<i>N</i>,<i>N</i>'-Bis(picolinoyl)hydrazine

Shao, Si‐Chang; Zhu, D. L.; Song, You; You, Xiao; Raj, S. Shanmuga Sundara; Fun, Hoong‐Kun

doi:10.1107/s0108270199009890

Cited by 9 publications

(16 citation statements)

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“…This is supported by the results of X-ray analysis of 1,2-dibenzoylhydrazine [4] and N,N'-bis(2-pyridinocarbonyl)hydrazine [5] in which a similar conformation of the C-C(=O)-NH-NH-C(=O)-C fragment is observed. The C (7) -O (2) carbonyl group lies virtually in the plane of the benzene ring (torsional angle O (2) -C ( The molecules in the crystal are bound in an infinite chain by hydrogen bonding with N (3) -H···O (1)' (1 -x, y, 1.5 -z) (H···O 1.83 Å, N-H···O 129°) and N 2) -H···O (2)' (0.5 -x, 0.5 -y, 1 -z) (H···O 2.00 Å, N-H···O 162°), the formation of which leads to lengthening of the C (6) -O (1) and C (7) -O (2) bonds to 1.226(3) and 1.233(3) Å respectively (mean value 1.210 Å [5]). It should be noted that the H(N (3) ) atom takes part in simultaneous formation of two hydrogen bonds.…”

supporting

confidence: 69%

mentioning

confidence: 99%

“…1, Tables 4,5) that the N-aroyl hydrazide fragment has an ap-ac-ap conformation (torsional angles C (4) -C (6) -N (2) -N (3) 172.7(2)°, C (6) -N (2) -N (3) -C (7) 99.8(3)°, and N (2) -N (3) -C (7) -C (8) -179.5(2)° which is apparently typical of N,N'-bis(2-arylcarbonyl)hydrazines. This is supported by the results of X-ray analysis of 1,2-dibenzoylhydrazine [4] and N,N'-bis(2-pyridinocarbonyl)hydrazine [5] in which a similar conformation of the C-C(=O)-NH-NH-C(=O)-C fragment is observed. The C (7) -O (2) carbonyl group lies virtually in the plane of the benzene ring (torsional angle O (2) -C ( The molecules in the crystal are bound in an infinite chain by hydrogen bonding with N (3) -H···O (1)' (1 -x, y, 1.5 -z) (H···O 1.83 Å, N-H···O 129°) and N 2) -H···O (2)' (0.5 -x, 0.5 -y, 1 -z) (H···O 2.00 Å, N-H···O 162°), the formation of which leads to lengthening of the C (6) -O (1) and C (7) -O (2) bonds to 1.226(3) and 1.233(3) Å respectively (mean value 1.210 Å [5]).…”

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confidence: 99%

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Study of the acylation reaction of 2,6-dimethyl-3,5-pyridinedicarboxylic acid hydrazides

Nesterova

Voevudsky

Samukha

et al. 2005

Chem Heterocycl Compd

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Keywords: aromatic acid halides, hydrazide, hydrazine hydrate, hydrazinolysis, X-ray analysis.The studies [1,2] demonstrated the possibility of a stepwise hydrazinolysis of the ester groups in diethyl 2,6-dimethyl-3,5-pyridinedicarboxylate with subsequent formation of 3-ethoxycarbonyl-2,6-dimethyl-5-pyridine-carboxylic acid hydrazide (1) and 2,6-dimethyl-3,5-dipyridinedicarboxylic acid dihydrazide (2) and then the corresponding hydrazones using aromatic aldehydes. It was found that the free ester group in the case of the hydrazones obtained from the monohydrazide 1 does not participate in the hydrazinolysis reaction.With the aim of investigating the chemical properties of the hydrazides 1 and 2 we have studied their acylation reaction with the aromatic acid halides 3a-h. This reaction occurs under base catalysis conditions using dry, refluxing acetonitrile. The choice of solvent and the temperature conditions are limited by the solubility of the hydrazides 1, 2 in organic solvents.The 3,5-pyridinedicarboxylic acid N-aroyl hydrazides 4, 5a-h formed in the reaction are neutralized using aqueous alcoholic sodium bicarbonate solution to give the corresponding bases 6, 7a-h (Tables 1-3). As is evident from the Table the most difficulty occurs in the reaction with 2-methoxybenzoyl chloride and this is evidently linked both with the lower electrophilicity of the reagent and with the steric hindrance generated by the ortho-methoxy group.The N-aroyl hydrazides 6, 7a-h are quite stable to acid and base hydrolysis but this occurs to give 2,6-dimethyl-3,5-pyridinedicarboxylic acid by refluxing for 6-10 h in 15% hydrochloric acid, virtually the same time being needed for the complete hydrolysis using a 2N aqueous alcohol solution of potassium hydroxide under reflux.The ester group of the monohydrazide 1 readily takes part in a hydrazinolysis reaction to give the dihydrazide 2 [1]. We were interested in the possible hydrazinolysis of the ester group in the obtained N-aroyl hydrazides 6a-h. It was found that prolonged reflux of both the bases 6a,b,e,f,h and the hydrochlorides __________________________________________________________________________________________

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supporting

confidence: 69%

mentioning

confidence: 99%

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confidence: 99%

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Study of the acylation reaction of 2,6-dimethyl-3,5-pyridinedicarboxylic acid hydrazides

Nesterova

Voevudsky

Samukha

et al. 2005

Chem Heterocycl Compd

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“…The torsional angles Au-N-N-Au (68.68(1)°) and C-N-N-C (65.74(1)°) and the dihedral angle of 87.5°be-tween the Au III -containing five-membered chelate rings illustrate a considerable twisted arrangement and thus partially interrupted p conjugation across the bridging ligand; two orthogonal molecular halves were found for the free ligand [6]. As a consequence of this twist and of the special coordinative features of the dicarbonylhydrazido ligands [3] (edge-sharing five-membered chelate rings) the two Au III ions exhibit a distance of only 3.974…”

Section: Introductionmentioning

confidence: 95%

“…The protonated form [5,6] H 2 L of the ligand has been studied before in connection with its anti-HIV and antitumor potential [7].…”

Section: Introductionmentioning

confidence: 99%

The complex (μ,η2:η2-L)[AuCl2]2, L2−=N,N′-bis(α-picolinoyl)hydrazido(2−), as obtained directly or through ring-opening reaction of 3,6-bis(2-pyridyl)-1,2,4,5-tetrazine

Dogan¹,

Schwederski²,

Schleid³

et al. 2004

Inorganic Chemistry Communications

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Novel diaroylhydrazine ligands as iron chelators: coordination chemistry and biological activity

et al. 2005

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The search for orally effective drugs for the treatment of iron overload disorders is an important goal in improving the health of patients suffering diseases such as beta-thalassemia major. Herein, we report the syntheses and characterization of some new members of a series of N-aroyl-N'-picolinoyl hydrazine chelators (the H2IPH analogs). Both 1:1 and 1:2 Fe(III):L complexes were isolated and the crystal structures of Fe(HPPH)Cl2, Fe(4BBPH)Cl2, Fe(HAPH)(APH) and Fe(H3BBPH)(3BBPH) were determined (H2PPH=N,N'-bis-picolinoyl hydrazine; H2APH=N-4-aminobenzoyl-N'-picolinoyl hydrazine, H23BBPH=N-3-bromobenzoyl-N'-picolinoylhydrazine and H24BBPH=N-(4-bromobenzoyl)-N'-(picolinoyl)hydrazine). In each case, a tridentate N,N,O coordination mode of each chelator with Fe was observed. The Fe(III) complexes of these ligands have been synthesized and their structural, spectroscopic and electrochemical characterization are reported. Five of these new chelators, namely H2BPH (N-(benzoyl)-N'-(picolinoyl)hydrazine), H2TPH (N-(2-thienyl)-N'-(picolinoyl)-hydrazine), H2PPH, H23BBPH and H24BBPH, showed high efficacy at mobilizing 59Fe from cells and inhibiting 59Fe uptake from the serum Fe transport protein, transferrin (Tf). Indeed, their activity was much greater than that found for the chelator in current clinical use, desferrioxamine (DFO), and similar to that observed for the orally active chelator, pyridoxal isonicotinoyl hydrazone (H2PIH). The ability of the chelators to inhibit 59Fe uptake could not be accounted for by direct chelation of 59Fe from 59Fe-Tf. The most effective chelators also showed low antiproliferative activity which was similar to or less than that observed with DFO, which is important in terms of their potential use as agents to treat Fe-overload disease.

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N,N'-Bis(picolinoyl)hydrazine

Cited by 9 publications

References 1 publication

Study of the acylation reaction of 2,6-dimethyl-3,5-pyridinedicarboxylic acid hydrazides

Study of the acylation reaction of 2,6-dimethyl-3,5-pyridinedicarboxylic acid hydrazides

The complex (μ,η2:η2-L)[AuCl2]2, L2−=N,N′-bis(α-picolinoyl)hydrazido(2−), as obtained directly or through ring-opening reaction of 3,6-bis(2-pyridyl)-1,2,4,5-tetrazine

Novel diaroylhydrazine ligands as iron chelators: coordination chemistry and biological activity

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