Photophysical properties of new anthracene-ended calix[4]resorcinols

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Reactions of 4-acylresorcinol derivatives with 3,5-di-tert-butyl-4-hydroxybenzyl acetate

Reactions of hydroxyphenylcarbonyl derivatives with 3,5-di-tert-butyl-4-hydroxybenzyl acetate under mild conditions gave novel functionalized diarylmethanes. Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 7, pp. 1128–1133, July, 2006.     

Practical generation of 3,5‐dimethoxybenzyllithium: application to the synthesis of 5‐substituted‐resorcinols

Reductive lithiation of 3,5‐dimethoxybenzyl methyl ether was successfully performed with lithium wire and a catalytic amount of naphthalene in dry tetrahydrofuran at ?15°C, leading to the quantitative generation of 3,5‐dimethoxybenzyllithium. This organometallic compound, which can be stored for at least 24 h, was trapped with a variety of different electrophiles, including, besides aldehydes, non‐functionalized and functionalized alkyl halides and an epoxide. Accordingly, it is a useful intermediate in the synthesis of 5‐substituted natural and non‐natural resorcinols. Copyright © 2003 John Wiley & Sons, Ltd.     

Synthesis of calix[4]resorcinarenes,containing phosphoryl fragments at the lower rim of the molecule

Reaction of resorcinol with phosphorylated acetals or ethoxyvinylphosphonic acid esters in acidic media leads to calix[4]resorcinarenes, containing dialkoxyphosphoryl fragments at the lower rim of the molecule. When the alkyl substituent in alkoxy groups at phosphorus atom is not very long, a partial hydrolysis of the initially formed products takes place to give calixarenes with alkoxyhydroxyphosphoryl fragments. Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 6, pp. 1102–1106, June, 2007.     

Novel first-generation dendrimers on calix[4]resorcinol core equipped with multiple triazole units

Novel first-generation dendrimers on the calix[4]resorcinol core with four branches each containing multiple 1,2,3-triazole units have been synthesized in one-step by acid catalyzed condensation of resorcinols with a new aldehyde dendron, namely, 4-{3,5-bis[(1-benzyl-1H-1,2,3-triazol-4-yl)- methoxy]benzyloxy}benzaldehyde (obtained by alkyne–azide cycloaddition). The reaction proceeds stereoselectively to form rccc-diastereoisomers in high yields.     

Synthesis and properties of <Emphasis Type="Italic">N</Emphasis>-[2,2-bis(2,4-dihydroxyaryl)ethyl]-<Emphasis Type="Italic">N</Emphasis>-methylamines and their hydrohalides

Condensation of one molecule of α-methylaminoacetaldehyde dimethyl acetal with two molecules of resorcinol or methylresorcinol in hydrohalogen acid solutions led to substituted N-(2,2-diarylethyl)-N-methylamine hydrohalides. Reactions of the corresponding amines with acetic anhydride, mono-and diisocyanates, and formaldehyde were studied. Conditions for formation of calixarene from resorcinol and α-methylaminoacetaldehyde dimethyl acetal were invented. Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 2, pp. 319–324, February, 2007.     

Design,synthesis and antiproliferative activity against human cancer cell lines of novel benzo-, benzofuro-, azolo- and thieno-1,3-thiazinone resorcinol hybrids

In this paper we report the design and synthesis of novel derivatives of the 4H-3,1-benzothiazinone type and heterocyclic analogues, i.e. benzofuro-, azolo- and thieno-1,3-thiazin-4-ones possessing 2,4-dihydroxyphenyl substituent. The compounds were obtained by the one-step reaction of aminobenzamides or heterocyclic aminocarboxamides with aryl-modified sulfinylbis[(2,4-dihydroxyphenyl)methanethione]. Evaluation of their antiproliferative potency against human cancer cell lines showed that the activity of some analogues was similar to that of cisplatin. The highest activity and low toxicity were found for 6-tert-butyl-2-(5-chloro-2,4-dihydroxyphenyl)-4H-thieno[3,2-d][1,3]thiazin-4-one. The structure–activity elucidation reveals that the most active compounds are those with a thienothiazin-4-one and benzofuro[3,2-d][1,3]thiazin-4-one skeleton and the presence of the hydrophobic substituent (Et, Cl) in the benzenediol moiety increases their antiproliferative potency. The ADMET properties of selected compounds including metabolic stability and toxicity profile were estimated in silico.