Reaktionen mit Dimethylformamid, 1. Mitt.: Synthese von Carbons�uredimethylamiden

Schindlbauer, H.

doi:10.1007/bf00904312

Cited by 33 publications

(15 citation statements)

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“…2-Mercapto-N,N-dimethylbenzamide (2) was prepared by using a reported procedure immediately prior to the reaction and used without purification. 58 35 mmol) in water (0.5 mL) was added at -5 to 0°C. To this mixture, 48% hexafluorophosphoric acid (1.5 mL) was added at 0°C and the mixture was stirred for 10 min.…”

Section: Methodsmentioning

confidence: 99%

New PET Imaging Agent for the Serotonin Transporter: [¹⁸F]ACF (2-[(2-Amino-4-chloro-5-fluorophenyl)thio]-N,N-dimethyl-benzenmethanamine)

et al. 2002

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A new F-18-labeled phenylthiophenyl derivative specific for imaging of serotonin transporters (SERT) in the brain by positron emission tomography (PET) is described. Fluorinated phenylthiophenyl derivative, ACF, 2-[(2-amino-4-chloro-5-fluorophenyl)thio]-N,N-dimethyl-benzenmethanamine, was prepared by first coupling 2,5-dichloro-4-nitroaniline with 2-mercapto-N,N-dimethylbenzamide. The amino group of the coupled adduct was converted to a fluoro group through a Schiemann reaction. Subsequently, a one pot reduction of both nitro and amide groups by BH(3)-tetrahydrofuran yielded the nonradioactive ACF (yield 25%). In vitro binding assays using cell membrane homogenates of LLC cells expressing SERT, dopamine transporters (DAT), or norepinephrine transporters (NET) showed excellent binding affinity and selectivity for SERT (K(i) = 0.05, 3020, and 650 nM for SERT, DAT, and NET, respectively). For preparation of the [(18)F]ACF, the NH(2) group of the initially coupled adduct was converted to the trimethylammonium salt, which was replaced by [(18)F]fluoride in the presence of Kryptofix 222 and potassium carbonate. The final product, [(18)F]ACF, was obtained after a borane and stannous chloride reduction reaction. The combined two step reaction gave a radiochemical yield of 10-15% (EOB) and a radiochemical purity of >99%. Synthesis of the novel PET tracer, [(18)F]ACF, as a probe for binding to SERT in the brain was successfully achieved. The new tracer [(18)F]ACF showed excellent brain penetration and selective localization after an iv injection in rats (brain uptake at 2, 30, 60, 120, and 240 min was 3.27, 1.28, 0.69, 0.21, and 0.06% dose/organ, respectively). The hypothalamus/cerebellum ratio at 60 min post iv injection was 3.55. This specific localization in the hypothalamus was blocked by pretreatment of (+)McN5652. This novel ligand is a potential PET tracer for in vivo evaluation of SERT in the brain.

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Section: Methodsmentioning

confidence: 99%

New PET Imaging Agent for the Serotonin Transporter: [¹⁸F]ACF (2-[(2-Amino-4-chloro-5-fluorophenyl)thio]-N,N-dimethyl-benzenmethanamine)

et al. 2002

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“…The propane sulfobetaines (3)(4)(5)(6)(7)(8)(9)(10)(11)(12) were prepared by reacting the corresponding N,N-dimethylamines with 1,3-propanesultone in ethyl acetate at room temperature (Scheme 2). 2,3 The products separated out from the solution as white solids which could be purified by recrystallisation.…”

Section: Methodsmentioning

confidence: 99%

“…4 The dimethylamides 22 and 23 in turn were prepared from hydrocinnamic acid and 3-phenylbutanoic acid respectively by reaction with DMF and thionyl chloride. The direct preparation of an N,N-dimethylamide by reacting a carboxylic acid with DMF and a co-reagent such as P 2 O 5 , [5][6][7][8] POCl 3 , 9,10 (COCl) 2 , 11-14 DCCI 15,16 or NaH 17 has been previously reported but, to the best of our knowledge, there are only two reports of the use of SOCl 2 for this purpose. 18,19…”

Section: Methodsmentioning

confidence: 99%

“…H NMR (400 MHz, CDCl 3 ): d = 0.89 (t, 3 H, J = 6 4. Hz, CH 3 ),1.26-1.40 [m, 6 H, CH 3 (CH 2 ) 3 ], 1.59 [q5 , 2 H, J = 7.1 Hz, CH 3 (CH 2 ) 3 CH 2 ], 2.18 (m, 2 H, CH 2 CH 2 N), 2.57 (t, 2 H, J = 7.7 Hz, ArCH 2 ), 2.70 (t, 2 H, J = 7.2 Hz, ArCH 2 ), 2.78 [s, 6 H, N(CH 3 ) 2 ], 2.96-2.99 (m, 2 H, CH 2 N), 7.08 and 7.11 (2´d, 4 H, J = 8.0 Hz, C 6 H 4 ),12.27 (br s, 1 H, HCl).13 C NMR (101 MHz, CDCl 3 ): d = 14.5 (CH 3 ), 23.0 (CH 3 CH 2 ), 26.0 (CH 2 CH 2 N), 29.4 (CH 2 ), 31.9 (CH 2 ), 32.1 (CH 2 ), 32.5 (ArCH 2 ), 35.9 (CH 2 Ar), 43.3 (NCH 3 ), 57.8 (CH 2 N), 128.6 (Ar, CH), 129.2 (Ar, CH), 136.7 (Ar, C-1/4), 141.7 (Ar, C-1/4). MS-EI: m/z = 247 (100%) [M + ], 202 (18%), 189 (14%), 175 (16%).…”

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confidence: 99%

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Synthesis of Quaternary Alkylammonium Sulfobetaines

Ward¹,

Davies²,

Hodges³

et al. 2002

Synthesis

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S y n t h e s i s o f Q u a t e r n a r y A l k y l a m m o n i u m S u l f o b e t a i n e s Abstract: A series of quaternary alkylammonium sulfobetaines of general formula RN + (CH 3 ) 2 (CH 2 ) n SO 3 -, where n = 2-4, have been synthesised by reacting the corresponding N,N-dimethylamines with either sodium 2-chloroethanesulfonate (n = 2), 1,3-propanesultone (n = 3), or 1,4-butanesultone (n = 4). Full details of the preparation of the required N,N-dimethylamines are reported.

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“…Reagents used in the synthesis were obtained from Aldrich and were of analytical grade. Compounds 1, 2, 10, and 12 were synthesized according to the literature methods [28][29][30][31][32] .…”

Section: Materials and Measurementsmentioning

confidence: 99%

Synthesis and in vitro evaluation of new diphenyl ether derivatives as serotonin transporter ligands

Guo

Chen

Jia

et al. 2008

Sci. China Ser. B-Chem.

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For the development of new ligands as potential imaging agents for the serotonin transporter (SERT), a series of diphenyl ether derivatives have been synthesized, characterized, and evaluated for their in vitro binding affinities to the SERT. Among the above compounds, 2-(2-((dimethylamino)methyl)-4-fluorophenoxy)-5-bromobenzenamine (15) and 2-(2-((dimethylamino)methyl)-4-fluorophenoxy)-5-iodobenzene amine (16) show high binding affinities for the SERT with K i values of 0.28 and 0.20 nmol·L 1 , respectively. They can be further labeled with carbon-11, fluorine-18, iodine-123 or bromine-76, and evaluated as useful imaging agents for the SERT. Moreover, the study of the structure-activity relationship (SAR) provides some useful information for the future design of new ligands. serotonin transporter, diphenyl ether, imaging agents, in vitro evaluation

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Reaktionen mit Dimethylformamid, 1. Mitt.: Synthese von Carbons�uredimethylamiden

Cited by 33 publications

References 0 publications

New PET Imaging Agent for the Serotonin Transporter: [¹⁸F]ACF (2-[(2-Amino-4-chloro-5-fluorophenyl)thio]-N,N-dimethyl-benzenmethanamine)

New PET Imaging Agent for the Serotonin Transporter: [¹⁸F]ACF (2-[(2-Amino-4-chloro-5-fluorophenyl)thio]-N,N-dimethyl-benzenmethanamine)

Synthesis of Quaternary Alkylammonium Sulfobetaines

Synthesis and in vitro evaluation of new diphenyl ether derivatives as serotonin transporter ligands

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Reaktionen mit Dimethylformamid, 1. Mitt.: Synthese von Carbons�uredimethylamiden

Cited by 33 publications

References 0 publications

New PET Imaging Agent for the Serotonin Transporter: [18F]ACF (2-[(2-Amino-4-chloro-5-fluorophenyl)thio]-N,N-dimethyl-benzenmethanamine)

New PET Imaging Agent for the Serotonin Transporter: [18F]ACF (2-[(2-Amino-4-chloro-5-fluorophenyl)thio]-N,N-dimethyl-benzenmethanamine)

Synthesis of Quaternary Alkylammonium Sulfobetaines

Synthesis and in vitro evaluation of new diphenyl ether derivatives as serotonin transporter ligands

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Product

Resources

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New PET Imaging Agent for the Serotonin Transporter: [¹⁸F]ACF (2-[(2-Amino-4-chloro-5-fluorophenyl)thio]-N,N-dimethyl-benzenmethanamine)

New PET Imaging Agent for the Serotonin Transporter: [¹⁸F]ACF (2-[(2-Amino-4-chloro-5-fluorophenyl)thio]-N,N-dimethyl-benzenmethanamine)