Regiospecific Functionalization of 1,3-Dihydro-2H-benzimidazol-2-one and Structurally Related Cyclic Urea Derivatives

Meanwell, Nicholas A.; Sit, Sing‐Yuen; Gao, Jinnian; Wong, Henry; Gao, Qi; Laurent, Denis R. St.; Balasubramanian, Neelakantan

doi:10.1021/jo00111a014

Cited by 50 publications

(45 citation statements)

References 6 publications

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“…16 The 5,5-dimethylimidazolidine-2,4-dione (1) itself was prepared by a standard procedure. 17 The synthesis of 3-arylsulfonylimidazolidine-2,4-diones (2a-d) was indicated in the IR spectra by the appearance of the absorptions for anti-symmetric and symmetric O=S=O stretchings in the narrow ranges of 1359-1357 cm -1 and 1168-1148 cm -1 .…”

Section: Resultsmentioning

confidence: 99%

“…The ethereal extract was discarded and aqueous layer was acidified to get the precipitates of immidazolidine-2,4-dione. General method for the synthesis of 3-arylsulfonylimidazolidine-2,4-diones 16 To a well stirred mixture of imidazolidine-2,4-dione (4.8 mmol), triethylamine (4.8 mmol) and catalytic amounts of DMAP, was dropwise added a solution of arylsulfonyl chloride (5.8 mmol) in an appropriate volume of dichloromethane and the reaction mixture was stirred at room temperature for three hours. The reaction mixture was diluted with 1N HCl till pH 2 and extracted with dichloromethane (3 × 25 mL).…”

Section: Synthesis Of 55-dimethylimidazolidine-24-dionementioning

confidence: 99%

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Synthesis and hypoglycemic activity of 5,5-dimethylarylsulfonylimidazolidine-2,4-diones

Kashif¹,

Ahmad²,

Hameed³

2008

Arkivoc

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1-Arylsulfonyl-5,5-dimethylimidazolidine-2,4-diones (3a-d) were prepared by the rearrangement of 3-arylsulfonyl-5,5-dimethylimidazolidine-2,4-diones (2a-d). Compounds (2a-d) were in turn synthesized by the reaction of arylsulfonyl chlorides with 5,5-dimethylimidazolidine-2,4-dione. All the synthesized compounds were characterized by modern spectroscopic techniques. Two of the synthesized compounds, (2a) and (3a), proved to be the stimulators of insulin release when used at concentrations of 100 µM.

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Section: Resultsmentioning

confidence: 99%

Section: Synthesis Of 55-dimethylimidazolidine-24-dionementioning

confidence: 99%

Synthesis and hypoglycemic activity of 5,5-dimethylarylsulfonylimidazolidine-2,4-diones

Kashif¹,

Ahmad²,

Hameed³

2008

Arkivoc

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“…Following the procedure of Li et al, 31 eluting with petroleum ether:EtOAc (1:0 to 1:1), afforded 4-(3-hydroxyphenyl)-3,5-dimethylisoxazole (27) (63 mg, 58%) as a colourless solid. The data are identical to those obtained using method 1.…”

Section: Ethyl 4-bromo-3-methylisoxazole-5-carboxylate (35)mentioning

confidence: 99%

“…MgSO4, filtered, and concentrated in vacuo. Purification of the oil by silica gel chromatography (Biotage; SNAP 10 g), eluting with petroleum ether and CH2Cl2 (1:0 to 3:1), afforded N-methyl-2-nitroaniline (73) (281 mg, 26% yield) as an orange solid: Rf 0.34 (petroleum ether:CH2Cl2 = 4:1); m.p [26][27][28]. [lit 20.…”

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confidence: 99%

Fragment-Based Identification of Ligands for Bromodomain-Containing Factor 3 of Trypanosoma Cruzi

Laurin¹,

Bluck²,

Chan³

et al. 2020

Preprint

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The Trypanosoma cruzi (T. cruzi) parasite is the cause of Chagas disease, a neglected disease endemic in South America. The life cycle of the T. cruzi parasite is complex and includes transitions between distinct life stages. This change in phenotype (without a change in genotype) could be controlled by epigenetic regulation, and might involve the bromodomain-containing factors 1-5 (TcBDF1-5). However, little is known about the function of the TcBDF1-5. Here we describe a fragment-based approach to identify ligands for T. cruzi bromodomain-containing factor 3 (TcBDF3). We expressed a soluble construct of TcBDF3 in E. coli, and used this to develop a range of biophysical assays for this protein. Fragment screening identified twelve compounds that bind to the TcBDF3 bromodomain. Based on this screen, we developed functional ligands containing a fluorescence or 19F reporter group, and a photo-crosslinking probe for TcBDF3. These tools compounds will be invaluable in future studies on the function of TcBDF3 and will provide insight into the biology of T. cruzi.

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“…For the crystal structures of other imidazo[4,5-b]pyridin-2ones, see: Kourafalos et al (2002); Meanwell et al (1995).…”

Section: Related Literaturementioning

confidence: 99%

6-Bromo-1-(1,2-propadienyl)-3-(2-propynyl)-1H-imidazo[4,5-b]pyridin-2(3H)-one

Dahmani¹,

Haoudi²,

Capet³

et al. 2010

Acta Cryst E

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The reaction of propargyl bromide and 6-bromo-1,3-dihydroimidazo[4,5-b]pyridin-2-one in refluxing dimethylformamide yields the title compound, C12H8BrN3O, which features nitrogen-bound propadienyl and propynyl substituents. The imidazolopyridine fused ring is planar (r.m.s. deviation = 0.012 Å); the propadienyl chain is coplanar with the fused ring as it is conjugated with it, whereas the propynyl chain is not as the nitrogen-bound C atom is a methylene linkage. The acetylenic H atom is hydrogen bonded to the carbonyl O atom of an adjacent molecule, forming a helical chain runnning along the b axis.

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Regiospecific Functionalization of 1,3-Dihydro-2H-benzimidazol-2-one and Structurally Related Cyclic Urea Derivatives

Cited by 50 publications

References 6 publications

Synthesis and hypoglycemic activity of 5,5-dimethylarylsulfonylimidazolidine-2,4-diones

Synthesis and hypoglycemic activity of 5,5-dimethylarylsulfonylimidazolidine-2,4-diones

Fragment-Based Identification of Ligands for Bromodomain-Containing Factor 3 of Trypanosoma Cruzi

6-Bromo-1-(1,2-propadienyl)-3-(2-propynyl)-1H-imidazo[4,5-b]pyridin-2(3H)-one

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