Synthesis of biologically active heterocyclic compounds from allenic and acetylenic nitriles and related compounds

2021 ◽  
Vol 0 (0) ◽  
Author(s):  
Marthe Carine Djuidje Fotsing ◽  
Dieudonné Njamen ◽  
Zacharias Tanee Fomum ◽  
Derek Tantoh Ndinteh
Keyword(s):  
Michael Addition ◽  
Heterocyclic Compounds ◽  
Biological Activities ◽  
Biologically Active ◽  
Polycyclic Compounds ◽  
One Step ◽  
Pharmaceutical Properties ◽  
Related Compounds ◽  
Acetylenic Acids ◽  
The Michael Addition

Abstract Cyclic and polycyclic compounds containing moieties such as imidazole, pyrazole, isoxazole, thiazoline, oxazine, indole, benzothiazole and benzoxazole benzimidazole are prized molecules because of the various pharmaceutical properties that they display. This led Prof. Landor and co-workers to engage in the synthesis of several of them such as alkylimidazolenes, oxazolines, thiazolines, pyrimidopyrimidines, pyridylpyrazoles, benzoxazines, quinolines, pyrimidobenzimidazoles and pyrimidobenzothiazolones. This review covers the synthesis of biologically active heterocyclic compounds by the Michael addition and the double Michael addition of various amines and diamines on allenic nitriles, acetylenic nitriles, hydroxyacetylenic nitriles, acetylenic acids and acetylenic aldehydes. The heterocycles were obtained in one step reaction and in most cases, did not give side products. A brief discussion on the biological activities of some heterocycles is also provided.

Biologically Active 2,5-Disubstituted-1,3,4-Oxadiazoles

2009 ◽  
Vol 2 (1) ◽  
pp. 390-406
Author(s):  
Harish Rajak ◽  
Murli Dhar Kharya ◽  
Pradeep Mishra
Keyword(s):  
Heterocyclic Compounds ◽  
Medical Literature ◽  
Biological Activities ◽  
Biologically Active ◽  
Pharmacological Properties ◽  
Clinical Use ◽  
Synthetic Drugs ◽  
Physiologic Activity ◽  
Pharmacologically Active

There are vast numbers of pharmacologically active heterocyclic compounds in regular clinical use. The presence of heterocyclic structures in diverse types of compounds is strongly indicative of the profound effects such structure exerts on physiologic activity, and recognition of this is abundantly reflected in efforts to find useful synthetic drugs. The 1,3,4-oxadiazole nucleus has emerged as one of the potential pharmacophore responsible for diverse pharmacological properties. Medical Literature is flooded with reports of a variety of biological activities of 2,5-Disubstituted-1,3,4-oxadiazoles. The present work is an attempt to summarize and enlist the various reports published on biologically active 2,5-disubstituted-1,3,4-oxadiazoles.

Fe3O4@L-arginine as a Reusable Catalyst for the Synthesis of Polysubstituted 2-Pyrrolidinones

2019 ◽  
Vol 6 (1) ◽  
pp. 61-68 ◽  
Author(s):  
Mohammad Ali Ghasemzadeh ◽  
Mohammad Hossein Abdollahi-Basir ◽  
Zahra Elyasi
Keyword(s):  
Heterocyclic Compounds ◽  
Structure Elucidation ◽  
Reaction Times ◽  
Biologically Active ◽  
Reusable Catalyst ◽  
Particle Sizes ◽  
Magnetic Nanocatalyst ◽  
Green Method ◽  
One Step ◽  
Good Agreement

Background: This research introduces an effective and green method for the synthesis of polysubstituted 2-pyrrolidinone derivatives as biologically-active heterocyclic compounds using multi- component reactions using Fe3O4@L-arginine as a reusable organocatalyst. Material and Method: The Fe3O4@L-arginine nanoparticles were prepared by a facile one-step approach and the structure elucidation of the magnetic nanocatalyst has been done using various spectroscopy techniques. Results: L-arginine-functionalized magnetite nanoparticles were obtained with particle sizes around 10 nm. Fe3O4@L-arginine exhibited strong catalytic activity to obtain some polysubstituted 2- pyrrolidinone. Conclusion: The considerable advantages of this research are short reaction times, excellent yields, simple workup procedure and reusability of the nanocatalyst which is in good agreement with green chemistry disciplines. The study on the reusability of the Fe3O4@L-arginine nanoparticles showed that the recovered catalyst could be reused six consecutive times.

A new four-component reaction involving the Michael addition and the Gewald reaction, leading to diverse biologically active 2-aminothiophenes

2017 ◽  
Vol 15 (18) ◽  
pp. 3892-3900 ◽  
Author(s):  
Joice Thomas ◽  
Sampad Jana ◽  
Mahendra Sonawane ◽  
Bert Fiey ◽  
Jan Balzarini ◽  
...  
Keyword(s):  
Michael Addition ◽  
Proliferative Activity ◽  
Biologically Active ◽  
Gewald Reaction ◽  
The Michael Addition

A Gewald-four component reaction has been successfully developed for the synthesis of a series of compounds containing an indole and a 2-aminothiophene moiety separated by a methylene spacer having anti-proliferative activity.

scholarly journals A New Method for the Synthesis of 2-Substituted Benzoxazoles from 2-Nitrophenol Derivatives and Aldehydes  

2021 ◽  
Vol 31 (3) ◽  
pp. 43-46
Keyword(s):  
Biological Activities ◽  
Catalyst System ◽  
Biologically Active ◽  
New Method ◽  
Redox Catalyst ◽  
High Pressure High Temperature ◽  
One Step ◽  
High Yields ◽  
Strong Acids ◽  
Single Reaction

Benzoxazole derivatives are one of the compounds with many interesting biological activities. Conventional methods are often performed under complex conditions using strong acids, expensive metal catalysts, requiring high pressure, high temperature, and under microwave irradiation. In this study, we reported a new method of benzoxazole synthesis with redox catalyst using FeCl3.6H2O and sulfur. This is a suitable, efficient, readily available and environmentally friendly catalyst system for redox and condensation reactions in one step at 100 oC. Applying this new method, we have synthesized eight 2-arylbenzoxazole derivatives with high yields (calculated according to 2-nitrophenol). This research is an important step forward in the synthesis of biologically active compounds containing the benzoxazole framework from readily available starting materials in a single reaction.

scholarly journals Chemistry and Biological Activities of 1,2,4-Triazolethiones—Antiviral and Anti-Infective Drugs

Molecules ◽  
2020 ◽  
Vol 25 (13) ◽  
pp. 3036
Author(s):  
Ashraf A. Aly ◽  
Alaa A. Hassan ◽  
Maysa M. Makhlouf ◽  
Stefan Bräse
Keyword(s):  
Natural Products ◽  
Heterocyclic Compounds ◽  
Biological Activities ◽  
Biologically Active ◽  
Biological Applications ◽  
Active Moiety ◽  
Interesting Class

Mercapto-substituted 1,2,4-triazoles are very interesting compounds as they play an important role in chemopreventive and chemotherapeutic effects on cancer. In recent decades, literature has been enriched with sulfur- and nitrogen-containing heterocycles which are used as a basic nucleus of different heterocyclic compounds with various biological applications in medicine and also occupy a huge part of natural products. Therefore, we shed, herein, more light on the synthesis of this interesting class and its application as a biologically active moiety. They might also be suitable as antiviral and anti-infective drugs.

Antioxidant, cytotoxic activity and pharmacokinetic studies by SwissAdme, Molinspiration, Osiris and DFT of PhTAD-substituted dihydropyrrole derivatives

2021 ◽  
Vol 17 ◽  
Author(s):  
Arif Ayar ◽  
Masuk Aksahin ◽  
Seda Mesci ◽  
Burak Yazgan ◽  
Melek Gül ◽  
...  
Keyword(s):  
Cytotoxic Activity ◽  
Cell Lines ◽  
Heterocyclic Compounds ◽  
Antioxidant Activities ◽  
Biological Activities ◽  
Molecular Structures ◽  
Biologically Active ◽  
Pharmacokinetic Studies ◽  
Ic50 Values ◽  
Mcf 7

Background: Pyrrole compounds having a heterocyclic structure are the most researched and biological activities such as antioxidant and anticancer. Objective: Herein is a first effort to study the significance of heterocyclic compounds to include pyrrole and triazolidine-3,5-dion moiety, on the pharmacokinetic, antioxidant activity and cytotoxic activity on MCF-7 and MCF-12A cell lines. Method: The molecular structures of compounds I-XIV were simulated by the theoretical B3LYP/DFT method. Pharmacokinetic studies of PhTAD-substituted heterocyclic compounds (I-XIV) were analyzed to show Lipinski's rules via in-silico methods of Swiss-ADME. The drug likeness calculations were carried out Molinspiration analyses. The some toxicity risk parameter can be quantified using Osiris. Antioxidant activities determined by DPPH, Fe+2 ions chelating and reducing. Cytotoxic activity measured by MTT and RTCA. Results: Compared with the DPPH activity, the metal chelating activity exhibited serious similar antioxidant effects by PhTAD substituted pyrrole compounds. The same compounds showed the highest activity among the two antioxidant activities. The IC50 values of the compounds are in the range of 12 and 290 µM in MCF-7 cell line. In the MTT and RTCA assays, All compounds showed cytotoxic activity, but about half of the fourteen compounds showed high cytotoxicity. IC50 values of the compounds are in the range of 5 and 54 µM for MTT and range of 1.5 and 44 µM for RTCA. Conclusion: Data of the antioxidant and cytotoxic activity of PhTAD-substituted dihydropyrrole-derived compounds in MCF-7 and MCF-12A cell lines confirmed that the compounds are a biologically active compound and is notable for anti-cancer researches.

Synthesis of Racemic [2-14C]Jasmonic acid*

1988 ◽  
Vol 43 (1-2) ◽  
pp. 29-31 ◽  
Author(s):  
Hans-Dieter Knöfel ◽  
Dieter Gross
Keyword(s):  
Jasmonic Acid ◽  
Michael Addition ◽  
One Step ◽  
The Michael Addition

(±)-[2-14C)Jasmonic acid has been synthesized in nearly 50% yield via the route of the Michael addition starting from 2-(2Z-pentenyl)-2-cyclopenten-1-one and diethyl [2-14C]malonate followed by saponification and decarboxylation of the Michael products in one step

Asymmetric Brønsted Acid-catalyzed Intramolecular aza-Michael Reaction – Enantioselective Synthesis of Dihydroquinolinones

2012 ◽  
Vol 67 (10) ◽  
pp. 1021-1029 ◽  
Author(s):  
Magnus Rueping ◽  
Stefan A. Moreth ◽  
Michael Bolte
Keyword(s):  
Michael Addition ◽  
Heterocyclic Compounds ◽  
Michael Reaction ◽  
Biological Activities ◽  
Enantioselective Synthesis ◽  
Bronsted Acid ◽  
Brønsted Acid ◽  
Brönsted Acid ◽  
Acid Catalyzed ◽  
High Yields

The enantioselective synthesis of 2-aryl-substituted 2,3-dihydroquinolin-4-ones, a class of heterocyclic compounds with interesting biological activities, has been achieved through a Brønsted acidcatalyzed enantioselective intramolecular Michael addition. The products are available in moderate to high yields and with good enantioselectivities.

TRYPTAMINES, CARBOLINES, AND RELATED COMPOUNDS: PART VI. STEREOCHEMISTRY OF THE MICHAEL ADDITION OF ETHYL MALONATE TO 1-CYCLOHEXENE CYANIDE

1960 ◽  
Vol 38 (4) ◽  
pp. 557-566 ◽  
Author(s):  
R. A. Abramovitch ◽  
J. M. Muchowski
Keyword(s):  
Michael Addition ◽  
Diethyl Malonate ◽  
Aminomethyl Derivative ◽  
Fischer Cyclization ◽  
Ethyl Malonate ◽  
Cis And Trans ◽  
Related Compounds ◽  
The Michael Addition

The Michael addition of diethyl malonate to 1-cyclohexene cyanide has been shown to give a mixture of the cis- and trans-diethyl 2-cyanocyclohexylmalonates in 72% and 28% yields respectively. The stereochemistry of the products was established by their unambiguous conversion to the respective cis- and trans-decahydroisoquinolines. Hydrogenation of a cyclohexane cyanide to the corresponding aminomethyl derivative takes place with retention of configuration. A number of substituted decahydroisoquinolines of known stereochemistry have been prepared. Decahydro-3,4-dioxoisoquinoline-4-phenylhydrazone underwent Fischer cyclization to a product assumed to be 2-oxo-octahydroindolo[2,3-d]isoquinoline indicating that the observation that 4-methyl-2,3-dioxopiperidine-3-phenylhydrazone did not undergo cyclization is not general for such 4-substituted piperidones.

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