scholarly journals Diversity-Oriented Synthesis: Amino Acetophenones as Building Blocks for the Synthesis of Natural Product Analogs

2021 ◽  
Vol 14 (11) ◽  
pp. 1127
Author(s):  
Mathias Eymery ◽  
Viet-Khoa Tran-Nguyen ◽  
Ahcène Boumendjel
Keyword(s):  
Drug Discovery ◽  
Natural Product ◽  
Organic Synthesis ◽  
Building Blocks ◽  
Structural Features ◽  
The Other ◽  
Pharmacological Properties ◽  
Diversity Oriented Synthesis ◽  
Fully Integrated ◽  
Lead Compounds

Diversity-Oriented Synthesis (DOS) represents a strategy to obtain molecule libraries with diverse structural features starting from one common compound in limited steps of synthesis. During the last two decades, DOS has become an unmissable strategy in organic synthesis and is fully integrated in various drug discovery processes. On the other hand, natural products with multiple relevant pharmacological properties have been extensively investigated as scaffolds for ligand-based drug design. In this article, we report the amino dimethoxyacetophenones that can be easily synthesized and scaled up from the commercially available 3,5-dimethoxyaniline as valuable starting blocks for the DOS of natural product analogs. More focus is placed on the synthesis of analogs of flavones, coumarins, azocanes, chalcones, and aurones, which are frequently studied as lead compounds in drug discovery.

Tetralone scaffolds and their potential therapeutic applications

2020 ◽  
Vol 17 ◽  
Author(s):  
Bhagwati Gauni ◽  
Krunal Mehariya ◽  
Anamik Shah ◽  
Srinivas Murty Duggirala
Keyword(s):  
Antitumor Activity ◽  
Organic Synthesis ◽  
Small Molecule ◽  
Heterocyclic Compounds ◽  
Biological Activities ◽  
Acetylcholinesterase Inhibitors ◽  
Building Blocks ◽  
Structural Features ◽  
Therapeutic Applications ◽  
Small Molecule Library

: Substituted tetralones have played a substantial role in organic synthesis due to their strong reactivity and suitability as a starting material for a range of synthetic heterocyclic compounds, pharmaceuticals along with biological activities as well as precursors of many natural products and their derivatives. Many α-tetralone derivatives are building blocks, that have been used in the synthesis of therapeutically functional compounds like some antibiotics, antidepressants, acetylcholinesterase inhibitors effective for treating Alzheimer’s disease and alkaloids possessing antitumor activity. In this review, there has been an attempt to explore the small molecule library having α-tetralone scaffold along with their diverse biological activities. Structural features of α-tetralone derivatives responsible for potential therapeutic applications are also described.

A stereolibrary of conformationally restricted amino acids based on pyrrolidinyl/piperidinyloxazole motifs

2015 ◽  
Vol 21 (6) ◽  
pp. 391-395 ◽  
Author(s):  
Oleksiy S. Artamonov ◽  
Taras Bulda ◽  
Tkhe Kyong Fam ◽  
Evgeniy Y. Slobodyanyuk ◽  
Dmitry M. Volochnyuk ◽  
...  
Keyword(s):  
Amino Acids ◽  
Natural Products ◽  
Drug Discovery ◽  
Carboxylic Acids ◽  
Building Blocks ◽  
Conformationally Restricted ◽  
Lead Compounds ◽  
Restricted Amino Acids

AbstractA stereolibrary of conformationally restricted oxazole-containing amino acids, namely all isomers of 5–pyrrolydinyl- and 5-piperidinyloxazole-4-carboxylic acids, were designed and synthesized in three steps by the reaction of the corresponding N-Boc-protected amino acids and ethyl isocyanoacetate. These natural products-inspired amino acids are valuable building blocks for the synthesis of peptidomimetics and potential lead compounds for drug discovery.

Regioselective N-alkylation of (2-chloroquinolin-3-yl) methanol with N-heterocyclic compounds using the Mitsunobu reagent

2011 ◽  
Vol 65 (3) ◽  
Author(s):  
Selvaraj Roopan ◽  
Fazlur-Rahman Khan ◽  
Jong Jin
Keyword(s):  
Natural Product ◽  
Organic Synthesis ◽  
Heterocyclic Compounds ◽  
Building Blocks ◽  
Natural Product Synthesis ◽  
Mitsunobu Reaction ◽  
Reaction Conditions ◽  
Diethyl Azodicarboxylate ◽  
Nitrogen Heterocyclic

AbstractThe Mitsunobu reaction is a well-established fundamental reaction and has been widely applied in organic synthesis. In this paper, under Mitsunobu conditions dehydration proceeds between (2-chloroquinolin-3-yl)methanol and nitrogen heterocyclic compounds such as quinazolinone, pyrimidone, 2-oxoquinoline in dry THF in the presence of triethylamine, triphenylphosphane and diethyl azodicarboxylate to give the corresponding products. As part of our recent research, we attempted to couple two N-heterocyclic compounds under Mitsunobu reaction conditions to provide efficient building blocks for natural product synthesis.

scholarly journals Acyl(imidoyl)ketenes: Reactive Bidentate Oxa/Aza-Dienes for Organic Synthesis

Symmetry ◽  
2021 ◽  
Vol 13 (8) ◽  
pp. 1509
Author(s):  
Ekaterina A. Lystsova ◽  
Ekaterina E. Khramtsova ◽  
Andrey N. Maslivets
Keyword(s):  
Drug Discovery ◽  
Organic Synthesis ◽  
High Selectivity ◽  
Building Blocks ◽  
Atom Economy ◽  
Thermal Generation ◽  
Modern Drug ◽  
Small Molecule Libraries ◽  
Intermolecular Reactions ◽  
High Yields

Polyfunctional building blocks are essential for the implementation of diversity-oriented synthetic strategies, highly demanded in small molecule libraries’ design for modern drug discovery. Acyl(imidoyl)ketenes are highly reactive organic compounds, bearing both oxa- and aza-diene moieties, conjugated symmetrically to the ketene fragment, enabling synthesis of various skeletally diverse heterocycles on their basis. The highlights of reactions utilizing acyl(imidoyl)ketenes are high yields, short reaction time (about several minutes), high selectivity, atom economy, and simple purification procedures, which benefits the drug discovery. The present review focuses on the approaches to thermal generation of acyl(imidoyl)ketenes, patterns of their immediate transformations via intra- and intermolecular reactions, including the reactions of cyclodimerization, in which either symmetric or dissymmetric heterocycles can be formed. Recent advances in investigations on mechanisms, identifications of intermediates, and chemo- and regioselectivity of reactions with participation of acyl(imidoyl)ketenes are also covered.

scholarly journals Review on Natural Coumarin Lead Compounds for Their Pharmacological Activity

2013 ◽  
Vol 2013 ◽  
pp. 1-14 ◽  
Author(s):  
K. N. Venugopala ◽  
V. Rashmi ◽  
B. Odhav
Keyword(s):  
Natural Product ◽  
Pharmacological Activity ◽  
Dietary Exposure ◽  
Herbal Remedies ◽  
Pharmacological Properties ◽  
Lead Compounds ◽  
Natural Coumarin ◽  
Low Toxicity ◽  
Anti Inflammatory

Coumarin (2H-1-benzopyran-2-one) is a plant-derived natural product known for its pharmacological properties such as anti-inflammatory, anticoagulant, antibacterial, antifungal, antiviral, anticancer, antihypertensive, antitubercular, anticonvulsant, antiadipogenic, antihyperglycemic, antioxidant, and neuroprotective properties. Dietary exposure to benzopyrones is significant as these compounds are found in vegetables, fruits, seeds, nuts, coffee, tea, and wine. In view of the established low toxicity, relative cheapness, presence in the diet, and occurrence in various herbal remedies of coumarins, it appears prudent to evaluate their properties and applications further.

Chemical Constituents and Bioactivities of Gorgonian Corals

2020 ◽  
Vol 24 (12) ◽  
pp. 1315-1330
Author(s):  
Hui Lei ◽  
Peng Jiang ◽  
Dan Zhang
Keyword(s):  
Biological Activities ◽  
Chemical Constituents ◽  
Structural Features ◽  
Mechanisms Of Action ◽  
Pharmacological Properties ◽  
Pharmacological Activities ◽  
Lead Compounds ◽  
Medicinal Value ◽  
Gorgonian Corals ◽  
New Compounds

Gorgonian corals are considered as a rich source of secondary metabolites with unique structural features and biological activities. A large number of novel metabolites with potent pharmacological properties have been isolated from gorgonian corals. Some of these compounds have exhibited to possess new mechanisms of action, which hold great promises as potential lead compounds in future marine drug development. This review aims to provide an overview of chemical constituents and biological activities of gorgonian corals from 2015 to December, 2019. Some 145 metabolites, including 16 sesquiterpenoids, 62 diterpenoids, 62 steroids and 5 alkaloids were reported during this period and their pharmacological activities were investigated. Moreover, the peculiar structure and potential medicinal value of these new compounds are discussed in this review.

scholarly journals Natural Product-Inspired Pyranonaphthoquinone Inhibitors of Indoleamine 2,3-Dioxygenase-1 (IDO-1)

2013 ◽  
Vol 66 (1) ◽  
pp. 40 ◽  
Author(s):  
David J. A. Bridewell ◽  
Jonathan Sperry ◽  
Jason R. Smith ◽  
Priambudi Kosim-Satyaputra ◽  
Lai-Ming Ching ◽  
...  
Keyword(s):  
Natural Products ◽  
Cell Viability ◽  
Natural Product ◽  
Structural Features ◽  
Lead Compounds ◽  
Indoleamine 2,3 Dioxygenase ◽  
Drug Concentrations ◽  
Cellular Context ◽  
In Cells

A series of pyranonaphthoquinone derivatives possessing structural features present in both natural products annulin B and exiguamine A have been shown to exhibit low micromolar inhibition of indoleamine 2,3-dioxygenase-1 (IDO-1). These inhibitors retain activity against the enzyme in a cellular context with an approximate one-log loss of dose potency against IDO-1 in cells. One particular analogue, triazole 8 shows good inhibition of IDO-1 along with little loss of cell viability at low drug concentrations. These results have extended the naphthoquinone series of novel IDO-1 inhibitors based on lead compounds from nature.

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