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, 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.
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.
COMPOSITIONS AND METHODS FOR MODULATING HAIR GROWTH
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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.
Permuted 2,4-thiazolidinedione (TZD) analogs as GLUT inhibitors and their in-vitro evaluation in leukemic cells
Aguilera, Renato J.,Choe, Jun-yong,Hess, Jessica D.,Iancu, Cristina V.,Macias, Lucasantiago Henze,Meyer-Almes, Franz-Josef,Mrowka, Piotr,Ramaa, C. S.,Schweipert, Markus,Tilekar, Kalpana,Upadhyay, Neha
, (2020/08/21)
Cancer is a heterogeneous disease, and its treatment requires the identification of new ways to thwart tumor cells. Amongst such emerging targets are glucose transporters (GLUTs, SLC2 family), which are overexpressed by almost all types of cancer cells; t
Synthesis and antimicrobial activity of a new series of thiazolidine-2,4-diones carboxamide and amino acid derivatives
Alhameed, Rakia Abd,Almarhoon, Zainab,Bukhari, Sarah I.,El-Faham, Ayman,De La Torre, Beatriz G.,Albericio, Fernando
, (2020/01/13)
Novel thiazolidine-2,4-dione carboxamide and amino acid derivatives were synthesized in excellent yield using OxymaPure/N,N'-diisopropylcarbodimide coupling methodology and were characterized by chromatographic and spectrometric methods, and elemental ana
