Synthesis and anticancer activity of benzotriazole derivatives

A series of benzotriazole (BTA) derivatives were synthesized as tyrosine protein kinase inhibitors using fragment-based design strategy. All desired compounds were synthesized with the reaction of benzotriazole, chloroacetonitrile and aromatic aldehyde using Ultrasonic-Microwave method and characterized by IR, ¹H and ¹³C-NMR, mass spectrometry (MS) and elemental analysis. The anticancer activity of these compounds was evaluated by CCK-8 method against carcinoma VX2, lung cancer A549, stomach cancer cell lines MKN45 and MGC in vitro. The results showed that all compounds showed good antiproliferative activity. In particular, compound 2.1 showed the most prominent inhibition of VX2 cell lines with IC₅₀ of 3.80 ± 0.75 μM. Compound 2.2 exhibited highly potent anticancer activity of stomach MGC cell lines with IC₅₀ of 3.72 ± 0.11 μM. A549 and MKN45 cell lines were sensitive to compound 2.5 with IC₅₀ of 5.47 ± 1.11 and 3.04 ± 0.02 μM, respectively.     

含苯并三唑色酮及1,3,4-噁二唑啉类化合物的合成

研究了一种简便的合成2位含氮杂环色酮类化合物的方法。1H-苯并三唑与ClCH~2COOH反应制得1H-苯并三唑-1-乙酸(1),以此为原料合成了一系列2位含1H-苯并三唑-1-甲基色酮(5)和相关的1,3,4-噁二唑衍生物(8)。     

Synthesis of substituted hydroxymethylene diphosphonic acids and their derivatives containing unsaturated fragments

Russian Journal of General Chemistry -     

Synthesis of actinomycin D analogs: XXIII. Actinocin derivatives containing azacrown fragments

A number of actinocin amides containing residues of aza-15-crown-5 and aza-18-crown-6 where crown fragments were separated from the heterocyclic chromophore by the residues of ω-amino acids were obtained as actinomycin D models.     

Synthesis and characterization of novel substituted and cyclic benzoquinone derivatives

Novel substituted benzoquinone compounds were synthesized from the reactions of p-chloranil and p-fluoranil with some thiols, amines, and diols in different reaction media. Interesting cyclic compounds like crown ether structures were obtained. The structures of all compounds were characterized by spectroscopic methods and microanalysis.     

Synthesis and properties of furan derivatives. 5. Synthesis of 2-substituted benzoxazoles containing furan fragments

The condensation of imidates and imidate hydrochlorides of furan acids with o-aminophenols gives furyl derivatives of 2-substituted benzoxazoles. Such compounds are also formed in the reaction of furan acids with o-aminophenol in the presence of boric acid.Communication 4, see [1].I. M. Gubkin State Petroleum and Gas Academy, 117917 Moscow. Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 7, pp. 896–901, July, 1996. Original article submitted April 16, 1996.     

Synthesis of novel hydropyrazolopyridine derivatives in solvent-free conditions via benzotriazole methodology

The reaction between 5-[N-(benzotriazol-1-ylmethyl)amino]-3-tert-butyl-1-phenylpyrazole or 5-amino-4-(benzotriazol-1-ylmethyl)-3-tert-butyl-1-phenylpyrazole with some unactivated and electron-rich alkenes has followed heterocyclization reactions to yield hydropyrazolopyridines, under solvent-free conditions, as predicted by benzotriazole methodology in contrast with those results obtained under solution. The reaction mechanism was proposed after fully spectroscopic analysis of final products and intermediates.     

Synthesis and properties of sym-triazine derivatives. 2. Synthesis of amino-sym-triazines containing fragments of sterically hindered phenol

The reaction of mono- and dichloro-sym-triazines with 4-hydroxy-3,5-di-tert-butyl-aniline was studied. N-substituted derivatives of 2,4,6-triamino-sym-triazine were synthesized, containing fragments of sterically hindered phenol.For article 1, see [1].Translated from Khimiya Geterotsiklicheskikh Soedinenii, No.12, pp. 1678–1682, December, 1984.     

Synthesis and properties of furan derivatives. 4. Synthesis of 2,5-disubstituted 1,3,4-oxadiazoles containing furan fragments

The condensation of hydrochloride sats of iminoesters of furan acids with hydrazides of carboxylic acids gives 2,5-disubstituted 1,3,4-oxadiazoles containing furan fragments. Such compounds are also formed in the condensation of hydrazides of 5-R-furan-2-carboxylic acids with hydrocloride salts of carboxylic acid iminoesters. The reaction of furan acids with hydrazine dihydrochloride in polyphosphoric acid gave symmetrically disubstituted 1,3,4-oxadiazoles containing furan fragments.Communication 3, see ref. [1].I. M. Gubkin State Petroleum and Natural Gas Institute, 117917, Moscow. Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 2, pp. 238–249, February, 1995. Original article submitted January 24, 1995.     

Synthesis of unsymmetrical hydroxybenzylphenols containing isobornyl fragments

4-(Bromomethyl)-2,6-diisobornylphenol was synthesized from 2,6-diisobornyl-4-methylphenol through intermediate 4-bromo-2,6-diisobornyl-4-methylcyclohexa-2,5-dien-1-one. Reactions of 4-(bromomethyl)-2,6-diisobornylphenol with 2,6- and 2,4-dialkylphenols gave new 4-(hydroxybenzyl)phenol derivatives containing bulky tert-butyl and isobornyl substituents.     

Synthesis and properties of symm-triazine derivatives. 4. Synthesis of 2,4,6-trisubstituted symm-triazines containing sterically-hindered phenol fragments

2,4,6-Trisubstituted symm-triazines containing sterically-hindered phenol fragments were synthesized by the cyclotrimerization of ethyl iminoesters. 2,4,6-Trimercapto-symm-triazine derivatives containing shielded phenol residues may be formed by the cyclotrimerization of the corresponding thiocyanates in acidic medium.For communication 3, see [1].Translated from Khimiya Geterosiklicheskikh Soedinenii, No. 1, pp. 107–113, January, 1986.     

Synthesis and absolute configurations of diastereomeric aziridine-2-carboxylic acid derivatives containing valine and hexafluorovaline fragments

Individual diastereomers of aziridine-2-carboxylic acid esters that contain R- and S-valine and R- and S-hexafluorovaline fragments were isolated by high-performance liquid chromatogrpahy (HPLC). The absolute configurations of both asymmetric centers of the diastereomeric esters were determined on the basis of the parameters of the PMR spectra (AB) and circular dichroism (the sign of the cotton effect at 200–220 nm).Communication 44 from the series Asymmetric unbridged nitrogen. See [1] for communication 43.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 10, pp. 1355–1358, October, 1985.     

Synthesis of isobornylphenols containing heterocyclic and benzylic fragments

The alkaloids salsolidine, salsoline and (R)-N-benzyl-l-phenylethylamine were added to 7-methyl-2-isobornylphenol using an aminomethylation reaction. Translated from Khimiya Prirodnykh Soedinenii, No. 4, pp. 367–368, July–August, 2008.     

Synthesis of derivatives of p-tert-butylcalix[4]arene containing on lower rim fragments of 2-aminoalkylbenzimidazoles

Reactions of calix[4]arene carboxymethoxy derivatives with 2-aminoalkylbenzimidazoles in the presence of dicyclohexylcarbodiimide and hydroxybenzotriazole afforded a series of p-tert-butylcalix[4]arene derivatives containing on the lower rim N-(2-benzimidazolylalkyl)carbamoylmethoxy fragments. The reaction carried out in the absence of hydroxybenzOtriazole resulted in macrocycles containing one N-(2-benzimidazolylalkyl)carbamoyl fragment and a fragment of N-(acyl)dicyclohexylisourea.