42749-18-8Relevant articles and documents
Synthetic (E)-3-phenyl-5-(phenylamino)-2-styryl-1,3,4-thiadiazol-3-ium chloride derivatives as promising chemotherapy agents on cell lines infected with HTLV-1
Chaves, Otávio Augusto,De Oliveira, Thais Silva,Echevarria, Aurea,Echevarria-Lima, Juliana,Netto-Ferreira, José C.,Paiva, Rojane O.,Sousa-Pereira, Danilo
, (2020/06/29)
Synthesis of four compounds belonging to mesoionic class, (E)-3-phenyl-5-(phenylamino)-2-styryl-1,3,4-thiadiazol-3-ium chloride derivatives (5a-d) and their biological evaluation against MT2 and C92 cell lines infected with human T-cell lymphotropic virus type-1 (HTLV-1), which causes adult T-cell leukemia/lymphoma (ATLL), and non-infected cell lines (Jurkat) are reported. The compounds were obtained by convergent synthesis under microwave irradiation and the cytotoxicity was evaluated using 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) assays. Results showed IC50 values of all compounds in the range of 1.51-7.70 μM in HTLV-1-infected and non-infected cells. Furthermore, it was observed that 5b could induce necrosis after 24 h for Jurkat and MT2 cell lines. The experimental (fluorimetric method) and theoretical (molecular docking) results suggested that the mechanism of action for 5b could be related to its capacity to intercalate into DNA. Moreover, the preliminary pharmacokinetic profile of the studied compounds (5a-d) was obtained through human serum albumin (HSA) binding affinity using multiple spectroscopic techniques (circular dichroism, steady-state and time-resolved fluorescence), zeta potential and molecular docking calculations. The interaction HSA:5a-d is spontaneous and moderate (Ka ～ 104 M-1) via a ground-state association, without significantly perturbing both the secondary and surface structures of the albumin in the subdomain IIA (site I), indicating feasible biodistribution in the human bloodstream.
Synthesis of mesoionic 4-(para-substituted phenyl-5-2,4-dichlorophenyl)-1, 3-4-thiadiazolium-2-aminides by direct cyclization via acylation of thiosemicarbazides
Britto, Marcelo Moreira,Almeida, Tania Mara Grigolli,Leitao, Andrei,Donnici, Claudio Luis,Lopes, Miriam Tereza Paz,Montanari, Carlos Alberto
, p. 3359 - 3369 (2007/10/03)
The synthesis of ten novel mesoionic 4-[para-substituted (H, CH 3, OCH3, NO2, Cl, Br, OH, t-C4H 9, C6H5, C4H9) phenyl-5-2,4-dichlorophenyl]-1,3-4-thiadiazolium-2-aminides, as hydrochlorides, are described. The synthesis strategy utilized the corresponding para-substituted isothiocyanates as starting materials to obtain the thiosemicarbazides through reaction with phenylhydrazine (61-98%), which were then submitted to acylation with 2,4-dichloro benzoyl chloride and direct cyclization to generate the desired substituted mesoionic compounds in good yields (ca. 80%). Copyright Taylor & Francis Group, LLC.
