scholarly journals One-pot multicomponent green Hantzsch synthesis of 1,2-dihydropyridine derivatives with antiproliferative activity

2020 ◽  
Vol 16 ◽  
pp. 2862-2869
Author(s):  
Giovanna Bosica ◽  
Kaylie Demanuele ◽  
José M Padrón ◽  
Adrián Puerta
Keyword(s):  
Antiproliferative Activity ◽  
Heterogeneous Catalysts ◽  
Aromatic Aldehydes ◽  
Significant Loss ◽  
Cancer Cell Growth ◽  
One Pot ◽  
Alumina Support ◽  
Human Solid Tumor ◽  
High Yields ◽  
Dihydropyridine Derivatives

A rapid route for obtaining unsymmetrical 1,2-dihydropyridines (1,2-DHPs) as opposed to 1,4-dihydropyridines (1,4-DHPs) has been achieved via a one-pot multicomponent Hantzsch reaction. A benign protocol has been developed for the preparation of various 1,2-dihydropyridine derivatives using heterogenized phosphotungstic acid on alumina support (40 wt %). High yields of over 75% have been accomplished in just 2–3.5 h after screening several heterogeneous catalysts and investigating the optimal reaction conditions. The catalyst chosen has passed the heterogeneity test and was shown to have the potential of being reused for up to 8 consecutive cycles before having a significant loss in activity. In addition, aromatic aldehydes gave the aforementioned regioisomer while the classical 1,4-DHPs were obtained when carrying out the reaction using aliphatic aldehydes. The preliminary study of the antiproliferative activity against human solid tumor cells demonstrated that 1,2-DHPs could inhibit cancer cell growth in the low micromolar range.

Synthesis of 3-(Cyclohexylamino)-2-arylimidazo[1,2-a]pyridine-8- carboxylic Acids Via an Efficient Three-component Condensation Reaction between Cyclohexylisocyanide and 2-Aminopyridine-3-carboxylic Acid in the Presence of Aromatic Aldehyde

2018 ◽  
Vol 21 (4) ◽  
pp. 298-301 ◽  
Author(s):  
Ghasem Marandi
Keyword(s):  
Biological Sciences ◽  
Carboxylic Acid ◽  
Carboxylic Acids ◽  
High Performance ◽  
Condensation Reaction ◽  
Aromatic Aldehydes ◽  
New Materials ◽  
One Pot ◽  
High Yields ◽  
Benzaldehyde Derivatives

Aim and Objective: The reaction of cyclohexylisocyanide and 2-aminopyridine-3- carboxylic acid in the presence of benzaldehyde derivatives in ethanol led to 3-(cyclohexylamino)-2- arylimidazo[1,2-a]pyridine-8-carboxylic acids in high yields. In a three component condensation reaction, isocyanide reacts with 2-aminopyridine-3-carboxylic acid and aromatic aldehydes without any prior activation. Material and Methods: The synthesized products have stable structures which have been characterized by IR, 1H, 13C and Mass spectroscopy as well as CHN-O analysis. Results: In continuation of our attempts to develop simple one-pot routes for the synthesis of 3- (cyclohexylamino)-2-arylimidazo[1,2-a]pyridine-8-carboxylic acids, aromatic aldehydes with divers substituted show a high performance. Conclusion: In conclusion, this study introduces the art of combinatorial chemistry using a simple one-pot procedure for the synthesis of new materials which are interesting compounds in medicinal and biological sciences.

Synthesis, Antiproliferative Activity and Molecular Docking of New Thiazole/Benzothiazole Fused Pyranopyrimidine Derivatives

2020 ◽  
Vol 17 (12) ◽  
pp. 951-958
Author(s):  
Pallava Nagaraju ◽  
Pedavenkatagari Narayana Reddy ◽  
Pannala Padmaja ◽  
Vinod G. Ugale
Keyword(s):  
Molecular Docking ◽  
Cell Lines ◽  
Antiproliferative Activity ◽  
Aromatic Aldehydes ◽  
Human Colon ◽  
Docking Studies ◽  
Human Colon Cancer ◽  
One Pot ◽  
Human Embryonic Kidney Cells ◽  
Heterocyclic Molecules

A new class of 4H,5H-benzo[4,5]thiazolo[3,2-a]pyrano[2,3-d]pyrimidin-5-one and 5H,6Hpyrano[ 2,3-d]thiazolo[3,2-a]pyrimidin-5-one derivatives were synthesized via the one-pot threecomponent reaction of 2-hydroxy-4H-benzo[4,5]thiazolo[3,2-a]pyrimidin-4-one and 7-hydroxy-5Hthiazolo[ 3,2-a]pyrimidin-5-one to various aromatic aldehydes and malononitrile. This domino transformation involves the formation of pyranopyrimidine ring by the formation of three C–C bonds and one C– O bond a single synthetic operation. As the products precipitate out of the reaction, simple filtration is enough to gather the products, and thus, there is no need for work-up or column-chromatography. The synthesized thiazole/benzothiazole fused pyranopyrimidine derivatives were evaluated for their antiproliferative activity against four cancer cell lines namely DU 145 (prostate cancer), Hela (Human cervical cancer), MDA-MB-231 (breast cancer), HT-29 (Human colon cancer) and normal cell line HEK293 (human embryonic kidney cells). The results demonstrated that synthesized compounds were selective in its cytotoxicity to cancer cells compared to normal cells. Among these compounds, 2-amino-9- methoxy-5-oxo-4-(3,4,5-trimethoxyphenyl)-4H,5H-benzo[4,5]thiazolo[3,2-a]pyrano[2,3-d]pyrimidine- 3-carbonitrile 4i exhibited the most potent antiproliferative activity against the tested cell lines. Molecular docking studies revealed that these active heterocyclic molecules bind selectively in the colchicine binding site of tubulin polymer.

scholarly journals Environ-Economic Synthesis and Characterization of Some New 1,2,4-Triazole Derivatives as Organic Fluorescent Materials and Potent Fungicidal Agents

2013 ◽  
Vol 2013 ◽  
pp. 1-19 ◽  
Author(s):  
Harshita Sachdeva ◽  
Rekha Saroj ◽  
Sarita Khaturia ◽  
Diksha Dwivedi
Keyword(s):  
Aromatic Aldehydes ◽  
New Drugs ◽  
Fluorescence Study ◽  
One Pot ◽  
Triazole Derivatives ◽  
Fluorescent Materials ◽  
Cyclocondensation Reaction ◽  
Practical Tool ◽  
High Yields

A multicomponent one-pot clean cyclocondensation reaction of 4-chloro-2-nitro aniline/amino acids and aromatic aldehydes/indole-2,3-diones with thiosemicarbazide in water yielding triazole/spiro indole-triazole derivatives in high yields and shorter reaction time and displaying excellent florescent property is reported. The developed MCR may provide a valuable practical tool for the synthesis of new drugs containing the title core fragment. All the newly synthesized compounds have been characterized by IR, 1HNMR, 13CNMR, and fluorescence study and also been screened for antimicrobial activity.

Silica sulfuric acid magnetic nanoparticle: an efficient and ecofriendly catalyst for synthesis of spiro[2-amino-4H-pyran-oxindole]s

2015 ◽  
Vol 93 (5) ◽  
pp. 546-549 ◽  
Author(s):  
Ali Reza Karimi ◽  
Meysam Sourinia ◽  
Zeinab Dalirnasab ◽  
Marzie Karimi
Keyword(s):  
Sulfuric Acid ◽  
Magnetic Nanoparticle ◽  
Ultrasound Irradiation ◽  
Significant Loss ◽  
Silica Sulfuric Acid ◽  
One Pot ◽  
External Magnet ◽  
Three Component Reaction ◽  
The One ◽  
High Yields

Silica sulfuric acid magnetic nanoparticles efficiently catalyze the one-pot, three-component reaction of isatins and malononitrile with dimedone, 1,3-dimethylbarbituric acid or 4-hydroxycoumarin in EtOH–H2O to afford the corresponding spiro[2-amino-4H-pyran-oxindole] derivatives in high yields under ultrasound irradiation at 60 °C. The heterogeneous nanocatalyst could be recovered easily from the reaction mixture using an external magnet and reused many times without significant loss of its catalytic activity.

scholarly journals Synthesis of Bis-2,3-dihydroquinazolin-4(1H)-ones and 2,3-Dihydroquinazolin-4(1H)-ones Derivatives with the Aid of Silica-Supported Preyssler Nanoparticles

2013 ◽  
Vol 2013 ◽  
pp. 1-14 ◽  
Author(s):  
Ali Gharib ◽  
Bibi Robabeh Hashemipour Khorasani ◽  
Manouchehr Jahangir ◽  
Mina Roshani ◽  
Reza Safaee
Keyword(s):  
Primary Amine ◽  
Ammonium Carbonate ◽  
Aromatic Aldehydes ◽  
Product Yield ◽  
Primary Amines ◽  
Isatoic Anhydride ◽  
One Pot ◽  
High Yields ◽  
First Time

One-pot three-component condensation of isatoic anhydride with primary amines or ammonium carbonate and aromatic aldehydes in refluxing ethanol in the presence of catalytic amounts of silica-supported preyssler nanoparticles (SPNP) afforded the corresponding 2,3-dihydroquinazolin-4(1H)-ones in high yields, and bis-dihydroquinazolinones were synthesized for the first time by a novel pseudo-five-component condensation of isatoic anhydride, a primary amine, and a dialdehyde in water. The catalyst is reusable and can be applied several times without any decrease in product yield.

One-pot multicomponent synthesis of β-acetamidoketones catalysed by pTSA1

2007 ◽  
Vol 85 (7-8) ◽  
pp. 479-482 ◽  
Author(s):  
Biswanath Das ◽  
Kongara Ravinder Reddy ◽  
Yallamalla Srinivas ◽  
Rathod Aravind Kumar
Keyword(s):  
Multicomponent Reaction ◽  
Acetyl Chloride ◽  
Reaction Times ◽  
Aromatic Aldehydes ◽  
Catalytic Amount ◽  
Multicomponent Synthesis ◽  
One Pot ◽  
High Yields ◽  
Three Component Coupling

A catalytic amount of pTSA has been found to be effective to carry out a one-pot three-component coupling of aromatic aldehydes, enolizable ketones or ketoesters, and acetonitrile in the presence of acetyl chloride to afford β-acetamidoketones in high yields. Short reaction times and inexpensive catalyst are main advantages of this protocol.Key words: β-acetamidoketone, pTSA, multicomponent reaction, diastereoselectivity.

CeCl3·7H2O as mild and efficient catalyst for the one-pot multicomponent synthesis of 8-aryl-7,8-dihydro[1,3]dioxolo[4,5-g]chromen-6-ones

2011 ◽  
Vol 76 (4) ◽  
pp. 235-241 ◽  
Author(s):  
Li-Qiang Wu ◽  
Wei-Lin Li ◽  
Fu-Lin Yan
Keyword(s):  
Aromatic Aldehydes ◽  
Environmentally Benign ◽  
Multicomponent Synthesis ◽  
One Pot ◽  
Efficient Catalyst ◽  
Solvent Free Conditions ◽  
Three Component Reaction ◽  
The One ◽  
High Yields ◽  
Work Up

A series of new 8-aryl-7,8-dihydro[1,3]dioxolo[4,5-g]chromen-6-ones were synthesized via a three-component reaction of 3,4-methylenedioxyphenol, aromatic aldehydes and Meldrum’s acid in the presence of CeCl3·7H2O under solvent-free conditions. The method provided several advantages such as easy work-up, high yields and environmentally benign procedure.

A Green Approach for the Synthesis of Novel 7,11-Dihydro-6H-chromeno[3,4-e]isoxazolo[5,4-b]pyridin-6-one Derivatives Using Acidic Ionic Liquid [C4mim][HSO4]

2016 ◽  
Vol 69 (9) ◽  
pp. 1049 ◽  
Author(s):  
Sudesh Kumari ◽  
M. Rajeswari ◽  
Jitender M. Khurana
Keyword(s):  
Ionic Liquid ◽  
Crystal Packing ◽  
Aromatic Aldehydes ◽  
Green Solvent ◽  
One Pot ◽  
X Ray ◽  
Acidic Ionic Liquid ◽  
Green Approach ◽  
Wide Range ◽  
High Yields

A multicomponent reaction capable of affording a wide range of novel 7,11-dihydro-6H-chromeno[3,4-e]isoxazolo[5,4-b]pyridin-6-one derivatives via one-pot three-component condensation of 4-hydroxycoumarin, aromatic aldehydes, and 5-amino-3-methylisoxazole in ionic liquid 1-butyl-3-methylimidazolium hydrogen sulfate ([C4mim][HSO4]) is reported. Structures have been confirmed by spectral and X-ray studies. Crystal packing of 4b has also been reported. Green solvent, short reaction time, easy workup, and high yields are the salient features of the present protocol.

One Pot Three Component Synthesis of 9-arylpolyhydroacridine Derivatives in an Ionic Liquid Medium

2005 ◽  
Vol 2005 (9) ◽  
pp. 600-602 ◽  
Author(s):  
Yu-Ling Li ◽  
Mei-Mei Zhang ◽  
Xiang-Shan Wang ◽  
Da-Qing Shi ◽  
Shu-Jiang Tu ◽  
...  
Keyword(s):  
Ionic Liquid ◽  
Ionic Liquids ◽  
Ammonium Acetate ◽  
Aromatic Aldehydes ◽  
Environmentally Benign ◽  
Reaction Conditions ◽  
One Pot ◽  
High Yields ◽  
Work Up ◽  
Ionic Liquid Medium

In this paper the preparation of 3,3,6,6-tetramethyl-9-aryl-1,2,3,4,5,6,7,8,9,10- decahydroacridin-1,8-dione derivatives from aromatic aldehydes, 5,5-dimethyl-1,3- cyclohexanedione and ammonium acetate in ionic liquids [bmim+][BF4-] is described. This new method has the advantages of easier work-up, milder reaction conditions, high yields and an environmentally benign procedure compared with other methods.

Nano ZrO2: an efficient, recyclable, and inexpensive catalyst for diastereoselective three-component Mannich reactions

2014 ◽  
Vol 92 (7) ◽  
pp. 659-664 ◽  
Author(s):  
M. Saeed Abaee ◽  
Elahe Akbarzadeh ◽  
Abbas Shockravi ◽  
Mohammad M. Mojtahedi ◽  
Hamid Reza Khavasi
Keyword(s):  
Spectroscopic Data ◽  
Room Temperature ◽  
Aromatic Aldehydes ◽  
Significant Loss ◽  
Mannich Reactions ◽  
X Ray ◽  
X Ray Crystallography ◽  
Aniline Derivatives ◽  
High Yields ◽  
Acyclic Ketones

A facile procedure is developed for the three-component Mannich reactions of several heterocyclic, homocyclic, and acyclic ketones by using catalytic quantities of nano ZrO2. As a result, the starting ketones undergo rapid reactions with a variety of aromatic aldehydes and aniline derivatives at room temperature to produce stereoselectively high yields of the corresponding anti β-amino ketones. Interestingly, the catalyst could be recycled for several runs in a row without significant loss of its activity. The structure of the products was assigned based on their spectroscopic data and the anti stereoselectivity was confirmed by X-ray crystallography.

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