- Three-Component Synthesis of 2-Alkylthiobenzoazoles in Aqueous Media
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A highly efficient three-component protocol for the synthesis of the 2-alkylthiobenzoazoles is described. Tetramethylthiuram disulfide (TMTD) cyclized with o -aminothiophenols, generating the intermediate 2-mercaptobenzothiazoles, and the successive C-S coupling with halogenated alkanes afforded a series of 2-alkyl-substituted thiobenzothiazoles smoothly in a one-pot process. This procedure could also be utilized for the preparation of 2-alkyl-substituted thiobenzoxazoles and 2-alkyl-substituted thiobenzimidazoles. Inexpensive and easily available starting materials, metal catalyst-free, broad substrate scope, and water as solvent are the features of this protocol.
- Chen, Jin-Quan,Dong, Zhi-Bing,Guo, Jia
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p. 1927 - 1933
(2020/07/03)
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- AlCl3-Promoted Synthesis of 2-Mercapto Benzoheterocycles by Using Sodium Dimethyldithiocarbamate as Thiocarbonyl Surrogate
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A simple, expeditious and high-efficiency synthetic method for the AlCl3-mediated one-pot preparation of 2-mercapto benzoheterocycles (2-mercapto benzothiazoles, benzoxazoles and benzimidazoles) is described. By the treatment of a series of S, O and N heteroatoms containing bifunctional molecules with sodium dimethyldithiocarbamate in AlCl3, the desired benzoheterocycles are obtained smoothly. The protocol can also be applied on the synthesis of a series of thiazolidine-2-thiones, imidazolidine-2-thiones. This novel synthetic approach has advantages such as ligand-free, high efficiency, short reaction time, readily available starting materials and simple experimental procedures.
- Liu, Xing,Zhang, Shi-Bo,Dong, Zhi-Bing
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p. 5406 - 5411
(2018/10/20)
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- An environmentally benign and efficient synthesis of substituted benzothiazole-2-thiols, benzoxazole-2-thiols, and benzimidazoline-2-thiones in water
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An efficient and practical method for the one-step synthesis of benzothiazole-2-thiols, benzoxazole-2-thiols and benzimidazoline-2-thiones by cyclization of 2-aminothiophenols, 2-aminophenols, and 1,2-phenylenediamines with tetramethylthiuram disulfide (TMTD) in water was described. The features of this method include metal/ligand-free, excellent yield, short reaction time and broad substrate scope. The method provides a facile and convenient preparation of some potentially biologically active compounds.
- Liu, Xing,Liu, Min,Xu, Wan,Zeng, Meng-Tian,Zhu, Hui,Chang, Cai-Zhu,Dong, Zhi-Bing
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p. 5591 - 5598
(2017/12/06)
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- Selective synthesis of 2-aminobenzoxazoles and 2-mercaptobenzoxazoles by using o-aminophenols as starting material
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2-Aminobenzoxazoles and 2-mercaptobenzoxazoles were selectively synthesized by treating o-aminophenols with dithiocarbamates and tetramethylthiuram disulfide (TMTD), respectively. With the promotion of NaH/CuI, the reaction of o-aminophenols with dithioca
- Liu, Min,Zeng, Meng-Tian,Xu, Wan,Wu, Li,Dong, Zhi-Bing
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supporting information
p. 4352 - 4356
(2017/10/17)
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- Elemental sulfur as a sulfuration agent in the copper-catalyzed C-H bond thiolation of electron-deficient arenes
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By utilizing elemental sulfur as the thiolation agent and oxidant, a copper-catalyzed direct C-H bond thiolation of electron-deficient arenes was demonstrated. Various electron-deficient arenes were proved to be suitable for this transformation. Preliminary mechanistic studies indicated that this reaction underwent a radical pathway, in which the trisulfur radical anion (S3-) might play a vital role. Meanwhile, KIE experiments suggested that C-H bond cleavage was not involved in the rate-determining step.
- Yan, Haiming,Huang, Zhiliang,Chen, Meng,Li, Cuiting,Chen, Ya,Gao, Meng,Lei, Aiwen
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supporting information
p. 8276 - 8279
(2017/10/23)
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- DERIVATIVES OF HETEROARYLSULFONAMIDES, THEIR PREPARATION AND THEIR APPLICATION IN HUMAN THERAPY
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The present invention concerns derivatives of heteroarylsulfonamides, notably as blockers of Kv potassium channels, and more particularly of channels Kv1.5, Kv4.3 or Kv11.1, their application in clinical therapy and their preparation methods. These compounds correspond to the following general formula (I): where R1 represents one or more substituents of the phenyl core X such as: hydrogen, halogen, trifluoromethyl, trifluoromethoxy, linear or branched C1-C4 alkyl, or linear or branched C1-C4 alkoxy, A represents oxygen or sulphur, B represents nitrogen when n=1 or 2 and D represents —C(═O)—, or B represents CH when n=0 and D represents —CH2O— or when n=1 and D represents —O—, R2 represents a hydrogen, a methyl, a fluorine or chlorine atom or a methoxy, HetAr represents a pyridyl or quinolyl group, possibly substituted by a group such as a linear or branched C1-C4 alkyl, a linear or branched C1-C4 alkoxy, a halogen, or a trifluoromethyl, and to their pharmaceutically acceptable salts.
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Paragraph 0067; 0068; 0069; 0070
(2013/07/19)
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- DERIVATIVES OF HETEROARYLSULFONAMIDES, THEIR PREPARATION AND THEIR APPLICATION IN HUMAN THERAPY
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The present invention concerns derivatives of heteroarylsulfonamides, notably as blockers of Kv potassium channels, and more particularly of channels Kv1.5, Kv4.3 or Kv11.1, their application in clinical therapy and their preparation methods. These compounds correspond to the following general formula (I): where R1 represents one or more substituents of the phenyl core X such as: hydrogen, halogen, trifluoromethyl, trifluoromethoxy, linear or branched C1-C4 alkyl, or linear or branched C1-C4 alkoxy, A represents oxygen or sulphur, B represents nitrogen when n=1 or 2 and D represents ?C(=O)-, or B represents CH when n=0 and D represents ?CH2O? or when n=1 and D represents ?O?, R2 represents a hydrogen, a methyl, a fluorine or chlorine atom or a methoxy, HetAr represents a pyridyl or quinolyl group, possibly substituted by a group such as a linear or branched C1-C4 alkyl, a linear or branched C1-C4 alkoxy, a halogen, or a trifluoromethyl, and to their pharmaceutically acceptable salts.
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Page/Page column 17
(2012/06/15)
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- Blue fluorescent dye-protein complexes based on fluorogenic cyanine dyes and single chain antibody fragments
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Fluoromodules are complexes formed upon the noncovalent binding of a fluorogenic dye to its cognate biomolecular partner, which significantly enhances the fluorescence quantum yield of the dye. Previously, several single-chain, variable fragment (scFv) antibodies were selected from a yeast cell surface-displayed library that activated fluorescence from a family of unsymmetrical cyanine dyes covering much of the visible and near-IR spectrum. The current work expands our repertoire of genetically encodable scFv-dye pairs by selecting and characterizing a group of scFvs that activate fluorogenic violet-absorbing, blue-fluorescing cyanine dyes, based on oxazole and thiazole heterocycles. The dye binds to both yeast cell surface-displayed and soluble scFvs with low nanomolar Kd values. These dye-protein fluoromodules exhibit high quantum yields, approaching unity for the brightest system. The promiscuity of these scFvs with other fluorogenic cyanine dyes was also examined. Fluorescence microscopy demonstrates that the yeast cell surface-displayed scFvs can be used for multicolor imaging. The prevalence of 405 nm lasers on confocal imaging and flow cytometry systems make these new reagents potentially valuable for cell biological studies.
- Zanotti, Kimberly J.,Silva, Gloria L.,Creeger, Yehuda,Robertson, Kelly L.,Waggoner, Alan S.,Berget, Peter B.,Armitage, Bruce A.
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supporting information; experimental part
p. 1012 - 1020
(2011/04/22)
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- DIAZEPANE COMPOUNDS WHICH MODULATE THE CB2 RECEPTOR
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Compounds of formula (I) are disclosed. Compounds according to the invention bind to and are agonists, antagonists or inverse agonists of the CB2 receptor, and are useful for treating inflammation. Those compounds which are agonists are additionally useful for treating pain.
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Page/Page column 26-27
(2009/05/30)
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- Regulatory molecules for the 5-HT3 receptor ion channel gating system
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Substituted benzoxazole derivatives which possess a nitrogen-containing heterocycle at C2 are selective partial agonists of the 5-HT3 receptor. Alteration of substituents on the benzoxazole nucleus affords both agonist-like and antagonist-like compounds, and uniquely modifies the function of the 5-HT3 receptor ion channel gating system. SAR and corroborative computational docking study for these partial agonists successfully explained structure and function of the 5-HT3 receptor.
- Yoshida, Satoshi,Watanabe, Takashi,Sato, Yasuo
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p. 3515 - 3523
(2008/02/07)
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- 4-(2-Pyridyl)piperazine-1-benzimidazoles as potent TRPV1 antagonists
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A series of 4-(2-pyridyl)piperazine-1-benzimidazole analogues based on compound 1 was synthesized and evaluated for TRPV1 antagonist activity in capsaicin-induced (CAP) and pH 5.5-induced (pH) FLIPR assays in a human TRPV1-expressing HEK293 cell line. Potent TRPV1 antagonists were identified through SAR studies. From these studies, several antagonists were found, with IC50 values ranging from 32 nM to ~5000 nM. Among these, 11 [IC50 = 90 nM (CAP) and 104 nM (pH)] was further evaluated and found to be orally available in rats (F% = 19.7).
- Shao, Bin,Huang, Jincheng,Sun, Qun,Valenzano, Kenneth J.,Schmid, Lori,Nolan, Scott
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p. 719 - 723
(2007/10/03)
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- A new 5-HT3 receptor ligand. II. Structure-activity analysis of 5-HT3 receptor agonist action in the gut
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Several modified 2-piperazinyl benzoxazole derivatives, which exhibit an agonistic effect on gastrointestinal motility, were synthesized and their effects on the contraction of guinea-pig ileum were examined. The quaternary piperazinyl benzoxazole structure has a restricted conformation and stereostructure compared to those of the other 5-HT3 receptor agonists, serotonin and meta-chlorophenylbiguanide. The mutual positions of the aromatic ring, nitrogen atom and terminal amine are considered to form the pharmacophore of the 5-HT3 receptor agonist in the gut. In the serotonin- evoked reflex bradycardia [Bezold-Jarisch (B-J) reflex] inhibition test using rats the B-J reflex-inducing ratio was different for each synthesized compound. These results suggest that, in these 5-HT3 receptor agonists, the substituents of the benzoxazole ring influence the B-J reflex-inducing activity in rats.
- Yamada, Megumi,Sato, Yasuo,Kobayashi, Kazuko,Konno, Fukio,Soneda, Tomoko,Watanabe, Takashi
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p. 445 - 451
(2007/10/03)
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- 3-[1-(2-Benzoxazolyl)hydrazino]propanenitrile derivatives: Inhibitors of immune complex induced inflammation
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3-[1-(2-Benzoxazolyl)hydrazino]propanenitrile derivatives were evaluated in the dermal and pleural reverse passive Arthus reactions in the rat. In the pleural test these compounds were effective in reducing exudate volume and accumulation of white blood cells. This pattern of activity was similar to that of hydrocortisone and different from that of indomethacin. The structural requirements for inhibiting the Arthus reactions were studied by systematic chemical modification of 1. These structure-activity relationship studies revealed that nitrogen 1' of the hydrazino group is essential for activity and must be electron rich, whereas chemical modifications of other sites of 1 had only a modest effect on activity.
- Haviv,Ratajczyk,DeNet,Kerdesky,Walters,Schmidt,Holms,Young,Carter
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p. 1719 - 1728
(2007/10/02)
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