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Structure-activity relationships for analogs of the tuberculosis drug bedaquiline with the naphthalene unit replaced by bicyclic heterocycles

Replacing the naphthalene C-unit of the anti-tuberculosis drug bedaquiline with a range of bicyclic heterocycles of widely differing lipophilicity gave analogs with a 4.5-fold range in clogP values. The biological results for these compounds indicate on average a lower clogP limit of about 5.0 in this series for retention of potent inhibitory activity (MIC90s) against M.tb in culture. Some of the compounds also showed a significant reduction in inhibition of hERG channel potassium current compared with bedaquiline, but there was no common structural feature that distinguished these.

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Reference£º
Benzodioxan,
1,4-Benzodioxane | C8H8O2 – PubChem

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TRIAZOLOPYRIDINE AND TRIAZOLOPYRIMIDINE INHIBITORS OF MYELOPEROXIDASE

The present invention provides compounds of Formula (I): wherein A and R1 are each as defined in the specification, and compositions comprising any of such novel compounds. These compounds are myeloperoxidase (MPO) inhibitors and/or eosinophil peroxidase (EPX) inhibitors, which may be used as medicaments.

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Reference£º
Benzodioxan,
1,4-Benzodioxane | C8H8O2 – PubChem

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4-(CONDENSED CYCLICMETHYL)-IMIDAZOLE-2-THIONES ACTING AS ALPHA2 ADRENERGIC AGONISTS

Compounds of Formula 1 where the variables have the meaning defined in the specification are agonists of alpha2 adrenergic receptors. Several compounds of the disclosure are specific or selective to alpha 2B and/or alpha2C adrenergic receptors in preference over alpha2A adrenergic receptors. Additionally some of the claimed compounds have no or only minimal cardivascular and/or sedatory activity. The compounds of Formula 1 are useful as medicaments in mammals, including humans, for treatment of diseases and or alleviations of conditions which are responsive to treatment by agonists of alpha2 adrenergic receptors. Compounds of Formula 1 which have no significant cardiovascular and/or sedatory activity are useful for treating pain and other conditions with minimal side effects.

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Reference£º
Benzodioxan,
1,4-Benzodioxane | C8H8O2 – PubChem

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ANTIBACTERIAL COMPOUNDS AND USES THEREOF

The present invention relates to compounds of formula (I) including any stereochemically isomeric form thereof, or pharmaceutically acceptable salts thereof, for the treatment of tuberculosis.

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Reference£º
Benzodioxan,
1,4-Benzodioxane | C8H8O2 – PubChem

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Practical synthesis of biaryl colchicinoids containing 3?,4?- catechol ether-based A-rings via Suzuki cross-coupling with ligandless palladium in water

Eight new biaryl colchicinoids containing 3?,4?-methylene or benzodioxy ether bridges were synthesized. The key synthetic step employed a ligandless, aqueous Suzuki cross-coupling reaction catalyzed by Pd(OAc) 2 with tetrabutylammonium bromide (TBAB) and potassium carbonate (K2CO3). The biaryl Suzuki products were typically formed in 5-30min and always in less than 1h.

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Reference£º
Benzodioxan,
1,4-Benzodioxane | C8H8O2 – PubChem

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PYRIDINONE DICARBOXAMIDE FOR USE AS BROMODOMAIN INHIBITORS

The present invention relates to compounds of formula (I) and salts thereof, pharmaceutical compositions containing such compounds and to their use in therapy.

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Reference£º
Benzodioxan,
1,4-Benzodioxane | C8H8O2 – PubChem

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In heterogeneous catalysis, the catalyst is in a different phase from the reactants. name: (2,3-Dihydrobenzo[b][1,4]dioxin-5-yl)methanol, At least one of the reactants interacts with the solid surface in a physical process called adsorption in such a way. 274910-19-9, name is (2,3-Dihydrobenzo[b][1,4]dioxin-5-yl)methanol. In an article£¬Which mentioned a new discovery about 274910-19-9

Benzofuran derivatives, their preparation and use

The present invention relates to benzofuran derivatives having general Formula (I) 1wherein A is selected from (1), (2), (3), (4) 2wherein Z is O or S; s is 0 or 1; q is 0 or 1; R4 is hydrogen, C1-6-alkyl, C2-6-alkenyl, C26-alkynyl, C1-6-alkyl-aryl, or C1-6-alkyl-O-aryl; D is a spacer group selected from branched or straight chain C1-6-alkylene, C2-6-alkenylene and C2-6-alkynylene; its enantiomers, and pharmaceutically acceptable acid addition salt thereof. The compounds are potently binding to the 5-HT1A receptor.

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Reference£º
Benzodioxan,
1,4-Benzodioxane | C8H8O2 – PubChem

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Example 6 2-(1,4-benzodioxan-5-yl)acetic acid (6). To a solution of 5-hydroxymethyl-1,4-benzodioxan (8.0 g, 48 mmol) in dichloromethane (200 mL) was added two droplets of N,N-dimethylformamide and thionyl chloride (5.0 mL, 68 mmol) at room temperature. After the resulting solution was boiled under reflux for 1 h and subsequently cooled to room temperature water (100 mL) was added. The phases were separated and the organic phase was dried (MgSO4) and the solvents evaporated in vacuo. A solution of the remaining oil (8.5 g, 46 mmol) was added to a mixture of sodium cyanide (5.0 g, 102 mmol) and N,N-dimethylformamide (100 mL) at room temperature. After stirring for 16 h at room temperature ice was added and the resulting slurry was extracted with diethyl ether (2*250 mL). The collected organic phases were washed with saturated calcium chloride, dried (Na2SO4) and the solvents were evaporated in vacuo. A mixture of the remaining oil (6.0 g, 34 mmol), ethanol (200 mL), sodium hydroxide (6.0 g) and water (6 mL) was boiled under reflux for 16 h. After evaporation of the solvents in vacuo, water (200 mL) was added and the resulting slurry was extracted with diethyl ether (2*200 mL). The collected organic phases were washed with brine, dried (Na2SO4) and the solvents were evaporated in vacuo affording 4.0 g (43%) of the title compound as an oil: 1H NMR (CDCl3) delta 3.65 (s, 2H), 4.15-4.30 (m, 4H), 6.70-6.85 (m, 3H).

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Reference£º
Patent; H. Lundbeck A/S; US2002/32205; (2002); A1;,
Benzodioxan
1,4-Benzodioxane | C8H8O2 – PubChem

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A solution of 20 (3.75 g, 32.3 mmol) in diethyl ether (80 mL) was cooled to 0 C and phosphorous tribromide (3.67 mL, 38.8 mmol) was added dropwise. The solution was stirred at 0 C for 10 min, then at r.t. for 1 h. Water (10 mL) was added cautiously to quench the excess of reagent and the mixture was diluted with diethyl ether and washed with water (3 x 50 mL). The combined organic layers were washed with brine (100 mL), dried over Na2S04, filtered and concentrated under reduced pressure to obtain 21 as a brown solid (4.61 g, 62%). 1H NMR (CDCI3) delta 6.91-6.77 (m, 3H), 4.52 (s, 2H), 4.35-4.33 (m, 2H), 4.29-4.27 (m, 2H). Found: [M+H- Br]=149.5.

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Reference£º
Patent; THE GLOBAL ALLIANCE FOR TB DRUG DEVELOPMENT, INC.; UPTON, Anna, Marie; COOPER, Christopher, Blair; MARCEL, Koenraad, Jozel Lodewijk; GUILLEMONT, Jerome, Emile Goerges; VAN DEN BROECK, Walter Marcel, Mathilde; PALMER, Brian, Desmond; MA, Zhenkun; (186 pag.)WO2017/155909; (2017); A1;,
Benzodioxan
1,4-Benzodioxane | C8H8O2 – PubChem

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Example 6 2-(1,4-benzodioxan-5-yl)acetic acid (6). To a solution of 5-hydroxymethyl-1,4-benzodioxan (8.0 g, 48 mmol) in dichloromethane (200 mL) was added two droplets of N,N-dimethylformamide and thionyl chloride (5.0 mL, 68 mmol) at room temperature. After the resulting solution was boiled under reflux for 1 h and subsequently cooled to room temperature water (100 mL) was added. The phases were separated and the organic phase was dried (MgSO4) and the solvents evaporated in vacuo. A solution of the remaining oil (8.5 g, 46 mmol) was added to a mixture of sodium cyanide (5.0 g, 102 mmol) and N,N-dimethylformamide (100 mL) at room temperature. After stirring for 16 h at room temperature ice was added and the resulting slurry was extracted with diethyl ether (2*250 mL). The collected organic phases were washed with saturated calcium chloride, dried (Na2SO4) and the solvents were evaporated in vacuo. A mixture of the remaining oil (6.0 g, 34 mmol), ethanol (200 mL), sodium hydroxide (6.0 g) and water (6 mL) was boiled under reflux for 16 h. After evaporation of the solvents in vacuo, water (200 mL) was added and the resulting slurry was extracted with diethyl ether (2*200 mL). The collected organic phases were washed with brine, dried (Na2SO4) and the solvents were evaporated in vacuo affording 4.0 g (43%) of the title compound as an oil: 1H NMR (CDCl3) delta 3.65 (s, 2H), 4.15-4.30 (m, 4H), 6.70-6.85 (m, 3H).

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Reference£º
Patent; H. Lundbeck A/S; US2002/32205; (2002); A1;,
Benzodioxan
1,4-Benzodioxane | C8H8O2 – PubChem