Derivatives of dihydropyrimido (4,5-b)-(1,4) benzthiazine and their pharmacological properties

Polezhaeva, A. I.; Roshchina, L. F.; Соколова, А. С.; Nemeryuk, M. P.; Pykhova, M. V.; Safonova, T. S.; Mashkovskii, M. D.

doi:10.1007/bf00760455

Cited by 2 publications

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“…Studies of the neuroleptic activity of the compounds were performed by A. I. Polezhaeva and L. F. Roshchina using measures characteristic of psychotropic agents using methods as described in [3]. …”

Section: Biological Methodsmentioning

confidence: 99%

Synthesis and properties of dipyrimido-[4,5-b][5,4-f]-1,4-thiazepine derivatives

Safonova¹,

Nemeryuk²,

Grineva³

et al. 2008

Pharm Chem J

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Derivatives of dipyrimido [4,5-b][5,4-f]-1,4-thiazepine were synthesized and some of their properties were studied.Continuing our reports on the search for biologically active substances among bi-and tricyclic 1,4-thiazine and 1,4-thiazepine systems [1, 4], we present here the synthesis of derivatives of the previously unknown heterocyclic dipyrimido [4,5-b][5,4-f]-1,4-thiazepine system.The interaction of 5-amino-6-mercaptopyrimidines I-V with 5-formyl-6-chloropyrimidine derivatives VI was studied. The primary products of the reaction of 4-dimethylamino-, 4-methylamino-, 4-methoxy-, and 4-methylthio-5amino-6-mercaptopyrimidines (I -IV) with 4-chloro-5-formyl-6-aminopyrimidine (VI) in methanol at 60 -65°C in the presence of an equimolar quantity of KOH were dipyrimidylsulfides VII -X.The IR spectra of compounds VII -X had absorption by an NH 2 group (3200 -3600 cm -1 ) and an aldehyde group (1680 cm -1 ), and the 1 H NMR spectrum showed signals from the CHO group with d 10.2 -10.3 ppm and from protons in the pyrimidine rings at C-2 and C-2¢ with d 7.77 -8.08 ppm, which is consistent with their structures. I, VII: R = N(CH 3 ) 2 ; II, VIII: R = HN(CH 3 ); III, IX: R = OCH 3 ; IV, X: R = SCH 3 ; V: R = NH 2

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Section: Biological Methodsmentioning

confidence: 99%

Synthesis and properties of dipyrimido-[4,5-b][5,4-f]-1,4-thiazepine derivatives

Safonova¹,

Nemeryuk²,

Grineva³

et al. 2008

Pharm Chem J

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“…In previous work [2,3], we described synthesis of derivatives of 1,4-thiazine tricyclic systems, which include substances with antitumor and psychotropic activity. In continuing these studies, we have developed a method for obtaining 4-alkoxy(amino)-8-nitro derivatives of pyrimido [4,5-b]-1,4-benzothiazepines 1a-d [1].…”

mentioning

confidence: 99%

Study of nitrogen- and sulfur-containing heterocycles. 54. Properties and conversions of pyrimido[4,5-b]-1,4-benzothiazepines. Synthesis of a novel heterocyclic system: Pyrimido[5,4-c]isoquinoline

Safonova

Nemeryuk

Grineva

et al. 2004

Chem Heterocycl Compd

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Keywords: pyrimidyl aryl sulfides, pyrimido[4,5-b]-1,4-benzothiazepine, pyrimido [5,4-c]isoquinoline.In previous work [2, 3], we described synthesis of derivatives of 1,4-thiazine tricyclic systems, which include substances with antitumor and psychotropic activity. In continuing these studies, we have developed a method for obtaining 4-alkoxy(amino)-8-nitro derivatives of pyrimido[4,5-b]-1,4-benzothiazepines 1a-d [1]. This work is devoted to study of the properties of compounds 1a-d and synthesis of novel derivatives of this heterocyclic system which are of interest for biological tests.In the first step of this work, we studied reduction of pyrimidobenzothiazepines 1a-c. We established that when these substances are treated with sodium borohydride in ethanol medium at 18-20°C, the dihydropyrimidobenzothiazepines 2a-c are smoothly formed. Their structure has been confirmed by the presence of absorption bands in the IR spectra of compounds 2a,b for the NH group in the 3280 cm -1 and 3380 cm -1 region respectively.For the example of compounds 1b and 2b, we established that their reduction by iron filings in acetic acid leads to 8-amino derivatives 2d and 2e. The compound 2e is also formed when pyrimidobenzothiazepine 2d is treated with sodium borohydride under the conditions for synthesis of derivatives 2a-c. Reactions of compound 2d with phenyl isocyanate and phenyl isothiocyanate yield derivatives 2f,g.

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Derivatives of dihydropyrimido (4,5-b)-(1,4) benzthiazine and their pharmacological properties

Cited by 2 publications

References 1 publication

Synthesis and properties of dipyrimido-[4,5-b][5,4-f]-1,4-thiazepine derivatives

Synthesis and properties of dipyrimido-[4,5-b][5,4-f]-1,4-thiazepine derivatives

Study of nitrogen- and sulfur-containing heterocycles. 54. Properties and conversions of pyrimido[4,5-b]-1,4-benzothiazepines. Synthesis of a novel heterocyclic system: Pyrimido[5,4-c]isoquinoline

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