2-(9-anthrylmethyl)amino-1[2-(1-pyrrolidinyl)ethyl]benzimidazole-fluorescent chemosensor on h+cations

FIELD: chemistry.

SUBSTANCE: invention relates to new derivatives of 1,2-disubstituted 2-aminobezimidazole, and more specifically to 2-(9-anthrylmethyl)amino-1-[2-(1-pyrrolidinyl)ethyl]benzimidazole of formula I: , which have properties of fluorescent chemosensor on H+ cations.

EFFECT: obtaining new fluorescent chemosensor on H+ cations.

1 dwg, 1 ex


The invention relates to new derivatives of some 1,2-disubstituted 2-aminobenzimidazole of benzimidazole, namely 2-(9-antimetal)amino-1-[2-(1-pyrrolidinyl)ethyl]benzimidazole of the formula I:

having the properties of fluorescent chemosensor on the cations H+.

Currently, quite a large number of compounds represented by the authors as an effective chemosensory on the hydrogen cations (J.F.Callan, A.P.de Silva, D.C.Magri. Luminescent sensors and switches in the early 21st century. Tetrahedron, 2005, No. 36, p.8551-8558; Wahren. Fluorescent and photochromic chemosensory. USP, 2001, No. 12, s-1174; B. Valeur, I. Leray. Design principles of fluorescent molecular sensors for cation recognition. Coord. Chem. Rev., 2000, v.205, No. 1, p.3-40), contain the receptor complex fragment responsible for the selective binding of the substrate, and the fluorophore, the so-called "signal" fragment molecules chemosensor, the optical properties of which change in the interaction of the receptor with the substrate. The function of the receptors in the proton chemosensor perform various nitrogen-containing structure - azaheterocycle, azagrebnaya, Zapadny, calixarenes. In most cases in these systems is so-called PET-effect (Photoinduced Electron Transfer) - fotoindutsiruemykh electron transfer (G.J.Kavarnos. Fundamentals of Photoinduced Electron Transfer. NY, Wiley-VCH, 1993, 359 p.). The receptor of the sensor, based on PET-effect I have is the electron donor, and fluorophore - acceptor. Upon excitation of the molecule is electron transfer from the highest occupied molecular orbital (wsmo) fluorophore at lowest unoccupied molecular orbital (NSMU). This allows you to be electronic transition with wsmo donor-receptor on wsmo acceptor is a fluorophore, thereby causing the quenching of fluorescence of the latter. When complexation occurs a sharp decrease in the energy wsmo receptor, resulting in electron transfer, wsmo fluorophore becomes energetically unfavorable. There is a free transition of the excited electron with the NSMU on wsmo fluorophore and the sensor starts to fluoresce. The effectiveness of such chemosensors is measured by two factors - the rate of change of the initial fluorescence intensity upon addition of the substrate and selective detection of a particular cation.

High interest in the dynamics of systems for the determination of cations H+due to the possibility of their use to determine the basicity of various physiological objects (X.Gao, Y.Zhang, .Wang. New boronic acid fluorescent reporter. Compounds. 2. A naphthalene-based on-off sensor functional at physiological pH, Org. Lett., 2003, No. 24, p.4615-4618). However dialkylaminoalkyl derivative of benzimidazole-2-amine and anthracene interesting from the point of view of its own biological activity (.Wang, J.-G.Delcros, J.Biggerstaff,.Phanstiel. Molecular requirements for targeting the polyamine transport system. Synthesis and biological evaluation of polyamine-anthracene conjugates. J. Med. Chem., 2003, No. 13, p.2672-2682; R.A.Gardner, J.-G.Delcros, F.Konate, F.Breitbeil, B.Martin, M.Sigman, M.Huang, O.Phanstiel. N1-Substituent effects in the selective delivery of polyamine conjugates into cells containing active polyamine transporters. J. Med. Chem., 2004, No. 24, R-6069; VAIDISOVA, Yetolmagan, V.i.minkin, Spa, Avestian, Navarova, Livramento, Whitecrow. Salts of 9-substituted 2-halogenopyrimidines[1,2-a]benzimidazole, and the halides of 1-substituted 3-halogenfrei-2-aminobenzimidazole, as well as their composition having hemorheological properties. RF patent № 2290404, 2006).

In 2003, 2-methyl-6-(4-methyl-1-piperazinil)benzo[de]isoquinoline-1,3-dione was proposed by the authors (J.Gan, K.Chen, C.-P.Chang, H.Tian, Luminescent properties and photo-induced electron transfer of naphthalimides with piperazine substituent. Dyes and Pigments, 2003, p.21-28) as an effective fluorescent sensor for the cations H+. In the interaction of this compound with an acid (however, the authors of this article are silent, what kind of acid was used) there is an increase in baseline fluorescence 76 times. The selectivity of the sensor has not been studied.

Synthesized and investigated chemosensor on the cations H+- 2,7-bis(4-dimethylaminophenyl)-9-(cycloheptatriene)fluoran (Z.Wang, G.Zheng, P.Lu. 9-(Cycloheptatrienylidene)fluorene derivative: remarkable ratiometric pH sensor and computing switch with NOR logic gate. Org. Lett., 2005, No. 17, p.3669-3672) is a very interesting fact is Ki vision touch of the dynamics of a class of compounds. When changing the pH of the solution (using sulfuric acid)containing the sensor, from 7,06 to 4.00 is the quenching of fluorescence in more than four times, and further acidification to pH 0,97 leads to flare-up fluorescence 27 times at pH 4.00 and 6.5 times at pH 7,06. Such "on-off" fluorescence under the influence of the pH stated by the authors as the basis for recording information.

One of the most efficient fluorescent sensors for cations N+is ethyl 4-(5-(4-(dimethylamino)phenyl)-1-(perftoralkil)-4,5-dihydro-3-pyrazolyl)benzoate (.J.Fahrni, L.Yang, D.G.VanDerveer. Tuning the photoinduced electron-transfer thermodynamics in 1,3,5-triaryl-2-pyrazoline fluorophores: X-ray structures, photophysical characterization, computational analysis and in vivo evaluation. J. Am. Chem. Soc., 2003, No. 13, p.3799-3812). When the protonation odnomomentnoe sulfuric acid is a flare-up of the original fluorescence 160 times. However, in this case, the authors have also not investigated the interaction of the received sensor with other cations.

In a series fluorophotometric of benzimidazole known 3-[2-diethyl-Mino)ethylamino]benzimidazo[2,1-a]Benz[de]isoquinoline-7-he, showing dynamics of activity in relation to the cations H+. When the protonation there is a change in the quantum yield of fluorescence depending on the pH of the medium (A.R. de Silva, H.Q.N.Gunaratne, P.L.M.Lynch, A.J.Patty, G.L.Spence. Luminescence and charge transfer. Part 3. The use of chromophores with ICT (internal charge trasfer) excited states in the construction of fluorescent PET (photoinduced electron transfer) pH sensors and related absorption pH sensors with aminoalkyl side chains. J. Chem. Soc., Perkin Trans. 2, 1993, p.1611-1616).

In a series of 1,2-disubstituted 2-aminobenzimidazole known compounds with different types of biological activity, such as antihistaminic activity (M.Menzer, G.Laban, H.-G.Kazmirowski, P.Meisel, E.Kretzschmar. Verfahren zur herstellung von 2-amino-benzimidazol-derivaten. DD 281383, 1990), antiviral (F.M.Sommen, K.J.L.M.Andries, J.E.G.Guillemont, K.P.M.-J.Meersman, J.F.A.Lacrampe, F.E.Janssens. Respiratory syncytial virus replication inhibitors. WO 0100611, 2001) and others

The closest structure is 1-(4-terbisil)-2-(4-piperidyl)aminobenzimidazole - drug Norastemizole, showing antihistamine activity (Y.Hong, R.P.Bakale, C.H.Senanayake. Methods for synthesizing 2-substituted imidazoles. WO 98/46571, 1998; D.A.Handley, Y.Hong, R.P.Bakale, C.H.Senanayake. Norastemizole. Drugs of the Future. 1998, vol.23, No. 9, p.966).

The technical result of the invention is a new derivative in a series of 1,2-disubstituted 2-aminobenzimidazole manifesting new for this series property highly efficient fluorescent chemosensor on the cations H+.

The technical result is achieved by the compound of formula I, the synthesis of which is in the interaction of 2-amino-1-[2-(1-pyrrolidinyl)ethyl]-

benzimidazole 9-anthraldehyde and restoration of the obtained 2-(9-EN-trimethylene)amino-1-[2-(1-pyrrolidinyl)ethyl]benzimidazole by sodium borohydride to 2-(9-antimetal)amino-1-[2-(1-pyrrolidinyl)ethyl]benzimidazole (I).

The structure of all the synthesized compounds is provided by elemental analysis, the data of IR - and NMR1N spectra. The IR spectrum of compound I, filmed in vaseline oil, there is a band of stretching vibrations of the secondary amino group at 3320 cm-1. The NMR spectrum1N. Amin, I present the signals from the protons of the amino group in the form of a broadened signal (δ 8,68), and the doublet from CH2group (δ ceiling of 5.60, J 3.3 Hz), directly related to the anthracene fragment.

Below is a synthesis technique proposed connection.

Example 1. 2-(9-Antimetal)amino-1-[2-(1-pyrrolidinyl)ethyl]-benzimidazole (I)

A mixture of 2.06 g (10 mmol) of 9-anthraldehyde and 2,30 (10 mmol) 2-amino-1-[2-(1-pyrrolidinyl)ethyl]benzimidazole (VAIDISOVA, Uwimana, Bampton, Neawanna, Oisemont, Vukov, Mcctravel.com. The method of obtaining derivatives of 2-amino-1-aminol-cyberseminar. Copyright certificate №1149592, 1984) in 70 ml of ethanol is boiled for 6 hours. To a solution of 2-(9-entremetier)amino-1-[2-(1-pyrrolidinyl)ethyl]benzimidazole in ethanol after heating was added 0.95 g (25 mmol) of sodium borohydride. The solution is stirred, diluted with water and the excess borohydride is neutralized with acetic acid. The precipitation is filtered off, washed with water and dried in air. Yield 3.50 g (83,2%). TPL=170-171° (acetonitrile). IR spectrum, ν, cm-1: 3320, 1460, 1355. An NMR spectrum1N, δ, ppm: 0,91-1,12 (4H, m, CH2CH2); 1,80-2,00 (4H, m, N(CH2) );2,60-by 2.73 (2H, m, NCH2); 3,80-to 3.92 (2H, m, HCH2; the ceiling of 5.60 (2H, d, CH2, J 3.3 Hz); of 6.96-8,54 (13H, m, arene. N); 8,68 (2H, user. s, NH). Found, %: C 79,89; N. Of 6.75; N Made 13.36. C28H28N4. Calculated, %: C 79,97; N. Of 6.71; N 13,32.

The study of dynamics properties

Methods of research. Assessment of the sensory ability of the compound I is carried out according to the fluorescence spectra in the field of local fluorescence of anthracene. To do this, to a solution of compound I (C=5×10-7mol/l) was added to the estimated five-fold molar excess triperoxonane acid, or acetate of a metal (Zn2+Cd2+, Cu2+,

With2+, Ni2+, Pb2+Hg2+), or their mixture and was stirred solution until the salt is completely dissolved. Then there was the shooting of the fluorescence spectra at wavelengthFluor=414 nm

(vasb=360 nm): initial solution and solutions containing in addition to the compounds I other cations. Shooting of luminescence spectra were carried out on an Hitachi 650-60.

The calculation of the relative changes in fluorescence intensity was performed according to the formula: OIF=I/I0where

I0is the initial fluorescence intensity of a solution of compound I;

I is the fluorescence intensity of a solution of compound I after addition of a fivefold molar excess of the cation.

The results tested the deposits

Spectral properties of amine I revealed its high-touch activity with respect to cations of N+.

Chemosensor I due to manifestations of PET-effect has a very weak fluorescence of anthracene type neutral solutions of acetonitrile in the excitation lightwosb.=360 nm (three individual area maximum 390-440 nm and a shoulder 460-470 nm). In the spectrum of emission of this compound is also observed band at 470-600 nm corresponding to the formation of excimer.

Complexation with various cations through the use of the electron density of the nitrogen atoms is significantly alters thermodynamics of PET-effect that leads to a change in fluorescence intensity. Adding acetates, Cu2+With2+, Ni2+, Pb2+Hg2+to a solution of sensor I causes a slight attenuation of the fluorescence intensity, whereas the ions H+dramatically increase the fluorescence intensity (I/I0=480) (see drawing).

The selectivity of this sensor was shown when added to the original solution of amine I a mixture of cations: H+, Zn2+Cd2+, Cu2+, Co2+, Ni2+, Pb2+Hg2+(each of the cations was taken in a five-fold molar excess relative to the compound (I). In this case, there is an increase relates the school fluorescence intensity (flare-up) 470 times. As can be seen, the deviation of the fluorescence intensity of a solution of compound I with the addition of a mixture of cations (H+, Zn2+Cd2+, Cu2+, Co2+, Ni2+, Pb2+Hg2+) from a solution of the compound I with the addition only of trichloroacetic acid (H+is insignificant and shows the high selectivity of this fluorescent chemosensor in relation to ions of N+. Add triethylamine, taken in an equivalent amount (in relation to the added acid), sour combined acetonitrile solution of amine I leads to complete restoration of the initial fluorescence intensity, indicating the reversibility of the process of protonation of the sensor I and the possibility of its reuse.

Studies have shown that 2-(9-antimetal)amino-1-[2-(1-pyrrolidinyl)ethyl]benzimidazole (I) is a highly sensitive and selective fluorescent sensor for cations H+.

2-(9-Antimetal)amino-1-[2-(1-pyrrolidinyl)ethyl]benzimidazole of the formula I


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