- Aerobic Visible-Light Induced Intermolecular S?N Bond Construction: Synthesis of 1,2,4-Thiadiazoles from Thioamides under Photosensitizer-Free Conditions
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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.
- Wang, Hui,Xie, Shihua,Zhu, Hongjun,Zhuo, Liang
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supporting information
p. 3398 - 3402
(2021/06/25)
-
- Efficient Synthesis and Bioevaluation of Novel Dual Tubulin/Histone Deacetylase 3 Inhibitors as Potential Anticancer Agents
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Novel dual HDAC3/tubulin inhibitors were designed and efficiently synthesized by combining the pharmacophores of SMART (tubulin inhibitor) and MS-275 (HDAC inhibitor), among which compound 15cwas found to be the most potent and balanced HDAC3/tubulin dual inhibitor with high HDAC3 activity (IC50= 30 nM) and selectivity (SI > 1000) as well as excellent antiproliferative potency against various cancer cell lines, including an HDAC-resistant gastric cancer cell line (YCC3/7) with IC50values in the range of 30-144 nM. Compound 15cinhibited B16-F10 cancer cell migration and colony formation. In addition, 15cdemonstrated significantin vivoantitumor efficacy in a B16-F10 melanoma tumor model with a better TGI (70.00%, 10 mg/kg) than that of the combination of MS-275 and SMART. Finally, 15cpresented a safe cardiotoxicity profile and did not cause nephro-/hepatotoxicity. Collectively, this work shows that compound 15crepresents a novel tubulin/HDAC3 dual-targeting agent deserving further investigation as a potential anticancer agent.
- Chen, Jianjun,Chen, Jingxuan,Huang, Junli,Li, Ling,Liu, Jin,Peng, Xiaopeng,Ren, Yichang,Sun, Zhiqiang
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p. 8447 - 8473
(2021/06/28)
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- Synthesis of imidazo[1,2-: C] thiazoles through Pd-catalyzed bicyclization of tert-butyl isonitrile with thioamides
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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.
- Peng, Xiangjun,Qin, Feng,Xu, Mengyue,Zhu, Shaojie,Pan, Yingming,Tang, Haitao,Meng, Xiujin,Wang, Hengshan
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supporting information
p. 8403 - 8407
(2019/09/30)
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- A efficient protocol for the synthesis of thioamides in [DBUH][OAc] at room temperature
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A novel, simple and eco-friendly method to synthesize thioamides from aryl nitriles and sodium sulfide (Na2S·9H2O) catalyzed by 1,8-diazabicyclo[5,4,0]undec-7-enium acetate ([DBUH][OAc]) ionic liquid (IL) at room temperature was developed in this paper. In this reaction, readily available inorganic salt (Na2S·9H2O) serves as the sulfur source, and various functional groups of aryl nitriles were well tolerated at room temperature. In addition, the products were easily separated from the IL which could be reused at least five times without considerable loss of its activity and applied in the green, concise synthesis of ethionamide.
- Cao, Xian-Ting,Qiao, Li,Zheng, Hui,Yang, Hui-Yong,Zhang, Peng-Fei
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p. 170 - 175
(2018/01/17)
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- Synthesis, crystal structure, anti-HIV, and antiproliferative activity of new oxadiazole and thiazole analogs
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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.
- Khan, Mahmood-ul-Hassan,Hameed, Shahid,Akhtar, Tashfeen,Al-Masoudi, Najim A.,Al-Masoudi, Wasfi A.,Jones, Peter G.,Pannecouque, Christophe
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p. 2399 - 2409
(2016/10/25)
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- Design and optimization of hybrid of 2,4-diaminopyrimidine and arylthiazole scaffold as anticancer cell proliferation and migration agents
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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.
- Zhou, Wenbo,Huang, Anling,Zhang, Yong,Lin, Qingxiang,Guo, Weikai,You, Zihua,Yi, Zhengfang,Liu, Mingyao,Chen, Yihua
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p. 269 - 280
(2015/04/27)
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- Powerful Antibacterial Activity of Phenyl-Thiolatobismuth(III) Complexes Derived from Oxadiazolethiones
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Seven novel 5-substituted phenylthiazole oxadiazolethiones: [Me-PTOT(H)], [MeO-PTOT(H)], [MeS-PTOT(H)], [F-PTOT(H)], [Cl-PTOT(H)], [Br-PTOT(H)], and [CF3-PTOT(H)], {where X-PTOT(H) = 5-[2-(4-X)thiazol-4-yl]-1,3,4-oxadiazole-2(3H)-thione, 4-X = C6H4}, were synthesised from their corresponding thioamides. From these seven heteroleptic thiolatobismuth complexes: BiPh(Me-PTOT)2 6, BiPh(MeO-PTOT)2 7, BiPh(MeS-PTOT)2 8, BiPh(F-PTOT)2 9, BiPh(Cl-PTOT)2 10, BiPh(Br-PTOT)2 11 and BiPh(CF3-PTOT)2 12 were synthesised and characterised. Complexes [10(DMSO)2] and [11(DMSO)2] were structurally characterised using X-ray diffraction. Evaluation of the antibacterial properties of the thiones and their BiIII complexes against Mycobacterium smegmatis, Staphylococcus aureus (S. aureus), Methicillin-resistant Staphylococcus aureus (MRSA), Vancomycin-resistant Enterococcus (VRE), Enterococcus faecalis (E. faecalis) and Escherichia coli (E. coli) showed that all bismuth(III) complexes were highly effective against all the bacteria, as demonstrated by very low MIC values (1.1-2.1 μM). Complexes BiPh(Me-PTOT)2 6, BiPh(Cl-PTOT)2 10 and BiPh(Br-PTOT)2 11, showed best activity against the multi-drug resistant bacteria VRE and MRSA with an MIC value of 1.0 μM. All these complexes and their corresponding thiones failed to show any prominent activity against M. smegmatis and E. coli, even at high concentrations. These complexes showed little or no toxicity towards mammalian COS-7 cells at 20 μg/mL. Seven heteroleptic thiolatobismuth(III) complexes [BiPh(X-PTOT)2] derived from a series of 5-substituted phenylthiazole oxadiazolethiones [X-PTOT(H)] provide powerful antibacterial action against the multi-resistant bacteria MRSA and VRE.
- Luqman, Ahmad,Blair, Victoria L.,Brammananth, Rajini,Crellin, Paul K.,Coppel, Ross L.,Andrews, Philip C.
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p. 4935 - 4945
(2015/11/02)
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- Metal-free, one-pot oxidative conversion of aldehydes to primary thioamides in aqueous media
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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.]
- Yadav, Arvind K.,Srivastava, Vishnu P.,Yadav, Lal Dhar S.
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p. 408 - 416
(2014/01/06)
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- Agonists for the adenosine A1 receptor with tunable residence time. a case for nonribose 4-amino-6-aryl-5-cyano-2-thiopyrimidines
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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.
- 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.
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supporting information
p. 3213 - 3222
(2014/05/20)
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- Novel and versatile synthesis of disubstituted 1,2-dihydro-1,2,4-triazol-3- ones
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A novel method for the synthesis of a wide range of 1,5-disubstituted 1,2-dihydro-1,2,4-triazol-3-ones is described. The key step involves a reaction between a dilithiated BOC-hydrazine and a N-alkoxycarbonylcarboximidothioate. A broad range of aryl and a
- Graham, Mark A.,Bethel, Paul A.,Burgess, Jonathan,Fairley, Gary,Glossop, Steve C.,Greenwood, Ryan D. R.,Jones, Clifford D.,Lovell, Scott,Swallow, Steve
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supporting information
p. 6078 - 6081
(2014/01/06)
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- A novel process for the synthesis of 3,5-diaryl-1,2,4-thiadiazoles from aryl nitriles
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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.
- Noei, Jalil,Khosropour, Ahmad Reza
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supporting information
p. 9 - 11
(2013/02/21)
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- Single-step microwave-mediated synthesis of oxazoles and thiazoles from 3-oxetanone: A synthetic and computational study
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The direct microwave-mediated condensation between 3-oxetanone and primary amides and thioamides has delivered moderate to good yields of (hydroxymethyl)oxazoles and (hydroxymethyl)thiazoles. The reactions use a sustainable solvent and only require short reaction times. These are highly competitive methods for the construction of two classes of valuable heteroarenes, which bear a useful locus for further elaboration. Electronic structure calculations have shown that the order of events involves chalcogen atom attack at sp3 carbon and alkyl-oxygen cleavage. The critical role of acid catalysis was shown clearly, and the importance of acid strength was demonstrated. The calculated barriers were also fully consistent with the observed order of thioamide and amide reactivity. Spontaneous ring opening involves a modest degree of C-O cleavage, moderating the extent of strain relief. On the acid-catalysed pathway, C-O cleavage is less extensive still, but proton transfer to the nucleofuge is well advanced with the carboxylic acid catalysts, and essentially complete with methanesulfonic acid. Open sesame: The direct microwave-mediated condensation between 3-oxetanone and primary amides and thioamides has delivered moderate to good yields of oxazoles and thiazoles. The reactions use a sustainable solvent, require only short reaction times and represent a highly competitive method for the construction of two classes of valuable heteroarenes. Electronic structure calculations have been used to probe a range of potential reaction mechanisms (see figure). Copyright
- Orr, David,Tolfrey, Alexandra,Percy, Jonathan M.,Frieman, Joanna,Harrison, Zo? A.,Campbell-Crawford, Matthew,Patel, Vipulkumar K.
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supporting information
p. 9655 - 9662
(2013/07/26)
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- A thiophosphoryl chloride assisted transformation of arylaldoximes to thioamides
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Primary benzothioamides were accessed from benzaldoximes (benzaldehyde oximes) via benzonitriles in a sequential tandem approach utilizing thiophosphoryl chloride as a dehydrating and thionating agent. Georg Thieme Verlag Stuttgart New York.
- Pandey, Lokesh Kumar,Pathak, Uma,Mathur, Sweta,Suryanarayana
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experimental part
p. 377 - 379
(2012/03/27)
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- O,O-Diethyl dithiophosphoric acid mediated direct synthesis of thioamides from aldehydes and ketones
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A general and convenient method for a one-pot conversion of aldehydes and ketones into thioamides has been developed. The protocol involves oximation of aldehydes and ketones followed by deoxygenative thioamidation of oximes with O,O-diethyl dithiophosphoric acid which acts as an acid as well a source of sulfur. The method is operationally simple, high yielding, and also applicable to the conversion of amides and nitriles into the corresponding thioamides.
- Yadav, Arvind K.,Srivastava, Vishnu P.,Yadav, Lal Dhar S.
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p. 7113 - 7116
(2013/01/15)
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- Synthesis and Antitumor Activity of 3-(2-Phenyl-1,3-thiazol-4-yl)-1H-indoles and 3-(2-Phenyl-1,3-thiazol-4-yl)-1H-7-azaindoles
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Given the potent antimicrobial, antiviral, and antitumor activities of many natural products, there is an increasing interest in the synthesis of new molecules based on natural compound scaffolds. Based on a 2,4-bis(3'-indolyl)imidazole skeleton, two new series of phenylthiazolylindoles and phenylthiazolyl-7-azaindoles were obtained by Hantzsch reaction between substituted phenylthioamides and the α-bromoacetyl derivatives. Some azaindole derivatives, tested at the National Cancer Institute against a panel of ~60 tumor cell lines derived from nine human cancer cell types, showed inhibitory effects against all cell lines investigated at micromolar to nanomolar concentrations. Two of them exhibited a high affinity for CDK1, with IC50 values of 0.41 and 0.85μM. These promising results will set the foundation for future investigations into the development of anticancer therapies. Marine mining: Given the promise of marine-derived bioactive indole alkaloids, we synthesized a series of phenylthiazolylindoles and phenylthiazolyl-7-azaindoles, and evaluated their antitumor activity against a panel of 60 cancer cell lines. Some derivatives showed IC50 values in the micromolar to nanomolar range.
- Diana, Patrizia,Carbone, Anna,Barraja, Paola,Montalbano, Alessandra,Parrino, Barbara,Lopergolo, Alessia,Pennati, Marzia,Zaffaroni, Nadia,Cirrincione, Girolamo
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experimental part
p. 1300 - 1309
(2012/05/05)
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- Efficient and green protocol for the synthesis of thioamides in C 6 (mim)2Cl2 as a dicationic ionic liquid
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A simple, efficient, facile and eco-friendly process for the synthesis of thioamides from nitriles using 1,6-bis(3methylimidazolium-1-yl)hexane chloride [C6(mim)2Cl2] as a dicationic ionic liquid (DIL) was developed. The ionic liquid was easily separated from the reaction mixture and was recycled at least four times without any loss of its activity.
- Khosropour,Noei,Mirjafari
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experimental part
p. 752 - 758
(2010/11/04)
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- Synthesis and in-vitro cytotoxicity of poly-functionalized 4-(2-arylthiazol-4-yl)-4H-chromenes
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A new series of 4-aryl-4H-chromenes bearing a 2-arylthiazol-4-yl moiety at the 4-position were prepared as potential cytotoxic agents. The in-vitro cytotoxic activity of the synthesized 4-aryl-4H-chromenes was investigated in comparison with etoposide, a well-known anticancer drug, using MTT colorimetric assay. Among them, the 2-(2-chlorophenyl)thiazol-4-yl analog 4b showed the most potent activity against nasopharyngeal epidermoid carcinoma KB, medulloblastoma DAOY, and astrocytoma 1321N1, and compound 4d bearing a 2-(4-chlorophenyl) thiazol-4-yl moiety at the 4-position of the chromene ring exhibited the best inhibitory activity against breast cancer cells MCF-7, lung cancer cells A549, and colon adenocarcinoma cells SW480 with IC50 values less than 5 μM. The ability of compound 4b to induce apoptosis was confirmed in a nuclear morphological assay by DAPI staining in the KB and MCF-7 cells.
- Mahmoodi, Majid,Aliabadi, Alireza,Emami, Saeed,Safavi, Maliheh,Rajabalian, Saeed,Mohagheghi, Mohammad-Ali,Khoshzaban, Ahad,Samzadeh-Kermani, Alireza,Lamei, Navid,Shafiee, Abbas,Foroumadi, Alireza
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experimental part
p. 411 - 416
(2011/08/05)
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- P4S10/dimethicone tandem: Efficient reagent for thionation of various aromatic amides and esters
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Organosulfur compounds are valuable because of their rich and varied chemistry especially in biological field. We report a new and efficient way for thionation of various aromatic amides and esters using P4S 10/ dimethicone tandem. The ease of handling and higher yield makes this protocol economical.
- Cho, Dongho,Ahn, Jiyoung,De Castro, Kathlia A.,Ahn, Hyunseok,Rhee, Hakjune
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supporting information; experimental part
p. 5583 - 5588
(2010/10/02)
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- AMPK MODULATORS
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The present invention relates to compounds and pharmaceutically acceptable salts, esters and prodrugs of Formula (I) or (II), which are useful as AMPK modulators effective in treating diabetes, obesity and cancer in a subject.
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Page/Page column 39
(2009/10/09)
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- 2-ARYL- AND 2-HETEROARYLTHIAZOLYL COMPOUNDS, METHODS FOR THEIR PREPARATION AND USE THEREOF
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The present invention discloses fused bicyclic 2-aryl- or 2-heteroarylthiazolyl compounds and their pharmaceutically acceptable salts and esters thereof, which are useful for inhibiting the growth of cancerous cells, inhibiting human breast carcinoma tumo
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Page/Page column 141; 142
(2009/10/22)
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- The BF3·OEt2-assisted conversion of nitriles into thioamides with Lawesson's reagent
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A method for the thiolysis of nitriles by applying Lawesson's reagent and facilitated by the addition of boron trifluoride-diethyl ether complex is reported. The method opens an easy access to primary thioamides. Aromatic, benzylic, and aliphatic nitriles were converted into the corresponding thioamides in high to quantitative yields (even in unfavorable cases, e.g., ortho-substitut-ed benzonitriles). The reaction was performed in 1,2-dimethoxyethane-tetrahydrofuran or toluene-diethyl ether solvent mixtures at 20-50°C, and exhibited considerable selectivity in the case of multifunctional nitrile substrates, such as cyanomethyl N-acetylphenylalaninate, benzoylacetonitrile, 4-cyanobenzamide, 4-acetylbenzonitrile, or pent-3-enenitrile. Georg Thieme Verlag Stuttgart.
- Nagl, Michael,Panuschka, Claudia,Barta, Andrea,Schmid, Walther
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experimental part
p. 4012 - 4018
(2009/05/27)
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- TiCl3OTf-[bmim]Br: a novel and efficient catalyst system for chemoselective one-pot synthesis of thioamides from arylaldoximes
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The combination of TiCl3OTf with 1-butyl-3-methylimidazolium bromide is found to be an efficient and novel catalytic system for chemoselective one-pot transformation of arylaldoximes to their corresponding thioamides in high to excellent yields.
- Noei, Jalil,Khosropour, Ahmad R.
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scheme or table
p. 6969 - 6971
(2009/04/07)
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- Phosphorus pentasulfide: A mild and versatile reagent for the preparation of thioamides from nitriles
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A simple, efficient, and new method has been developed for the synthesis of thioamides from nitriles. The reaction of a variety of aromatic and aliphatic nitriles in the presence of phosphorus pentasulfide afforded the corresponding thioamides in high yields. This method is easy, rapid, and high-yielding for the synthesis of thioamides from nitriles. Georg Thieme Verlag Stuttgart.
- Kaboudin, Babak,Elhamifar, Dawood
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p. 224 - 226
(2007/10/03)
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- METHODS AND COMPOSITIONS FOR MODULATING SPHINGOSINE-1-PHOSPHATE (S1P) RECEPTOR ACTIVITY
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The present invention relates to compounds which modulate the activity of the SI P1 receptor, the use of these compounds for treating conditions associated with signaling through the S1 P1 receptor, and pharmaceutical compositions comprising these compounds.
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Page/Page column 104-105
(2010/10/20)
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- Practical routes to the triarylsulfonyl chloride intermediate of a β3 adrenergic receptor agonist
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A β3 adrenergic receptor agonist was prepared on a multi-kilogram scale in high yield and purity via a convergent synthesis. A key intermediate in this synthesis was an arylthiazolylbenzenesulfonyl chloride. The triaryl segment of this sulfonyl chloride was assembled at the thiazole ring via coupling of α-haloketone and thiobenzamide precursors (Hantzsch synthesis). Three strategies for introducing the para-sulfonyl chloride moiety were developed and evaluated. The sulfonation/chlorination and diazotization/chlorosulfonylation routes were found the most efficient.
- Ikemoto, Norihiro,Liu, Jinchu,Brands, Karel M.J.,McNamara, James M.,Reider, Paul J.
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p. 1317 - 1325
(2007/10/03)
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- CONVERSION OF NITRILES TO THIOAMIDES UNDER THE ACTION OF THE BINARY THIONYLATING SYSTEM PHOSPHORUS DITHIOACID-ALCOHOL
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Binary systems of phosphorus dithioacid-methanol and phosphorus pentasulfide-methanol are effective hydrosulfonating systems for the conversion of aromatic nitriles to the corresponding primary thioamides.In ternary systems nitrile-phosphorus dithioacid-alcohol from one to four parallel processes can occur.The structure of the phosphorus dithioacids has little effect, whereas the structures of the nitrile and alcohol substantially influence both the rate of the processes and the possible pathway.The reactivity of alcohols in these reactions drops with increasing volume of the hydrocarbon radical.
- Zabirov, N. G.,Shamsevaleev, F. M.,Cherkasov, R. A.
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- Effects of varying solvents and of the addition of sulfur on the rate of thiohydrolysis of aromatic nitriles
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Maximal rates of formation of thioamides from m- and p-substituted benzonitriles were obtained by bubbling H2S through solutions of the nitrile in pyridine containing a 0.11 mol fraction of triethylamine or in 95percent ethanol containing about 0.22 mol fraction triethylamine; at other mol fractions the rate fell off sharply.The Hammett p value of +2.3 in pyridine indicates that HS- is the reactive species.The addition of enough sulfur to saturate the solution leads to about a 3-fold enhancement of rate, probably because of the formation of polysulfide ions in trace amounts.
- Abbas, Khamis,Edward, John T.
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p. 3075 - 3078
(2007/10/02)
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- 2(4-Fluorophenyl)-4,5,-bis(4-methoxyphenyl)thiazole and method of use
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Novel triaryl thiazole compounds are useful as analgesic agents. In particular, 2-(4-halophenyl)-4,5-bis(4-methoxyphenyl)thiazoles are used. These compounds are prepared by condensation of a substituted thiobenzamide with a substituted desyl chloride.
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