3774-99-0Relevant articles and documents
Synthesis of some new derivatives of thiazolopyrimidines and hydrolysis of its arylidene derivative
Nagarajaiah,Khazi, Imtiyaz Ahmed M.,Begum, Noor Shahina
, p. 467 - 479 (2015)
A new ammonium acetate-assisted, convenient and efficient procedure for the synthesis of arylidene derivatives of thiazolopyrimidine is described. The main advantages of this protocol is that it is economical, short reaction time, commonly available chemicals, and ease of isolation of products. In addition, a new series of thiazole-fused pyrimidines were synthesized and hydrolysis of one of its arylidene derivative studied. All the compounds were characterized by analytical and spectroscopic methods. Further, the structure of hydrolyzed product and two other compounds were confirmed by X-ray crystal structure analysis. The crystal structures are stabilized by intermolecular C-H.O, C-H.N, C-H.π and π.π weak interactions. The anti-microbial screening was done on the compounds in order to test their anti-bacterial and anti-fungal activities. [Figure not available: see fulltext.]
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)
Discovery of 2,4-thiazolidinedione-tethered coumarins as novel selective inhibitors for carbonic anhydrase IX and XII isoforms
Eldehna, Wagdy M.,Taghour, Mohammed S.,Al-Warhi, Tarfah,Nocentini, Alessio,Elbadawi, Mostafa M.,Mahdy, Hazem A.,Abdelrahman, Mohamed A.,Alotaibi, Ohoud J.,Aljaeed, Nada,Elimam, Diaaeldin M.,Afarinkia, Kamyar,Abdel-Aziz, Hatem A.,Supuran, Claudiu T.
, p. 531 - 541 (2022/01/13)
Different 2,4-thiazolidinedione-tethered coumarins 5a–b, 10a–n and 11a–d were synthesised and evaluated for their inhibitory action against the cancer-associated hCAs IX and XII, as well as the physiologically dominant hCAs I and II to explore their selec
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.
Synthesis and characterization of pine-cone derived carbon-based solid acid: A green and recoverable catalyst for the synthesis of pyra-no_pyrazole, amino-benzochromene, amidoalkyl naphthol and thiazoli-dinedione derivatives
Ghorbani, Fatemeh,Pourmousavi, Seied Ali,Kiyani, Hamzeh
, p. 66 - 81 (2021/03/19)
In this report, SO3H-functionalized Carbon nanoparticles (Pine-SO3H) with high acid density have been synthesized by the thermal treatment of sulfuric acid with Pine-Cone as carbon-based at 180oC in a sealed autoclave in a
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.
Synthesis, anticancer, and antibacterial studies of benzylidene bearing 5-substituted and 3,5-disubstituted-2,4-thiazolidinedione derivatives
Sethi, Navjot Singh,Prasad, Deo Nandan,Singh, Rajesh K.
, p. 369 - 379 (2021/03/03)
Aim: To develop novel compounds having potent anticancer and antibacterial activities. Background: Several studies have proved that benzylidene analogues of clinical 2,4-TZDs, such as troglitazone and ciglitazone, have more potent antiproliferative activity than their parent com-pounds. Literature studies also revealed that the attachment of more heterocyclic rings, containing nitrogen on 5th position of 2,4-TZD, can enhance the antimicrobial activity. Hence, attachment of various moieties on the benzylidene ring may produce safe and effective compounds in the future. Objective: The objective of the present study was to synthesize a set of novel benzylidene ring containing 5-and 3-substituted-2,4-thiazolidinedione derivatives and evaluate them for their anti-cancer and antibacterial activity. Method: The synthesized compounds were characterized by IR, NMR, mass, and elemental stud-ies. The in vitro cytotoxicity studies were performed for human breast cancer (MCF-7) and human lung cancer (A549) cells and HepG2 cell-line and compared to standard drug doxorubicin by MTT assay. Antimicrobial activity of the synthesized 2,4-thiazolidinediones derivatives was carried out using the cup plate method with slight modification. Result: The results obtained showed that TZ-5 and TZ-13 exhibited good antiproliferative activity against A549 cancer cell-line, whereas TZ-10 exhibited moderate antiproliferative activity against HepG2 cell-line when compared to standard drug doxorubicin. TZ-5 also exhibited reasonable activity against the MCF-7 cell-line with doxorubicin as standard. TZ-4, TZ-5, TZ-6, TZ-7, and TZ-16 exhibited remarkable antibacterial activity against Gram positive and moderate activity against Gram negative bacteria with the standard drug ciprofloxacin. Conclusion: Attachment of heterocyclic rings containing nitrogen as the hetero atom improves the anticancer and antimicrobial potential. Attachment of electronegative elements like halogens can also enhance the antimicrobial activity. Further structure modifications may lead to the development of more potent 2,4-TZD leads that can be evaluated for further advanced studies.
COMPOSITIONS AND METHODS FOR MODULATING HAIR GROWTH
-
Page/Page column 75-77, (2020/07/21)
The present disclosure relates to compounds that are capable of inhibiting the mitochondrial pyruvate carrier and promoting hair growth. The disclosure further relates to methods of promoting hair growth or treating conditions or disorders affecting hair growth, such as baldness or alopecia.
Ultrasound-assisted one-pot green synthesis of new N- substituted-5-arylidene-thiazolidine-2,4-dione-isoxazoline derivatives using NaCl/Oxone/Na3PO4 in aqueous media
álvarez, Eleuterio,Arshad, Suhana,Bougrin, Khalid,El Alaoui, Nour-Eddine,Karrouchi, Khalid,Tachallait, Hamza,Talha, Aicha,Thari, Fatima Zahra
, (2020/07/02)
A rapid and green method for the synthesis of novel N-thiazolidine-2,4-dione isoxazoline derivatives 5 from N-allyl-5-arylidenethiazolidine-2,4-diones 3 as dipolarophiles with arylnitrile oxides via 1,3-dipolar cycloaddition reaction. The corresponding N-allyl substituted dipolarophiles were prepared by one-pot method from thiazolidine-2,4-dione with aldehydes using Knoevenagel condensation followed by N-allylation of thiazolidine-2,4-dione in NaOH aqueous solution under sonication. In addition, the isoxazoline derivatives 5 were synthesized by regioselective and chemoselective 1,3-dipolar cycloaddition using inexpensive and mild NaCl/Oxone/Na3PO4 as a Cl source, oxidant and/or catalyst under ultrasonic irradiation in EtOH/H2O (v/v, 2:1) as green solvent. All synthesized products are furnished in good yields in the short reaction time, and then their structures were confirmed by NMR, mass spectrometry and X-ray crystallography analysis.
Novel thiazolidinedione-hydroxamates as inhibitors of Mycobacterium tuberculosis virulence factor Zmp1
?lachtová, Veronika,?ebela, Marek,Torfs, Eveline,Oorts, Lauren,Cappoen, Davie,Berka, Karel,Bazgier, Václav,Brulíková, Lucie
, (2019/11/28)
Zinc metalloprotease 1 (Zmp1) is an extracellular enzyme, which has been found essential for the intracellular survival and pathogenesis of Mycobacterium tuberculosis. In this work, we designed and synthesized a series of novel thiazolidinedione-hydroxamates and evaluated in silico their drug-likeness behavior. Then, their inhibitory properties towards a recombinant Zmp1 from Mycobacterium tuberculosis were analyzed by MALDI-TOF MS. Nine of the tested compounds were found to inhibit the enzymatic reaction more effectively than the generic metalloprotease inhibitor phosphoramidon. Furthermore, the synthesized thiazolidinedione-hydroxamate hybrids were evaluated for their in vitro antimycobacterial activity and acute cytotoxicity using whole-cell assays. Results showed that none of the hybrids exhibited acute cytotoxicity against RAW264.7 macrophages. Whereas extracellular antimycobacterial activity was limited, RAW264.7 macrophage infection results showed that a majority of the hybrids inhibited the intracellular growth of Mycobacterium tuberculosis at a concentration of 100 and 10 μM. The thiazolidinedione-hydroxamate compound 2n was considered to be the best candidate of the evaluated library.
