2548-79-0Relevant articles and documents
Aerobic Visible-Light Induced Intermolecular S?N Bond Construction: Synthesis of 1,2,4-Thiadiazoles from Thioamides under Photosensitizer-Free Conditions
Wang, Hui,Xie, Shihua,Zhu, Hongjun,Zhuo, Liang
supporting information, p. 3398 - 3402 (2021/06/25)
Aerobic visible-light induced intermolecular S?N bond construction has been achieved without the addition of photosensitizer, metal, or base. With this strategy, 1,2,4-thiadiazoles can be obtained from thioamides. Preliminary mechanistic investigation suggested that the excited state of thioamides undergoes a single-electron-transfer (SET) process to afford thioamidyl radicals, which can be further transformed into a 1,2,4-thiadiazole through desulfurization and oxidative cyclization. The reaction has good functional group tolerance and represents a green method for the construction of S?N bonds.
Regioselective C-C cross-coupling of 1,2,4-thiadiazoles with maleimides through iridium-catalyzed C-H activation
Tian, Ting,Dong, An-Shun,Chen, Dan,Cao, Xian-Ting,Wang, Guannan
supporting information, p. 7664 - 7668 (2019/08/30)
A regioselective C-C cross-coupling of 1,2,4-thiadiazoles with maleimides through iridium catalysis was developed. This transformation tactically linked the 1,2,4-thiadiazoles and succinimides together, and the novel molecules formed may have potential biological activity.
Synthesis of imidazo[1,2-: C] thiazoles through Pd-catalyzed bicyclization of tert-butyl isonitrile with thioamides
Peng, Xiangjun,Qin, Feng,Xu, Mengyue,Zhu, Shaojie,Pan, Yingming,Tang, Haitao,Meng, Xiujin,Wang, Hengshan
supporting information, p. 8403 - 8407 (2019/09/30)
Building new biological molecules is challenging. Herein, imidazo[1,2-c]thiazoles were synthesized as a new class of heterobicyclic analogs through Pd-catalyzed cascade bicyclization from isonitriles with thioamides. The bicyclic scaffolds were constructed by inserting three molecules of isonitrile into two molecules of thioamide and then cyclizing them in a one-pot procedure. In vitro antitumor studies of these new compounds were conducted by using the MTT assay, and compound 3c showed excellent inhibitory effects against HepG2 at 7.06 ± 0.68 μM.
Synthesis, crystal structure, anti-HIV, and antiproliferative activity of new oxadiazole and thiazole analogs
Khan, Mahmood-ul-Hassan,Hameed, Shahid,Akhtar, Tashfeen,Al-Masoudi, Najim A.,Al-Masoudi, Wasfi A.,Jones, Peter G.,Pannecouque, Christophe
, p. 2399 - 2409 (2016/10/25)
A series of 2-adamantyl-5-arylthiazolyl-1,3,4-oxadiazoles 7a–x together with thiazoles 13 and 14 were synthesized. Compounds 7a–l, 13, and 14 were tested in vitro with the aim of identifying novel lead compounds active against human immunodeficiency virus type-1 and human immunodeficiency virus type-2 activity in MT-4 cells. Title compounds were also tested against representatives of Gram-positive and Gram-negative bacteria (Staphylococcus aureus, Salmonella spp.), various mycobacterial strains (Mycobacterium fortuitum and Mycobacterium smegmatis), yeast (Candida albicans), and mold (Aspergillus fumigatus). None of the compounds showed antiviral or antimicrobial activity, except compounds 13 and 14 exhibited anti-human immunodeficiency virus-1 activity with EC50 values of 1.79 and 2.39 μM with Selectivity index = 18 and 4, respectively. On the other hand, compounds 7a and 7j showed a marked cytotoxicity against the human CD4+ lymphocytes (MT-4). Therefore, 7a and 7j were evaluated for their antiproliferative activity against two solid tumor-derived cell lines, which exhibited IC50 values of 8.1 ± 0.10 μM and 4.8 ± 0.08 μM against Hep-G2 cell lines, respectively.
Design, synthesis and Structure-activity relationship studies of new thiazole-based free fatty acid receptor 1 agonists for the treatment of type 2 diabetes
Li, Zheng,Qiu, Qianqian,Xu, Xue,Wang, Xuekun,Jiao, Lei,Su, Xin,Pan, Miaobo,Huang, Wenlong,Qian, Hai
supporting information, p. 246 - 257 (2016/03/08)
The free fatty acid receptor 1 (FFA1/GPR40) has attracted interest as a novel target for the treatment of type 2 diabetes. Several series of FFA1 agonists including TAK-875, the most advanced compound terminated in phase III studies due to concerns about liver toxicity, have been hampered by relatively high molecular weight and lipophilicity. Aiming to develop potent FFA1 agonists with low risk of liver toxicity by decreasing the lipophilicity, the middle phenyl of TAK-875 was replaced by 11 polar five-membered heteroaromatics. Subsequently, systematic exploration of SAR and application of molecular modeling, leads to the identification of compound 44, which was an excellent FFA1 agonist with robustly hypoglycemic effect both in normal and type 2 diabetic mice, low risks of hypoglycemia and liver toxicity even at the twice molar dose of TAK-875. Meanwhile, two important findings were noted. First, the methyl group in our thiazole series occupied a small hydrophobic subpocket which had no interactions with TAK-875. Furthermore, the agonistic activity revealed a good correlation with the dihedral angle between thiazole core and the terminal benzene ring. These results promote the understanding of ligand-binding pocket and might help to design more promising FFA1 agonists.
Design and optimization of hybrid of 2,4-diaminopyrimidine and arylthiazole scaffold as anticancer cell proliferation and migration agents
Zhou, Wenbo,Huang, Anling,Zhang, Yong,Lin, Qingxiang,Guo, Weikai,You, Zihua,Yi, Zhengfang,Liu, Mingyao,Chen, Yihua
, p. 269 - 280 (2015/04/27)
Therapeutics of metastatic or triple-negative breast cancer are still challenging in clinical. Herein we demonstrated the design and optimization of a series of hybrid of 2,4-diaminopyrimidine and arylthiazole derivatives for their anti-proliferative properties against two breast cancer cell lines (MCF-7 as human breast cancer and MDA-MB-231 as triple-negative breast cancer). More importantly, some of those compounds with potent antiproliferative activities also indicated excellent inhibitory activities against MDA-MB-231 cell migration. These results suggested that the new series of hybridation of aryl-thiazoles and aminopyrimidines could be identified and developed as novel highly potential anticancer agents against the triple-negative breast cancer as well as metastatic one in the future.
Metal-free, one-pot oxidative conversion of aldehydes to primary thioamides in aqueous media
Yadav, Arvind K.,Srivastava, Vishnu P.,Yadav, Lal Dhar S.
supporting information, p. 408 - 416 (2014/01/06)
One-pot tandem reactions of a variety of aldehydes with aqueous ammonia, molecular iodine, and O,O-diethyl dithiophosphoric acid readily afford the corresponding primary thioamides. This is an inexpensive, practical, and metal-free way of accessing various thioamides from aldehydes in aqueous media. The pure products are obtained simply by filtration followed by successive washing with aqueous sodium thiosulfate and water. [Supplementary materials are available for this article. Go to the publisher's online edition of Synthetic Communications for the following free supplemental resource(s): Full experimental and spectral details.]
Agonists for the adenosine A1 receptor with tunable residence time. a case for nonribose 4-amino-6-aryl-5-cyano-2-thiopyrimidines
Louvel, Julien,Guo, Dong,Agliardi, Marta,Mocking, Tamara A. M.,Kars, Roland,Pham, Tan Phát,Xia, Lizi,De Vries, Henk,Brussee, Johannes,Heitman, Laura H.,Ijzerman, Adriaan P.
supporting information, p. 3213 - 3222 (2014/05/20)
We report the synthesis and evaluation of previously unreported 4-amino-6-aryl-5-cyano-2-thiopyrimidines as selective human adenosine A 1 receptor (hA1AR) agonists with tunable binding kinetics, this without affecting their nanomolar affinity for the target receptor. They show a very diverse range of kinetic profiles (from 1 min (compound 52) to 1 h (compound 43)), and their structure-affinity relationships (SAR) and structure-kinetics relationships (SKR) were established. When put in perspective with the increasing importance of binding kinetics in drug discovery, these results bring new evidence of the consequences of affinity-only driven selection of drug candidates, that is, the potential elimination of slightly less active compounds that may display preferable binding kinetics.
Crystal landscape of primary aromatic thioamides
Eccles, Kevin S.,Morrison, Robin E.,Maguire, Anita R.,Lawrence, Simon E.
, p. 2753 - 2762 (2014/06/23)
The crystal landscape of a series of primary aromatic thioamides is described, displaying similar characteristic intermolecular hydrogen-bonding interactions in the solid state to those observed in their widely studied amide analogues, including R22(8) dimers and C(4) chains. In a number of cases, high Z′ values were observed in the structures. On the basis of the observed solid-state features, the thioamide functional group, which is a strong hydrogen-bond donor and moderate acceptor, offers considerable potential as a key moiety for crystal engineering.
A novel process for the synthesis of 3,5-diaryl-1,2,4-thiadiazoles from aryl nitriles
Noei, Jalil,Khosropour, Ahmad Reza
supporting information, p. 9 - 11 (2013/02/21)
A novel and efficient process for the synthesis of 3,5-diaryl-1,2,4- thiadiazoles from aryl nitriles in 1-butyl-3-methylimidazolium bromide promoted by (NH4)2S and TCT-DMSO is described.
