- Revisiting Hydroxyalkylation of Phenols with Cyclic Carbonates
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Described is a tetrabutylammonium fluoride-mediated hydroxyalkylation reaction of phenols with cyclic carbonates. This operationally simple method enables the synthesis of a variety of aryl β-hydroxyethyl ethers in good to excellent yields with a very small amount of catalyst loading (0.1–1 mol%). Of particular note is the efficient conversion of aromatic diols and phloroglucinol to the corresponding bis- and tris-hydroxyethylated products. To further showcase the versatility of this protocol, guaifenesin was prepared with a single step by the condensation of guaiacol and glycerol carbonate. We also developed a flow ethoxylation process permitting the continuous synthesis of multiflorol. (Figure presented.).
- Kao, Shih-Chieh,Lin, Yi-Ching,Ryu, Ilhyong,Wu, Yen-Ku
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supporting information
p. 3639 - 3644
(2019/07/10)
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- Synthesis and antileishmanial activity of 1,3-bis(aryloxy)propan-2-amines
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We describe herein the antileishmanial activity of 1,3-bis(aryloxy)propan-2-amines, prepared in four simple steps from epichlorohydrin. Among the evaluated compounds, three (4o, 4q, and 4r) displayed considerable activity against Leishmania amazonensis promastigote forms, with IC50 values below 10 μM. We also analyzed the effects of the nature and the position of ring substituent on activity. Two amines (4m and 4o) showed excellent profiles in the treatment of L. amazonensis-infected macrophages, reducing the parasite burden by more than 95% in tested concentrations.
- Lavorato, Stefania N.,Duarte, Mariana C.,Lage, Daniela P.,Tavares, Carlos A. P.,Coelho, Eduardo A. F.,Alves, Ricardo J.
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p. 1052 - 1072
(2017/04/14)
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- 1,3-Bis(aryloxy)propan-2-ols as potential antileishmanial agents
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We describe herein the synthesis and antileishmanial activity of 1,3-bis(aryloxy)propan-2-ols. Five compounds (2, 3, 13, 17, and 18) exhibited an effective antileishmanial activity against stationary promastigote forms of Leishmania amazonensis (IC50??15.0?μm), and an influence of compound lipophilicity on activity was suggested. Most of the compounds were poorly selective, as they showed toxicity toward murine macrophages, except 17 and 18, which presented good selective indexes (SI?≥?10.0). The five more active compounds (2, 3, 13, 17, and 18) were selected for the treatment of infected macrophages, and all of them were able to reduce the number of internalized parasites by more than 80%, as well as the number of infected macrophages by more than 70% in at least one of the tested concentrations. Altogether, these results demonstrate the potential of these compounds as new hits of antileishmanial agents and open future possibilities for them to be tested in in vivo studies.
- Lavorato, Stefania N.,Duarte, Mariana C.,Lage, Daniela P.,Tavares, Carlos A. P.,Coelho, Eduardo A. F.,Alves, Ricardo J.
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p. 981 - 986
(2017/10/05)
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- An efficient synthesis of 1-(2-Methoxyphenoxy)-2,3-epoxypropane: Key intermediate of β-adrenoblockers
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An efficient process for the preparation of 1-(2-methoxyphenoxy)-2,3- epoxypropane, a key intermediate for the synthesis of ranolazine is described.
- Madivada, Lokeswara Rao,Anumala, Raghupathi Reddy,Gilla, Goverdhan,Kagga, Mukkanti,Bandichhor, Rakeshwar
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p. 1660 - 1664
(2013/02/25)
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- IMPROVED PROCESS FOR THE PREPARATION OF RANOLAZINE
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The present invention provides an improved process for the preparation of ranolazine of formula I and pharmaceutically acceptable salts thereof, by reacting 2,6-dimethylaniline derivative with chloroacetyl chloride in the presence of base in water and resulting amide intermediate is reacted with piperazine and the resulting piperazinc derivative is further condensed with an appropriate oxirane derivative ( prepared by the reaction of 2-methoxyphenol with epichlorohydrin in the presence of base using phase transfer catalyst) in an inert solvent, and highly pure ranolazine is isolated and converted to its acid salts using excess of mineral acid.
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Page/Page column 12; 14
(2008/12/05)
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- Antitussive and mucus regulating 2-substituted thiazolidines
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2-Substituted thiazolidines compounds having formula I STR1 wherein X is a CH2, O or S, R is hydroxy or an acyloxy, alkyloxy, alkenyloxy or alkinyloxy group, R1 is hydrogen or a group of formula STR2 R2 is hydrogen or a free or esterified carboxy group, Ra and Rb are hydrogen or methyl, p is zero or 1, R3 is a C1 -C2 alkylsulphonyl group, a phenyl or p-Cl phenyl, p-methylsulphonyl group or an acyl group; are useful as mucus regulating, antitussive and antibronchospastic agents.
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- Hypocholesterolemic activity of 1,3 bis(substituted phenoxy) 2 propanones
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A series of 1,3 bis (substituted phenoxy) 2 propanones was found to be active hypocholesterolemic agents at 10 mg/kg/day. The p chloro and p methyl substituted phenoxy compounds possess the highest activity. These compounds did not possess the estrogenic and antifertility activities of the related previously reported derivatives of the bis (β phenylethyl) ketone series. The 1,3 bis (p methylphenoxy) 2 propanone (7) also lowered serum triglycerides and glycerol which appeared to be due to increased levels of serum lipase and reduced activity of liver lipase. There was reduced incorporation of free fatty acids into complex lipids by the liver. Cholesterol was excreted faster in the treated animals.
- Piantadosi,Hall,Wyrick,Ishaq
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p. 222 - 229
(2007/10/12)
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