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A series of N-heterocyclic analogs of muricadienin, a precursor of various acetogenins, were synthesized, and their biological activity was studied. It was revealed that the linking group between the N-methylpyrazole/imidazole part and the hydrophobic alkadienyl chain affects the ability of these compounds to induce apoptosis and cause cell cycle arrest. Compound 3b showed the highest cytotoxic activity. [ABSTRACT FROM AUTHOR]

The stereoselective synthesis of (5Z,9Z)-tetradeca-5,9-diene-1,14-dioic acid was carried out using Ti-catalyzed homo-cyclomagnesiation of 2-(hepta-5,6-dien-1-yloxy)tetrahydro-2H-pyran. Intermolecular esterification of this dicarboxylic acid with polyether acetylenic alcohols in the presence of carbodiimides was used to synthesize the corresponding monoesters and symmetric diesters. Using the intramolecular oxidative coupling of terminal triple bonds of the latter compounds, polyether macrodiolides containing 1Z,5Z-diene and 1,3-diyne fragments were synthesized. [ABSTRACT FROM AUTHOR]

New symmetric aryl-substituted derivatives of acetogenins were synthesized using the Ti-catalyzed homo-cyclomagnesiation of aryl-substituted 1,2-dienes at the key step. Ruthenium catalyzed oxidative cyclization of symmetric aryl-substituted 1Z,5Z-dienes was used to synthesize diols and ketols containing a tetrahydrofuran fragment. Diastereoselective reduction of ketols with L-selectride yielded target diols. In addition, by oxidation of ketols with Dess—Martin periodinane, diketones were synthesized in high yields. [ABSTRACT FROM AUTHOR]

The stereoselective synthesis of (5Z,9Z)-tetradeca-5,9-diene-1,14-diol was carried out by the catalytic homo-cyclomagnesiation of oxygen-containing 1,2-diene. Selective syntheses of macrocyclic and linear compounds containing pharmacophoric 1Z,5Z-diene and alkynylcarbinol fragments were carried out after the transformation of (5Z,9Z)-tetradeca-5,9-diene-1,14-diol into the corresponding dialdehyde. [ABSTRACT FROM AUTHOR]

Based on (5Z,9Z)-tetradeca-5,9-diene-1,14-dioic acid, previously undescribed polyether aromatic macrodiolides were synthesized in good yields (53–67%). The cytotoxicity of the resulting macrocyclic compounds in vitro against tumor Jurkat cells, K562 cells, conditionally normal Hek293 cell lines and normal fibroblasts was the assessment carried out. The ability of the most active macrodiolide to induce apoptosis toward Jurkat cells and influence the cell cycle was studied. [ABSTRACT FROM AUTHOR]

An efficient method has been developed for the synthesis of 2,5-dialkyl-substituted tetrahydrofurans, analogues of natural acetogenins. A series of tetrahydrofurans of this type have been obtained using the Ti-catalyzed homo-cyclomagnesiation of terminal 1,2-dienes at the key stage. By Ru-catalyzed oxidation of symmetrical nZ,(n+4)Z—dienes, ketols containing a tetrahydrofuran fragment were synthesized. Diastereoselective reduction of the carbonyl group of these ketols with L-selectride leads to diols, whereas oxidation of their hydroxyl groups with the Dess—Martin periodinane results in the formation of previously unreported diketones in quantitative yields. [ABSTRACT FROM AUTHOR]

Based on (5Z,9Z)-tetradeca-5,9-diene-1,14-dioic acid, previously undescribed polyether aromatic macrodiolides were synthesized in good yields (53–67%). The cytotoxicity of the resulting macrocyclic compounds in vitro against tumor Jurkat cells, K562 cells, conditionally normal Hek293 cell lines and normal fibroblasts was the assessment carried out. The ability of the most active macrodiolide to induce apoptosis toward Jurkat cells and influence the cell cycle was studied.

Stereoselective synthesis of (7Z,11Z)-octadeca-7,11-diene-1,18-dioic acid was carried out using a homo-cyclomagnesiation reaction of 2-(nona-7,8-dien-1-yloxy)tetrahydro-2H-pyran. After Steglisch esterification of the synthesized acid and polyester acetylenes in the presence of DCC and DMAP, the corresponding diesters were synthesized in good yields (67–75%). Based on symmetric diesters with terminal triple bonds, polyether macrodiolides containing conjugated triple bonds and pharmacophoric cis,cis-1,5-diene fragments in their structure were synthesized for the first time.

Stereoselective synthesis of (7Z,11Z)-octadeca-7,11-diene-1,18-dioic acid was carried out using a homo-cyclomagnesiation reaction of 2-(nona-7,8-dien-1-yloxy)tetrahydro-2H-pyran. After Steglisch esterification of the synthesized acid and polyester acetylenes in the presence of DCC and DMAP, the corresponding diesters were synthesized in good yields (67–75%). Based on symmetric diesters with terminal triple bonds, polyether macrodiolides containing conjugated triple bonds and pharmacophoric cis,cis-1,5-diene fragments in their structure were synthesized for the first time. [ABSTRACT FROM AUTHOR]