Assembly of New Heterocycles through an Effective Use of Bisaldehydes by Using a Sequential GBB/Ugi Reaction

Kaur, Tanpreet; Gautam, Ram Nayan; Sharma, Anuj

doi:10.1002/asia.201601009

Cited by 21 publications

(6 citation statements)

References 49 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Truly catalyst free reactions are only recently reported by Sharma et al, but seem to work exclusively in a reaction using 2-aminothiazole under microwave conditions. [160,161,171,172,196] In some of the catalyst-free reactions, a carboxylic acid functional group was found in one of the three components that facilitated the reaction in good yields, although it must be noted, that the use of carboxylic acids will show Passerini poisoning. This side reaction is driven by the presence of 3 components; aldehyde, isocyanide and carboxylic acid that allow for the P-3CR to happen (Scheme 19).…”

Section: Catalysts In the Gbb-3crmentioning

confidence: 99%

The Groebke‐Blackburn‐Bienaymé Reaction

2019

View full text Add to dashboard Cite

Imidazo[1,2‐a]pyridine is a well‐known scaffold in many marketed drugs, such as Zolpidem, Minodronic acid, Miroprofen and DS‐1 and it also serves as a broadly applied pharmacophore in drug discovery. The scaffold revoked a wave of interest when Groebke, Blackburn and Bienaymé reported independently a new three component reaction resulting in compounds with the imidazo[1,2‐a]‐heterocycles as a core structure. During the course of two decades the Groebke Blackburn Bienaymé (GBB‐3CR) reaction has emerged as a very important multicomponent reaction (MCR), resulting in over a hundred patents and a great number of publications in various fields of interest. Now two compounds derived from GBB‐3CR chemistry received FDA approval. To celebrate the first 20 years of GBB‐chemistry, we present an overview of the chemistry of the GBB‐3CR, including an analysis of each of the three starting material classes, solvents and catalysts. Additionally, a list of patents and their applications and a more in‐depth summary of the biological targets that were addressed, including structural biology analysis, is given.

show abstract

Section: Catalysts In the Gbb-3crmentioning

confidence: 99%

The Groebke‐Blackburn‐Bienaymé Reaction

2019

View full text Add to dashboard Cite

show abstract

“…However, a few studies have been performed on the use of bis ‐benzaldehydes as a starting material for the preparation of novel compounds with different applications such as redox flow battery, [ 25 ] biofunctional dynamic covalent polymer, [ 26 ] allosteric effectors of hemoglobin, [ 27 ] fluorescence‐based assay, [ 28 ] in Groebke–Blackburn–Bienayme/Ugi reactions, [ 29 ] electrical conductivity, [ 30 ] macrocyclization, [ 31 ] breaking and mending of the porphyrin, [ 32 ] and a broad spectrum of biological activities. [ 16,23 ]…”

Section: Introductionmentioning

confidence: 99%

Novel 2‐cyanoacrylamido‐4,5,6,7‐tetrahydrobenzo[b]thiophene derivatives as potent anticancer agents

Sroor

Aboelenin

Mahrous

et al. 2020

Archiv der Pharmazie

View full text Add to dashboard Cite

Ethyl 2-acrylamido-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxylate as well as its corresponding bis-derivatives, 5-10, with aliphatic linkers were synthesized, fully characterized, and tested as novel anticancer agents. The targeted compounds, 5-10, were obtained by the Knoevenagel condensation reactions of bis-o-or-p-aldehyde with a molar ratio of ethyl 2-(2-cyanoacetamido)-4,5,6,7tetrahydrobenzo[b]thiophene-3-carboxylate of 2 in the presence of piperidine in excellent yields (93-98%). The in vitro anticancer activities of the prepared compounds were evaluated against HepG2, MCF-7, HCT-116, and BJ1 cells. Compounds 7 and 9 emerged as the most promising compounds, with IC 50 values of 13.5 and 32.2 µg/ml, respectively, against HepG2 cells, compared with the reference drug doxorubicin (IC 50 : 21.6 µg/ml). Real-time reverse-transcription polymerase chain reaction was used to measure the changes in expression levels of the COL10A1 and COL11A1, ESR1, and ERBB2, or AXIN1 and CDKN2A genes within the treated cells, as genetic markers for colon, breast, or liver cancers, respectively. Treatment of the colon cancer cells with compounds 5, 9, and 10, or breast and liver cancers cells with compounds 7, 8, 9, and 10 downregulated the expression of the investigated tumor markers. The DNA damage values (depending on comet and DNA fragmentation assays) increased significantly upon treatment of colon cancer cells with compounds 5, 9, and 10, and breast and liver cells with compounds 8, 9, and 10. The structure-activity relationship suggested that the increase of the chain of the alkyl linker increases the anticancer activity and the compounds with bis-cyanoacrylamide moieties are more active than those with one cyanoacrylamide moiety.

show abstract

“…In this way, a variety of transformations involving Groebke–Blackburn–Bienaymé (GBB)/Hantzsch, and Biginelli/Ugi-azide sequential reactions were reported by Shahrisa [29]. Similarly, Sharma and co-workers disclosed a related approach [30]. Moreover, 2,4-diaminopyrimidine underwent selective GBB processes leading to a single monoadduct, which reacted again with another isocyanide/aldehyde pair to yield a 5-component adduct in a selective manner.…”

Section: Reviewmentioning

confidence: 99%

Selectivity in multiple multicomponent reactions: types and synthetic applications

Ghashghaei

Seghetti

2019

Beilstein J. Org. Chem.

View full text Add to dashboard Cite

Multiple multicomponent reactions reach an unparalleled level of connectivity, leading to highly complex adducts. Usually, only one type of transformation involving the same set of reactants takes place. However, in some occasions this is not the case. Selectivity issues then arise, and different scenarios are analyzed. The structural pattern of the reactants, the reaction design and the experimental conditions are the critical factors dictating selectivity in these processes.

show abstract

Assembly of New Heterocycles through an Effective Use of Bisaldehydes by Using a Sequential GBB/Ugi Reaction

Cited by 21 publications

References 49 publications

The Groebke‐Blackburn‐Bienaymé Reaction

The Groebke‐Blackburn‐Bienaymé Reaction

Novel 2‐cyanoacrylamido‐4,5,6,7‐tetrahydrobenzo[b]thiophene derivatives as potent anticancer agents

Selectivity in multiple multicomponent reactions: types and synthetic applications

Contact Info

Product

Resources

About