Synthesis and Pharmacological Evaluation of α,α-Disubstituted Derivatives of Phenylacetamide and 1-Naphthylacetamide

Casadio, S; Pala, G; Bruzzese, T.; Crescenzi, E; Marazzi-Uberti, E; Coppi, G

doi:10.1021/jm00329a010

Cited by 7 publications

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“…Recent reports of analgesic and anti inflammatory properties have appeared for a variety of chemical categories of compounds. Among aniline and anilide derivatives prepared (181)(182)(183)(184)(185)(186)(187)(188)(189)(190)(191)(192)(193) were some analogues of methadone, among which stereospecificity require ments did not conform to those for methadone compounds (183). p-Butoxy phenylacetamide was reported to be more potent than phenacetin and aminopyrine, but less than morphine (184) .…”

Section: Oxotremorine Arecolinementioning

confidence: 99%

“…p-Butoxy phenylacetamide was reported to be more potent than phenacetin and aminopyrine, but less than morphine (184) . Among the series of aryl substi tuted acetic acids (185), nitriles (186), and ami des (187,188), analgesic and anti-inflammatory activities usually were greater among naphthyl than phenyl derivatives. Analgesic, anti-inflammatory, or both activities were ob served among new series of phenetidines (189), alkylpiperizine esters (190) , N-antipyryloxamides (191), arylacethydroxamic acids (192), 2,3-bis-(p-meth oxyphenyl) indoles (193), some aminoguanidine sympathetic blockers (194), and imidazoles (195), and pyridobenzimidazoles (196).…”

Section: Oxotremorine Arecolinementioning

confidence: 99%

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Some Relationships Between Chemical Structure and Pharmacological Activities

Cavallito¹

1968

Annu. Rev. Pharmacol.

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Earlier reviews in this series dealt with some relationships of chemical structure with biological activities (1-3) i the present assignment is restricted essentially to pharmacologically active compounds. As with the earlier re views, the published literature is not covered exhaustively, but some new re ports and observations are included which appeared from about September, 1964 [termination of coverage of last review (1)] to May, 1967. Where useful for purposes of relationship, selected older literature is cited.Over the years attempts have been made to devise general hypotheses pertaining to structure-activity relationships (SAR) and drug mechanisms of action. Recent efforts include variations of receptor occupancy hypotheses (Ariens, Stephenson), rate or kinetic hypotheses (Paton), and more chemi cally descriptive concepts (Belleau and others). In reviewing publications of the past two years that could be considered pertinent to SAR, one is im pressed by the gulf that exists between most synthesizers of new molecules and the developers of general hypotheses. For example, from 310 complete articles published in J. Med. Chern. (1965-66), only six made reference to these hypotheses either as stimuli for the project or as vehicles for cor relating SAR. This might indicate that the hypotheses are sterile or inade quate for either predictive or correlative purposes or that there is little in terest or inclination among most investigators in relating specific observa tions to general hypotheses. Most of these hypothes,t!s have indeed offered little that is of substantive value from a chemical perspective of devising novel molecules of biological interest. However, the efforts are commendable and some of these hypotheses may evolve and develop into theories with use ful correlative and predictive values. As hypotheses become more chemically descriptive, one can anticipate that there will be a greater consideration of such hypotheses by the designers of new, biologically interesting molecules.Their more recent concepts have been summarized by Ariens (4) and Paton (5). Shortcomings of the Ariens and Stephenson receptor occupancy and the Paton rate hypotheses have been analyzed by Belleau (6) as back ground for discussion of his "conformational perturbation" hypothesis.Bloom & Goldman (7) further consider these and modify and extend some of Belleau's views in proposing a "dynamic receptor hypothesis" relevant to catecholamine-adenine mononucleotide interactions in adrenergic mech anisms. These reviews are recommended to the cautious reader; space does 39 Annu. Rev. Pharmacol. 1968.8:39-66. Downloaded from www.annualreviews.org Access provided by New York University -Bobst Library on 05/14/15. For personal use only.Quick links to online content Further ANNUAL REVIEWS

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Section: Oxotremorine Arecolinementioning

confidence: 99%

Section: Oxotremorine Arecolinementioning

confidence: 99%

Some Relationships Between Chemical Structure and Pharmacological Activities

Cavallito¹

1968

Annu. Rev. Pharmacol.

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“…The synthesis and antiinflammatory activity of aisopropy 1-a-[2-(dimethy lamino) ethyl ] -1 -napht hy lacetamide (1) has been reported. 2 If one envisions formation of a bond between the central C atom of the sidechain f-Pr group and the C-8 position of the naphthalene ring of 1, then the acenaphthene 2 is derived. In this paper, we describe the synthesis and antiinflammatory activity of this "bridged" compound, as well as the chemistry of some intermediates.…”

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confidence: 99%

Acenaphthene chemistry. 2. Synthesis and antiinflammatory activity of 1-[2-(dimethylamino)ethyl]-2,2-dimethyl-1-acenaphthenecarboxamide

Levine¹

1971

J. Med. Chem.

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Antiinflammatory Acenaphthene Derivatives (MgSOi), and the solvent was removed to yield 1.28 g of 25, a yellowish oil, ir (neat) 2110 cm-1 (azide). A soln of LAH (0.570, 15.0 mmoles) in 25 ml of anhyd Et20 was refluxed for 2 hr after which the crude azide 25 in 50 ml of anhyd Et20 was added at such a rate as to maintain reflux. The reaction mixt was refluxed for 2 hr after which "wet" Et20 followed by H20 was added to decomp the excess LAH. The aq layer was extd several times with Et20 and the combined Et20 fractions were washed with H20 and satd NaCl soln and dried (MgSOi), and the solvent was removed to yield a colorless oil, 1.525 g. Chromatog on silica gel, eluting with 5% MeOH-CHCU, afforded a colorless oil, 0.850 g. Formation of the HC1 salt and recrystn (EtOH-Et20) afforded 0.567 g (51%) of 23, mp 132-134°. en/¿/wo-2-Amino-3-(3,4-dihydroxyphenyl)butane -HC1(3).-To ery

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α‐Isopropyl‐α‐(2‐Dimethylaminoethyl)‐1‐Naphthacetamide 1505‐95‐9

2004

Sax's Dangerous Properties of Industrial Materials

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Synthesis and Pharmacological Evaluation of α,α-Disubstituted Derivatives of Phenylacetamide and 1-Naphthylacetamide

Cited by 7 publications

References 0 publications

Some Relationships Between Chemical Structure and Pharmacological Activities

Some Relationships Between Chemical Structure and Pharmacological Activities

Acenaphthene chemistry. 2. Synthesis and antiinflammatory activity of 1-[2-(dimethylamino)ethyl]-2,2-dimethyl-1-acenaphthenecarboxamide

α‐Isopropyl‐α‐(2‐Dimethylaminoethyl)‐1‐Naphthacetamide 1505‐95‐9

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