Efficient preparation of substituted 5,6,7,8-tetrahydroquinolines and octahydroacridine derivatives

Sielemann, Dirk; Keuper, Ralf; Risch, Nikolaus

doi:10.1002/(sici)1521-3897(199907)341:5<487::aid-prac487>3.0.co;2-j

Cited by 16 publications

(7 citation statements)

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“…mp 172.5–173.5°C 22), 1‐(4‐bromophenyl)‐3‐dimethylamino‐1‐propanone hydrochloride 18 (mp 194–195°C; lit. mp 193°C 23), 1‐(4‐biphenyl‐1‐yl)‐3‐dimethylamino‐1‐propanone hydrochloride 19 (mp 187–188°C; lit. mp 182–183°C 24), 3‐dimethylamino‐1‐(naphthalen‐1‐yl)‐1‐propanone hydrochloride 20 (mp 156–157°C; lit.…”

Section: Methodsmentioning

confidence: 99%

A Novel Antifungal Agent with Broad Spectrum: 1‐(4‐Biphenylyl)‐3‐(1H‐imidazol‐1‐yl)‐1‐propanone

Roman¹,

Mareș

Nastasa

2012

Archiv der Pharmazie

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A series of (1-substituted aryl)-3-(1H-imidazol-1-yl)-1-propanones was synthesized through the N-alkylation of imidazole with 3-dimethylamino-1-(substituted aryl)-1-propanone hydrochlorides (ketonic Mannich bases). A second series of N(1) -substituted imidazoles was obtained by the reduction of the carbonyl function of the imidazole-ketones in the previous series by means of NaBH(4) . All of the compounds were evaluated for antifungal activity against 16 strains of Candida, and 3-(1H-imidazol-1-yl)-1-(4-biphenylyl)-1-propanone emerged as a broad-spectrum antifungal agent. Several 3-(1H-imidazol-1-yl)-1-(2'-(substituted benzyl)oxyphenyl)-1-propanones were also active towards Candida kefyr.

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Section: Methodsmentioning

confidence: 99%

A Novel Antifungal Agent with Broad Spectrum: 1‐(4‐Biphenylyl)‐3‐(1H‐imidazol‐1‐yl)‐1‐propanone

Roman¹,

Mareș

Nastasa

2012

Archiv der Pharmazie

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“…First, the Pt II temperature probe was synthesized by using a straight‐forward synthetic method 10b. 19 In a modified Lewis method for the first step of the synthesis, 2‐(4‐bromophenyl)‐5,6,7,8‐tetrahydroquinoline (Br‐thq)20 and K 2 PtCl 4 were heated to generate the μ‐chloro‐bridged precursor dimer and, subsequently, in a second step, by introducing ligand 2,2,6,6‐tetramethylheptane‐3,5‐dione (acac), the target complex [platinum(II)(2‐(4‐bromophenyl)‐5,6,7,8‐tetrahydroquinoline)(2,2,6,6‐tetramethylheptane‐3,5‐dione)] was isolated in a yield of 65 %. For oxygen sensing, nanoparticles that were made from poly(styrene‐ co ‐1‐vinylpyrrolidone) (PS‐ co ‐PVP)21 were doped with platinum(II)‐5,10,15,20‐tetrakis(2,3,4,5,6‐pentafluorophenyl)porphyrin (PtTFPP).…”

Section: Resultsmentioning

confidence: 99%

“…2‐(4‐Bromophenyl)‐5,6,7,8‐tetrahydroquinoline,20 as well as the dimer19f and the complex,10b, 19 were synthesized according to modified literature procedures.…”

Section: Methodsmentioning

confidence: 99%

“…[10b, 19] In a modified Lewis method for the first step of the synthesis, 2-(4-bromophenyl)-5,6,7,8-tetrahydroquinoline (Br-thq) [20] and K 2 PtCl 4 were heated to generate the m-chloro-bridged precursor dimer and, subsequently, in a second step, by introducing ligand 2,2,6,6-tetramethylheptane-3,5-dione (acac), the target complex [platinum(II)(2-(4-bromophenyl)-5,6,7,8-tetrahydroquinoline)(2,2,6,6-tetramethylheptane-3,5-dione)] was isolated in a yield of 65 %. [10b, 19] In a modified Lewis method for the first step of the synthesis, 2-(4-bromophenyl)-5,6,7,8-tetrahydroquinoline (Br-thq) [20] and K 2 PtCl 4 were heated to generate the m-chloro-bridged precursor dimer and, subsequently, in a second step, by introducing ligand 2,2,6,6-tetramethylheptane-3,5-dione (acac), the target complex [platinum(II)(2-(4-bromophenyl)-5,6,7,8-tetrahydroquinoline)(2,2,6,6-tetramethylheptane-3,5-dione)] was isolated in a yield of 65 %.…”

Section: The Emission Of the Temperature Indicator [Pt II A C H T U mentioning

confidence: 99%

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Referenced Dual Pressure‐ and Temperature‐Sensitive Paint for Digital Color Camera Read Out

Fischer

Karakus

Meier

et al. 2012

Chemistry A European J

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The first fluorescent material for the referenced simultaneous RGB (red green blue) imaging of barometric pressure (oxygen partial pressure) and temperature is presented. This sensitive coating consists of two platinum(II) complexes as indicators and a reference dye, each of which is incorporated in appropriate polymer nanoparticles. These particles are dispersed in a polyurethane hydrogel and spread onto a solid support. The emission of the (oxygen) pressure indicator, PtTFPP, matches the red channel of a RGB color camera, whilst the emission of the temperature indicator [Pt(II) (Br-thq)(acac)] matches the green channel. The reference dye, 9,10-diphenylanthracene, emits in the blue channel. In contrast to other dual-sensitive materials, this new coating allows for the simultaneous imaging of both indicator signals, as well as the reference signal, in one RGB color picture without having to separate the signals with additional optical filters. All of these dyes are excitable with a 405 nm light-emitting diode (LED). With this new composite material, barometric pressure can be determined with a resolution of 22 mbar; the temperature can be determined with a resolution of 4.3 °C.

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“…The hydrazones K2,K 3,K 5,K 6,K 7,K 8,K 9 and K10 werereported fort he first time byt hiss tudyw iththeir synthesis,spectralanalysisand theircytotoxica ctivities while mono Mannichbases D1-D10 [34][35][36][37][38][39][40][41][42][43]a nd the hydrazones K1 and K4 werereported in literature [7,30]. 1 Ha nd 13 CN MR (Table 3)and high resolution MS…”

Section: Resultsmentioning

confidence: 99%

Synthesis of some Mannich bases with dimethylamine and their hydrazones and evaluation of their cytotoxicity against Jurkat cells

Küçükoğlu¹,

Gül

Atalay

et al. 2011

Arzneimittelforschung

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1-Aryl-3-dimethylamino-1-propanone hydrochlorides type mono Mannich bases, D series, and corresponding hydrazone derivatives, K series, were synthesized and their cytotoxicity was tested against Jurkat cells (transformed human T-lymphocytes). The aryl part was changed as phenyl in D1 and K1, 4-methylphenyl in D2 and K2, 4-methoxyphenyl in D3 and K3, 4-hydroxyphenyl in D4 and K4, 4-chlorophenyl in D5 and K5, 3-methoxyphenyl in D6 and K6, 4-fluorophenyl in D7 and K7, 4-bromophenyl in D8 and K8, 3-hydroxyphenyl in D9 and K9, and 2-acetylthiophene in D10 and K10. Of the compounds synthesized, K2, K3, K5, K6, K7, K8, K9, and K10 are reported for the first time. Cytotoxic activities of the D and K series were compared with each other to see alterations in bioactivity depending on the chemical structures in Jurkat cells. Cytotoxicities of the compounds synthesized were also compared with the reference compound, 5-fluorouracil (CAS 148-82-3). Mono Mannich bases, D1 (3.60 times), D2 (4.45 times), D3 (2.46 times), D4 (3.52 times), D5 (5.18 times), D6 (3.20 times), D7 (3.23 times), D8 (3.95 times), D9 (3.36 times) and D10 (3.99 times) had 2.46-5.18 times higher cytotoxic potency than the reference compound 5-fluorouracil against Jurkat cells, while hydrazones K1 (4.92 times), K2 (4.65 times), K3 (6.04 times), K4 (6.34 times), K5 (4.67 times), K6 (5.12 times), K7 (5.39 times), K8 (8.31 times), K9 (4.65 times) and K10 (8.65 times) had 4.65-8.65 times higher cytotoxic potency than the reference compound 5-fluorouracil against the same cell line. On the other hand, hydrazone compounds K1 (1.37 times), K3 (2.46 times), K4 (1.80 times), K6 (1.60 times), K7 (1.67 times), K8 (2.11 times), K9 (1.38 times), and K10 (2.17 times) had 1.37-2.46 times higher cytotoxic potency than their corresponding mono Mannich bases. The results of this study suggest that hydrazones were better compounds compared with the corresponding mono Mannich bases in terms of cytotoxicity, and they may serve as model compounds to develop new cytotoxic agents for further studies.

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Efficient preparation of substituted 5,6,7,8-tetrahydroquinolines and octahydroacridine derivatives

Cited by 16 publications

References 0 publications

A Novel Antifungal Agent with Broad Spectrum: 1‐(4‐Biphenylyl)‐3‐(1H‐imidazol‐1‐yl)‐1‐propanone

A Novel Antifungal Agent with Broad Spectrum: 1‐(4‐Biphenylyl)‐3‐(1H‐imidazol‐1‐yl)‐1‐propanone

Referenced Dual Pressure‐ and Temperature‐Sensitive Paint for Digital Color Camera Read Out

Synthesis of some Mannich bases with dimethylamine and their hydrazones and evaluation of their cytotoxicity against Jurkat cells

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