Z. I. Zhilina

1, 4-benzdiazepines, their cyclic homologs and analogs: XVI. Synthesis, properties, and pharmacological activity of 3-substituted 1,2-dihydro-3H-1,4-benzdiazepin-2-ones

Ear l i e r we investigated the connection between s t ruc ture and proper t ies of 1 ,2-dihydro-3H-1,4-benzdiazepin-2-ones and-2-thiones, substituted in positions 1, 5, and 7 [1-4 ]. Striving to obtain information on the effect of substituents in the 3 -m position of 1 ,2-dihydro-3H-1,4-benzdiazepine sys t em (A) on proper t ies of compounds of the given se r ies , we synthesized 3-a lkyl , 3-hydroxy, 3 -acy loxyl , 2 -d ihydro -3H-1 ,4benz diazepin-2-ones (I, II, III) and 3 ,7-d ich loro-5-phenyl l ,2 -d ihydro-3H-1 ,4-benzdiazepin-2-one hydrochloride (IV), and also studied cer ta in proper t ies of the obtained mater ia ls , for example, their pharmacological activity.

Induction of cytochrome p-450 by tetraphenylporphyrin-Sn4+

The intensive study of inducers of microsomal mono-oxygenases (MOG) is linked with prospects for creating substances on their basis which will stimulate detoxication processes and protect the internal medium of the organism against xenobiotics of varied nature. Effective inducers of MOG (as well as inhibitors) can also be used to control, at the molecular level, processes of adaptation and compensation of disturbed functions arising during the action of chemicals on the body [6]. This paper gives data obtained in a study of a representative of a new class of MOG inducers, mainly porphyrins and their metallocomp!exes.

Chemical transformations and evaluation of the basicities of 4,5-dihydropyrrolo[1,2,3-e,f][1,5]benzodiazepin-6(7h)-ones

The alkaline hydrolysis, amidation, and methylation of 4,5-dihydropyrrolo[1,2,3-e,f][1,5]benzodiazepin-6(7H)-one derivatives under various conditions were investigated. The ionization constants (pKα) for 1,2-dimethyl-4,5-dihydro[1,2,3-e,f][1,5]benzodiazepin-6(7H)-one were calculated by the Hammett indicator method, and two values, viz., pKα1 = −2.37 and pKα2= 5.53, which were ascribed to protonation of the diazepine ring and the indole ring of the molecule, respectively, were obtained.

4,5-dihydro-6h-pyrrolo[1,2,3-d,e]quinoxalin-5-ones

The synthesis of 1-R1-2-R2-8-R3-4,5-dihydro-6H-pyrrolo[1,2,3-d,e]quinoxalin-5-one derivatives (where R1 = CH3, C2H5; R2 = CH3, COOC2H5; R3 = H, CH3, C2H5O, Cl, Br) is described. The physicochemical properties of these derivatives were also studied.

1,4-Benzodiazepines, their cyclic homologs and analogs. XXVIII. 1,2-Dihydro-3h-1,4-benzodiazepin-2-ones with heterocyclic substituents in position 3

In recent years, polynuclear heterocyclic compounds based on 1,4-benzodiazepines have been prepared, which have a high activity towards the central nervous system (CNS) [2-7]. During studies on the connection between the structure and the pharmacological properties of 1,4-benzodiazepines, we synthesized derivatives of this class of types I-III. Compounds I were prepared by condensing 5-substituted 2-aminobenzophenones with tryptophan ethyl ester hydrochloride (method i) of the acid chloride of tryptophan (method 2) (Table I). Table i shows that compounds I are obtained in higher yields by the second method than by the first.

Mass spectra of 3-arylidene-1H-2,3-dihydro-1,4-benzodiazepin-2-ones

The scheme of the fragmentation of arylidene derivatives of 5-phenyl-1,4-benzodiazepin-2-ones was established by means of high-resolution mass spectrometry. One of the principal fragmentation pathways of these compounds is cleavage of the 2C-3C and 4N-5C bonds to give two fragments. Depending on the substituents in the arylidene portion of the molecule, the charge is localized primarily on one or the other of these fragments. The mechanism of the formation of the [ArCH2]+ ions observed in the mass spectra of all of the investigated compounds was established on the basis of the mass spectrum of the 1N-deuterium-labeled compound. The specific fragmentation pathways due to the ortho effect of the nitro group are discussed.