- Access to Thiazole via Copper-Catalyzed [3+1+1]-Type Condensation Reaction under Redox-Neutral Conditions
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A new strategy for thiazoles via copper-catalyzed [3+1+1]-type condensation reaction from oximes, anhydrides and potassiumthiocyanate (KSCN) is developed herein. The transformation has good functional group tolerance and various thiazoles were formed smoothly in good to excellent yields under mild reaction conditions. This process involves copper-catalyzed N-O/C-S bond cleavages, activation of vinyl sp2 C-H bond, and C-S/C-N bond formations which are under redox-neutral conditions as well as operational simplicity.
- Tang, Xiaodong,Yang, Jidan,Zhu, Zhongzhi,Zheng, Meifang,Wu, Wanqing,Jiang, Huanfeng
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p. 11461 - 11466
(2016/11/28)
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- Exploration and Optimization of an Efficient One-pot Sequential Synthesis of Di/tri-substituted Thiazoles from α-Bromoketones, Thioacids Salt, and Ammonium Acetate
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Exploration of scope of an optimized one-pot sequential procedure for preparing of 2,4-di- and 2,4,5-tri-substituted thiazoles has been accomplished. The synthesis was performed by the initial formation of a β-keto-thioester intermediate from nucleophilic substitution of α-bromoketones with thioacid potassium salts, followed by treatment with ammonium acetate and one equivalent of acetic acid in toluene to form imine intermediate eventually leading to cyclization yielding thiazoles. This procedure should be highlighted with a flexible way to control the substitution pattern around thiazole ring by choosing appropriately substituted α-bromoketones even containing acid labile functionality and thioacid potassium salts, and thus its applicability is very wide.
- Venkateswararao, Eeda,Jalani, Hitesh B.,Manoj,, Manickam,Jung, Sang-Hun
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p. 1449 - 1456
(2016/09/24)
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- Lipase and deep eutectic mixture catalyzed efficient synthesis of thiazoles in water at room temperature
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Lipase bio-catalyst or ammonium based deep eutectic mixture efficiently catalyzed aqueous phase synthesis of methyl-thiazole and amino-thiazole derivatives. The simple ammonium deep eutectic catalyst, easily synthesized from choline chloride and urea, is inexpensive, recyclable and bio-degradable, making it suitable for industrial applications. Springer Science+Business Media, LLC 2012.
- Lobo, Hyacintha Rennet,Singh, Balvant Shyam,Shankarling, Ganapati Subray
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p. 1369 - 1375
(2013/01/15)
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- Efficient synthesis of 2,4-disubstituted thiazoles under grinding
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A simple and convenient protocol is described for the preparation of 2,4-disubstituted thiazoles via a condensation reaction of -halo carbonyl compounds with thiourea or thioacetamide at room temperature, under grinding, in good yields.
- Heravi, Majid M.,Poormohammad, Nargess,Beheshtiha, Yahia S.,Baghernejad, Bita
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experimental part
p. 579 - 582
(2011/04/22)
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- Synthesis, characterization, and antimicrobial evaluation of oxadiazole congeners
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A series of 1,3-oxazole, 1,3-thiazole, isomeric 1,2,4-oxadiazole, 1,3,4-oxadiazole, and 1,2,3,4-tetrazole heterocycles was synthesized. All the compounds shared as a common feature the presence of a 4-hydroxyphenyl substituent. The structures of the synthesized compounds were confirmed by MS, 1H-NMR, and elemental analysis. In vitro antimicrobial activity for all the newly synthesized compounds at concentrations of 200-25 μg/mL was evaluated against Gram+ve organisms such as methicillin-resistant Staphylococcus aureus (MRSA), Gram-ve organisms such as Escherichia coli (E. coli), and the fungal strain Aspergillus niger (A. niger) by the cup plate method. Ofloxacin and ketoconazole (10 μg/mL) were used as reference standards for antibacterial and antifungal activity, respectively. Compounds 15, 16, and 20 showed notable antibacterial and antifungal activities at higher concentrations (200 μg/mL), whereas 17-19 were found to display significant antibacterial or antifungal activity (25-50 μg/mL) against the Gram+ve, Gram-ve bacteria, or fungal cells used in the present study.
- Sadek, Bassem,Fahelelbom, Khairi Mustafa Salem
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experimental part
p. 4339 - 4347
(2011/08/10)
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- Novel bisaryl substituted thiazoles and oxazoles as highly potent and selective peroxisome proliferator-activated receptor δ agonists
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The discovery, synthesis, and optimization of compound 1 from a high-throughput screening hit to highly potent and selective peroxisome proliferator-activated receptor δ (PPARδ) agonists are reported. The synthesis and structure-activity relationship in this series are described in detail. On the basis of a general schematic PPAR pharmacophore model, scaffold 1 was divided into headgroup, linker, and tailgroup and successively optimized for PPAR activation using in vitro PPAR transactivation assays. A (2-methylphenoxy)acetic acid headgroup, a flexible linker, and a five-membered heteroaromatic center ring with two hydrophobic aryl substituents were required for efficient and selective PPARδ activation. The fine-tuning of these aryl substituents led to an array of highly potent and selective compounds such as compound 38c, displaying an excellent pharmacokinetic profile in mouse. In an in vivo acute dosing model, selected members of this array were shown to induce the expression of pyruvate dehydrogenase kinase-4 (PDK4) and uncoupling protein-3 (UCP3), genes that are known to be involved in energy homeostasis and regulated by PPARδ in skeletal muscle.
- Epple, Robert,Cow, Christopher,Xie, Yongping,Azimioara, Mihai,Russo, Ross,Wang, Xing,Wityak, John,Karanewsky, Donald S.,Tuntland, Tove,Nguyê?-Tran, Van T. B.,Ngo, Cara Cuc,Huang, David,Saez, Enrique,Spalding, Tracy,Gerken, Andrea,Iskandar, Maya,Seidel, H. Martin,Tian, Shin-Shay
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experimental part
p. 77 - 105
(2010/04/30)
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- A rapid and high-yielding synthesis of thiazoles and aminothiazoles using tetrabutylammonium salts
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A convenient method for the synthesis of thiazoles and aminothiazoles by treatment of phenacyl bromides with thioamides/thiourea in the presence of tetrabutylammonium hexafluorophosphate (Bu4NPF6) at room temperature was developed. The products having high yields were formed rapidly (within 15 min). The method is simple, rapid and practical, generating thiazole derivatives in excellent isolated yields. The structures of the newly synthesized products were identified by FT-IR, 1H NMR, 13C NMR spectroscopy and elemental analysis data. The Japan Institute of Heterocyclic Chemistry.
- Kocabas, Erdal,Sariguney, Ahmet Burak,Coskun, Ahmet
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experimental part
p. 2849 - 2854
(2011/04/16)
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- Efficient and expeditious synthesis of di- and trisubstituted thiazoles in PEG under catalyst-free conditions
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An efficient and expeditious catalyst-free protocol was developed for the construction of di- and trisubstituted thiazoles from -haloketones and thioureas/thioamides in PEG. The reaction was carried out at ambient temperature, and the products were obtained in excellent isolated yields (91-98%). Additionally, PEG could be recovered easily and was reused without evident loss in activity.
- Zhu, Dongjian,Chen, Jiuxi,Xiao, Huilong,Liu, Miaochang,Ding, Jinchang,Wu, Huayue
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experimental part
p. 2895 - 2906
(2009/12/03)
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- An efficient, catalyst- and solvent-free synthesis of imidazo[1,2-a] pyridines and 2,4-disubstituted thiazoles on grinding
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An efficient synthesis of imidazo[1,2-a]pyridines and 2,4-disubstituted thiazoles in excellent yield under catalyst-and solvent-free conditions at room temperature on grinding has been developed. The important features of this method are that it is reasonably fast, very clean, high yielding, simple workup and environmentally benign.
- Zhu, Dongjian,Chen, Jiuxi,Wu, Dengze,Liu, Miaochang,Ding, Jinchang,Wu, Huayue
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experimental part
p. 84 - 86
(2009/10/15)
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- Liquid-phase organic synthesis of thiazoles using poly(ethylene glycol)-bound sulfonyl chloride resin
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Reaction of poly(ethylene glycol) (PEG)-bound sulfonic acid with thionyl chloride formed difunctionalized PEG-bound sulfonyl chloride, which was treated with α-hydroxyketones, followed by treatment with thioamides in the presence of potassium carbonate, to afford thiazoles in good yields with a facile workup procedure. Copyright Taylor & Francis Group, LLC.
- Liu, Xiao-Ling,Wang, Qiu-Ying,Sheng, Shou-Ri,Xu, Chen,Cai, Ming-Zhong
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p. 3338 - 3345
(2008/12/22)
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- Efficient synthesis of 2,4-disubstituted thiazoles using ionic liquid?under ambient conditions: a practical approach towards?the?synthesis of Fanetizole
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A highly efficient and rapid synthesis of 2-amino-4-arylthiazoles and 2-methyl-4-arylthiazole from α-bromoketone and thiourea/thioamide is described using room temperature ionic liquid at ambient conditions. The method is simple, rapid and practical, generating thiazole derivatives in excellent isolated yields. This protocol is utilized for a commercially feasible synthesis of an anti-inflammatory agent, Fanetizole.
- Potewar, Taterao M.,Ingale, Sachin A.,Srinivasan, Kumar V.
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p. 11066 - 11069
(2011/05/18)
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- ANTIBACTERIAL AGENTS
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Compounds of formula (I) have antibacterial activity wherein R represents hydrogen or 1, 2 or 3 optional substituents; W is =C(R1)- or =N-; R1 is hydrogen or an optional substituent and R2 is hydrogen, methyl, or fluorine; or R1 and R2 taken together are -CH2-, -CH2CH2-, -O-, or, in either orientation, -O- CH2- Or -OCH2CH2-; R3 is a radical of formula -(Alk1)m-(Z)p-(Alk2)n-Q wherein m, p and n are independently 0 or 1, provided that at least one of m, p and n is 1, Z is -O-, -S-, -S(O)-, -S(O2)-, -NH-, -N(CH3)-, -N(CH2CH3)-, -C(=O)-, -O-(C=O)-, -C(=O)-O-, or an optionally substituted divalent monocyclic carbocyclic or heterocyclic radical having 3 to 6 ring atoms; or an optionally substituted divalent bicyclic heterocyclic radical having 5 to 10 ring atoms; Alk1 and Alk2 are optionally substituted C1C6 alkylene, C2-C6 alkenylene, or C2-C6 alkynylene radicals, which may optionally terminate with or be interrupted by -O-, -S-, -S(O)-, -S(O2)-, -NH-, -N(CH3)-, or -N(CH2CH3)-; and Q is hydrogen, halogen, nitrile, or hydroxyl or an optionally substituted monocyclic carbocyclic or heterocyclic radical having 3 to 6 ring atoms; or an optionally substituted bicyclic heterocyclic radical having 5 to 10 ring atoms.
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Page/Page column 111; 136
(2010/11/28)
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- COMPOUNDS AND COMPOSITIONS AS PPAR MODULATORS
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The invention provides compounds, pharmaceutical compositions comprising such compounds and methods of using such compounds to treat or prevent diseases or disorders associated with the activity of the Peroxisome Proliferator-Activated Receptor (PPAR) families, particularly the activity of PPAR.
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Page/Page column 42-43
(2010/02/14)
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- COMPOUNDS, METHODS AND FORMULATIONS FOR THE ORAL DELIVERY OF A GLUCAGON LIKE PEPTIDE (GLP)-1 COMPOUND OR AN MELANOCORTIN 4 RECEPTOR (MC4) AGONIST PEPTIDE
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The present invention relates to novel compounds, methods, and formulations useful for the oral delivery of a GLP-1 compound or an MC4 agonist peptide.
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Page/Page column 13-15
(2008/06/13)
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- Progress in the proxifan class: heterocyclic congeners as novel potent and selective histamine H3-receptor antagonists
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Histamine H3 receptors are critically involved in the pathophysiology of several disorders of the central nervous system (CNS). Among other families of H3-receptor ligands, the proxifan class has recently been described to contain numerous potent histamine H3-receptor antagonists, e.g. ciproxifan or imoproxifan. In the present study, we report on the design of novel heterocyclic proxifan analogues and their antagonist potencies at histamine H3 receptors. The new compounds were tested for in vitro and in vivo H3-receptor antagonist potencies in different species as well as for H3-receptor selectivity vs. H1 and H2 receptors. In vitro, all compounds investigated proved to be potent H3-receptor antagonists in the rat as well as in the guinea-pig. In addition, they showed good to high oral CNS potency in vivo in mice. Especially, oxadiazole derivatives 24-26 displayed nanomolar antagonist activity in vitro and high potency in vivo (ED50=0.47-0.57 mg/kg). The results show that the additional heteroaromatic moieties might act as bioisosteres of the ketone or oxime moieties of ciproxifan or imoproxifan, respectively, and might cause divergent pharmacokinetic properties. Thus, these novel H3-receptor antagonists are interesting leads for further development. Copyright
- Grassmann, Sven,Sadek, Bassem,Ligneau, Xavier,Elz, Sigurd,Ganellin, C. Robin,Arrang, Jean-Michel,Schwartz, Jean-Charles,Stark, Holger,Schunack, Walter
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p. 367 - 378
(2007/10/03)
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