Estrogens and antiestrogens. Modern synthetic approaches to directed modification of estra-1,3,5(10)-triene steroids: goals, reactions, and methods

2021 ◽  
Author(s):  
Yuriy Kuznetsov ◽  
Inna Levina ◽  
Igor Zavarzin
Keyword(s):  
Organic Synthesis ◽  
Hormonal Therapy ◽  
Medicinal Chemistry ◽  
Steroid Nucleus ◽  
Aromatic Fragment ◽  
The Past ◽  
Natural Estrogens ◽  
Wide Range ◽  
Synthetic Approaches

The monograph summarizes the information over the past 20 years on the currently widely used and promising methods for the synthesis of estra-1,3,5(10)-triene derivatives by modifying natural estrogens - estrone and estradiol. The main practical goals of modifying this class of steroids and achievements in the chemistry of steroidal antiestrogens, which are promising drugs for hormonal therapy, are considered. Special attention is paid to the stereochemical features of the reactions and the specific problems of modification of the steroid nucleus of estratrienes associated with the presence of an aromatic fragment in their structure. In addition, the data on the reactivity and stereochemical aspects of the transformations of 13-epiestratriene steroids were summarized. The monograph is intended for a wide range of specialists in the field of organic synthesis, organic, bioorganic, and medicinal chemistry.

An Efficient Cascade Synthesis of Ethyl 3-Amino-5-oxoisoxazolidine-4-carboxylate Derivatives

Synthesis ◽  
2017 ◽  
Vol 49 (18) ◽  
pp. 4341-4349
Author(s):  
Runtao Li ◽  
Runrun Li ◽  
Qiang Wei ◽  
Xin Wang ◽  
Zemei Ge
Keyword(s):  
Organic Synthesis ◽  
Medicinal Chemistry ◽  
Wide Range

An efficient cascade synthesis of ethyl 3-amino-5-oxoisoxa­zolidine-4-carboxylate derivatives from diethyl 2-(ethoxymethyl­ene)malonate, different hydroxylamines and various amines is developed. This approach tolerates a wide range of amines affording highly functionalized isoxazolidine derivatives, which are expected to be important in organic synthesis and medicinal chemistry.

scholarly journals Recent Developments in the Synthesis of Pyrido[1,2-a]benzimidazoles

Synthesis ◽  
2018 ◽  
Vol 50 (11) ◽  
pp. 2131-2149 ◽  
Author(s):  
Kamal Kapoor ◽  
Parthasarathi Das ◽  
Rajni Khajuria ◽  
Sk. Rasheed ◽  
Chhavi Khajuria
Keyword(s):  
Transition Metal ◽  
Medicinal Chemistry ◽  
Type I ◽  
Type Ii ◽  
Aromatic Rings ◽  
Metal Free ◽  
Wide Range ◽  
Recent Developments ◽  
Metal Catalyzed ◽  
Synthetic Approaches

Pyrido[1,2-a]benzimidazole is one of the most important azaheterocyclic compounds consisting of three fused aromatic rings. Molecules containing this core have displayed a wide range of applications in the field of medicinal chemistry. The synthesis of pyrido[1,2-a]benzimidazole and its derivatives has attracted organic chemists because of its tremendous utility in interdisciplinary branches of chemistry. In this context, this review discusses the main advances in the synthesis of pyrido[1,2-a]benzimidazoles via metal-mediated and metal-free reactions from 2000 to 2016.1 Introduction2 Synthetic Approaches to Pyrido[1,2-a]benzimidazoles2.1 Type I: Transition-Metal-Catalyzed Methods2.2 Type II: Metal-Free Approaches3 Conclusion

scholarly journals Synthetic Strategies in the Preparation of Phenanthridinones

Molecules ◽  
2021 ◽  
Vol 26 (18) ◽  
pp. 5560
Author(s):  
Rajeshwar Reddy Aleti ◽  
Alexey A. Festa ◽  
Leonid G. Voskressensky ◽  
Erik V. Van der Eycken
Keyword(s):  
Natural Products ◽  
Organic Synthesis ◽  
Medicinal Chemistry ◽  
Coupling Reactions ◽  
Structural Importance ◽  
Wide Range ◽  
Biaryl Coupling ◽  
Synthetic Methodologies

Phenanthridinones are important heterocyclic frameworks present in a variety of complex natural products, pharmaceuticals and displaying wide range of pharmacological actions. Its structural importance has evoked a great deal of interest in the domains of organic synthesis and medicinal chemistry to develop new synthetic methodologies, as well as novel compounds of pharmaceutical interest. This review focuses on the synthesis of phenanthridinone scaffolds by employing aryl-aryl, N-aryl, and biaryl coupling reactions, decarboxylative amidations, and photocatalyzed reactions.

Triflic Anhydride (Tf2O)-Activated Transformation of Amides, Sulfoxides and Phosphorus Oxides via Nucleophilic Trapping

Synthesis ◽  
2021 ◽  
Author(s):  
Hai Huang ◽  
Jun Yong Kang
Keyword(s):  
Organic Chemistry ◽  
Organic Synthesis ◽  
Phosphorus Oxide ◽  
Synthetic Organic Chemistry ◽  
The Past ◽  
Mechanistic Pathway ◽  
Trifluoromethanesulfonic Anhydride ◽  
Wide Range ◽  
Electrophilic Activation ◽  
Nucleophilic Trapping

Trifluoromethanesulfonic anhydride (Tf2O) has found a wide range of applications in synthetic organic chemistry as a strong electrophilic activator leading to the transient generation of a triflate intermediate. This versatile triflate intermediate undergoes nucleophilic trapping with diverse nucleophiles to yield novel compounds. In this review, we describe the features and applications of triflic anhydride in organic synthesis reported in the past decade, especially in amide, sulfoxide, and phosphorus oxide chemistry through electrophilic activation. A plausible mechanistic pathway of each important reaction is also discussed.

Regioselective Synthesis of Diverse Thio-, Seleno-substituted 1,2,3-Triazoles

2020 ◽  
Vol 23 (22) ◽  
pp. 2379-2401
Author(s):  
Lin-Lin Zhang ◽  
Qin-Pei Wu ◽  
Zhi-Bin Xu
Keyword(s):  
Organic Synthesis ◽  
Reaction Mechanisms ◽  
Material Science ◽  
Medicinal Chemistry ◽  
Synthetic Methods ◽  
Regioselective Synthesis ◽  
Internal Alkynes ◽  
Synthetic Approaches

: Thio-, seleno-substituted triazoles are useful scaffolds employed in the fields of organic synthesis, medicinal chemistry, and material science. A number of synthetic approaches to efficient formation of thio- and seleno-triazoles have been disclosed, including the interception of copper(I) triazolides generated in-situ, cycloaddition of internal alkynes (thio-, halo-, and metalated alkynes) to azides, and the coupling of azides and nonalkyne substrates. This mini-review intends to summarize the synthetic methods toward thio-, seleno-1,2,3-triazoles and the relative reaction mechanisms.

scholarly journals An Overview of Coumarin as a Versatile and Readily Accessible Scaffold with Broad-Ranging Biological Activities

2020 ◽  
Vol 21 (13) ◽  
pp. 4618 ◽  
Author(s):  
Francesca Annunziata ◽  
Cecilia Pinna ◽  
Sabrina Dallavalle ◽  
Lucia Tamborini ◽  
Andrea Pinto
Keyword(s):  
Scientific Community ◽  
Medicinal Chemistry ◽  
Biological Activities ◽  
Natural Compounds ◽  
Natural Sources ◽  
Wide Range ◽  
Living Organisms ◽  
Privileged Structures ◽  
Synthetic Approaches ◽  
Critical Overview

Privileged structures have been widely used as an effective template for the research and discovery of high value chemicals. Coumarin is a simple scaffold widespread in Nature and it can be found in a considerable number of plants as well as in some fungi and bacteria. In the last years, these natural compounds have been gaining an increasing attention from the scientific community for their wide range of biological activities, mainly due to their ability to interact with diverse enzymes and receptors in living organisms. In addition, coumarin nucleus has proved to be easily synthetized and decorated, giving the possibility of designing new coumarin-based compounds and investigating their potential in the treatment of various diseases. The versatility of coumarin scaffold finds applications not only in medicinal chemistry but also in the agrochemical field as well as in the cosmetic and fragrances industry. This review is intended to be a critical overview on coumarins, comprehensive of natural sources, metabolites, biological evaluations and synthetic approaches.

Boron in Medicinal and Organic Chemistry

2021 ◽  
Vol 25 ◽  
Author(s):  
João Lucas Bruno Prates ◽  
Aline Renata Pavan ◽  
Jean Leandro dos Santos
Keyword(s):  
Organic Synthesis ◽  
Boronic Acid ◽  
Medicinal Chemistry ◽  
Therapeutic Agent ◽  
Chemical Properties ◽  
Cross Coupling ◽  
Review Article ◽  
Coupling Reactions ◽  
The Past ◽  
Cross Coupling Reactions

: Nowadays, boron-containing compounds have gained researchers’ attention because of the wide versatility and applicability of this element in both organic and medicinal chemistry. Since its discovery, its use in medicinal chemistry was neglected due to its possible toxic effects. However, in the past years, boron-containing compounds did not show such effects, and some drugs have already been approved by the Food and Drug Administration to treat diseases, including cancer, infections, and inflammation. Several boron-containing compounds are used in organic and medicinal chemistry, either as a reagent or therapeutic agent. The chemical properties of this element make its use possible in organic synthesis as a reducing agent and catalyst, mainly in cross-coupling reactions. Among boron-containing compounds, boranes, azaborines, benzoxaborole, boronic acid, and boron derivatives are most commonly described. This review article discusses the main properties of boron-containing compounds, their preparation by organic synthesis, as well as their applications in organic synthesis and medicinal chemistry fields, developing new perspectives for further investigations.

Regioselective C–H selenylation of heteroarenes under metal-free conditions

2021 ◽  
Vol 25 ◽  
Author(s):  
Ricardo F. Schumacher ◽  
Roberta Cargnelutti ◽  
Adriane Sperança ◽  
Jean C. Kazmierczak ◽  
Thiago Anjos ◽  
...  
Keyword(s):  
Supramolecular Chemistry ◽  
Organic Synthesis ◽  
Medicinal Chemistry ◽  
Optoelectronic Devices ◽  
Literature Survey ◽  
Organoselenium Compounds ◽  
Metal Free ◽  
The Past ◽  
Target Molecules ◽  
Safe Access

Selenium-containing heteroarenes consist of a synthetically valuable family of compounds that found applications in many different areas, such as organic synthesis, medicinal chemistry, supramolecular chemistry, and optoelectronic devices construction. Over the past decade, many advances have been achieved to the synthesis of these substances, and this review aims to cover a literature survey of the direct selenylation of heteroarenes under metal-free conditions, which represents one of the most powerful synthetic strategies for the preparation of those target molecules. The construction of new C-Se bonds through selective C-H functionalization reactions has become useful and atom-economical. The widespread adoption of metal-free approaches has emerged as versatile, sustainable, and safe access to these organoselenium compounds. Among the features of these new protocols are the use of mild oxidants and halogen-based catalysts, inorganic bases, as well as photo-induced reactions, and electrosynthesis.

scholarly journals Recent Advances on Synthetic Methodology Merging C–H Functionalization and C–C Cleavage

Molecules ◽  
2020 ◽  
Vol 25 (24) ◽  
pp. 5900
Author(s):  
Hamid Azizollahi ◽  
José-Antonio García-López
Keyword(s):  
Organic Synthesis ◽  
Recent Progress ◽  
Transition Metal Catalysis ◽  
Synthetic Methodology ◽  
Straightforward Manner ◽  
Metal Catalysis ◽  
Radical Intermediates ◽  
Wide Range ◽  
Radical Initiators ◽  
Synthetic Approaches

The functionalization of C–H bonds has become a major thread of research in organic synthesis that can be assessed from different angles, for instance depending on the type of catalyst employed or the overall transformation that is carried out. This review compiles recent progress in synthetic methodology that merges the functionalization of C–H bonds along with the cleavage of C–C bonds, either in intra- or intermolecular fashion. The manuscript is organized in two main sections according to the type of substrate in which the cleavage of the C–C bond takes place, basically attending to the scission of strained or unstrained C–C bonds. Furthermore, the related research works have been grouped on the basis of the mechanistic aspects of the different transformations that are carried out, i.e.,: (a) classic transition metal catalysis where organometallic intermediates are involved; (b) processes occurring via radical intermediates generated through the use of radical initiators or photochemically; and (c) reactions that are catalyzed or mediated by suitable Lewis or Brønsted acid or bases, where molecular rearrangements take place. Thus, throughout the review a wide range of synthetic approaches show that the combination of C–H and C–C cleavage in single synthetic operations can serve as a platform to achieve complex molecular skeletons in a straightforward manner, among them interesting carbo- and heterocyclic scaffolds.

Direct Access to Highly Functionalised Benzimidazoles and Benzoxazoles from a Common Precursor

Synthesis ◽  
2019 ◽  
Vol 51 (21) ◽  
pp. 4006-4013 ◽  
Author(s):  
Amanda Garrido ◽  
Pierre-Olivier Delaye ◽  
François Quintin ◽  
Mohamed Abarbri ◽  
Pedro Lameiras ◽  
...  
Keyword(s):  
Organic Synthesis ◽  
Building Block ◽  
Medicinal Chemistry ◽  
Direct Access ◽  
One Pot ◽  
Metal Free ◽  
Mild Conditions ◽  
Common Precursor ◽  
Biological Interest ◽  
Wide Range

Benzoxazole and benzimidazole are commonly encountered heterocycles in medicinal chemistry and their functionalisation around 1-, 2-, 5-, and/or 6-positions provides a wide range of molecules of biological interest. In this manuscript, a straightforward preparation of diversely and highly substituted benzimidazoles and benzoxazoles on these positions, from a common starting material, a 3,3-dibromoacrolein, is described. Such acrolein derivatives are almost never described in the literature or used as ‘building-block’ for organic synthesis. The double electrophilicity of this substrate was found to be advantageous for condensation with two equivalents of various 1,2-diaminobenzene or 2-aminophenol derivatives. This one-pot reaction performed under metal-free and mild conditions allows the creation of three new carbon–heteroatom bonds and affords the desired heterocycles.

Sign in / Sign up

Export Citation Format

Share Document