<i>N′</i>‐(3‐Amino‐1<i>H</i>‐isoindol‐1‐ylidene)‐R‐carbohydrazides and Their Amide‐Type Isomerism

Hordiyenko, Olga V.; Biitseva, Angelina V.; Kornilov, M. Yu.; Brosse, Nicolas; Hocquet, Alexandre; Jamart‐Grégoire, Brigitte; Шишкин, Олег В.; Zubatyuk, Roman I.

doi:10.1002/ejoc.200600063

Cited by 12 publications

(16 citation statements)

References 22 publications

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“…Recently, the crystal structures and biological properties of a large number of hydrazone derivatives and their metal complexes have been reported [1][2][3][4][5]. As part of the ongoing investigation of this class of compounds, the crystal structure of anew hydrazone derivative is reported in this paper.…”

Section: Discussionmentioning

confidence: 98%

“…The molecular structure of the title compound consists of a [3,4]dioxolebenzohydrazide and a2 -chloro-5-nitrobenzylidene groups that are located on opposite sides of the C=N bond showing an E configuration. The dihedral angle between the two substituted benzene rings C1-C6 and C9-C14 …”

Section: Discussionmentioning

confidence: 99%

“…

Source of material [3,4]Dioxolebenzohydrazide (18.2 mg, 0.1 mmol) was dissolved in methanol (10 ml), then 2-chloro-5-nitrobenzaldehyde (18.6 mg, 0.1 mmol) was added slowly into the solution, and the mixture was stirred at room temperature for 3h.The resulting solution was left in air for afew days, yielding colorless block-shaped crystals.

Experimental details

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confidence: 99%

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Crystal structure of [3,4]dioxole-N′-(2-chloro-5- nitrobenzylidene)benzohydrazide, C15H10ClN3O5

Wu¹,

Lin²,

Sun³

et al. 2009

Zeitschrift Für Kristallographie - New Crystal Structures

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Section: Discussionmentioning

confidence: 98%

Section: Discussionmentioning

confidence: 99%

“…

Experimental details

…”

mentioning

confidence: 99%

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Crystal structure of [3,4]dioxole-N′-(2-chloro-5- nitrobenzylidene)benzohydrazide, C15H10ClN3O5

Wu¹,

Lin²,

Sun³

et al. 2009

Zeitschrift Für Kristallographie - New Crystal Structures

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“…We may assume that these compounds are similar in structure to previously studied N',N"-1H-isoindole-1,3-diylidenedicarbohydrazides and exist in a symmetrical tautomeric form. We should note that the disubstitution products also could not be obtained in a similar reaction from phthalodinitrile [8]. However, they can be synthesized either from 1,3-substituted 1H-isoindoles -from highly reactive 1,1,3-trichloro-1H-isoindole [24] or from 1-imino-1H-isoindole-3-amine [25].…”

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confidence: 99%

“…The reaction of dinitrile 5 with an equivalent amount of hydrazides was carried out by the method described by Hordiyenko et al [8]. Analysis of the mixture of crude products by LC/MS showed that all the hydrazides taken, except cyclopropanecarboxylic acid hydrazide, react with dinitrile 5 to give a mixture of structural isomers, N'- (7-amino-2,4-dimethyl-5H-pyrrolo[3,4-b]pyridin-5-ylidene)carbohydrazides 6b-d and N'- (5-amino-2,4-dimethyl-7H-pyrrolo[3,4-b]pyridin-7-ylidene)carbohydrazides 7b-d.…”

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confidence: 99%

4,6-Dimethylpyridine-2,3-dicarbonitrile and its reaction with N-acylhydrazines

Rudenko

Kucherak

Толмачев

et al. 2011

Chem Heterocycl Comp

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Heterocyclic 1,2-dicarbonitriles such as 2,3-dicyanoazines hold considerable interest as precursors of azaphthalocyanine dyes used in the preparation of highly stable dyes, new functional materials for nonlinear optics, photoconductors, liquid crystals, electrochromic devices, solar energy devices, color monitors, laser systems for information storage [1][2][3], and in photodynamic therapy [4].Heterocyclic 1,2-dicarbonitriles also serve as convenient starting blocks in the synthesis of condensed heterocycles. Analysis of the literature data showed that the reactions of 2,3-dicyanopyridines with N-nucleophiles, in particular, with amines, have hardly been studied [5][6][7]. In a study of the heterocyclization reactions of N-acylhydrazines with phthalodinitrile [8], pyridine-2,3-dicarbonitriles have attracted special attention, specifically 4,6-dimethylpyridine-2,3-dicarbonitrile. On one hand, the result of the cyclization reaction cannot be unequivocally predicted due to the asymmetry of this compound due to the presence of the nitrogen atom in the ring. Furthermore, the presence of a methyl group at C-4 in this dicarbonitrile may affect the regioselectivity of the reaction. Several products whose structures were not established have been formed in the reaction of pyridine-2,3-dicarbonitrile with ammonia or acid hydrazides [9].The method for the synthesis of 2,3-dicyanopyridine involving conversion of derivatives of pyridine-2,3-dicarboxylic acid [10] cannot be used for the preparation of alkyl-substituted pyridine-2,3-dicarbonitriles. 2-Halopyridines already containing a nitrile group at C-3 of the pyridine ring have been used in an approach to the synthesis of alkyl-substituted pyridine-2,3-dicarbonitriles. The introduction of a second cyano group by nucleophilic substitution of halogen atoms by a cyanide ion should lead to alkyl-substituted pyridine-

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Identification of 1,3‐Diiminoisoindoline Carbohydrazides as Potential Antimalarial Candidates

et al. 2011

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A series of inhibitors of plant enzymes of the non-mevalonate pathway from herbicide research efforts at BASF were screened for antimalarial activity in a cell-based assay. A 1,3-diiminoisoindoline carbohydrazide was found to inhibit the growth of Plasmodium falciparum with an IC(50) value <100 nM. Synthesis of a variety of derivatives allowed an improvement of the initial antimalarial activity down to IC(50) =18 nM for the most potent compound, the establishment of a structure-activity relationship, and the evaluation of the cytotoxic profile of the diiminoisoindolines. Furthermore, interesting configurational and conformational aspects for this class of compounds were studied by computational and X-ray crystal structure analysis. Some of the compounds can act as tridentate ligands, forming 2:1 ligand-iron(III) complexes, which also display antimalarial activity in the nanomolar IC(50) range, paired with low cytotoxicity.

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N′‐(3‐Amino‐1H‐isoindol‐1‐ylidene)‐R‐carbohydrazides and Their Amide‐Type Isomerism

Cited by 12 publications

References 22 publications

Crystal structure of [3,4]dioxole-N′-(2-chloro-5- nitrobenzylidene)benzohydrazide, C15H10ClN3O5

Crystal structure of [3,4]dioxole-N′-(2-chloro-5- nitrobenzylidene)benzohydrazide, C15H10ClN3O5

4,6-Dimethylpyridine-2,3-dicarbonitrile and its reaction with N-acylhydrazines

Identification of 1,3‐Diiminoisoindoline Carbohydrazides as Potential Antimalarial Candidates

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