scholarly journals The Ugi-Smiles Reaction on Steroids: Discovery of Bioactive N,N-Disubstituted 3- Aminoestrones

2020 ◽  
Author(s):  
Cecilia Attorresi ◽  
Bruno Falcone ◽  
Evelyn Bonifazi ◽  
Gabriel Gola ◽  
Andrea Barquero ◽  
...  
Keyword(s):  
Multicomponent Reaction ◽  
Biological Activities ◽  
Steric Effects ◽  
Efficient Synthesis ◽  
Reaction Conditions ◽  
Antiviral Activities ◽  
Steroidal Derivatives

The Ugi-Smiles multicomponent reaction is a powerful tool for obtaining <i>N-</i>arylamines from acidic phenols and has been widely used for gaining access to structurally diverse scaffolds. In this work we demonstrate that this isocyanide-based coupling can be used for the straightforward and efficient synthesis of <i>N,N-</i>disubstituted 3-aminoestrones, steroidal derivatives that usually show interesting biological activities. In this sense, we analyzed the scope and limitations of the reaction when applied to aromatic nitrosteroids and found that the outcome is highly influenced by the steric effects imposed by the steroidal skeleton. After optimization of the reaction conditions a set of thirteen N-substituted 3-aminoestromes were obtained, some of them with interesting antiproliferative and antiviral activities.

scholarly journals The Ugi-Smiles Reaction on Steroids: Discovery of Bioactive N,N-Disubstituted 3- Aminoestrones

2020 ◽  
Author(s):  
Cecilia Attorresi ◽  
Bruno Falcone ◽  
Evelyn Bonifazi ◽  
Gabriel Gola ◽  
Andrea Barquero ◽  
...  
Keyword(s):  
Multicomponent Reaction ◽  
Biological Activities ◽  
Steric Effects ◽  
Efficient Synthesis ◽  
Reaction Conditions ◽  
Antiviral Activities ◽  
Steroidal Derivatives

The Ugi-Smiles multicomponent reaction is a powerful tool for obtaining <i>N-</i>arylamines from acidic phenols and has been widely used for gaining access to structurally diverse scaffolds. In this work we demonstrate that this isocyanide-based coupling can be used for the straightforward and efficient synthesis of <i>N,N-</i>disubstituted 3-aminoestrones, steroidal derivatives that usually show interesting biological activities. In this sense, we analyzed the scope and limitations of the reaction when applied to aromatic nitrosteroids and found that the outcome is highly influenced by the steric effects imposed by the steroidal skeleton. After optimization of the reaction conditions a set of thirteen N-substituted 3-aminoestromes were obtained, some of them with interesting antiproliferative and antiviral activities.

Metal and Non-Metal Catalysts in the Synthesis of Five-Membered S-Heterocycles

2019 ◽  
Vol 16 (2) ◽  
pp. 258-275 ◽  
Author(s):  
Navjeet Kaur
Keyword(s):  
Organic Synthesis ◽  
Biological Activities ◽  
Reaction Times ◽  
Research Field ◽  
Environmentally Benign ◽  
Metal Catalyst ◽  
Efficient Synthesis ◽  
Heterocyclic Molecules ◽  
The Past ◽  
Harsh Conditions

Background:A wide variety of biological activities are exhibited by N, O and S containing heterocycles and recently, many reports appeared for the synthesis of these heterocycles. The synthesis of heterocycles with the help of metal and non-metal catalyst has become a highly rewarding and important method in organic synthesis. This review article concentrated on the synthesis of S-heterocylces in the presence of metal and non-metal catalyst. The synthesis of five-membered S-heterocycles is described here.Objective:There is a need for the development of rapid, efficient and versatile strategy for the synthesis of heterocyclic rings. Metal, non-metal and organocatalysis involving methods have gained prominence because traditional conditions have disadvantages such as long reaction times, harsh conditions and limited substrate scope.Conclusion:The metal-, non-metal-, and organocatalyst assisted organic synthesis is a highly dynamic research field. For ßthe chemoselective and efficient synthesis of heterocyclic molecules, this protocol has emerged as a powerful route. Various methodologies in the past few years have been pointed out to pursue more sustainable, efficient and environmentally benign procedures and products. Among these processes, the development of new protocols (catalysis), which avoided the use of toxic reagents, are the focus of intense research.

DFT Study and Synthesis of Novel Bioactive Bispyrazole Using Mg/AlLDH as a Solid Base Catalyst

2020 ◽  
Vol 14 ◽  
Author(s):  
Soufiane Akhramez ◽  
Youness Achour ◽  
Mustapha Diba ◽  
Lahoucine Bahsis ◽  
Hajiba Ouchetto ◽  
...  
Keyword(s):  
Dft Calculations ◽  
Experimental Finding ◽  
Biological Activities ◽  
Condensation Reaction ◽  
Aromatic Aldehydes ◽  
Mechanistic Study ◽  
Knoevenagel Reaction ◽  
Solid Base ◽  
Reaction Conditions ◽  
Aryl Aldehyde

Background: In this study, an efficient synthesis of novel bispyrazole heterocyclic molecules by condensation of substituted aromatic aldehydes with 1,3-diketo-N-phenylpyrazole by using Mg/Al-LDH as heterogeneous catalyst is reported. The attractive features of this protocol are as follows: mild reaction conditions, good yields and easiness of the catalyst separation from the reaction mixture. Further, a mechanistic study has been performed by using DFT calculations to explain the observed selectivity of the condensation reaction between aryl aldehyde and 1,3-diketo-N-phenylpyrazole via Knoevenagel reaction. The local electrophilicity/ nucleophilicity that allows explaining correctly the experimental finding. Methods: The bispyrazole derivatives 3a-m were prepared by condensation reaction of substituted aromatic aldehydes with 1,3-diketo-Nphenylpyrazole by using Mg/Al-LDH as heterogeneous catalyst under THF solvent at the refluxing temperature. Objective: To synthesize a novel bispyrazole heterocyclic molecule may be have important biological activities and thus can be good candidates for pharmaceutical applications. Results: This protocol describes the Synthesis of Bioactive Compounds under mild reaction conditions, good yields and easiness of the catalyst separation from the reaction mixture. Further, a mechanistic study has been performed by using DFT calculations to explain the observed selectivity of the condensation reaction between aryl aldehyde and 1,3-diketo-N-phenylpyrazole via Knoevenagel reaction. The local electrophilicity/ nucleophilicity that allows explaining correctly the experimental finding. Conclusion: In summary, the pharmacologically interesting bis-pyrazole derivatives have been synthesized through Mg/Al-LDH as a solid base catalyst, in THF as solvent. Thus, the synthesized bioactive compounds containing the pyrazole ring may be have important biological activities and thus can be good candidates for pharmaceutical applications. Therefore, the catalyst Mg/Al-LDH showed high catalytic activity. Besides, a series of bispyrazole molecules were synthesized with a good yield and easy separation of the catalyst by simple filtration. Moreover, DFT calculations and reactivity indexes are used to explain the selectivity of the condensation reaction between aryl benzaldehyde and 1,3-diketo-Nphenylpyrazole via Knoevenagel reaction, and the results are in good agreement with the experimental finding.

scholarly journals Synthesis and Biological Evaluation of a Novel Glycidyl Metharcylate/Phaytic Acid-Based on Bagasse Xylan Composite Derivative

Polymers ◽  
2021 ◽  
Vol 13 (13) ◽  
pp. 2084
Author(s):  
Mingkun Li ◽  
Heping Li ◽  
Hongli Liu ◽  
Zhiming Zou ◽  
Chaoyu Xie
Keyword(s):  
Lung Cancer ◽  
Thermal Stability ◽  
Ionic Liquid ◽  
Molecular Docking ◽  
Phytic Acid ◽  
Biological Activities ◽  
Biological Evaluation ◽  
Potential Candidate ◽  
Reaction Conditions ◽  
Cell Proliferation Inhibition

The development of natural biomass materials with excellent properties is an attractive way to improve the application range of natural polysaccharides. Bagasse Xylan (BX) is a natural polysaccharide with various biological activities, such as antitumor, antioxidant, etc. Its physic-chemical and biological properties can be improved by functionalization. For this purpose, a novel glycidyl metharcylate/phytic acid based on a BX composite derivative was synthesized by a free radical polymerization technique with glycidyl metharcylate (GMA; GMABX) and further esterification with phytic acid (PA; GMABX-PA) in ionic liquid. The effects of the reaction conditions (i.e., temperature, time, initiator concentration, catalyst concentration, GMA concentration, PA concentration, mass of ionic liquid) on grafting rate(G), conversion rate(C) and degree of substitution(DS) are discussed. The structure of the composite material structure was confirmed by FTIR, 1H NMR and XRD. SEM confirmed the particle morphology of the composite derivative. The thermal stability of GMABX-PA was determined by TG-DTG. Molecular docking was further performed to study the combination mode of the GMABX-PA into the active site of two lung cancer proteins (5XNV, 2EB2) and a blood cancer protein (2M6N). In addition, tumor cell proliferation inhibition assays for BX, GMABX-PA were carried out using the 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetraz -olium bromide (MTT) method. The results showed that various reaction conditions exhibited favorable gradient curves, and that a maximum G of 56% for the graft copolymerization and a maximum DS of 0.267 can be achieved. The thermal stability was significantly improved, as demonstrated by the fact that there was still 60% residual at 800 °C. The molecular docking software generated satisfactory results with regard to the evaluated binding energy and combining sites. The inhibition ratio of GMABX-PA on NCI-H460 (lung cancer cells) reached 29.68% ± 4.45%, which is five times higher than that of BX. Therefore, the material was shown to be a potential candidate for biomedical applications as well as for use as a heat resistant material.

scholarly journals Design of bifunctional quaternary phosphonium salt catalysts for CO2 fixation reaction with epoxides under mild conditions

2016 ◽  
Vol 18 (17) ◽  
pp. 4611-4615 ◽  
Author(s):  
Shiyao Liu ◽  
Naoki Suematsu ◽  
Keiji Maruoka ◽  
Seiji Shirakawa
Keyword(s):  
Co2 Fixation ◽  
Phosphonium Salt ◽  
Cyclic Carbonates ◽  
Efficient Synthesis ◽  
Reaction Conditions ◽  
Mild Conditions ◽  
Phosphonium Iodide ◽  
Fixation Reaction ◽  
Quaternary Phosphonium Salt

An efficient synthesis of cyclic carbonates from epoxides and CO2 under mild reaction conditions was achieved via the use of a designed bifunctional quaternary phosphonium iodide catalyst.

scholarly journals A Simple and Efficient Synthesis of Highly Substituted Indeno[1,2-b]pyrrole and Acenaphtho[1,2-b]pyrrole Derivatives by Tandem Three-Component Reactions

Molecules ◽  
2018 ◽  
Vol 23 (11) ◽  
pp. 3031 ◽  
Author(s):  
Xiaodong Tang ◽  
Songlei Zhu ◽  
Ying Ma ◽  
Ren Wen ◽  
Lanqi Cen ◽  
...  
Keyword(s):  
Environmentally Benign ◽  
Efficient Synthesis ◽  
Reaction Conditions ◽  
Dicarbonyl Compounds ◽  
Pyrrole Derivatives ◽  
Three Component Reaction ◽  
High Yields ◽  
Operational Simplicity

A green, convenient and tandem procedure for the efficient synthesis of highly substituted indeno[1,2-b]pyrrole and acenaphtho[1,2-b]pyrrole derivatives by domino three-component reaction of tryptamine/benzylamine, 1,3-dicarbonyl compounds and ninhydrin/ acenaphthenequinone is described. The significant features of this procedure were characterized by mild reaction conditions, high yields, operational simplicity and it being environmentally benign.

Late-Stage Sulfoximination: Improved Synthesis of the Anticancer Drug Candidate Atuveciclib

Synthesis ◽  
2018 ◽  
Vol 51 (04) ◽  
pp. 971-975 ◽  
Author(s):  
Vincent Reboul ◽  
Thomas Glachet ◽  
Xavier Franck
Keyword(s):  
Anticancer Drug ◽  
Late Stage ◽  
Drug Candidate ◽  
Efficient Synthesis ◽  
Reaction Conditions

An efficient synthesis of racemic atuveciclib was accomplished in five steps with an excellent 51% overall yield, using cheap reagents and mild reaction conditions. The key sulfoximination reaction was realized during the last step of the synthesis from the corresponding sulfide.

An efficient synthesis of methyl 2-cyano-3,12-dioxoursol-1,9-dien-28-oate (CDDU-methyl ester): analogues, biological activities, and comparison with oleanolic acid derivatives

2014 ◽  
Vol 12 (28) ◽  
pp. 5192-5200 ◽  
Author(s):  
Liangfeng Fu ◽  
Qi-Xian Lin ◽  
Karen T. Liby ◽  
Michael B. Sporn ◽  
Gordon W. Gribble
Keyword(s):  
Methyl Ester ◽  
Oleanolic Acid ◽  
Biological Activities ◽  
Efficient Synthesis

An efficient synthesis of methyl 2-cyano-3,12-dioxoursol-1,9-dien-28-oate (CDDU-methyl ester).

ChemInform Abstract: An Efficient Synthesis of Benzimidazoles via a Microwave Technique and Evaluation of Their Biological Activities.

ChemInform ◽  
2013 ◽  
Vol 44 (41) ◽  
pp. no-no
Author(s):  
Bahittin Kahveci ◽  
Emre Mentese ◽  
Musa Oezil ◽  
Serdar Uelker ◽  
Murat Ertuerk
Keyword(s):  
Biological Activities ◽  
Efficient Synthesis ◽  
Microwave Technique

Efficient synthesis of pyrido[2,3-d]pyrimidine-7-carboxylic acids catalyzed by a TiO2/SiO2 nanocomposite in aqueous media at room temperature

2018 ◽  
Vol 73 (9) ◽  
pp. 641-645 ◽  
Author(s):  
Sepehr Sadegh-Samiei ◽  
Shahrzad Abdolmohammadi
Keyword(s):  
Heterogeneous Catalyst ◽  
Carboxylic Acids ◽  
Room Temperature ◽  
Aqueous Media ◽  
Reaction Times ◽  
Molar Ratio ◽  
Efficient Synthesis ◽  
Reaction Conditions ◽  
Moderate Reaction ◽  
Recyclable Heterogeneous Catalyst

AbstractA novel and efficient synthesis of eight 5-aryl-1,3-dimethyl-2,4-dioxo-1,2,3,4,5,8-hexahydropyrido[2,3-d]pyrimidine-7-carboxylic acids using a TiO2/SiO2 nanocomposite with a molar ratio of 1:1 as a recyclable heterogeneous catalyst is described. The desired products, five of which are new, are formed in short reaction times (2–3 h) with high to excellent yields (94%–98%) under very moderate reaction conditions (room temperature, aqueous media).

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