- Structure activity relationship of organic alcohol and esters for antidepressant-like activity
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The synthesized compounds 1-7 were evaluated for their antidepressant activity, among which 2-phenylethyl alcohol 1 and isoamyl phenylacetate 3 showed 43 % and 37 % reduction in immobility time in mice using forced swim test, thereby, displaying antidepressant-like activity. Compound 1 and 3 were equipotent and both these compounds were 2x effective than the standard drug phenelzine. Considering other esters it appears that a decrease in alkyl chain length or addition of either NO2 or OH groups to the phenyl ring caused a marked decline in the antidepressant-like activity.
- Perveen, Shahnaz,Yasmeen, Arfa,Khan, Muhammad Aitmaud,Dar, Ahsana,Jafri, Rehana,Ahmed, Amir
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experimental part
p. 14 - 17
(2011/01/03)
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- Protic acid immobilized on solid support as an extremely efficient recyclable catalyst system for a direct and atom economical esterification of carboxylic acids with alcohols
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(Chemical Equation Presented) A convenient and clean procedure of esterification is reported by direct condensation of equimolar amounts of carboxylic acids with alcohols catalyzed by an easy to prepare catalyst system of perchloric acid immobilized on silica gel (HClO4-SiO2). The direct condensation of aryl, heteroaryl, styryl, aryl alkyl, alkyl, cycloalkyl, and long-chain aliphatic carboxylic acids with primary/secondary alkyl/cycloalkyl, allyl, propargyl, and long-chain aliphatic alcohols has been achieved to afford the corresponding esters in excellent yields. Chiral alcohol and N-t-Boc protected chiral amino acid also resulted in ester formation with the representative carboxylic acid or alcohol without competitive N-t-Boc deprotection and detrimental effect on the optical purity of the product demonstrating the mildness and chemoselectivity of the procedure. The esters of long-chain (>C10) acids and alcohols are obtained in high yields. The catalyst is recovered and recycled without significant loss of activity. The industrial application of the esterification process is demonstrated by the synthesis of prodrugs of ibuprofen and a few commercial flavoring agents. Other protic acids such as H2SO4, HBr, TfOH, HBF4, and TFA that were adsorbed on silica gel were less effective compared to HClO4-SiO2 following the order HClO4-SiO 2 ? H2SO4-SiO2 > HBr-SiO 2 > TfOH-SiO2 ? HBF4-SiO2 ≈ TFA-SiO2. When HClO4 was immobilized on other solid supports the catalytic efficiency followed the order HClO4-SiO 2 > HClO4-K10 > HClO4-Al 2O3 (neutral) > HClO4-Al2O 3 (acidic) > HClO4-Al2O3 (basic).
- Chakraborti, Asit K.,Singh, Bavneet,Chankeshwara, Sunay V.,Patel, Alpesh R.
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supporting information; experimental part
p. 5967 - 5974
(2009/12/24)
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- Esterification in dry media using ferric perchlorate adsorbed on silica gel
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Adsorption of Fe(ClO4)3(H2O)6 onto chromatographic grade silica gel in the presence of alcohol ( to be used for esterification ) produces a supported reagent, Fe(ClO4)3(ROH)6/SiO2. This reagent, has been found effective for the rapid and high yield of esters, on grinding in the presence of carboxylic acids using pestle and mortar in the solid state.
- Parmar, Anupama,Kaur, Jatinder,Goyal, Rita,Kumar, Baldev,Kumar, Harish
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p. 2821 - 2826
(2007/10/03)
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- An efficient use of zeolite catalysts for esterification of carboxylic acids
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A mild and practical method (batch process) for the esterification of carboxylic acids with alcohols using zeolite catalysts in good to excellent yields is described. The esterification of phenylacetic acid with ethanol has also been carried out in very high yield using continuous flow fixed bed reactor.
- Gumaste, Vikas K.,Deshmukh,Bhawal
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p. 1174 - 1179
(2007/10/03)
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- Transesterification of methyl arylacetates wtih lithium alkoxides
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A series of methyl arylacetates were transesterified in excellent yields using lithium alkoxides derived from primary, secondary, and tertiary aliphatic alcohols, benzyl alcohols, and allyl alcohol.
- Bhawal,Khanapure,Biehl
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p. 112 - 114
(2007/10/02)
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- Conversion of Aromatic Ketones into α-Arylalkanoic Acids. Part 2. Routes Employing Peracid, Chlorine, or Nitrous Acid
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Further methods for effecting the oxidative rearrangement of 1-arylalkanones to α-arylalkanoic esters have been investigated.It has been shown that appropriate α-iodoacetals, readily prepared from the ketones, can be converted into esters on treatment either with a peracid or with chlorine.Using the latter reagent, α-chlorination of the ester can be an unwanted side reaction with some substrates and the factors governing by-product formation are discussed.It is demonstrated that, employing chlorine, the process can be made catalytic in iodine.The acetals of 2-amino-1-arylalkanones have also been shown to give high yields of esters under diazotising conditions adding support to the suggestion that the ion, ArC(OR)2CHR', or an incipient version of the ion, is a key intermediate in the process.
- Higgins, Stanley D.,Thomas, C. Barry
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p. 1483 - 1488
(2007/10/02)
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