose, compound 3 was demonstrated to cross the intestinal membrane by using the facilitative GLUT2 transport.
Synthesis and evaluation of in?vivo antioxidant, in?vitro antibacterial, MRSA and antifungal activity of novel substituted isatin N-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)thiosemicarbazones
Thanh, Nguyen Dinh,Giang, Nguyen Thi Kim,Quyen, Tran Ha,Huong, Doan Thi,Toan, Vu Ngoc
, p. 532 - 543 (2016/08/12)
Some new isatin N-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)thiosemicarbazones 4a-t with different substituents at 1-, 5- and 7-positions of isatin ring have been synthesized by reaction of N-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)thiosemicarbazide 2 with corresponding isatins 3a-t. Compounds 4a-t were evaluated in?vivo for antioxidant activity and in?vitro for anti-microorganism activities. The MIC values were found for Gram positive bacteria (MIC?=?1.56–6.25?μM), for Gram negative bacteria (MIC?=?12.5?μM), and for fungi Aspergillus niger (MIC?=?3.12–12.5?μM), Fusarium oxysporum (MIC?=?6.25–12.5?μM) and Saccharomyces cerevisiae (MIC?=?6.25–12.5?μM). Regarding the antioxidant activity, the SOD, GHS-Px and catalase activities of 4c-i and 4m-r were MIC?=?10.57–10.85, 0.27–0.93 and 345.45–399.75 unit/mg protein, respectively. Compounds 4e-h had MIC values of 0.78, 1.56, and 3.12?μM for three clinical MRSA isolates. Compound 4e showed the selective cytotoxic effects against some cancer (LU-1, HepG2, MCF7, P338, SW480, KB) cell lines and normal fibroblast cell line NIH/3T3.