Hypo-.beta.-lipoproteinemic agents. 1. Bicyclo[2.2.2]octyloxyaniline and its derivatives

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

doi:10.1021/jm00245a004

Cited by 15 publications

(3 citation statements)

References 3 publications

(4 reference statements)

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“…Changes in plasma levels of cholesterol and triglycerides after repeated oral application are determined by standard analytical procedures. Assays allow differentiating between atherogenic VLDL and LDL and nonatherogenic HDL cholesterol [43]. For further details regarding animal models, see [44].…”

Section: Introductionmentioning

confidence: 99%

Cardiovascular Drugs

Hollmann¹,

Lehmann²,

Albrecht³

et al. 2000

Ullmann's Encyclopedia of Industrial Chemistry

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Section: Introductionmentioning

confidence: 99%

Cardiovascular Drugs

Hollmann¹,

Lehmann²,

Albrecht³

et al. 2000

Ullmann's Encyclopedia of Industrial Chemistry

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“…Antimalarial enhancement of primaquine by 5-phenoxylation was described earlier. 1 In an effort to achieve the optimal substitution pattern for this series, we have synthesized the compounds included in Table I. Having found that 4-methylprimaquine2 was less toxic than its (1) E. H. Chen, A. J. Saggiomo, K. Tanabe, B. L. Verma, and E.…”

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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“…The proposed5 "three points of attachment" model of the interaction of the muscarinic antagonist with the receptor explains neither the role of the second aromatic ring nor the role of substitution in the ring. Some impairment of binding has been reported at the receptor level due to ring (1) Sternbach, L. H.; Kaiser, S. J. Am.…”

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confidence: 99%