Hypobetalipoproteinemic agents. 2. Compounds related to 4-(1-adamantyloxy)aniline

Lednicer, Daniel; We, Heyd; De, Emmert; Re, TenBrink; Pe, Schurr; Ce, Day

doi:10.1021/jm00187a016

Cited by 14 publications

(3 citation statements)

References 2 publications

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“…22 Treatment of a solution of 1-adamantanethiol in DMF-C 6 H 6 with NaH and fluoronitrobenzene and subsequent heating afforded 4-(adamantylthio)nitrobenzene (eq 13). 22 Treatment of a solution of 1-adamantanethiol in DMF-C 6 H 6 with NaH and fluoronitrobenzene and subsequent heating afforded 4-(adamantylthio)nitrobenzene (eq 13).…”

Section: Synthesis Of 4-(1-adamantylthio)aniline and Its Derivativesmentioning

confidence: 99%

1-Adamantanethiol

Kang

Britton

2010

Encyclopedia of Reagents for Organic Synthesis

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Section: Synthesis Of 4-(1-adamantylthio)aniline and Its Derivativesmentioning

confidence: 99%

1-Adamantanethiol

Kang

Britton

2010

Encyclopedia of Reagents for Organic Synthesis

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“…We have previously reported the hypobetalipoproteinemic activity of agents related to 4-(l-bicyclo[2.2.2]octyloxy)aniline (l)1 and the more potent 4-(l-1 2, R = H 3, R = (CH2)5 adamantyloxy)aniline (2).2 This activity consists of a reduction of the atherogenic heparin precipitating lipoproteins (HPL) and also the HPL to cholesterol ratio in the cholesterol-cholic acid fed rat. 3 Ultracentrifugation studies with the piperidine 3 have demonstrated that not only are the atherogenic, lower density (d <1.040 g/mL) lipoproteins reduced as desired, but the high density lipoproteins (1.040 < d < 1.21 g/mL), which may well be antiatherogenic,4…”

mentioning

confidence: 99%

Modifications of primaquine as antimalarials. 3. 5-Phenoxy derivatives of primaquine

Nodiff¹,

Tanabe²,

Chen³

et al. 1982

J. Med. Chem.

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and 5% methanol, v/v). Commercial Raney nickel was purchased from W.R. Grace Co. (no. 30). Silica gel was purchased from EM .5-Hydroxy-6-methoxy-4-methyl-8-nitroquinoline (2). 4-Methyl-5,6-dimethoxy-8-nitroquinoline4 (6.21 g, 25 mmol) was dissolved in EtOH (100 mL) containing concentrated HC1 (4.7 mL). The mixture was heated under reflux for 21 h, cooled to 10 °C, and filtered. The solid was washed with cold (10 °C) EtOH (18 mL), followed by petroleum ether (15 mL), and air-dried to yield 5.41 g (92%) of the title compound, mp 253-257 °C dec.Anal. (CuH10N2O4) C, , N.5-Chloro-6-methoxy-4-methyl-8-nitroquinoline (3). A solution of the above 5-hydroxyquinoline (5.25 g, 0.022 mol) in P0C13 (75 mL) was heated at 80 °C for 2 h. The reaction mixture was poured onto ice and basified with excess NH4OH. The tan solid was filtered to give 5.8 g of crude product. This material was purified via column chromatography over silica gel and eluted with CHC13. The fast-moving yellow band was collected and concentrated to give 3.9 g (69%) of the title compound, mp 167-169 °C. Anal. (CUH9C1N203) C, H, Cl, N.6-Methoxy-4-methyl-8-nitro-5-[3-(trifluoromethyl)phenoxyjquinoline (4a). To a solution of 3-(trifluoromethyl)phenol (4.1 g) in 2-ethoxyethanol (45 mL) containing KOH (1.37 g) was added the above 5-chloroquinoline (5.7 g, 0.023 mol). The mixture was heated at reflux for 8 h and allowed to cool overnight. The solid was filtered and washed well with cold EtOH to give 5.9 g (69%) of the title compound, mp 206-208 6C. An analytical

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“…emic activity of agents related to 4-(l-bicyclo[2.2.2]octyloxy)aniline (l)1 and the more potent 4-(l-1 2, R = H 3, R = (CH2)5 adamantyloxy)aniline (2).2 This activity consists of a reduction of the atherogenic heparin precipitating lipoproteins (HPL) and also the HPL to cholesterol ratio in the cholesterol-cholic acid fed rat. 3 Ultracentrifugation studies with the piperidine 3 have demonstrated that not only are the atherogenic, lower density (d <1.040 g/mL) lipoproteins reduced as desired, but the high density lipoproteins (1.040 < d < 1.21 g/mL), which may well be antiatherogenic,4 5"6 7are increased.…”

mentioning

confidence: 99%