Bisindoles. 7. Synthesis of di(5-indolyl) sulfone

The parent compound of a new heterocyclic system, viz., di(5-indolyl) sulfone, was synthesized by the classical scheme of the Fischer reaction by means of polyphosphoric acid. The starting dihydrazine was obtained from 4,4'-dichlorodiphenyl sulfone.See [1] for Communication 6.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 11, pp. 1508–1510, November, 1980.     

Bisindoles. 14. Electrophilic substitution reactions in the di(5-indolyl) oxide series

Chemistry of Heterocyclic Compounds - Some electrophilic substitution reactions in the di(5-indolyl) oxide series were studied. The Vilsmeier and Mannich reactions and diazo coupling and...     

Bisindoles. 26. Synthesis of 7,7-dichlorobis (5-indolyl) methane

7,7-Dichloro-2,2-dicarbethoxybis (5-indolyl) methane has been synthesized by cyclization of the 3,3-dichloro-4,4-diphenylmethanedihydrazone of ethyl pyruvate. Subsequent hydrolysis and decarboxylation of the corresponding diacid gave the unsubstituted 7,7-dichlorobis (5-indolyl) methane. The syn-syn, syn-anti, and anti-anti forms of 3,3-dichloro-4,4-diphenylmethanedihydrazone of ethyl pyruvate have been separated and characterized.For Communication 25, see [1].Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 8, pp. 1062–1065, August, 1988.     

Bisindoles. 15. Acidic condensation of bis(2-ethoxycarbonyl-5-indolyl) oxide and bis(2-ethoxycarbonyl-5-indolyl)methane with aromatic aldehydes

The acidic condensation of bis (2-ethoxycarbonyl-5-indolyl) oxide and bis(2-ethoxycarbonyl-5-indolyl)methane with aromatic aldehydes was studied. Bis(3-chloro) compounds with labile chlorine atoms, by nucleophilic substitution of which the corresponding dimethylamino, hydroxy, methoxy, acetoxy, cyano, and mercapto derivatives were obtained, were isolated.See [1] for communication 14.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 3, pp. 365–368, March, 1983.     

Synthesis of 5-(3-indolyl)oxazole natural products. Structure revision of Almazole D

The synthesis and utility of β-oxotryptamine and β-oxytryptophan ester synthons provide a convenient entry to 5-(3-indolyl)oxazole natural products leading to a structure revision of almazole D.     

Synthesis of new di-(3-indolyl)arenes

1,4-Di-(3-indolyl)benzene 6 and 2,8-di-(3-indolyl)dibenzofuran 12 were synthesized from 1,4-diacetylbenzene and 2,8-diacetyldibenzofuran, respectively, via indole synthetic strategies. Investigation into the acid-catalysed formation of macrocyclic systems from these di-(3-indolyl)arenes led to the development of the 18-membered macrocycle 14 from the diindolylbenzene 6, which was capable of undergoing complexation with nickel(II) ions.     

Synthesis and transformation of (N-substituted 2-methyl-5-methoxy-3-indolyl)succinic acids

The reaction of N-substituted 2-methyl-5-methoxyindoles with maleic anhydride gave the corresponding (2-methyl-5-methoxy-3-indolyl)succinic anhydrides, which were hydrolyzed to acids and converted to monoamides by reaction with primary or secondary amines.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 11, pp. 1525–1527, November, 1972.     

Indole derivatives CXV. Synthesis and some transformations of 5-(3-indolyl)isoxazole-3-carboxylic acid

5-(3-Indolyl)isoxazole-3-carboxylic acid and its amide and hydrazide were obtained from ethyl 5-(3-indolyl)isoxazole-3-carboxylate. When 5-(3-indolyl)isoxazole-3-carboxylate is heated, it undergoes decarboxylation with isomerization to 3-(-cyanoacetyl)indole; when it is heated in alcohol with hydrazine and phenylhydrazine in the presence of copper, it undergoes isomerization to 5-(3-indolyl)pyrazole-3-carboxylic and 1-phenyl-5-(3-indolyl)-pyrazole-3-carboxylic acids. 5-(3-Indolyl)pyrazole-3-carboxylic acid hydrazide is formed when a solution of ethyl 5-(3-indolyl)isoxazole-3-carboxylate is refluxed with hydrazine in 96% alcohol.See [1] for communication CXIV.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 7, pp. 936–938, July, 1978.     

Bisindoles 27. Electrophilic substitution reactions of 7,7-dichlorobis(5-indolyl)methanes

Formylation, aminomethylation and acetylation have been studied as the most characteristic electrophilic substitution reactions of 7,7-dichlorobis(5-indolyl)-methane and its diethyl ester.For Communication 26 see [1].Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 10, pp. 1363–1366, October, 1989.     

Synthesis of di(adamantylalkyl) tosyloxymethylphosphonates and di(adamantyloxyalkyl) tosyloxymethylphosphonates

A simple method for the synthesis of esters of tosyloxymethylphosphonic acid based on the adamantane series of alcohols and diethyl tosyloxymethyl phosphonate was developed. The di(adamantylalkyl) and di(adamantyloxyalkyl) tosyloxymethylphosphonates are of interest as key compounds in the synthesis of antiviral drugs of the nucleoside phosphonate class.     

Indole derivatives C. Synthesis of ω-(3-indolyl)alkyl bromides

-(3-Indolyl)alkyl bromides, the structure of which was confirmed by alternative synthesis from-(3-indolyl)alkanols, were obtained by a modified Borodin-Hunsdiecker reaction from mercury salts of-(3-indolyl)alkanoie acids.See [1] for communication XCIX.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 11, pp. 1493–1495, November, 1974.     

Cytotoxic di(8-quinolyl) disulfides

It has been shown that the nature of the substituent and its position in the quinoline ring markedly affects the antitumor activity and toxicity of di(8-quinolyl) disulfides. The greatest cytotoxicity in the series of methyl derivatives was shown by the 7-, 6-, and 3-isomers towards HT-1080 (human fibrosarcoma) and MG-22A (mouse hepatoma) tumor cells while the 2-methyl derivatives generally have no effect on these cells. High cytotoxicity was also shown (LC₅₀ <1 μg/ml) by other 7-substituted compounds (Cl, PhO, PhS) but they also appear to be highly toxic towards normal NIH 3Y3 mouse embryonic fibroblasts. A similar trend was observed in the series of 5-substituted compounds (NH₂, Cl, OMe, NO₂) which were highly active towards tumor cells but were toxic to normal cells. The best selectivity was found for the 6-substituted quinolines, the 6-methoxy derivative at low concentration brought about the death of tumor cells but appeared much less toxic towards normal fibroblasts (LC₅₀ 100 μg/ml with a corresponding LD₅₀ of 874 mg/kg ). __________ Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 5, pp. 750–754, May 2007.     

Synthesis and characterization of beta-cyclodextrin inclusion complex containing di(8-hydroxyquinoline) magnesium

The beta-cyclodextrin (beta-CD) inclusion complex containing di(8-hydroxyquinoline)magnesium was prepared. The product was characterized by NMR, IR, differential thermal thermogravimetric analysis (DT-TGA), spectrofluorimetry, and elemental analysis, indicating the formation of inclusion complex in which the quinoline rings of the guest were encapsulated within the beta-CD cavities. The Job's method provided 2:1 stoichiometry for the inclusion complex between beta-CD and di(8-hydroxyquinoline)magnesium. The association constant calculated with the modified Benesi-Hildebrand equation at 25 degrees C was determined. And the mean association constant was 3577 (L/mol)2, R.S.D. was 2.58%. The thermal stability and solubility of di(8-hydroxyquinoline)magnesium were improved when forming inclusion complex.     

Synthesis and Cytotoxicity of Derivatives of Di(3-indolyl) Selenide

A method has been developed for the synthesis of di(3-indolyl) selenides. From indole and SeO₂. N-Alkyl derivatives of di(3-indolyl) selenide have been obtained in the two-phase system alkyl halide–solid K₂CO₃ (or KOH)–18-crown-6–toluene. It was discovered that N-unsubstituted di(3-indolyl) selenides possess high cytotoxicity on HT-1080 and MG-22A tumor cell lines.     

Synthesis of di(polyfluoroalkyl) ethers

New procedures for preparing di(polyfluoroalkyl) ethers by reactions of polyfluoropropyl chlorosulfonites with polyfluorinated alcohols were tested.Translated from Zhurnal Prikladnoi Khimii, Vol. 77, No. 9, 2004, pp. 1573–1574.Original Russian Text Copyright © 2004 by Rakhimov, Nalesnaya, Vostrikova.     

Synthesis of macrocyclic systems derived from di-(2-indolyl)heteroarenes

A number of new 3,6-di-(2-indolyl)-dibenzofuran and carbazole derivatives have been prepared from dibenzofuran and carbazole linkers via the Fischer indole synthesis. The bis-indoles were successfully formylated at C3 and the resulting dicarbaldehydes were combined with diamines to generate indole based imine macrocyclic systems.     

Aroylnitrile oxide cyclizations. 2. Synthesis of (3-aroylisoxazol-5-yl)alkanoic acids

Intermolecular cyclization of 1,3-dipolar aroylnitrile oxides to terminal alkynols followed by phase transfer catalyzed oxidation provided a short, convenient route to several novel (3-aroylisoxazol-5-yl)alkanoic acids.     

Synthesis and physical properties of N-2-phenylethyl- and N-2-(3-indolyl)ethyl-5′-deoxy-5′-adenosineacetamides

The synthesis and physical properties of N-2-phenylethyl- and N-2-(3-indolyl)ethyl-5′-deoxy-5′-adenosineacetamides ( 2 and 3 ), which are stable compounds of phenylalanyl- and tryptophanyl-AMPs, are described.