Carcinogenic nitrogen compounds. Part LXI. The Skraup reaction with diamines derived from acenaphthene and anthracene

Buu‐Hoï, Ng. Ph.; Dufour, M.

doi:10.1039/j39680002070

Cited by 7 publications

(7 citation statements)

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“…3-Amino-1,2-dihydroindeno[1,7- gh ]quinoline ( 35 ) was prepared from 32 according to the literature procedure . It was then converted into its acetyl derivative 36 in quantitative yield by acetic anhydride in THF: mp 226−227 °C (after crystallization from methanol); 1 H NMR (CDCl 3 + DMSO- d 6 ) 2.22 (s, 3, CH 3 ), 3.39 (m, 4, CH 2 ), 7.45−7.50 (q, 1, H-8), 7.94−7.97 (d, 1.…”

Section: Methodsmentioning

confidence: 99%

“…Four different azaphenanthrene analogues of azonafide ( 42 − 45 ), with nitrogen replacing CH at either the 8 or the 11 position, were prepared from aminoacenaphthenes as shown in Scheme . When the Skraup reaction was run on 5-aminoacenaphthene ( 30 ), the product was 1,2-dihydroindeno[1,7- gh ]quinoline 33 . Oxidation of 33 with potassium dichromate in acetic acid gave anhydride 39 directly, and treatment with N , N -dimethylethylenediamine in ethanol and toluene at reflux then afforded 8-azaphenanthrene derivative 42 (5-[2‘-(dimethylamino)ethyl]-5,6-dihydro-4 H -quinolino[6,7,8- de ]isoquinoline-4,6-dione).…”

Section: Chemistrymentioning

confidence: 99%

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Analogues of Amonafide and Azonafide with Novel Ring Systems

et al. 2000

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Three new types of amonafide and azonafide analogues were synthesized and screened in a panel of human solid tumor cells and murine L1210 leukemia cells. The structural types included tetrahydroazonafides, which have the naphthalene chromophore of amonafide within the anthracene nucleus of azonafide; phenanthrene analogues, in which the linear anthracene nucleus is replaced by the bent phenanthrene nucleus; and azaphenanthrenes. The tetrahydroazonafides were generally intermediate in potencies between amonafide and azonafide against the tumor cells, but some of them had high potencies against the L1210 cells and were more potent against the MDR strain than the sensitive strain. The phenanthrene and azaphenanthrene analogues showed no improvement on the potencies of the anthracenes.

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Section: Methodsmentioning

confidence: 99%

Section: Chemistrymentioning

confidence: 99%

Analogues of Amonafide and Azonafide with Novel Ring Systems

et al. 2000

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“…1 Synthesis of N 4 ,N 4 ,N 9 ,N 9 -Tetraethylquinolino[7,8-h]quinoline-4,9-diamine (26). Excess neat diethylamine (20 mL) was added to 17 (100 mg, 0.258 mmol) and heated under reflux for 48−72 h. Water (50 mL) was added, and the residue was extracted (27). Sodium sulfite (0.084 g, 6.667 mmol) and 16 (0.050 g, 0.167 mmol) in water (10 mL) was refluxed for 4 h. The solvent was removed, and the crude reaction mixture was dissolved in DMSO and filtered then precipitated with EtOAc to give 27 (0.093 g, 26%).…”

Section: ■ Experimental Sectionmentioning

confidence: 99%

“…The first is one of access. The synthesis of quinolinoquinoline 2 and its derivatives is not simple, and there has been a low supply of these compounds. ,− The second relates to coordination environment. The five-membered ring formed on coordination of phenanthroline to a metal 4 can accommodate a wide range of metals with little distortion to either the ligand or the metal.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Basicity Studies of Quinolino[7,8-h]quinoline Derivatives

et al. 2020

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Quinolino[7,quinoline is a superbasic compound, with a pK aH in acetonitrile greater than that of 1,8-bis(dimethylaminonaphthalene) (DMAN), although its synthesis and the synthesis of its derivatives can be problematic. The use of halogen derivatives 4,9-dichloroquinolino[7,8h]quinoline (16) and 4,9-dibromoquinolino[7,8-h]quinoline ( 17) as precursors has granted the formation of a range of substituted quinolinoquinolines. The basicity and other properties of quinolinoquinolines can be modified by the inclusion of suitable functionalities. The experimentally obtained pK aH values of quinolino[7,8-h]quinoline derivatives show that N 4 ,N 4 ,N 9 ,N 9 -tetraethylquinolino[7,8-h]quinoline-4,9-diamine ( 26) is more superbasic than quinolino[7,8-h]quinoline. Computationally derived pK aH values of quinolinoquinolines functionalized with dimethylamino (NMe 2 ), 1,1,3,3-tetramethylguanidino (NC(NMe 2 ) 2 ) or N,N,N′,N′,N″,N″-hexamethylphosphorimidic triamido (NP(NMe 2 ) 3 ) groups are significantly greater than those of quinolino[7,8-h]quinoline. Overall, electron-donating functionalities are observed to increase the basicity of the quinolinoquinoline moiety, while the substitution of electron-withdrawing groups lowers the basicity.

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“…It has long been recognized that the aza derivatives of carcinogenic polycyclic hydrocarbons can themselves act as carcinogens (Cook & Thomson 1945). More recently it has been shown that diaza derivatives are particularly pertinent in this context (Pai & Ranadive 1965;Buu-Hoi et a1 1967, 1968. To extend our studies of such polycyclic compounds (Bloomfield et a1 1986;Upton 1986Upton , 1992Tucker et a1 1993a, b), a series of diazabenzo[c]phenanthrenes has been prepared and screened, prompted by the isosteric relationship between benzo[c]phenanthrene 1 and its diaza analogue 2.…”

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confidence: 99%

Novel 5,8-Diazabenzo[c]phenanthrenes: Synthesis and Mutagenicity

Upton

Jaeda

Upton

1998

Journal of Pharmacy and Pharmacology

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The polycyclic aromatic hydrocarbons have been recognized as carcinogens and mutagens since the early part of this century. More recently their aza and polyaza derivatives have been shown to have the same biological activity. A major source of these compounds is the combustion of fresh or metamorphosed plant materials; this contributes to the environmental burden of, and exposure to, these carcinogens. We report the synthesis and characterization of a series of novel 5,8-diazabenzo[c]phenanthrenes which are isosteric with the known epidermal carcinogen benzo[c]phenanthrene but have not yet been reported as components of soot or diesel particulate matter. The synthesis of the compounds exploits a versatile, double Friedlander reaction between the appropriately substituted 2,2'-diaminobenzophenone and beta-diketones, with yields of purified product ranging from 30-90%. The nucleophilic substitution of these diazabenzophenanthrenes with ethanolamine is also described. This strategy will enable further elaboration of these heterocyclic nuclei at a later date. Mutagenicity testing of these agents was performed using spot tests and in Ames plate-incorporation assays using Escherichia coli WP2 and WP2uvrA as test organisms. The plate-incorporation assays were performed in the presence or absence of metabolic enzymes contained in the S9 liver fraction from Aroclor 1254-induced rats, to investigate whether bioactivation of the diazabenzophenanthrenes contributed to their toxicity. No differences between these two protocols were observed, with neither test showing reversion to prototrophic behaviour. Furthermore, the compounds were not toxic to the test organism. These initial results suggest that these compounds are not mutagenic in the Ames tests employed.

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Carcinogenic nitrogen compounds. Part LXI. The Skraup reaction with diamines derived from acenaphthene and anthracene

Cited by 7 publications

References 0 publications

Analogues of Amonafide and Azonafide with Novel Ring Systems

Analogues of Amonafide and Azonafide with Novel Ring Systems

Synthesis and Basicity Studies of Quinolino[7,8-h]quinoline Derivatives

Novel 5,8-Diazabenzo[c]phenanthrenes: Synthesis and Mutagenicity

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