- A practical synthesis of 3-n-propylphenol, a component of tsetse fly attractant blends
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A practical synthesis of the tsetse fly attractant 3-n-propylphenol involves the Grignard reaction of 3-hydroxybenzaldehyde and ethylmagnesium bromide affording a benzylic alcohol-type phenol derivative that upon catalytic hydrogenation gives the title product in 75% overall yield. Selection of the right solvent mixture and temperature range for the Grignard reaction is crucial for the kilogram-scale preparation of the target compound.
- Ujvary, Istvan,Mikite, Gyula
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- Efficient Transfer Hydrogenation of Ketones using Methanol as Liquid Organic Hydrogen Carrier
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Herein, we demonstrate an efficient protocol for transfer hydrogenation of ketones using methanol as practical and useful liquid organic hydrogen carrier (LOHC) under Ir(III) catalysis. Various ketones, including electron-rich/electron-poor aromatic ketones, heteroaromatic and aliphatic ketones, have been efficiently reduced into their corresponding alcohols. Chemoselective reduction of ketones was established in the presence of various other reducible functional groups under mild conditions.
- Garg, Nidhi,Paira, Soumen,Sundararaju, Basker
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p. 3472 - 3476
(2020/05/29)
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- 5-LIPOXYGENASE INHIBITORY THIAZOLES
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The invention concerns a thiazole of the formula I, wherein Ar1 is optionally substituted aryl of up to 10 carbon atoms; A is a direct link to X, or is (1-6C)alkylene, (3-6C)alkenylene, (3-6C)alkynylene or cyclo(3-6C)alkylene; X is oxy, thio, sulphinyl, sulphonyl or imino; Ar2 is optionally substituted phenylene, or a 6-membered heterocyclene moiety containing up to three nitrogen atoms; R1 is hydrogen, (1-6C)alkyl, (2-6C)alkenyl, (2-6C)alkynyl or substituted (1-4C)alkyl; R2 is hydrogen, (1-6C)alkyl, (3-6C)alkenyl, (3-6C)alkynyl, substituted (1-4C)alkyl or (2-6C)alkanoyl; Q is optionally substituted thiazolyl; or a pharmaceutically-acceptable salt thereof. The invention also concerns processes for the manufacture of a thiazole of the formula I, or a pharmaceutically-acceptable salt thereof, and pharmaceutical compositions containing said thiazole
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- (Methoxyalkyl)thiazoles: A new series of potent, selective, and orally active 5-lipoxygenase inhibitors displaying high enantioselectivity
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(Methoxyalkyl)thiazoles are novel 5-lipoxygenase (5-LPO) inhibitors that are neither redox agents nor iron chelators. Consideration of a hypothetical model of the enzyme active site led to this series which is exemplified by 1-[3(naphth-2-ylmethoxy)phenyl]-1-(thiazol-2-yl)propyl methyl ether (2d, ICI211965). 2d inhibits cell-free guinea pig 5-LPO activity, LTC4 synthesis in plasma free mouse macrophages, and LTB4 synthesis in rat and human blood (IC50s 0.1 μM, 8nM, 0.5 μM, and 0.4 μM, respectively) but does not inhibit the synthesis of cyclooxygenase products at concentrations up to 50 μM in macrophages and 100 μM in blood. 2d is orally active in rat (ex vivo ED50 10 mg/kg in blood taken in 1h after dosing). SAR studies show that high in vitro potency requires methoxy, thiazolyl, and naphthyl groups and depends critically on the substitution pattern. (Methoxyalkyl)thiazoles are chiral. Resolution of 1-methoxy-6-(naphth-2-ylmethoxy)-1-(thiazol-2-yl)indan (2j, ICl216800) shows that (+)-2j is 50-150-fold more potent than (-)-2j in in vitro assays. Thus, (methoxyalkyl)thiazoles are a new series of orally active, selective 5-LPO inhibitors and represent the first class of inhibitors in which inhibition is mediated by specific, enantioselective interactions with the enzyme.
- Bird,Bruneau,Crawley,Edwards,Foster,Girodeau,Kingston,McMillan
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p. 2176 - 2186
(2007/10/02)
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- Thiazole derivatives having a 5-lipoxygenase-inhibiting activity
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The invention concerns a thiazole of the formula I, wherein Ar1 is optionally substituted aryl of up to 10 carbon atoms;, A is a direct link to X, or is (1-6C)alkylene, (3-6C)alkenylene, (3--6C)alkynylene or cyclo(3-6C)alkylene;, X is oxy, thio, sulphinyl, sulphonyl or imino;, Ar2 is optionally substituted phenylene,or a 6-membered heterocyclene moiety containing up to three nitrogen atoms;, R1 is hydrogen, (1-6C)alkyl, (2-6C)alkenyl, (2-6C)alkynyl or substituted (1-4C)alkyl;, R2 is hydrogen, (1-6C)alkyl, (3-6C)alkenyl, (3-6C)alkynyl, substituted (1-4C)alkyl or (2-6C)alkanoyl;, Q is optionally substituted thiazolyl;, or a pharmaceutically-acceptable salt thereof. The invention also concerns processes for the manufacture of a thiazole of the formula I, or a pharmaceutically-acceptable salt thereof, and pharmaceutical compositions containing said thiazole.
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- Naturally Occurring Dibenzofurans. Part 6. Synthesis of Didymic Acid
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The synthesis of the lichen dibenzofuran didymic acid (1) (3-hydroxy-7-methoxy-1-pentyl-9-propyldibenzofuran-2-carboxylic acid) by intramolecular Ullmann coupling of methyl 5-bromo-4-(2-bromo-5-methoxy-3-propylphenoxy)-2-methoxy-6-pentylbenzoate (34) and methyl 5-iodo-4-(2-iodo-5-methoxy-4-nitro-3-propylphenoxy)-2-methoxy-6-pentylbenzoate (32) and appropriate further transformations, is described.
- Carvalho, Christopher F.,Sargent, Melvyn V.
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p. 1621 - 1626
(2007/10/02)
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