- Novel synthesis of 2-Aminothiazoles via Fe(III)-Iodine-catalyzed Hantzsch-type condensation
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A novel iron-iodine catalyzed one pot synthesis of 2-aminothiazoles from methyl aryl ketones and thiourea is demonstrated. This protocol can be considered as a catalyzed version of the classical Hantzsch aminothiazole synthesis as it enables the in situ generation of α-iodoketones in the reaction medium using catalytic amount of iodine leading to Hantzsch condensation with thiourea. The supply of iodine for multiple catalytic cycles is ensured by using catalytic amounts of iron as it enables iodide to iodine oxidation. The generality of this protocol is also well established in this manuscript by synthesizing a variety of 2-aminothiazoles from different ketones and thiourea.
- Ujwaldev, Sankuviruthiyil M.,Harry, Nissy Ann,Neetha, Mohan,Anilkumar, Gopinathan
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supporting information
p. 646 - 653
(2020/10/20)
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- 2-Amino-4-arylthiazoles through One-Pot Transformation of Alkylarenes with NBS and Thioureas
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Treatment of alkylarenes with N-bromosuccinimide in a mixture of ethyl acetate and water at 60 °C, a mixture of acetonitrile and water at 80 °C, or a mixture of diethyl carbonate and water under irradiation with a tungsten lamp, followed by a reaction with thioureas or arenethioamides provided the corresponding 2-amino- 4-arylthiazoles or 2,4-diarylthiazoles in good to moderate yields, respectively, in one pot. The present reaction is an efficient one-pot transformation method of alkylarenes into 2-amino-4-arylthiazoles and 2,4-diarylthiazoles directly under mild and transition-metal-free conditions.
- Shibasaki, Kaho,Togo, Hideo
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p. 2520 - 2527
(2019/04/04)
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- Synthesis of 2-aminothiazoles from styrene derivatives mediated by 1,3-dibromo-5,5-dimethylhydrantoin (DBH)
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An efficient procedure for the synthesis of 2-aminothiazoles via DBH-mediated oxidative cyclization of styrenes and thioureas is reported. Various alkenes were successfully transformed to the corresponding 2-aminothiazoles in yields of 10–81% via a two-step one-pot manner using DBH as both the bromine source and oxidant. The method can be readily carried out in gram-scale and successfully applied to the synthesis of anti-inflammatory drug fanetizole using styrene as starting material.
- Ma, Chunhua,Miao, Yuqi,Zhao, Minghao,Wu, Ping,Zhou, Jianglu,Li, Zhi,Xie, Xilei,Zhang, Wei
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p. 3602 - 3607
(2018/05/26)
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- Synthesis and biological evaluation of novel thiazole- VX-809 hybrid derivatives as F508del correctors by QSAR-based filtering tools
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The most common CF mutation, F508del, impairs the processing and gating of CFTR protein. This deletion results in the improper folding of the protein and its degradation before it reaches the plasma membrane of epithelial cells. Present correctors, like VX809 only induce a partial rescue of the mutant protein. Our previous studies reported a class of compounds, called aminoarylthiazoles (AATs), featuring an interesting activity as correctors. Some of them show additive effect with VX809 indicating a different mechanism of action. In an attempt to construct more interesting molecules, it was thought to generate chemically hybrid compounds, blending a portion of VX809 merged to the thiazole scaffold. This approach was guided by the development of QSAR analyses, which were performed based on the F508del correctors so far disclosed in the literature. This strategy was aimed at exploring the key requirements turning in the corrector ability of the collected derivatives and allowed us to derive a predictive model guiding for the synthesis of novel hybrids as promising correctors. The new molecules were tested in functional and biochemical assays on bronchial CFBE41o-cells expressing F508del-CFTR showing a promising corrector activity.
- Liessi, Nara,Cichero, Elena,Pesce, Emanuela,Arkel, Maria,Salis, Annalisa,Tomati, Valeria,Paccagnella, Matteo,Damonte, Gianluca,Tasso, Bruno,Galietta, Luis J.V.,Pedemonte, Nicoletta,Fossa, Paola,Millo, Enrico
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p. 179 - 200
(2017/12/28)
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- Novel 2-(2,4-dioxo-1,3-thiazolidin-5-yl)acetamides as antioxidant and/or anti-inflammatory compounds
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A series of novel N-(4-aryl-1,3-thiazol-2-yl)-2-(2,4-dioxo-1,3-thiazolidin- 5-yl)acetamides (4a-k) and N-(1,3-benzothiazol-2-yl)-2-(2,4-dioxo-1,3- thiazolidin-5-yl)acetamide derivatives (4l-o) are synthesized and evaluated for their anti-inflammatory and antioxidant activity (DPPH radical scavenging, superoxide anion scavenging, lipid peroxide inhibition, erythrocyte hemolytic inhibition). Compounds 4k and 4l have exhibited good antioxidant activity in four assays, while compounds 4c, 4d , 4m, 4n and 4o have shown good DPPH radical scavenging efficacy. Compounds 4a, 4h , 4i, 4k, 4m and 4n have possessed excellent anti-inflammatory activity. N-[4-(o-methoxyphenyl)-1,3-thiazol-2-yl]- 2-(2,4-dioxo-1,3-thiazolidin-5-yl) acetamide (4k) and N-(6-nitro-/methoxy-1,3- benzothiazol-2-yl)-2-(2,4-dioxo-1,3-thiazolidin-5-yl)acetamide (4m and 4n) have exhibited both antioxidant and anti-inflammatory activities.
- Koppireddi, Satish,Komsani, Jayaram Reddy,Avula, Sreenivas,Pombala, Sujitha,Vasamsetti, Satishbabu,Kotamraju, Srigiridhar,Yadla, Rambabu
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p. 305 - 313
(2013/10/01)
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- An efficient, uncatalyzed, and rapid synthesis of thiazoles and aminothiazoles under microwave irradiation and investigation of their biological activity
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A convenient method for the synthesis of thiazoles by treatment of -bromoketones with thioamides (Hantzsch synthesis) in the absence of catalysts under microwave irradiation has been developed. The products were formed rapidly in excellent yields. An efficiency comparison of time, yield, and effort clearly proved the microwave technique to be superior. The structures of the newly synthesized compounds were characterized by spectroscopic data and elemental analyses. The synthesized compounds were tested for their biological activity. Depending on the substituents, some of the thiazoles exhibit very good antibacterial or antifungal activity.
- Gaikwad, Sudhakar A.,Patil, Amol A.,Deshmukh, Madhukar B.
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experimental part
p. 103 - 109
(2010/05/02)
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- QUINAZOLINEDIONE DERIVATIVES AS TRPA1 MODULATORS
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The present invention provides Quinazolinedione derivatives as TRPA (Transient Receptor Potential subfamily A) modulators. In particular, compounds described herein are useful for treating or preventing diseases, conditions and/or disorders modulated by T
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Page/Page column 17
(2010/01/31)
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- PHTHALIMIDE DERIVATIVES AS TRPA1 MODULATORS
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The present invention provides TRPA (Transient Receptor Potential subfamily A) modulators. In particular, compounds described herein are useful for treating or preventing diseases, conditions and/or disorders modulated by TRPAl (Transient Receptor Potential subfamily A, member 1) modulators. Also provided herein are processes for preparing compounds described herein, intermediates used in their synthesis, pharmaceutical compositions thereof, and methods for treating or preventing diseases, conditions and/or disorders modulated by TRPAl.
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Page/Page column 29
(2009/10/22)
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- MODULATORS OF GLUCOCORTICOID RECEPTOR, AP-1, AND/OR NF-κB ACTIVITY AND USE THEREOF
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Novel non-steroidal compounds are provided which are useful in treating diseases associated with modulation of the glucocorticoid receptor, AP-1, and/or NF-κB activity including inflammatory and immune diseases, obesity and diabetes having the structure o
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Page/Page column 76
(2008/12/05)
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