Synthesis and properties of fluorine-containing heterocyclic compounds. 8. .alpha.-(2-Pyridyl)- and .alpha.-(2-piperidyl)-2-(trifluoromethyl)-4-azaphenanthrenemethanols

Loy, Myrna; Joullié, Madeleine M.

doi:10.1021/jm00263a032

Cited by 19 publications

(8 citation statements)

References 7 publications

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“…37 The preparation and physicochemical properties of the rest of the compounds have been described elsewhere: 1k,r,s; 38 1l-o, 2a,b,i,q; 39 and 2k, 3c,d. 40 …”

Section: Methodsmentioning

confidence: 99%

“…The primary journals which first described the preparation and physicochemical properties of compounds listed in Tables −3 are as follows: 1a,c ; 1b,e,g,h ; 1d ; 1f,i,p,q ; 1j,t ; 2c − h,j,l − p ; and 3a,b . The preparation and physicochemical properties of the rest of the compounds have been described elsewhere: 1k,r,s ; 1l − o, 2a,b,i,q ; and 2k, 3c,d…”

Section: Methodsmentioning

confidence: 99%

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Molecular Electronic Properties of a Series of 4-Quinolinecarbinolamines Define Antimalarial Activity Profile

Bhattacharjee

Karle

1996

J. Med. Chem.

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A detailed computational study on a series of 4-quinolinecarbinolamine antimalarials was performed using the semiempirical Austin model 1 (AM1) quantum chemical method to correlate the electronic features with antimalarial activity and to illuminate more completely the fundamental molecular level forces that affect the function and utility of the compounds. Ab initio (3-21G level) calculations were performed on mefloquine, the lead compound in this series, to check the reliability of the AM1 method. Electron density in specific regions of the molecules appears to play the pivotal role toward activity. A large laterally extended negative potential in the frontal portion of the nitrogen atom of the quinoline ring and the absence of negative potential over the molecular plane are crucial for the potent antimalarials. These electrostatic features are likely to be the modulator of hydrophobicity or lipophilicity of the compounds and, hence, determine their activities. The magnitude of the positive potential located by the hydroxyl hydrogen atom also correlates with potent antimalarial activity. Two negative potential regions occur near the hydroxyl oxygen and piperidyl nitrogen atoms. The two negative potential regions and the positive potential located by the hydroxyl hydrogen atom are consistent with intermolecular hydrogen bonding with the cellular effectors. The present modeling study should aid in efficient designing of this class of antimalarial agents.

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“…37 The preparation and physicochemical properties of the rest of the compounds have been described elsewhere: 1k,r,s; 38 1l-o, 2a,b,i,q; 39 and 2k, 3c,d. 40 …”

Section: Methodsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

Molecular Electronic Properties of a Series of 4-Quinolinecarbinolamines Define Antimalarial Activity Profile

Bhattacharjee

Karle

1996

J. Med. Chem.

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“…Several 4,5-disubstituted 2-(trifluoromethyl)-1,10-phenanthrolines are known, , but 2-(trifluoromethyl)-1,10-phenanthroline (tfm-phen) has not been reported. We initially attempted the synthesis of tfm-phen by a Skraup−Doebner−Von Miller reaction using α,β-unsaturated carbonyl 4 (Scheme ) and 8-aminoquinoline. , However, isolation of the aldehyde 4 from Et 2 O proved difficult due its high volatility .…”

Section: Resultsmentioning

confidence: 99%

Oxidatively Resistant Ligands for Palladium-Catalyzed Aerobic Alcohol Oxidation

2011

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The complex [(neocuproine)Pd(OAc)] 2 [OTf] 2 (1) catalyzes the aerobic oxidation of 2-heptanol at room temperature, but competitive ligand oxidation leads to low catalyst lifetimes. In an effort to mitigate the oxidative degradation of the ligand, a variety of Pd complexes ligated by fluorinated phenanthrolines (bis-2,9-(trifluoromethyl)-1,10-phenanthroline (btfm-phen), 4-methyl-2-(trifluoromethyl)-1,10-phenanthroline (tfmm-phen), and 2-(o-difluorophenyl)-1,10-phenanthroline (odfp-phen)) were prepared and tested. Active catalyst precursors were generated by in situ conproportionation of (N-N)Pd(OAc) 2 and [(N-N)Pd(NCCH 3 ) 2 [OTf] 2 . Pd complexes derived from tfmm-phen catalyzed the aerobic oxidation of 2-heptanol at room temperature with up to 22 turnovers, nearly double that of 1.

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“…For example, 10-(4-methylpiperazin-l-yl)pyrido[4,3- b ][l,4]benzothiazepine possesses potent antidepressant-like activity . Benzonaphthyridine analogs are known as antagonists of 5-HT 4 receptors, antitumor agents, potential antimalarials, α-adrenoreceptor blockers, PKC inhibitors, and cancer cell growth inhibitors . Thus far, a few studies have been directed toward the synthesis of pyridobenzothazepines and benzo[ c ][1,5] or benzo[ c ][1,7]naphthyridines.…”

Section: Introductionmentioning

confidence: 99%

A New Strategy toward Fused-Pyridine Heterocyclic Scaffolds: Bischler−Napieralski-type Cyclization, Followed by Sulfoxide Extrusion Reaction

Guo

Dang

et al. 2007

J. Comb. Chem.

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Method development was completed for a new strategy to obtain fused-pyridine heterocyclic scaffolds. The synthetic route entails a Bischler-Napieralski-type reaction as the key step, followed by a sulfoxide extrusion reaction. The reactions of 3-amino-2-arylthiopyridines or 3-amino-4-arylthiopyridines and carboxylic acids promoted by a Lewis acid such as SnCl4 yielded novel tricyclic pyridobenzothiazepines, which could be readily converted to their corresponding oxidized products via a sequence of sulfur oxidations and eventually to benzonaphthyridines via a sulfoxide extrusion. The synthetic strategy provides an efficient way to access libraries of novel structurally diversified heterocyclic compounds with potential pharmaceutical or biological activities.

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Synthesis and properties of fluorine-containing heterocyclic compounds. 8. .alpha.-(2-Pyridyl)- and .alpha.-(2-piperidyl)-2-(trifluoromethyl)-4-azaphenanthrenemethanols

Abstract: Synthesis and Properties of Fluorine-Containing Heterocyclic Compounds. 8. a-(2-Pyridyl)-and a-( 2-Piperidyl)-2-(trifluoromethyl)-4-azaphenanthrenemethanols

Cited by 19 publications

References 7 publications

Molecular Electronic Properties of a Series of 4-Quinolinecarbinolamines Define Antimalarial Activity Profile

Molecular Electronic Properties of a Series of 4-Quinolinecarbinolamines Define Antimalarial Activity Profile

Oxidatively Resistant Ligands for Palladium-Catalyzed Aerobic Alcohol Oxidation

A New Strategy toward Fused-Pyridine Heterocyclic Scaffolds: Bischler−Napieralski-type Cyclization, Followed by Sulfoxide Extrusion Reaction

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