Effect of Structure of 1-Substituted Isatins on Direction of Their Reactions with Some Acetohydrazide Ammonium Derivativ
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ct of Structure of 1-Substituted Isatins on Direction of Their Reactions with Some Acetohydrazide Ammonium Derivatives A. V. Bogdanova,*, A. D. Voloshinaa, A. S. Sapunovaa, N. V. Kulika, and V. F. Mironova a A.E.
Arbuzov Institute of Organic and Physical Chemistry, Federal Research Center “Kazan Scientific Center of the Russian Academy of Sciences,” Kazan, 420088 Russia *e-mail: [email protected] Received April 8, 2020; revised April 8, 2020; accepted April 18, 2020
Abstract—The reaction of 1-acylisatins with Girard’s reagent T proceeds with elimination of the acyl substituent and the formation of isatin-3-hydrazone with a quaternary nitrogen atom in the side chain. Depending on the structure of the substituent in position 1, 1-(aminomethyl)isatins reacted with the Girard’s reagent T to form hydrazones either with the elimination of the aminomethyl substituent or with its retention. Isatin derivatives containing no substituents in the aromatic fragment exhibit moderate activity against gram-positive bacteria S. aureus 209p and B. cereus 8035. Low hemotoxicity of the obtained compounds was revealed. Keywords: isatin, hydrazones, heterocycles, antimicrobial activity, ammonium salts
DOI: 10.1134/S1070363220090029 Isatin (1H-indole-2,3-dione) and its derivatives have a planar cyclic structure with a high degree of conjugation. They are widely used in the design of organic functional materials for various purposes [1–6]. Isatin easily undergoes deep modification, its derivatives belong to the class of privileged heterocyclic structures [7, 8], on the basis of which biologically active substances of a broad spectrum of action have been designed. Therefore, most of publications on the synthesis and reactions of isatin and its derivatives belongs to the field of pharmaceutical chemistry [9–12]. Isatin derivatives have high antiviral, antifungal, antibacterial, antiproliferative, antitumor, anti-inflammatory, antidiabetic, antihypertensive and anticonvulsant activity (Scheme 1) [13–21]. Taking into account the numerous data on the synthesis and study of the biological activity of Mannich
bases obtained from isatin [10, 22–24], we attempted to functionalize a series of 1-(aminomethyl)isatins with acetylhydrazides with a quaternary nitrogen in position 2. At the first stage, the Girard’s reagent T 5 was introduced into the raction with isatins 1–4. The reaction was carried out with heating in ethanol in the presence of catalytic amounts of trifluoroacetic acid (Scheme 2). Analysis of the 1H, 13C NMR and mass spectra of the reaction product 9 indicated the absence of an aminomethyl substituent at position 1 of the heterocycle. The mass spectrum of compound 9 contained a peak of the cation with a mass of 261. The 1H and 13C NMR spectra of compound 9 completely coincided with those described earlier [25–27]. The reactions of isatins 3 and 4 with reagent 5 furnished 2-(piperazin-1-yl)pyrimidine and ciprofloxacin, respectively. 1-Acylisatins
Scheme 1.
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BOGDANOV et al. Scheme 2.
Scheme 3.
6–8 reacted with reagent
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