3774-99-0Relevant articles and documents
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Andreasch
, p. 73 (1889)
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A synthesis of phosphorylated 2,4-dioxothiazolidine derivatives
Yavari, Issa,Sanaeishoar, Tayebeh,Piltan, Mohammad,Azad, Leila
, p. 1612 - 1619 (2011)
The zwitterionic 1:1 intermediates generated from trialkyl phosphites and dialkyl acetylenedicarboxylates are trapped by 2,4-thiazolidinedione and 5-arylidene-2,4-thiazolidinediones to produce dialkyl 2-(2,4-dioxothiazolidin-3- yl)-3-(dialkoxyphosphoryl)
Synthesis, α-glucosidase and α-amylase inhibitory activities, acute toxicity and molecular docking studies of thiazolidine-2,4-diones derivatives
Fettach, Saad,Thari, Fatima Zahra,Hafidi, Zakaria,Tachallait, Hamza,Karrouchi, Khalid,El achouri, Mohammed,Cherrah, Yahia,Sefrioui, Hassan,Bougrin, Khalid,Faouzi, My El Abbes
, (2021/04/26)
In the present study, a series of thiazolidine-2,4-diones derivatives (3a–3e) and (4a–4e) were synthesized and characterized by 1H NMR, 13C NMR and ESI-MS spectrometry. All compounds were screened for their α-glucosidase and α-amylase inhibitory activities. In vitro biological investigations revealed that most of compounds were active against α-glucosidase with IC50 values in the range of 43.85 ± 1.06 to 380.10 ± 1.02 μM, and α-amylase with IC50 in the range of 18.19 ± 0.11 to 208.10 ± 1.80 μM. Some of the tested compounds were found to be more potent inhibitors than the clinical drug Acarbose (IC50glucosidase = 97.12 ± 0.35 μM and IC50amylase = 2.97 ± 0.004 μM). The lead compounds were evaluated for their acute toxicity on Swiss mice and found to be completely non-toxic with LD > 2000 mg/kg BW. Furthermore, the Structure–activity relationship (SAR) and the binding interactions of all compounds with the active site of α-glucosidase and α-amylase were confirmed through molecular docking and stabilizing energy calculations. This study has identified the inhibitory potential a new class of synthesized thiazolidine-2,4-diones in controlling both hyperglycemia and type 2 diabetes mellitus. Furthermore, the theoretical binding mode of the target molecules was evaluated by molecular docking studies against the 3D Crystal Structure of human pancreatic α-amylase (PDB ID: 1B2Y) and α-glucosidase (PDB ID: 3W37) Communicated by Ramaswamy H. Sarma.
Development of Novel Mitochondrial Pyruvate Carrier Inhibitors to Treat Hair Loss
Liu, Xiaoguang,Flores, Aimee A.,Situ, Lisa,Gu, Wen,Ding, Hui,Christofk, Heather R.,Lowry, William E.,Jung, Michael E.
, p. 2046 - 2063 (2021/02/16)
Herein, we report the synthesis and evaluation of novel analogues of UK-5099 both in vitro and in vivo for the development of mitochondrial pyruvate carrier (MPC) inhibitors to treat hair loss. A comprehensive understanding of the structure-activity relationship was obtained by varying four positions of the hit compound, namely, the alkyl group on the N1 position, substituents on the indole core, various aromatic and heteroaromatic core structures, and various Michael acceptors. The major discovery was that the inhibitors with a 3,5-bis(trifluoromethyl)benzyl group at the N1 position were shown to have much better activity than JXL001 (UK-5099) to increase cellular lactate production. Additionally, analogue JXL069, possessing a 7-azaindole heterocycle, was also shown to have significant MPC inhibition activity, which further increases the chemical space for drug design. Finally, more than 10 analogues were tested on shaved mice by topical treatment and promoted obvious hair growth on mice.
