Hypotensive Agents. IV.<sup>1</sup> Hydrogenated Dialkylaminoalkyl Isoindole Derivatives<sup>2</sup>

Rice, Leonard M.; Grogan, Charles H.; Reid, E. Emmet

doi:10.1021/ja01116a010

Cited by 20 publications

(11 citation statements)

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“…We prepared all of our succinimides by direct reaction of the amine and succinic anhydride at room temperature to yield first the amic acid which, in most cases, was not isolated but was heated directly to 160-170" in an oil-bath for two hours to cyclize the amic acid to the imide. We have previously reported a new method of synthesis of N-alkyl saccharins and their reduction with lithium aluminum hydride (11) and six series of dialkylaminoalkyl isoindoles in various states of hydrogenation obtained by reduction of the corresponding imides with lithium aluminum hydride (12). The present paper further demonstrates the general applicability of the reduction of appropriate phthalimides and endophthalimides in various states of ring hydrogenation to obtain N-substituted hydrogenated isoindoles.…”

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confidence: 57%

N-Alkyl Imides and Their Reduction by Means of Lithium Aluminum Hydride

Rice¹,

Reid²,

Grogan³

1954

J. Org. Chem.

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During the past several years we have prepared a relatively large number of cyclic bases which have been screened for hypotensive activity as hydrochlorides and quaternary salts. We have found with the majority of compounds prepared in the several series studied so far that the bases could be prepared conveniently and in good yields by the reduction of the corresponding imides with lithium aluminum hydride. As a result of this continued study we have prepared a large number of N-alkyl-and N-dialkyl-aminoalkyl imides as intermediates in the synthesis of the desired bases.A survey of the literature concerning the particular series of imides that we wish to report here revealed that one t o several members had been reported in each series but that in many cases the physical data were scanty. Also, the previously reported imides, prepared by a variety of methods, are scattered in many sources in the literature. We have prepared the present four series of N-alkyl imides, in amounts varying from 4 to 90 grams, by a single general method and have assembled complete data on boiling points, melting points, densities, and refractive indices.In the present article we wish to report the N-alkyl succinimides from butyl through dodecyl (I) ; the N-alkyl-cis-A4-tetrahydrophthalimides, methyl through dodecyl (11) ; the N-alkyl-cis-3, 6-endomethylene-A4-tetrahydrophthalimides, butyl through dodecyl (111) ; and the N-alkyl hexahydrophthalimides, methyl through dodecyl (IV). 0 0 0 0

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confidence: 57%

N-Alkyl Imides and Their Reduction by Means of Lithium Aluminum Hydride

Rice¹,

Reid²,

Grogan³

1954

J. Org. Chem.

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“…The amidoacidification of maleic anhydride copolymer with N , N -dimethylamino-1-propyl amine (DMAPA) was performed analogously to the model reaction [ 18 , 44 , 49 , 50 , 51 , 52 , 53 , 54 , 55 , 56 , 57 , 58 , 59 , 60 ]. The amine was added dropwise to a dimethylformamide DMF solution of the copolymer.…”

Section: Resultsmentioning

confidence: 99%

Synthesis, Characterization, and Antimicrobial Properties of Peptides Mimicking Copolymers of Maleic Anhydride and 4-Methyl-1-pentene

Szkudlarek

Heine

Keul

et al. 2018

IJMS

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Synthetic amphiphilic copolymers with strong antimicrobial properties mimicking natural antimicrobial peptides were obtained via synthesis of an alternating copolymer of maleic anhydride and 4-methyl-1-pentene. The obtained copolymer was modified by grafting with 3-(dimethylamino)-1-propylamine (DMAPA) and imidized in a one-pot synthesis. The obtained copolymer was modified further to yield polycationic copolymers by means of quaternization with methyl iodide and dodecyl iodide, as well as by being sequentially quaternized with both of them. The antimicrobial properties of obtained copolymers were tested against Escherichia coli, Pseudomonas aeruginosa, Staphylococcus epidermidis, and Staphylococcus aureus. Both tested quaternized copolymers were more active against the Gram-negative E. coli than against the Gram-positive S. aureus. The copolymer modified with both iodides was best when tested against E. coli and, comparing all three copolymers, also exhibited the best effect against S. aureus. Moreover, it shows (limited) selectivity to differentiate between mammalian cells and bacterial cell walls. Comparing the minimum inhibitory concentration (MIC) of Nisin against the Gram-positive bacteria on the molar basis instead on the weight basis, the difference between the effect of Nisin and the copolymer is significantly lower.

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“…Rice and coauthors [7,8,[78][79][80] obtained series of hexa-and octahydroisoindoles and their "bridged" derivatives 52 with various substituents at the nitrogen. On the basis of these compounds quaternary salts 53 with clearly defined biological activity were obtained, e.g., see [7].…”

Section: Reduction Of Carbonyl Groups In Phthalimides and Phthalimidinesmentioning

confidence: 99%

“…Phthalimides and phthalimidines are similar in structure to isoindoles, are easily obtainable, and are therefore often used in the synthesis of isoindoles [2,3,5] and their isologs [7][8][9][10][78][79][80][81][82][83][84][85][86].…”

Section: Reduction Of Carbonyl Groups In Phthalimides and Phthalimidinesmentioning

confidence: 99%

4,7-Dihydro-, 4,5,6,7-tetrahydro-, and octahydroisoindoles (and methanoisoindoles). (Review)

Marinicheva

Губина

2004

Chem Heterocycl Compd

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Hypotensive Agents. IV.¹ Hydrogenated Dialkylaminoalkyl Isoindole Derivatives²

Cited by 20 publications

References 4 publications

N-Alkyl Imides and Their Reduction by Means of Lithium Aluminum Hydride

N-Alkyl Imides and Their Reduction by Means of Lithium Aluminum Hydride

Synthesis, Characterization, and Antimicrobial Properties of Peptides Mimicking Copolymers of Maleic Anhydride and 4-Methyl-1-pentene

4,7-Dihydro-, 4,5,6,7-tetrahydro-, and octahydroisoindoles (and methanoisoindoles). (Review)

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Hypotensive Agents. IV.1 Hydrogenated Dialkylaminoalkyl Isoindole Derivatives2

Cited by 20 publications

References 4 publications

N-Alkyl Imides and Their Reduction by Means of Lithium Aluminum Hydride

N-Alkyl Imides and Their Reduction by Means of Lithium Aluminum Hydride

Synthesis, Characterization, and Antimicrobial Properties of Peptides Mimicking Copolymers of Maleic Anhydride and 4-Methyl-1-pentene

4,7-Dihydro-, 4,5,6,7-tetrahydro-, and octahydroisoindoles (and methanoisoindoles). (Review)

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Hypotensive Agents. IV.¹ Hydrogenated Dialkylaminoalkyl Isoindole Derivatives²