Histone deacetylase inhibitorを用いた新しい分化誘導療法の可能性

Insights into the Recent Synthetic Advances of Organoselenium Compounds

In the present review, we discuss recent progress in the field of C-Z bond formation reactions (Z = S, Se, Te) catalyzed by transition metals. Two complementary methodologies are considered─catalytic cross-coupling reactions and catalytic addition reactions. The development of advanced catalytic systems is aimed at improved catalyst efficiency, reduced catalyst loading, better cost efficiency, environmental concerns, and higher selectivity and yields. The important rise of research efforts in sustainability and green chemistry areas is critically assessed. The paramount role of mechanistic studies in the development of a new generation of catalytic systems is addressed, and the key achievements, problems, and challenges are summarized for this field.

Transition-Metal-Catalyzed C-S, C-Se, and C-Te Bond Formations via Cross-Coupling and Atom-Economic Addition Reactions. Achievements and Challenges.

A practical approach for the regioselective synthesis of 3-arylthioindoles has been accomplished using a combination of 1-aryltriazene/CS2 as a new sulfenylation source. The methodology employs molecular iodine as a catalyst and is compatible with a variety of structurally diverse reactants.

Iodine-Catalyzed Synthesis of 3-Arylthioindoles Employing a 1-Aryltriazene/CS2 Combination as a New Sulfenylation Source.

Palladium‐Catalyzed Picolinamide‐Directed Benzylic C(sp3)−H Chalcogenation with Diaryl Disulfides and Diphenyl Diselenide

Fe(III)-Catalyzed direct C3 chalcogenylation of indole: The effect of iodide ions

Base-Promoted Direct Chalcogenylation of 2-Naphthols

One‐Pot Synthesis of 3‐Halo‐2‐organochalcogenylbenzo[b]chalcogenophenes from 1‐(2,2‐Dibromovinyl)‐2‐organochalcogenylbenzenes

Breast and ovarian cancer are the most common cancers in women. Available cancer treatments, in general, have limited efficacy and frequent, undesirable side effects. Recently, scientists have focused on searching for new epigenetic modulators such as inhibitors of DNA methyltransferases and histone deacetylases (HDACs), with novel properties and selectivity. We report the synthesis of seven new analogs of Santacruzamate A. Molecular modeling showed that compounds 3–9 presented the best binding energies (kcal/mol) against HDAC4 compared to that of crystallographic ligand. The compounds were evaluated against MCF-7 and MDA-MB-231 (breast cancer), TOV-21G (ovarian adenocarcinoma), and WI-26VA4 (non-tumor lung fibroblasts) cells. Compound 5, the most potent and selective of the series, exhibited remarkably enhanced anticancer potency, with IC50 values for the tumor cells of 24.3–44.93 μM, compared with that of etoposide (12–18.57 μM) and doxorubicin (2.1–4.37 μM). Further investigation showed that compound 5 could promote DNA damage, increase the activity of caspases-3 and -9, and upregulate mRNA levels of p21, TP53, and BAK, suggesting apoptotic cell death of the tumor cells via the intrinsic pathway. This study demonstrated that synthetic analogs of santacruzamate A with zinc-linked groups are effective for improving both HDAC inhibition and antitumor activity.

Synthesis, cytotoxic activity, and mode of action of new Santacruzamate A analogs

Transition metal catalysed direct sulfanylations of unreactive C-H bonds have become a unique and straightforward synthetic strategy in late-stage C-S bond formation of relevant complex molecules. Such transformations represent a breakthrough in modern synthetic organic chemistry, as they offer unusual reactivity patterns and avoid pre-functionalization of the starting materials. Despite inherent challenges in activating/functionalizing unreactive C-H bonds, a considerable number of different transition metals have shown the ability to selectively catalyze these processes toward C-S bond formation. In this sense, this review article covers the development and mechanistic analysis of the direct sulfanylation of Csp3-H and Csp2-H bonds through transition metal catalysed reactions in the last two decades, providing an essential guide for organic chemists working on this research area.

Diego Seckler

Papers

Fe(III)-Catalyzed direct C3 chalcogenylation of indole: The effect of iodide ions

Base-Promoted Direct Chalcogenylation of 2-Naphthols

One‐Pot Synthesis of 3‐Halo‐2‐organochalcogenylbenzo[b]chalcogenophenes from 1‐(2,2‐Dibromovinyl)‐2‐organochalcogenylbenzenes

Synthesis, cytotoxic activity, and mode of action of new Santacruzamate A analogs

Transition metal catalysed direct sulfanylation of unreactive C-H bonds: an overview of the last two decades.