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Lantsetti, N. A.; Ryabova, S. Yu.; Алексеева, Л. М.; Shashkov, Alexander S.; Граник, В. Г.

doi:10.1023/a:1015520621450

Cited by 6 publications

(8 citation statements)

References 2 publications

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“…Another interesting d-carboline synthesis was developed based on 3-(N¢-phenyl-N¢-w-chloroacetyl)amino-2-formylindole (173) [173]. Reaction of 173 and pyridine formed an intermediate pyridinium salt (174) in which the methylene had highly acidic CH bonds.…”

Section: Scheme 53mentioning

confidence: 99%

Carbolines. Part I: Comparison of some methods for the synthesis of α-, γ-, and δ-carbolines (a review)

Smirnova¹,

Golovko²,

Граник³

2011

Pharm Chem J

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The main trends in the development of the chemistry of a-, g-, and d-carbolines are generalized. Syntheses of carbolines based on pyridine derivatives (including the Fischer synthesis, Graebe-Ullmann reaction, thermal decomposition of azides, photochemical cyclization of anilinopyridines, arylation of substituted pyridines and piperidones, etc.) and based on indole derivatives are described. Published data about the biological activity of compounds belonging to these series are summarized.Four classes of pyridoindoles, i.e., carbolines (1 -4), are known. Of these, b-carbolines (2) have been studied most completely. Numerous studies, including several reviews [1 -3], have addressed the synthesis and various properties of this class of compounds. The properties of the other carbolines have been studied in less detail, e.g., their syntheses and chemical and physicochemical properties have not yet been discussed and compared in the literature.A detailed comparison seems especially important because precisely such an analysis can expose the basic features that make these classes chemically and biologically significant. This is especially important during research directed at the discovery of new biologically active compounds. Because the large volume of literature dedicated to b-carbolines makes it practically impossible to discuss it in a single review, the present review is limited to a comparison of the other carbolines only, the syntheses of which have been discussed much less in the literature. We intend to discuss the main trends in the development of the chemistry of a-, g-, and d-carbolines without pretending to include all literature in its entirety in order to compare the potential of finding novel effective drugs in these series. We discuss first reviews dedicated to pyridoindoles [2 -5], including a rather recent review of g-carbolines [6]. Then we switch to chemical approaches to the synthesis of selected carboline derivatives, noting briefly publications on their biological properties.Pyridoindoles (carbolines), including pyrido[4,3-b]indoles (g-carbolines), some of which exhibit a broad spectrum of biological activity, are definitely interesting. Drugs of this class already exist, e.g., neuroleptic carbidine 5 (Carbidinum or Stobadine) and dimebon antihistamine drugs 6 (Dimebonum) and diazoline 7 (Diazolinum or Omeril) [7,8]. Furthermore, dimebon exhibited pronounced anti-NMDA (N-methyl-D-asparate, ED 50 = 42 mg/kg i.p.) and anticalcium activity (blocks calcium channels, IC 50 = 57 mM) and inhibited acetylcholinesterase (ACE) and butyrylcholinesterase (BuCE) (IC 50 = 42 and 7.9 mM, respectively) in in vitro tests. It also had pronounced cognitive-stimulant properties in in vivo tests for a neurotoxic 654 0091-150X/11/4412-0654

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Section: Scheme 53mentioning

confidence: 99%

Carbolines. Part I: Comparison of some methods for the synthesis of α-, γ-, and δ-carbolines (a review)

Smirnova¹,

Golovko²,

Граник³

2011

Pharm Chem J

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“…1 H NMR, δ: 6.00 (d, 1 H, H(9), J = 8.2 Hz); 6.83 (t, 1 H, H (8), J = 8.2 Hz); 7.32 (t, 1 H, H(7)); 7.00, 8.34 (A 2 B 2 system, 4 H, H(2´), H(6´), H(3´), H(5´)); 7.50, 7.75 (both m, 3 H each, H (6) and H(2´), H(6´), H(3´)-H(5´)); 8.50 (s, 1 H, H(4)); 8.60 (br.s, 2 H, NH 2 ); 12.1 (br.s, 1 H, N(5)H). 1 H NMR, δ: 6.00 (d, 1 H, H(9), J = 8.2 Hz); 6.83 (t, 1 H, H (8), J = 8.2 Hz); 7.32 (t, 1 H, H(7)); 7.00, 8.34 (A 2 B 2 system, 4 H, H(2´), H(6´), H(3´), H(5´)); 7.50, 7.75 (both m, 3 H each, H (6) and H(2´), H(6´), H(3´)-H(5´)); 8.50 (s, 1 H, H(4)); 8.60 (br.s, 2 H, NH 2 ); 12.1 (br.s, 1 H, N(5)H).…”

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A new method for the synthesis of [1,4]diazepino[6,5-b]indole derivatives

et al. 2006

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Reactions of 3 [(N aryl N chloroacetyl)amino] 2 formylindoles with substituted anilines gave 1,4 diaryl 2 oxo 1,2,3,6 tetrahydro[1,4]diazepino[6,5 b]indol 4 ium chlorides and those with 4 aminopyridine yielded 4 amino 1 (1 aryl 2 oxo 2,5 dihydro 1H pyrido[3,2 b]indol 3 yl)pyridinium chlorides. Reduction of 1,2,3,6 tetrahydrodiazepinoindol 4 ium chlorides af forded the corresponding hexahydro derivatives. An alternative synthesis of 1 (4 nitrophenyl) 3 oxo 4 phenyl 1,2,3,4,5,6 hexahydro[1,4]diazepino[6,5 b]indole from 3 [N (4 nitro phenyl)amino] 2 [(phenylimino)methyl]indole was developed. The method involves the fol lowing sequence of transformations: reduction, chloroacetylation, and intramolecular alky lation.

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“…Recently, 1,2 we have developed a new approach to the synthesis of [1,4]diazepino [6,5 b]indole 4 oxides and studied their reduction with various agents, including formamidinesulfinic acid.…”

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“…Reduction of cyclic nitrones such as [1,4]diazepino [6,5 b]indole 4 oxides 1 with formamidinesulfinic acid (used for the first time for this purpose) afforded mixtures of tetra hydro (2) and hexahydro [1,4]diazepino [6,5 b]indoles (3) (Scheme 1). It was found that the para substituents R in the phenyl group bound to the N(1) atom noticeably af fect the reaction outcome, although they are very distant from the reactive site.…”

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On the reduction of 1-aryl-2-oxo-1,2,3,6-tetra-hydro[1,4]diazepino[6,5-b]indole 4-oxides

et al. 2004

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Electrochemical reduction of 1 aryl 2 oxo 1,2,3,6 tetrahydro[1,4]diazepino [6,5 b]indole 4 oxides, 2 oxo 1 phenyl 1,2,3,6 tetrahydro[1,4]diazepino [6,5 b]indole, and 2 oxo 1 phenyl 1,2,3,4,5,6 hexahydro[1,4]diazepino [6,5 b]indole was studied. The results obtained were com pared with previous data for the reduction of 4 oxides with formamidinesulfinic acid. Key words: [1,4]diazepino[6,5 b]indole 4 oxide, formamidinesulfinic acid, electrochemi cal reduction. Recently, 1,2 we have developed a new approach to the synthesis of [1,4]diazepino[6,5 b]indole 4 oxides and studied their reduction with various agents, including formamidinesulfinic acid.Both tetra and hexahydrodiazepinoindoles can be ob tained, depending on the reducing agent. Reduction of cyclic nitrones such as [1,4]diazepino[6,5 b]indole 4 oxides 1 with formamidinesulfinic acid (used for the first time for this purpose) afforded mixtures of tetra hydro (2) and hexahydro[1,4]diazepino[6,5 b]indoles (3) (Scheme 1). It was found that the para substituents R in the phenyl group bound to the N(1) atom noticeably af fect the reaction outcome, although they are very distant from the reactive site. It was demonstrated 1,2 that the reduction of the N(4)=C(5) bond is favored by electron withdrawing substituents but prevented by electron do nating ones. The significant role of the substituent was attributed to the known positive bridging effect 3,4 charac teristic of compounds with two aromatic fragments (here, benzene and indole) bridged by an O, S, or N atom (as in our case). Such aromatic fragments have the tendency toward efficient p-π conjugation. 3,4The reality of this effect in a system containing a 3 aryl aminoindole fragment was proved by our 1 H NMR study 5 of deuterium exchange in 1 acetyl 3 arylaminoindoles (4a,b). The deuterium exchange rate was higher for com pound 4b (R = 4 Cl): its 1 H NMR spectrum recorded in CD 3 COOD immediately upon the dissolution showed no sig nal for the indole C(2)H pro ton. The slower deuterium ex change in indole 4a than in 4b is probably due to the elec tron withdrawing effect of the NO 2 group, which weakens the electron donating effect of the exo NH fragment.Thus, the para substituent R in the phenyl group af fects the electron density at position 2 of the indole sys tem even in 3 arylaminoindoles and we do not find it surprising that this effect extends to the C=N bond at position 2 of the indole fragment in diazepinoindoles 1.The goal of the present work was to compare the re sults obtained by chemical (with formamidinesulfinic acid) and electrochemical reduction of diazepinoindoles 1.The redox properties of N oxides of aromatic hetero cycles, tertiary amines, and azomethine derivatives have been documented. 6,7 The effect of the nature of the sub stituent on the half wave potential (E 1/2 ) of the reduction Scheme 1 R = 4 NO 2 (a), Cl (b)

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Cited by 6 publications

References 2 publications

Carbolines. Part I: Comparison of some methods for the synthesis of α-, γ-, and δ-carbolines (a review)

Carbolines. Part I: Comparison of some methods for the synthesis of α-, γ-, and δ-carbolines (a review)

A new method for the synthesis of [1,4]diazepino[6,5-b]indole derivatives

On the reduction of 1-aryl-2-oxo-1,2,3,6-tetra-hydro[1,4]diazepino[6,5-b]indole 4-oxides

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