1931

DOI: 10.1039/jr9310002447

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CCCXXXV.—Researches in the phenanthridine series. Part I. A new synthesis of phenanthridine homologues and derivatives

Gilbert T. Morgan¹,

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Preparation Of Intermediates1

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Cited by 75 publications

(41 citation statements)

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“…Phenyl 6-methylphenanthridin-8-yl carbamate and diphenyl 6-methylphenanthridine-3,8-diyl dicarbamate were used as the starting material for the synthesis procedure (Scheme 2). Protected phenanthridines were prepared in four steps, starting from the commercially available 2-aminobiphenyl, by the Morgan-Walls reaction 27 based on the middle pyridine ring formation by intramolecular electrophilic cyclization of the 2-amidobiphenyl derivative using POCl3. Removal of phenyloxycarbonyl protection from compounds 1 and 2 was achieved by heating at 120C under acidic condition.…”

Section: Synthesismentioning

confidence: 99%

The phenanthridine biguanides efficiently differentiate between dGdC, dAdT and rArU sequences by two independent, sensitive spectroscopic methods

¹

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²

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³

et al. 2011

Mol. BioSyst.

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At submicromolar concentrations two novel phenanthridine biguanides exhibit distinctly different spectroscopic signals for dGdC and dAdT sequences, respectively, by opposite fluorimetric changes (quenching for dGdC and increase for dAdT) and especially bis -biguanide derivative gives opposite ICD response (negative ICD for dGC and strong positive for dAdT). This speci fic signalling was explained by ability of compounds to switch binding mode from intercalation into dGdC to minor groove binding into dAdT sequences. Both compounds bind to rArU by intercalation, yielding different fluorimetric and CD response in compariso n to any of aforementioned ds-DNA. Moreover, both compounds revealed significantly higher affinity toward ds-polynucleotides in comparison to previously studied alkylamine-and urea-analogues. Furthermore, DNA/RNA binding properties of novel compounds could be controlled by pH, due to the protonation of heterocyclic nitrogen. Low in vitro cytotoxicity of both compounds against human cell lines makes them interesting spectrophotometric probes.

“…Phenyl 6-methylphenanthridin-8-yl carbamate and diphenyl 6-methylphenanthridine-3,8-diyl dicarbamate were used as the starting material for the synthesis procedure (Scheme 2). Protected phenanthridines were prepared in four steps, starting from the commercially available 2-aminobiphenyl, by the Morgan-Walls reaction 27 based on the middle pyridine ring formation by intramolecular electrophilic cyclization of the 2-amidobiphenyl derivative using POCl3. Removal of phenyloxycarbonyl protection from compounds 1 and 2 was achieved by heating at 120C under acidic condition.…”

Section: Synthesismentioning

confidence: 99%

The phenanthridine biguanides efficiently differentiate between dGdC, dAdT and rArU sequences by two independent, sensitive spectroscopic methods

¹

,

²

,

³

et al. 2011

Mol. BioSyst.

View full text Add to dashboard Cite

At submicromolar concentrations two novel phenanthridine biguanides exhibit distinctly different spectroscopic signals for dGdC and dAdT sequences, respectively, by opposite fluorimetric changes (quenching for dGdC and increase for dAdT) and especially bis -biguanide derivative gives opposite ICD response (negative ICD for dGC and strong positive for dAdT). This speci fic signalling was explained by ability of compounds to switch binding mode from intercalation into dGdC to minor groove binding into dAdT sequences. Both compounds bind to rArU by intercalation, yielding different fluorimetric and CD response in compariso n to any of aforementioned ds-DNA. Moreover, both compounds revealed significantly higher affinity toward ds-polynucleotides in comparison to previously studied alkylamine-and urea-analogues. Furthermore, DNA/RNA binding properties of novel compounds could be controlled by pH, due to the protonation of heterocyclic nitrogen. Low in vitro cytotoxicity of both compounds against human cell lines makes them interesting spectrophotometric probes.

“…Compound XIV was prepared from 9-chloromethylphenanthridine (5). Compound XIV was prepared from 9-chloromethylphenanthridine (5).…”

Section: Preparation Of Intermediatesmentioning

confidence: 99%

UNSYMMETRICALLY DISUBSTITUTED PIPERAZINES. II. HISTAMINE ANTAGONISTS¹

1949

J. Org. Chem.

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When tested by the tracheal chain method (1, 2) the known benzylmethyl and benzylethyl piperazines (3) were found to have about 1% and 0.4% respectively of the antihistaminic activity of dimethylaminoethyl benzhydryl ether (Benadryl). This suggested that N-methylpiperazines having "-substituents containing two or three rings might show activities comparable to those of currently available histamine antagonists and that among such substituents the benzhydryl group would be close to the optimal size.A variety of derivatives of methylpiperazine, whose properties are shown in Table I, were therefore prepared to ascertain (a) whether the benzhydryl radical was in fact of the optimal size and (b) whether it would be possible to combine the features of antihistaminic and bronchodilator drugs. This latter point early received a negative answer which was not unexpected since attempts to combine in one compound the virtues of two physiologically active types usually result in a substance lacking the advantages of either. Compound X I was much less potent than benzhydrylmethylpiperazine and Compounds XI1 and XI11 had only vestigial activity. Bronchodilator action was also negligible.In respect to point (a), Compounds I-VI had activities intermediate between those of benzylmethylpiperazine and benzhydrylmethylpiperazine (4). Compounds VII-X and XIV-XV again showed little or no activity. It is evident that the benzhydryl group is, at any rate, close to the optimal size. The inferior potency of Compounds XI-XI11 can be interpreted as meaning that hydrophilic groups in this portion of the molecule are undesirable. EXPERIMENTALWith 1,be exception of Compounds I11 and X I I , all the substances listed in Table I were prepared by the direct reaction of methylpiperazine with the appropriate halide. The intermediates for I, 11, and XI11 were bromides, the rest chlorides. The reactions leading to Compounds IV-VI and XIV-XV were carried out in ethanol, the others without solvent except that a little benzene was usually added to ensure adequate mixing. The benzhydryl chloride precursors t o Compounds VII-X react by the SN1 scheme requiring absence of hydroxylic solvents. It is probable from the poor yield of Compound V that a-naphthylmethyl chloride also reacts largely by the "unimolecular" mechanism. In the preparation of Compounds X I and XI11 hydroxylic solvents presumably would not be objectionable. Aside from these variations the preparations were of standard type and can be generalized. Two equivalents of methylpiperazine were employed t o one of halide and the mixture was heated on the steam-bath for two t o ten hours dependent on the expected reactivity of the halide. When ethanol was present it was evaporated a t this point. The reaction mixture was then partitioned between ether and water, the ethereal layer being washed with water 1 The work here reported is part of a joint program carried out in collaboration with a 2 Present address, Wesleyan University, Middletown, Connecticut. pharmacological group in these laboratories....

“…15 Outros métodos empregam derivados de bifenila substituídos na posição 2, por exemplo a reação de Pictet-Hubert 16 e a sua modificação de MorganWalls, 17 aplicada à síntese de fenantridinas seguida por oxidação, 18 ou a ciclização do etil carbamato de 2-aminobifenila, 19 e a reação de 2-aminobifenila com fosgênio (Figura 2, E), 20 ou a sequência de reações envolvendo a nitração, redução e desidratação aplicada ao ácido bifenil-2-carboxílico, 21 e a oxidação de bifenil-2-carboxamidas (Figura 2, D). 22 Além destes métodos, as fenantridinonas (1) podem ser obtidas pelo rearranjo térmico de 2-alcoxifenantridinas 23 ou cicloadições de Diels-Alder, 24 ou, fotoquimicamente, por irradiação de aril-hidrazonas de benzotriazol (Figura 2, B), 25 ou por foto-desidro--halogenação de benzoilanilinas (Figura 2, C), [26][27][28] foto-ciclo-adição de estirenos com isoquinolinonas, 29 ou por pirólise de derivados de 3-arilidenoamino-1,2,3-benzotriazin-4-onas 30 e de benzoilbenzotriazóis (Figura 2, B).…”

Section: Introductionunclassified

Synthesis of Phenanthridinone Derivatives by Direct Arylation. Characterization of the Absorption and Emission Spectra for Representative Examples

et al. 2016

Química Nova

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publicado na web em 18/02/2015 SYNTHESIS OF PHENANTHRIDINONE DERIVATIVES BY DIRECT ARYLATION. CHARACTERIZATION OF THE ABSORPTION AND EMISSION SPECTRA FOR REPRESENTATIVE EXAMPLES. The phenanthridinone heterocyclic system has attracted considerable attention in recent years due to the diverse array of physical, chemical and pharmacological properties demonstrated by natural and synthetic derivatives. As a consequence there has been considerable development of synthetic methodology for the synthesis of this and related heterocyclic ring systems. The synthetic literature is discussed and is compared with a direct arylation methodology for the intramolecular cyclization of tertiary (2-iodo)benzoylamides to generate the biaryl bond of these compounds. The efficient methodology allowed the synthesis of a number of previously unknown phenanthridinone products. The photoluminescent properties of representative examples were characterized and it is proposed that the previously unknown compound 1s reveals dual fluorescence in a manner similar to the known compound 1r.

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