Synthesis of 1-Hydroxy(and 1-Alkoxy, 1-Acyloxy)-1H-indoles and evaluations of their suppressive activities against tumor growth through inhibiting lactate dehydrogenase A.

Inhibition of lactate dehydrogenase (LDH) has emerged as a promising cancer therapy strategy due to its essential role in the metabolic transformation of cancer cells. In this study, 53 derivatives of 1-hydroxy(and 1-alkoxy, 1-acyloxy)indoles were designed, synthesized, and biologically evaluated. Several multi-substituted 1-hydroxy(and 1-alkoxy, 1-acyloxy)indole compounds exhibited inhibitory activity against the LDH-A isoform (LDHA).

An Efficient Method for the Selective Syntheses of Sodium Telluride and Symmetrical Diorganyl Tellurides and the Investigation of Reaction Pathways.

Studies on organotellurium compounds have not been extensively conducted due to a lack of tolerable synthetic methods, difficult isolation processes, and their chemical instabilities. Overcoming these hurdles, we developed an efficient and mild method for the selective synthesis of symmetrical diorganyl tellurides , a representative class of organotellurium compounds, using a proper reducing reagent. The reaction condition was optimized for the selective formation of by forming the telluride dianion (Te) using a reducing reagent, sodium borohydride (NaBH), and then followed by the addition of organyl halides.

Studies on the selective synthesis of diorganyl diselenides using potassium hydroxide and mechanistic investigations of the reaction pathway.

Methods of selectively synthesizing diorganyl diselenides (R-Se-Se-R) without using harmful reducing agents are presented. We optimized the reaction conditions for the selective formation of the diselenide dianion (Se) and the corresponding diorganyl diselenides using basic reagents (, KOH), while suppressing the formation of side products, such as diorganyl selenides (R-Se-R) or multiselenides (R-Se-R; ≥ 3). Furthermore, we have suggested and examined the reaction pathways responsible for the formation of the desired diorganyl diselenides 1 and side products 2 and 3.

Studies on the Selective Syntheses of Sodium Ditelluride and Dialkyl Ditellurides.

Studies on the selective synthetic method for dialkyl ditellurides , a representative class of organyl tellurium compounds, were presented. Considering the difficulty in conducting previous harsh reactions and in suppressing the formation of dialkyl tellurides as side products, we optimized reaction conditions for selective syntheses of sodium ditelluride and the corresponding dialkyl ditellurides . We reduced tellurium to sodium ditelluride by using NaBH and subsequently, treated the obtained sodium ditelluride with alkyl halides (RX) to give the target compounds .

Syntheses of New Multisubstituted 1-Acyloxyindole Compounds.

The syntheses of novel 1-acyloxyindole compounds and the investigations on reaction pathways are presented. Nitro ketoester substrate , obtained in a two-step synthetic process, underwent reduction, intramolecular addition, nucleophilic 1,5-addition, and acylation to afford 1-acyloxyindoles in one pot. Based on the systematic studies, we established the optimized reaction conditions for focusing on the final acylation step of the intermediate 1-hydroxyindole .

An Efficient Method for Selective Syntheses of Sodium Selenide and Dialkyl Selenides.

The studies on the selective synthesis of dialkyl selenide compounds were presented. Overcoming the complexity and difficulty of selenides (R-Se-R) and/or multiselenides (R-Se-R; ≥ 2), we aimed to optimize the reaction condition for the tolerable preparation of sodium selenide (NaSe) by reducing Se with NaBH, and then to achieve selective syntheses of dialkyl selenides by subsequently treating the obtained sodium selenide with alkyl halides (RX). Consequently, various dialkyl selenides were efficiently synthesized in good-to-moderate yields.

One-Pot Synthesis of Novel Multisubstituted 1-Alkoxyindoles.

Studies on a one-pot synthesis of novel multisubstituted 1-alkoxyindoles and their mechanistic investigations are presented. The synthesis of was successfully achieved through consecutive four step reactions from substrates . The substrates , prepared through a two-step synthetic sequence, underwent three consecutive reactions of nitro reduction, intramolecular condensation, and nucleophilic 1,5-addition to provide the intermediates, 1-hydroxyindoles , which then were alkylated in situ with alkyl halide to afford the novel target products .

Syntheses and binding affinities of 6-nitroquipazine analogues for serotonin transporter. Part 5: 2'-Substituted 6-nitroquipazines.

Five C2'-substituted 6-nitroquipazine (6-NQ) derivatives were prepared and evaluated in terms of their biological abilities (K(i)) to displace [(3)H]citalopram binding to serotonin transporter. The relationship between their structure and biological activities revealed that shorter alkyl groups tend to possess higher binding affinity. Both compounds 12a and 12c were found to have the equally highest binding affinity (K(i)=0.