Thiazole and benzothiazole derivatives of cytisine

Saprykina, V. A.; Виноградова, В. И.; Ambartsumova, R. F.; Ibragimov, T. F.; Shakhidoyatov, Kh. M.

doi:10.1007/s10600-006-0182-7

Cited by 12 publications

(7 citation statements)

References 5 publications

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“…2,4 The thiazole ring is known to be a part of vitamin B1, cocarboxylase, and the cyclic system of penicillin. 5 Thiazole itself and its derivatives are of importance in biological systems as anti-inflammatory, analgesic agents and inhibitors on lipoxygenase activities. 6,7 Schiff bases constitute an interesting class of chelating agents, capable of coordination with one or more metal ions to form mononuclear as well as polynuclear metal complexes.…”

Section: Introductionmentioning

confidence: 99%

Experimental and ab initio Computational Studies on Dimethyl-(4-{4-{3-methyl-3-phenyl-cyclobutyl)-thiazol-2-yl]-hydrazonomethyl}-phenyl)-amine

Yüksektepe¹,

Saraçoğlu²,

Çalışkan³

et al. 2010

Bulletin of the Korean Chemical Society

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A new hydrazone derivative compound has been synthesized and characterized by IR, 1 H-NMR, 13 C-NMR and UV-vis. spectroscopy techniques, elemental analysis and single-crystal X-ray diffraction (XRD). The new compound crystallizes in monoclinic space group C2/c. In addition to the crystal structure from X-ray experiment, the molecular geometry, vibrational frequencies and frontier molecular orbitals analysis of the title compound in the ground state have been calculated by using the HF/6-31G(d, p), B3LYP/6-311G(d, p) and B3LYP/6-31G(d, p) methods. The computed vibrational frequencies are used to determine the types of molecular motions associated with each of the observed experimental bands. To determine conformational flexibility, molecular energy profile of (1) was obtained by semi-empirical (AM1) calculation with respect to a selected degree of torsional freedom, which was varied from -180 o to +180 o in steps of 10 o . Molecular electrostatic potential of the compound was also performed by the theoretical method.

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Section: Introductionmentioning

confidence: 99%

Experimental and ab initio Computational Studies on Dimethyl-(4-{4-{3-methyl-3-phenyl-cyclobutyl)-thiazol-2-yl]-hydrazonomethyl}-phenyl)-amine

Yüksektepe¹,

Saraçoğlu²,

Çalışkan³

et al. 2010

Bulletin of the Korean Chemical Society

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“…On the other hand, the chiral 3,7-diazobicyclo[3.3.1]nonane skeleton is interesting for studying structural features of substituted cytisines [3][4][5][6]. Until now, a large number of cytisine derivatives with various groups on the N atom have been synthesized [7][8][9][10][11][12], including acryloyl groups [13], thiazoles, benzthiazoles [11], and 1,2,4-thiadiazole groups [12]. In continuation of our research on transformations of 1 [11,12] and in order to find biologically active compounds in this series, we synthesized acyl derivatives via acylation of 1 with acetic anhydride and acid chlorides.…”

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confidence: 99%

“…Until now, a large number of cytisine derivatives with various groups on the N atom have been synthesized [7][8][9][10][11][12], including acryloyl groups [13], thiazoles, benzthiazoles [11], and 1,2,4-thiadiazole groups [12]. In continuation of our research on transformations of 1 [11,12] and in order to find biologically active compounds in this series, we synthesized acyl derivatives via acylation of 1 with acetic anhydride and acid chlorides. The acylating agents were acetic anhydride; benzoyl-and o-bromo-and p-nitrobenzoyl chlorides; and crotonyl and cinnamoyl chlorides.…”

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confidence: 99%

Structural features of N-acylcytisines

et al. 2009

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747.945+547.79+548.737 G. Genzhemuratova, M. G. Levkovich, and Kh. M. ShakhidoyatovN-Acyl cytisine derivatives were synthesized by acylation with acetic anhydride; benzoyl and o-bromo-and p-nitrobenzoyl chlorides; and crotonyl and cinnamoyl chlorides. The structures of the synthesized compounds were studied using IR, PMR, and x-ray structure analysis (XSA). PMR spectra of the N-acylcytisines in solution typically had two rotational isomers around the N12-CO bond. Conformational analysis was performed using XSA for the position of the acyl group relative to the cytisine core. Bond lengths and angles of the acyl groups involved in the conjugation were analyzed.The broad spectrum of biological activity of cytisine (1) and its derivatives [1, 2] makes them a promising class for practical application. On the other hand, the chiral 3,7-diazobicyclo[3.3.1]nonane skeleton is interesting for studying structural features of substituted cytisines [3][4][5][6]. Until now, a large number of cytisine derivatives with various groups on the N atom have been synthesized [7][8][9][10][11][12], including acryloyl groups [13], thiazoles, benzthiazoles [11], and 1,2,4-thiadiazole groups [12]. In continuation of our research on transformations of 1 [11,12] and in order to find biologically active compounds in this series, we synthesized acyl derivatives via acylation of 1 with acetic anhydride and acid chlorides. The acylating agents were acetic anhydride; benzoyl-and o-bromo-and p-nitrobenzoyl chlorides; and crotonyl and cinnamoyl chlorides. The reaction with acetic anhydride occurred with an excess of it. Acylation by the acid chlorides occurred in anhydrous toluene under reflux: R = -ÑH 3 (2); -Ñ 6 H 5 (3); -Ñ 6 H 4 -Br-o (4); -C 6 H 4 -NO 2 -n (5); -CH=CH-C 6 H 5 (6); -CH=CH-CH 3 (7) Acylation of 1 by acid chlorides was carried out without a HCl acceptor. Atom N12 of ring C played this role. Structures of 2-7 were confirmed by IR and PMR spectra and by an x-ray structure analysis (XSA) for N-o-bromobenzoylcytisine (4), N-p-nitrobenzoylcytisine (5), and N-crotonylcytisine (6).IR spectra contained absorption bands at 1643-1653 cm -1 (ν CO ) and 1634-1647 (ν CO ). The physicochemical properties of 2, 3, and 7 agreed with those published. PMR spectra of the N-acylcytisines in solution characteristically showed several rotational isomers around the N12-CO and CO-R bonds. They could produce spectra of several conformers or simply give very broad spectral lines because the barriers to rotation were small. In several instances resonances could not be unambiguously assigned.

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“…For general background, see: Fu et al (2005); Saprykina et al (2006). For a related structure, see: Cheng (2007).…”

Section: Related Literaturementioning

confidence: 99%

Methyl 2-(2-amino-1,3-thiazol-4-yl)-2-[(Z)-methoxycarbonylmethoxyimino]ethanoate

et al. 2009

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In the molecule of the title compound, C9H11N3O5S, the thiazole ring is oriented at dihedral angles of 87.33 (3) and 87.18 (3)° with respect to the planar (r.m.s. deviations 0.0136 and 0.0139 Å) methyl ester groups. The dihedral angle between the methyl ester groups is 44.20 (3)°. In the crystal structure, intermolecular N—H⋯N, N—H⋯O and C—H⋯O hydrogen bonds link the molecules along the a axis, through R 2 2(8) and R 2 2(22) ring motifs, forming infinite two-dimensional polymeric sheets. π–π Contacts between the thiazole rings [centroid–centroid distance = 3.536 (2) Å] may further stabilize the structure.

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Thiazole and benzothiazole derivatives of cytisine

Cited by 12 publications

References 5 publications

Experimental and ab initio Computational Studies on Dimethyl-(4-{4-{3-methyl-3-phenyl-cyclobutyl)-thiazol-2-yl]-hydrazonomethyl}-phenyl)-amine

Experimental and ab initio Computational Studies on Dimethyl-(4-{4-{3-methyl-3-phenyl-cyclobutyl)-thiazol-2-yl]-hydrazonomethyl}-phenyl)-amine

Structural features of N-acylcytisines

Methyl 2-(2-amino-1,3-thiazol-4-yl)-2-[(Z)-methoxycarbonylmethoxyimino]ethanoate

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