98. The isomeric 1-carboxy-4-, -3-, and -2-methylcyclohexane-1-acetic acids

Desai, R. D.; Hunter, R. F.; Khan, G. M.; Saharia, G. S.

doi:10.1039/jr9360000416

Cited by 9 publications

(4 citation statements)

References 0 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The cycloalkanone II was subjected to Strecker synthesis using either toluidine or anisidine in the presence of potassium cyanide and glacial acetic acid to give the respective nitriles IIIa–d . Partial hydrolysis of III using sulfuric acid at room temperature yielded the respective amide derivatives IVa–d . The cyano methyl group was introduced using paraformaldehyde and potassium cyanide in glacial acetic acid to afford compounds Va–d which were subjected to hydrolysis using sodium hydroxide in ethanol to furnish the corresponding acids VIa–d .…”

Section: Resultsmentioning

confidence: 99%

See 1 more Smart Citation

Synthesis, molecular modeling studies, and anticonvulsant evaluation of novel 1‐((2‐hydroxyethyl)(aryl)amino)‐N‐substituted cycloalkanecarboxamides and their acetate esters

Aboul‐Enein

El‐Azzouny

Amin

et al. 2018

Archiv der Pharmazie

View full text Add to dashboard Cite

A series of 1-((2-hydroxyethyl)(aryl)amino)-N-substituted cycloalkanecarboxamides IXa-l and their acetate esters Xa-l were designed and synthesized as new anticovulsant agents. The evaluation of the anticonvulsant effect was performed in vivo by subcutaneous pentylenetetrazole (scPTZ) and maximal electroshock (MES) tests in mice. Further, neurotoxicity, hepatotoxicity, and acute toxicity were determined. All the new candidates displayed 100% anticonvulsant activity in the scPTZ screen in the dose range of 0.0057-0.283 mmol/kg. The most potent compounds in the scPTZ screen were Xh (ED 50 = 0.0012 mmol/kg), Xd (ED 50 = 0.002 mmol/kg), Xf (ED 50 = 0.004 mmol/kg), IXj (ED 50 = 0.0047 mmol/kg), Xl (ED 50 = 0.0076 mmol/kg), and Xi (ED 50 = 0.008 mmol/kg). They exhibited higher fold activity in the anticonvulsant potential than the gold standards, phenobarbital and ethosuximide. Compound Xf was active in both scPTZ and MES screens. It showed ED 50 of 0.016 mmol/kg in MES screen. In the neurotoxicity screens, none of the test compounds displayed any minimal motor impairment at the maximum administered dose. The 3D pharmacophore model using Biova 1 Discovery Studio 2016 programs exhibited high fit value. The anticonvulsant evaluation results were compatible with the molecular modeling study. K E Y W O R D S 1-[(2-hydroxyethyl)(aryl)amino]-N-

show abstract

Section: Resultsmentioning

confidence: 99%

“…Compounds IIIa–e , IVa–f , Va–d , VIa–d , VIIa–d , VIIIa–f were prepared according to adopted procedures . Please also see the Supporting Information for further details.…”

Section: Methodsmentioning

confidence: 99%

Synthesis, molecular modeling studies, and anticonvulsant evaluation of novel 1‐((2‐hydroxyethyl)(aryl)amino)‐N‐substituted cycloalkanecarboxamides and their acetate esters

Aboul‐Enein

El‐Azzouny

Amin

et al. 2018

Archiv der Pharmazie

View full text Add to dashboard Cite

show abstract

“…As shown in Scheme 2 and Table 2, under ultrasound irradiation at 41-50 o C for 2.5-9 h, without any extra solvent, the synthesis of ethyl cycloalkylidene cyanoacetate (4a-4f) were carried out in good yields (55%-89%). The results are better than those afforded by conventional methods [20][21][22][23][24]. For example, under ultrasound at 41 °C for 2.5 h, provided 4 b in 84% yield; whereas the conventional method refluxing in benzene for 4-6 h gave 4b in 75.5% yield [20].…”

Section: Synthesis Of Ethyl α-Cyanocinnamates Catalyzed By Nh 4 Oac-acohmentioning

confidence: 99%

Some Applications of Ultrasound Irradiation in Organic Synthesis

Li¹,

Wang²,

Chen³

et al. 2005

COS

144

View full text Add to dashboard Cite

The chemical applications of ultrasound, "sonochemistry", have become an exciting new field of research during the past decade. Scientists now know that the chemical effects of ultrasound are diverse and include substantial improvements in both stoichiometric and catalytic chemical reactions. In some cases, ultrasonic irradiation can increase reactivities by nearly a million fold. The chemical effects of ultrasound fall into homogeneous sonochemistry of liquids, heterogeneous sonochemistry of liquid-liquid or liquid-solid systems. In this paper, some recent applications of ultrasound in organic synthesis, such as, Knoevenagel condensation, Claisen-Schmidt condensation, Michael addition, Pinacol coupling reaction, Bucherer-Bergs reaction and Biginelli reaction, are reviewed. b 1/1.2 2.5 (4~6[20]) 41 (80[20]) 84 (75.5[20]) c 1/1.2 6 (48[21]) 45~48 (heating [21]) 62 (50[21]) d 1/1 9 41 55 (no rection[22]) e 1/1.2 5(8[23]) 41(80[23]) 89 (85[23]) f 1/1.2 7.5 41 74 g 1/1 21 41~50 36 (E/Z=2/1) h 1/1.2 13 (24[24]) 41~50 (refluxing [24]) 31 (E/Z=2/1) (8[24]) a The mole ratio is ketone / ethyl cyanoacetate.

show abstract

“…Only very few samples of 4-substituted cyclohexanone cyanohydrins have been reported in the literature (5)(6)(7)(8)(9). In all cases, mixtures of cis/trans isomers are obtained.…”

Section: Introductionmentioning

confidence: 95%

Hydroxynitrile lyase-catalyzed addition of HCN to 4-substituted cyclohexanones: stereoselective preparation of tetronic acids

Effenberger¹,

Roos²,

Kobler³

et al. 2002

Can. J. Chem.

View full text Add to dashboard Cite

The addition of HCN to 4-alkylcyclohexanones 1 to give cyanohydrins 2 is strongly catalyzed by hydroxynitrile lyases (HNLs). With PaHNL, from bitter almond, trans-addition occurs almost exclusively, yielding trans-2. With MeHNL, from cassava, cis-addition is preferred to give cis-2. cis-Selectivity is nearly quantitative, especially for cyclohexanones with larger 4-substituents. Comparable results with respect to the stereoselectivity were observed in the HNL-catalyzed addition of HCN to 4-alkoxycyclohexanones 3a-g. In contrast, the stereoselectivity in the HNLcatalyzed addition to 4-alkanoyloxycyclohexanones 3h-k is very poor. The transformation of cis-4-propylcyclohexanone cyanohydrin (2c) into the corresponding cis-spirotetronic acid 7 occurs without any isomerization.

show abstract

98. The isomeric 1-carboxy-4-, -3-, and -2-methylcyclohexane-1-acetic acids

Cited by 9 publications

References 0 publications

Synthesis, molecular modeling studies, and anticonvulsant evaluation of novel 1‐((2‐hydroxyethyl)(aryl)amino)‐N‐substituted cycloalkanecarboxamides and their acetate esters

Synthesis, molecular modeling studies, and anticonvulsant evaluation of novel 1‐((2‐hydroxyethyl)(aryl)amino)‐N‐substituted cycloalkanecarboxamides and their acetate esters

Some Applications of Ultrasound Irradiation in Organic Synthesis

Hydroxynitrile lyase-catalyzed addition of HCN to 4-substituted cyclohexanones: stereoselective preparation of tetronic acids

Contact Info

Product

Resources

About