A heterocyclic quinone was used in the Nenitzescu reaction for the first time. New tricyclic compounds - pyrrolo[3,2-e]- and furo[3,2-e]indazoles - were synthesized by the condensation of 1,3-diphenyl-4,7-dioxoindazole with various enamines.

3-p-Nitrophenylaminobenzofuran was obtained by the reaction of 2,3-dihydrobenzofuran-3-one with p-nitroaniline and was used in the Vilsmeier reaction for the synthesis of 2-formyl-3-p-nitrophenylaminobenzofuran. Treatment of the latter with malononitrile led to 1-p-nitrophenyl-2-imino-3-cyano-1,2-dihydropyrido[3,2-b]benzofuran.

3-Ethylhexahydropyrazino[3,2,1-jk]carbazole is converted into hexahydro[1,4]diazocino[7,8,1-jk]carbazoles by the action of methyl propiolate and acetylacetylene in acetonitrile and into 1-methoxy9-(β-vinylethylamino)ethylcarbazoles by the action of acetylenedicarboxylic ester and methyl propiolate in methanol. 3-Benzyl-substituted pyrazinocarbazole does not react with alkynes.

The present review covers general aspects related to the metabolism of organic compounds, primarily, of biologically active azaheterocycles used as drugs. Compounds of this type occupy a dominant place among known drugs. Data on the main chemical processes determining the pathways of principal biotransformations, such as redox reactions, hydrolysis, alkylation, acylation, various conjugations, isomerizations, and condensations, are summarized. The metabolisms of heterocycles is considered based on the ring size of the substrate.

ChemInformVolume 42, Issue 11 Heterocyclic Compounds ChemInform Abstract: Novel Pyrano[3,2-b]indole Derivatives: Synthesis and Some Properties. N. S. Masterova, N. S. Masterova Antibiot. State Sci. Cent., Moscow 117003, RussiaSearch for more papers by this authorS. Yu. Ryabova, S. Yu. Ryabova Antibiot. State Sci. Cent., Moscow 117003, RussiaSearch for more papers by this authorL. M. Alekseeva, L. M. Alekseeva Antibiot. State Sci. Cent., Moscow 117003, RussiaSearch for more papers by this authorM. I. Evstratova, M. I. Evstratova Antibiot. State Sci. Cent., Moscow 117003, RussiaSearch for more papers by this authorS. S. Kiselev, S. S. Kiselev Antibiot. State Sci. Cent., Moscow 117003, RussiaSearch for more papers by this authorV. G. Granik, V. G. Granik Antibiot. State Sci. Cent., Moscow 117003, RussiaSearch for more papers by this author N. S. Masterova, N. S. Masterova Antibiot. State Sci. Cent., Moscow 117003, RussiaSearch for more papers by this authorS. Yu. Ryabova, S. Yu. Ryabova Antibiot. State Sci. Cent., Moscow 117003, RussiaSearch for more papers by this authorL. M. Alekseeva, L. M. Alekseeva Antibiot. State Sci. Cent., Moscow 117003, RussiaSearch for more papers by this authorM. I. Evstratova, M. I. Evstratova Antibiot. State Sci. Cent., Moscow 117003, RussiaSearch for more papers by this authorS. S. Kiselev, S. S. Kiselev Antibiot. State Sci. Cent., Moscow 117003, RussiaSearch for more papers by this authorV. G. Granik, V. G. Granik Antibiot. State Sci. Cent., Moscow 117003, RussiaSearch for more papers by this author First published: 17 February 2011 https://doi.org/10.1002/chin.201111155Read the full textAboutPDF ToolsRequest permissionExport citationAdd to favoritesTrack citation ShareShare Give accessShare full text accessShare full-text accessPlease review our Terms and Conditions of Use and check box below to share full-text version of article.I have read and accept the Wiley Online Library Terms and Conditions of UseShareable LinkUse the link below to share a full-text version of this article with your friends and colleagues. Learn more.Copy URL Share a linkShare onFacebookTwitterLinkedInRedditWechat No abstract is available for this article. Volume42, Issue11March 15, 2011 RelatedInformation

The published data on nitrogen (II) oxide donors related to C-nitro compounds are generalized and described systematically. The key classes of these compounds and the possible mechanisms of their transformations under hydrolytic conditions and in living organisms are considered. The attention is focused on C-nitro compounds as potential medicinal agents for treating abroad range of diseases (cardiovascular diseases,tuberculosis,cancer, etc.). The bibliography includes 106 references.

Published data on the chemical and biological properties of α-, γ-, and δ-carbolines are reviewed.

The reactions of 2-dicyanomethylidene-3-ethoxymethylidene-2,3-dihydroindole with hydrazine hydrate and phenylhydrazine afforded 2,3-diamino-4-cyanopyrido[4,3- b ]indole and 3-amino-2-anilino-4-cyanopyrido[4,3- b ]indole, respectively, and the reactions of the latter compounds with dimethylformamide diethyl acetal were studied. The reactions of 2,3-diamino-4-cyanopyrido[4,3- b ]indole with benzaldehyde, ethyl acetoacetate, and acetylacetone were investigated. First representatives of new heterocyclic systems, viz ., [1,2,4]triazolo[1’,5’:1,6]-pyrido[4,3- b ]indole and pyrazolo[1’,5’:1,2]pyrido[4,3- b ]indole, were synthesized. The structure of ethyl 6-cyano-5-[( E )-(dimethylamino)methylideneamino]-2-methyl-7 H -pyrazolo-[1’,5’:1,2]pyrido[4,3- b ]indole-1-carboxylate was established by X-ray diffraction.

Amidinohydrazones were prepared by the condensation of 4-arylamino-2-oxo-5-formyl-1,2-dihydropyridine-3-carbonitriles and 4-arylamino-2-oxo-1,2-dihydropyridine-3-carbaldehydes with aminoguanidinium carbonate with the purpose to investigate their biological activity as putative NO donors. The reaction of 5- и 3-formylpyridones with diguanidinium carbonate was studied. The formation of stable complexes of 4-arylamino-5-formyl-2-oxo-1,2-dihydropyridine-3-carbonitriles with aminoguanidine and guanidine was discovered. Amidinohydrazones obtained possess antiinflammatory, antidiabetic, and antihypertensive activities.

Reactions of salts of 1,3,5-triazine dinitromethyl derivatives with nitrogen dioxide that result mainly in 1,3,5-triazinenitrolic acids are investigated. The behavior of nitrolic acid in electroreduction at a mercury drop electrode at various pH was studied; oxygen was shown to accelerate the process. The promoting effect of nitrolic acids on the activity of soluble guanylate cyclase of human platelets was shown. The studied nitrolic acids are active donors of nitric oxide, a universal and important regulator of cell metabolism functions. NO-releasing properties of furoxans are investigated.

Acid treatment of β-(3-acetoxyindol-2-yl)-α-cyanoacrylic acid derivatives (ethyl ester and nitrile) with aqueous or gaseous HCl afforded novel 3-substituted 2-oxo-2,5-dihydropyra-no[3,2- b ]indoles. 2-Oxo-2,5-dihydropyrano[3,2- b ]indole-3-carbonitrile was converted into ethyl 2-oxo-2,5-dihydropyrano[3,2- b ]indole-3-carboximidate.

New 1-aryl-6-[2-(dimethylamino)vinyl]4-oxo-1,4-dihydropyrimidine-5-carbonitriles and 4-arylamino-2-oxo-1,2-dihydropyridine-3-carbonitriles containing electron-withdrawing substituents in the benzene ring were synthesized from enamino amides and dimethylformamide dialkylacetals. The influence of various dimethylformamide acetals on the yield of 3-(4-chloro-anilino)-2-cyano-5-(dimethylamino)penta-2,4-dienoic acid N-(dimethylamino)methyl-ideneamide was investigated in the reaction of these acetals with 3-(4-chloroanilino)-2-cyanocrotonamide. New 4-arylamino-5-formyl-2-oxo-1,2-dihydropyridine-3-carbonitriles and 4-arylamino-2-oxo-1,2-dihydropyridine-3-carbaldehydes containing electron-withdrawing substituents in the benzene ring were synthesized. The latter compounds were converted into new substituted l,6-naphthyridinones by the action of various CH acids. A new approach to the synthesis of 4-(4-fluoroanilino)-5-formyl-2-oxo-1,2-dihydropyridine-3-carbonitrile using dimethylformamide diisopropylacetal under mild conditions was developed. The comparative reactivity of the formyl group in the reactions of 4-arylamino-5-formyl-2-oxo-1,2-dihydropyridine-3-carbonitriles and in 4-arylamino-2-oxo-1,2-dihydropyridine-3-carb-aldehydes with malononitrile was determined using HPLC.

Reactions of 3-acetoxy-2-(2,2-dicyanovinyl)indole with hydrazine hydrate and methyl-and phenylhydrazines afforded new indolin-3-one derivatives, namely, 2-[(3,5-diaminopyrazol-4-yl)methylidene]indolin-3-ones. Reactions of the compounds obtained with acetic anhydride and DMF and DMAA dimethyl acetals were studied. Cyclization of 2-[(3,5-diamino-1H-pyrazol4-yl)methyridene]-1,2-dihydro-3 H-indolinone gave 3-amino-1,5-dihydropyrazolo-[4’,3’:5,6]pyrido[3,2-b]indole, a representative of a novel heterocyclic system.

New 2-oxo-4-arylamino-5-formyl-3-cyano-1,2-dihydropyridines and 2-oxo-4-arylamino3-formyl-1,2-dihydropyridines containing electron-acceptor substituents in the phenyl ring were synthesized, the interaction of these formylpyridones with different CH-acids to produce new substituted 1,6-naphthyridinones was carried out 3-Nitro-2-oxo-l-aryl-5-chloro-l,2-dihydro-l,6naphthyridines were synthesized, its' interaction with morpholine and 4-aminopyridine was investigated. The ratio of reactivity of formyl group in 2-oxo-4-arylamino-5-formyl-3-cyano-l,2dihydropyridines and in 2-oxo-4-arylamino-3-formyl-1,2-dihydropyridines in the reaction with malononitrile was determined using HPLC.