- 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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- 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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- Serotonin 5-HT3 receptor partial activator
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This invention provides a serotonin 5-HT3 receptor partial activator which has a serotonin 5-HT3 receptor activating action, in addition to its serotonin 5-HT3 receptor antagonism, and does not cause constipation as a side effect. Particularly, based on the finding that newly synthesized benzoxazole derivatives typified by the compounds of the following formula (2) have strong serotonin 5-HT3 receptor antagonism and serotonin 5-HT3 receptor activating action, this invention provides these benzoxazole derivatives as serotonin 5-HT3 receptor partial activators. In the above formula, R1 to R4 may be the same or different from one another and each represents a hydrogen atom, a halogen atom, a substituted or unsubstituted lower alkyl group, a substituted or unsubstituted lower alkenyl group or a substituted or unsubstituted amino group, or two groups of R1 and R2 may be linked together to form a ring structure, namely benzene ring; R5 represents a hydrogen atom, a substituted or unsubstituted lower alkyl group or a substituted or unsubstituted lower alkenyl group; and m is an integer of 1 to 4.
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- Benzoxazole derivatives as novel 5-HT3 receptor partial agonists in the gut
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A series of benzoxazoles with a nitrogen-containing heterocyclic substituent at the 2-position was prepared and evaluated for 5-HT3 partial agonist activity on isolated guinea pig ileum. The nature of the substituent at the 5-position of the benzoxazole ring affected the potency for the 5-HTs receptor, and the 5-chloro derivatives showed increased potency and lowered intrinsic activity. 5-Chloro-7-methyl-2-(4-methyl-1- homopiperazinyl)benzoxazole (6v) exhibited a high binding affinity in the same range as that of the 5-HT3 antagonist granisetron, and its intrinsic activity was 12% of that of 5-HT. Compound 6v inhibited 5-HT-evoked diarrhea but did not prolong the transition time of glass beads in the normal distal colon even at a dose of 100 times the ED50 for diarrhea inhibition in mice. Compounds of this type are expected to be effective for the treatment of irritable bowel syndrome without the side effect of constipation.
- Sato, Yasuo,Yamada, Megumi,Yoshida, Satoshi,Soneda, Tomoko,Ishikawa, Midori,Nizato, Tetsutaro,Suzuki, Kokichi,Konno, Fukio
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p. 3015 - 3021
(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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