- Substituted pyrimidine compound and application thereof
-
The present invention discloses a substituted pyrimidine compound, which has a structure represented by a general formula I, wherein each substituent is defined in the specification. According to thepresent invention, the compound has a broad-spectrum bactericidal activity, can provide excellent prevention and control effects on cucumber downy mildew, wheat powdery mildew, corn rust disease, riceblast, cucumber anthracnose and the like, and particularly can provide good prevention effects on powdery mildew, corn rust disease and rice blast.
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Page/Page column 0434-0437
(2021/09/01)
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- 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
-
supporting information
p. 3398 - 3402
(2021/06/25)
-
- Structural and Activity Relationships of 6-Sulfonyl-8-Nitrobenzothiazinones as Antitubercular Agents
-
The benzothiazinone (BTZ) scaffold compound PBTZ169 kills Mycobacterium tuberculosis by inhibiting the essential flavoenzyme DprE1, consequently blocking the synthesis of the cell wall component arabinans. While extraordinarily potent against M. tuberculosis with a minimum inhibitory concentration (MIC) less than 0.2 ng/mL, its low aqueous solubility and bioavailability issues need to be addressed. Here, we designed and synthesized a series of 6-methanesulfonyl substituted BTZ analogues; further exploration introduced five-member aromatic heterocycles as linkers to attach an aryl group as the side chain. Our work led to the discovery of a number of BTZ derived compounds with potent antitubercular activity. The optimized compounds 6 and 38 exhibited MIC 47 and 30 nM, respectively. Compared to PBTZ169, both compounds displayed increased aqueous solubility and higher stability in human liver microsomes. This study suggested that an alternative side-chain modification strategy could be implemented to improve the druglike properties of the BTZ-based compounds.
- Chiarelli, Laurent R.,Fan, Dongguang,Han, Quanquan,Lu, Yu,Qiao, Chunhua,Shi, Rui,Stelitano, Giovanni,Wang, Bin,Huszár, Stanislav,Miku?ová, Katarína,Savková, Karin
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supporting information
p. 14526 - 14539
(2021/10/26)
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- Optimization, Structure-Activity Relationship, and Mode of Action of Nortopsentin Analogues Containing Thiazole and Oxazole Moieties
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Plant diseases seriously endanger plant health, and it is very difficult to control them. A series of nortopsentin analogues were designed, synthesized, and evaluated for their antiviral activities and fungicidal activities. Most of these compounds displayed higher antiviral activities than ribavirin. Compounds 1d, 1e, and 12a, with excellent antiviral activities, emerged as novel antiviral lead compounds, among which 1e was selected for further antiviral mechanism research. The mechanism research results indicated that these compounds may play an antiviral role by aggregating viral particles to prevent their movement in plants. Further fungicidal activity tests revealed that nortopsentin analogues displayed broad-spectrum fungicidal activities. Compounds 2p and 2f displayed higher antifungal activities against Alternaria solani than the commercial fungicides carbendazim and chlorothalonil. Current research has laid a foundation for the application of nortopsentin analogues in plant protection.
- Guo, Jincheng,Hao, Yanan,Ji, Xiaofei,Wang, Ziwen,Liu, Yuxiu,Ma, Dejun,Li, Yongqiang,Pang, Huailin,Ni, Jueping,Wang, Qingmin
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p. 10018 - 10031
(2019/10/05)
-
- Mo (CO)6-assisted Pd-supported magnetic graphene oxide-catalyzed carbonylation-cyclization as an efficient way for the synthesis of 4(3H)-quinazolinones
-
In this paper, a novel catalyst is introduced based on the immobilization of palladium on modified magnetic graphene oxide nanoparticles. The catalyst is characterized by several methods, including transmission electron microscopy, scanning electron microscopy, X-ray fluorescence, vibrating-sample magnetometer, Fourier transform-infrared and dynamic light scattering (DLS) analysis. The activity of the catalyst was investigated in the synthesis of 4(3H)-quinazolinones via Pd-catalyzed carbonylation-cyclization of N-(2-bromoaryl) benzimidamides by Mo (CO)6. The Mo (CO)6 is used as a carbon monoxide source for performing the reaction under mild conditions. The catalyst showed good reusability, and no change in activity was observed after 10?cycles of recovery.
- Bahadorikhalili, Saeed,Ansari, Samira,Hamedifar, Haleh,Ma'mani, Leila,Babaei, Mohsen,Eqra, Rahim,Mahdavi, Mohammad
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-
- Regioselective C-C cross-coupling of 1,2,4-thiadiazoles with maleimides through iridium-catalyzed C-H activation
-
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.
- Tian, Ting,Dong, An-Shun,Chen, Dan,Cao, Xian-Ting,Wang, Guannan
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supporting information
p. 7664 - 7668
(2019/08/30)
-
- Synthesis of imidazo[1,2-: C] thiazoles through Pd-catalyzed bicyclization of tert-butyl isonitrile with thioamides
-
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)
-
- 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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- A simple method for synthesis of thioamides and application in synthesis of 1,2,4-thiadiazoles
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A novel, simple protocol is disclosed for the synthesis of 1,2,4-thiadiazoles starting from thioamides with Na2-eosin Y-sensitized titanium dioxide as catalyst through visible light irradiation (7 W blue LED light) and only 0.3 mol% catalysts were used. The raw material thioamides is prepared by aryl nitriles and sodium sulfide (Na2S9H2O) in DMF and in this reaction, readily available, inexpensive inorganic salt (Na2S9H2O) serves as the sulfur source and various functional groups of aryl nitriles were well and thioamides were synthesized successfully in gram-scale.
- Cao, Xian Ting,Yang, Huiyong,Zheng, Hui,Zhang, Pengfei
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p. 509 - 517
(2018/03/27)
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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, synthesis and Structure-activity relationship studies of new thiazole-based free fatty acid receptor 1 agonists for the treatment of type 2 diabetes
-
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.
- Li, Zheng,Qiu, Qianqian,Xu, Xue,Wang, Xuekun,Jiao, Lei,Su, Xin,Pan, Miaobo,Huang, Wenlong,Qian, Hai
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supporting information
p. 246 - 257
(2016/03/08)
-
- Design and optimization of hybrid of 2,4-diaminopyrimidine and arylthiazole scaffold as anticancer cell proliferation and migration agents
-
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)
-
- Domino aryne precursor: Efficient construction of 2,4-disubstituted benzothiazoles
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An aryne precursor with a potential to perform domino aryne chemistry was proposed and synthesized. The reaction of this reagent with benzothioamide derivatives could afford 2,4-disubstituted benzothiazole with sequential incorporation of C-S, C-N, and C-C bonds on the consecutive three positions of the aryne precursor.
- Shi, Jiarong,Qiu, Dachuan,Wang, Juan,Xu, Hai,Li, Yang
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supporting information
p. 5670 - 5673
(2015/05/20)
-
- 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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- CATHEPSIN CYSTEINE PROTEASE INHIBITORS
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This invention relates to a novel class of compounds which are cysteine protease inhibitors, including but not limited to, inhibitors of cathepsins K, L, S and B. These compounds are useful for treating diseases in which inhibition of bone resorption is indicated, such as osteoporosis.
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Page/Page column 51; 52; 60
(2015/04/28)
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- CATHEPSIN CYSTEINE PROTEASE INHIBITORS
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This invention relates to a novel class of compounds which are cysteine protease inhibitors, including but not limited to, inhibitors of cathepsins K, L, S and B. These compounds are useful for treating diseases in which inhibition of bone resorption is indicated, such as osteoporosis.
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Page/Page column 58; 59; 69
(2015/04/28)
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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)
-
- Crystal landscape of primary aromatic thioamides
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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.
- Eccles, Kevin S.,Morrison, Robin E.,Maguire, Anita R.,Lawrence, Simon E.
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p. 2753 - 2762
(2014/06/23)
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- FUSED HETEROCYCLIC COMPOUNDS AND THEIR USE
-
The present invention provides compounds of formula (I) and pharmaceutically acceptable salts, hydrates and solvates thereof for use in the treatment of cancer:
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-
Page/Page column 34; 35
(2014/03/25)
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- 3H-1,2,4-Dithiazol-3-one compounds as novel potential affordable antitubercular agents
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Small molecules with oxathiazol-2-one moiety were recently reported as potent inhibitors of Mycobacterium bovis var. bacilli Calmette-Guérin (BCG), among which HT1171 was the most potent and selective proteasome inhibitor. Herein we synthesized a series of novel compounds by bioisosteric replacement of the oxathiazol-2-one ring with 3H-1,2,4-dithiazol-3-one, and also fifteen 1,3,4-oxathiazol-2-one molecules in order for potency comparison and structure-activity relationship elucidation since their antibacterial effects on the virulent strains were not evaluated before. All the compounds were assessed for antitubercular activities on the virulent H37Rv strain by a serial dilution method. Among the tested compounds, 3H-1,2,4-dithiazol-3-one compound 4n was found to be the most active with a lowest MIC90 value of 1 μg/mL. Furthermore, the cytotoxicities of all the compounds against normal human liver cell line L02 were determined by an MTT method. Compound 4n displayed a lower inhibitory ratio than HT1171 at the concentration of 100 μM, indicating its better safety profile.
- Yang, Jianzhong,Pi, Weiyi,Xiong, Li,Ang, Wei,Yang, Tao,He, Jun,Liu, Yuanyuan,Chang, Ying,Ye, Weiwei,Wang, Zhenling,Luo, Youfu,Wei, Yuquan
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p. 1424 - 1427
(2013/03/14)
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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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- Development of new deoxycytidine kinase inhibitors and noninvasive in vivo evaluation using positron emission tomography
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Combined inhibition of ribonucleotide reductase and deoxycytidine kinase (dCK) in multiple cancer cell lines depletes deoxycytidine triphosphate pools leading to DNA replication stress, cell cycle arrest, and apoptosis. Evidence implicating dCK in cancer cell proliferation and survival stimulated our interest in developing small molecule dCK inhibitors. Following a high throughput screen of a diverse chemical library, a structure-activity relationship study was carried out. Positron Emission Tomography (PET) using 18F-L-1-(2′-deoxy-2′-FluoroArabinofuranosyl) Cytosine (18F-L-FAC), a dCK-specific substrate, was used to rapidly rank lead compounds based on their ability to inhibit dCK activity in vivo. Evaluation of a subset of the most potent compounds in cell culture (IC50 = ~1-12 nM) using the 18F-L-FAC PET pharmacodynamic assay identified compounds demonstrating superior in vivo efficacy.
- Murphy, Jennifer M.,Armijo, Amanda L.,Nomme, Julian,Lee, Chi Hang,Smith, Quentin A.,Li, Zheng,Campbell, Dean O.,Liao, Hsiang-I.,Nathanson, David A.,Austin, Wayne R.,Lee, Jason T.,Darvish, Ryan,Wei, Liu,Wang, Jue,Su, Ying,Damoiseaux, Robert,Sadeghi, Saman,Phelps, Michael E.,Herschman, Harvey R.,Czernin, Johannes,Alexandrova, Anastassia N.,Jung, Michael E.,Lavie, Arnon,Radu, Caius G.
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supporting information
p. 6696 - 6708
(2013/10/01)
-
- Optimizing thiadiazole analogues of resveratrol versus three chemopreventive targets
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Chemoprevention is an approach to decrease cancer morbidity and mortality through inhibition of carcinogenesis and prevention of disease progression. Although the trans stilbene derivative resveratrol has chemopreventive properties, its action is compromised by weak non-specific effects on many biological targets. Replacement of the stilbene ethylenic bridge of resveratrol with a 1,2,4-thiadiazole heterocycle and modification of the substituents on the two aromatic rings afforded potential chemopreventive agents with enhanced potencies and selectivities when evaluated as inhibitors of aromatase and NF-κB and inducers of quinone reductase 1 (QR1).
- Mayhoub, Abdelrahman S.,Marler, Laura,Kondratyuk, Tamara P.,Park, Eun-Jung,Pezzuto, John M.,Cushman, Mark
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experimental part
p. 510 - 520
(2012/03/10)
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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)
-
- 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
-
experimental part
p. 752 - 758
(2010/11/04)
-
- Novel selective thiazoleacetic acids as CRTH2 antagonists developed from in silico derived hits. Part 1
-
Structure-activity relationships of three related series of 4-phenylthiazol-5-ylacetic acids, derived from two hits emanating from a focused library obtained by in silico screening, have been explored as CRTH2 (chemoattractant receptor-homologous molecule expressed on Th2 cells) antagonists. Several compounds with double digit nanomolar binding affinity and full antagonistic efficacy for human CRTH2 receptor were obtained in all subclasses. The most potent compound was [2-(4-chloro-benzyl)-4-(4-phenoxy-phenyl)-thiazol-5-yl]acetic acid having an binding affinity of 3.7 nM and functional antagonistic effect of 66 nM in a BRET and 12 nM in a cAMP assay with no functional activity for the other PGD2 DP receptor (27 μM in cAMP).
- Rist, ystein,Grimstrup, Marie,Receveur, Jean-Marie,Frimurer, Thomas M.,Ulven, Trond,Kostenis, Evi,Hoegberg, Thomas
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scheme or table
p. 1177 - 1180
(2010/06/15)
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- GHRELIN MODULATING COMPOUNDS AND COMBINATIONS THEREOF
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Compounds that modulate GHS-R are described, for examples compounds formula (I).
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Page/Page column 132-133
(2009/01/20)
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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.
-
scheme or table
p. 6969 - 6971
(2009/04/07)
-
- Sulfonamide compounds and uses thereof
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Compounds that modulate GHS-R are described, for examples compounds formula (I)
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Page/Page column 34
(2010/11/25)
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- Methods for minimizing thioamide impurities
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Methods for minimizing the formation of thioamide compounds using decoy agents during reactions, such as thionations of carbonyl compounds containing nitrite groups, are provided.
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Page/Page column 7
(2008/06/13)
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- Reactions of some ortho and para halogenated aromatic nitriles with ethylenediamine: Selective synthesis of imidazolines
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The reaction of ethylenediamine (EDA) with ortho and/or para halogenated benzonitriles did not lead to the imidazolines expected: a competitive aromatic nucleophilic substitution (SNAr) was observed instead. The selective synthesis of these imidazolines was performed by nucleophilic addition of EDA to thiobenzamide derivatives. The difference in reactivity between the nitrile and thioamide derivatives was estimated by a frontier orbital approach at the RHF/6-31G** level which predicted a greater reactivity of substituted thiobenzamides towards the nucleophilic addition of EDA.
- Crane, Louis J.,Anastassiadou, Maria,Stigliani, Jean-Luc,Baziard-Mouysset, Geneviève,Payard, Marc
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p. 5325 - 5330
(2007/10/03)
-
- Substituted 1,3-thiazole compounds, their production and use
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(1) A 1,3-thiazole compound of which the 5-position is substituted with a 4-pyridyl group having a substituent including no aromatic group or (2) a 1,3-thiazole compound of which the 5-position is substituted with a pyridyl group having at the position adjacent to a nitrogen atom of the pyridyl group a substituent including no aromatic group has an excellent p38 MAP kinase inhibitory activity.
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-
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- SUBSTITUTED THIAZOLE DERIVATIVES BEARING 3-PYRIDYL GROUPS, PROCESS FOR PREPARING THE SAME AND USE THEREOF
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The present invention provides a pharmaceutical composition having a steroid C17,20-lyase inhibitory activity, which is useful as a prophylactic or therapeutic agent of prostatism, tumor such as breast cancer and the like, more particularly, a steroid C17,20-lyase inhibitor containing a compound represented by the formula: wherein A1 is an aromatic hydrocarbon group optionally having substituents or a heterocyclic group optionally having substituents, one of A2 and A3 is a hydrogen atom, a halogen atom, a C1-4 aliphatic hydrocarbon group optionally having substituents or an optionally esterified carboxyl group, the other of A2 and A3 is an aromatic hydrocarbon group optionally having substituents or a heterocyclic group optionally having substituents, and at least one of A1, A2 and A3 is a 3-pyridyl group optionally having substituents, or a salt thereof or a prodrug thereof.
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Page/Page column 40
(2008/06/13)
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- 5-PYRIDYL-1,3-AZOLE COMPOUNDS, PROCESS FOR PRODUCING THE SAME AND USE THEREOF
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An optionally N-oxidized compound represented by the formula: wherein R1 represents hydrogen, hydrocarbon, heterocycle, amino, acyl, R2 represents an aromatic group, R3 represents hydrogen, pyridyl, aromatic hydrocarbon, X represents oxygen, optionally oxidized sulfur, Y represents a bond, an oxygen, optionally oxidized sulfur, a group represented by the formula NR4 (R4 represents hydrogen, hydrocarbon or acyl) and Z represents a bond or a divalent acyclic hydrocarbon, or a salt thereof has an excellent adenosine A3 receptor antagonistic activity and is used as an agent for preventing or treating diseases related to an adenosine A3 receptor. Furthermore, the compound (I) or a salt thereof has p38 MAP kinase inhibitory activity and TNF-α inhibitory activity and is used as an agent for preventing or treating diseases related to p38 MAP kinase and diseases related to TNF-α.
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Referential example 16
(2008/06/13)
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- Synthesis and anti-angiogenic activity of 6-(1,2,4-thiadiazol-5-yl)-3-amino pyridazine derivatives
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General screening for inhibitors of microvessel growth in vitro in the rat aortic ring assay led to the discovery of a novel series of thiadiazole pyridazine compounds with potential anti-angiogenic activity. Chemical optimization produced orally active compounds with potent in vitro and in vivo anti-angiogenesis and anti-tumor activities.
- Bongartz, Jean-Pierre,Stokbroekx, Raymond,Van der Aa, Marcel,Luyckx, Marcel,Willems, Marc,Ceusters, Marc,Meerpoel, Lieven,Smets, Gerda,Jansen, Tine,Wouters, Walter,Bowden, Charlie,Valletta, Lisa,Herb, Mark,Tominovich, Rose,Tuman, Robert
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p. 589 - 591
(2007/10/03)
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- Diaryl substituted thiazoles useful in the treatment of fungal infections
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Disclosed is a novel class of thiazole, thiadiazole, and oxadiazole compounds which are substituted at their nuclear carbons by aromatic moieties. These compounds exhibit antifungal activity against a variety of fungi including strains which have proven to be resistant to treatment with known antifungal agents such as Fluconazole.
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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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- 4-(Substituted phenyl thiazolyl)-3-hydroxy-3-pyrroline-2,5-diones
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Novel 4-(substituted thiazolyl)-3-hydroxy-3-pyrroline-2,5-diones are disclosed which inhibit glycolic acid oxidase and thus are useful in the treatment and prevention of calcium oxalate renal lithiasis.
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