Cytotoxic 1,5-diaryl-3-oxo-1,5-pentadienes: An assessment and comparison of membrane permeability using Caco-2 and MDCK monolayers

Singh, Ravi Shankar Prasad; Michel, Deborah; Das, Umashankar; Dimmock, Jonathan R.; Alcorn, Jane

doi:10.1016/j.bmcl.2014.09.074

Cited by 14 publications

(5 citation statements)

References 15 publications

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“…The C–H alkenylation is another important C–C bond-forming reaction. Olefinated organic molecules like vinylarenes play a significant role as key intermediates in organic synthesis and are also present in various natural products as well as drug molecules [ 65 – 68 ]. Though there are traditional methods available for C–H olefinations they suffer from some disadvantages such as for example requiring prefunctionalized substrates as in case of the Heck cross-coupling [ 69 – 70 ].…”

Section: Reviewmentioning

confidence: 99%

Pyridine C(sp²)–H bond functionalization under transition-metal and rare earth metal catalysis

Sindhe¹,

Reddy²,

Rajkumar³

et al. 2023

Beilstein J. Org. Chem.

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Pyridine is a crucial heterocyclic scaffold that is widely found in organic chemistry, medicines, natural products, and functional materials. In spite of the discovery of several methods for the synthesis of functionalized pyridines or their integration into an organic molecule, new methodologies for the direct functionalization of pyridine scaffolds have been developed during the past two decades. In addition, transition-metal-catalyzed C–H functionalization and rare earth metal-catalyzed reactions have flourished over the past two decades in the development of functionalized organic molecules of concern. In this review, we discuss recent achievements in the transition-metal and rare earth metal-catalyzed C–H bond functionalization of pyridine and look into the mechanisms involved.

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Section: Reviewmentioning

confidence: 99%

Pyridine C(sp²)–H bond functionalization under transition-metal and rare earth metal catalysis

Sindhe¹,

Reddy²,

Rajkumar³

et al. 2023

Beilstein J. Org. Chem.

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“…A major interest in our laboratories is the design, synthesis and antineoplastic evaluation of 1,5-diaryl-3-oxo-1,4-pentadienes mounted on a variety of scaffolds, which give rise to series 1 (Figure 1). Most previous studies of structurally-related compounds were conducted without or with very low numbers of normal cells at the same time as cancer cell lines, making it difficult to compare tumor-specificity between compounds [1][2][3][4][5][6][7][8][9][10]. Among these previous 10 papers, three papers are from our research group [5][6][7].…”

Section: Introductionmentioning

confidence: 99%

“…Most previous studies of structurally-related compounds were conducted without or with very low numbers of normal cells at the same time as cancer cell lines, making it difficult to compare tumor-specificity between compounds [1][2][3][4][5][6][7][8][9][10]. Among these previous 10 papers, three papers are from our research group [5][6][7]. Our group used four human oral squamous cell carcinoma cell lines (Ca9-22, HSC-2, HSC-3, HSC-4) with three human normal oral mesenchymal cells (HGF, HPLF, HPC) [5,6] and human CRL1790 (non-malignant colon cells) [10].…”

Section: Introductionmentioning

confidence: 99%

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Cytotoxic Tumour-Selective 1,5-Diaryl-3-Oxo-1,4-Pentadienes Mounted on a Piperidine Ring

et al. 2021

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A series of 3,5-bis(benzylidene)-4-piperidones 2a–u were prepared as candidate cytotoxic agents. In general, the compounds are highly toxic to human gingival carcinoma (Ca9-22), human squamous carcinoma-2 (HSC-2) and human squamous carcinoma-4 (HSC-4) neoplasms, but less so towards non-malignant human gingival fibroblast (HGF), human periodontal ligament fibroblast (HPLF) and human pulp cells (HPC), thereby demonstrating tumour-selective toxicity. A further study revealed that most of the compounds in series 2 were more toxic to the human Colo-205 adenocarcinoma cell line (Colo-205), human HT29 colorectal adenocarcinoma cells (HT-29) and human CEM lymphoid cells (CEM) neoplasms than towards non-malignant human foreskin Hs27 fibroblast line (Hs27) cells. The potency of the cytotoxins towards the six malignant cell lines increased as the sigma and sigma star values of the aryl substituents rose. Attempts to condense various aryl aldehydes with 2,2,6,6-tetramethyl-4-piperidone led to the isolation of some 1,5-diaryl-1,4-pentadien-3-ones. The highest specificity for oral cancer cells was displayed by 2e and 2r. In the case of 2r, its selective toxicity exceeded that of doxorubicin and melphalan. The enones 2k, m, o have the highest SI values towards colon cancer and leukemic cells. Both 2e,r inhibited mitosis and increased the subG1 population (with a transient increase in G2/M phase cells). Slight activation of caspase-3, based on the cleavage of poly(ADP-ribose)polymerase (PARP) and procaspase 3, was detected.

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“…For instance, derivatives of phenols, aldehydes, and ketones, viz., imines, oximes, hydrazones, etc., are some examples of transient DGs that have been utilized in C–H bond functionalizations. − However, new transient directing groups for the selective C–H functionalizations are still highly desirable as well as appreciable. o -Alkenylanilines are important building blocks in many organic transformations and are prevalent in many bioactive compounds …”

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confidence: 99%

Transformable Transient Directing Group-Assisted C(sp²)–H Activation: Synthesis and Late-Stage Functionalizations of o-Alkenylanilines

et al. 2022

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The isocyanate group in aryl isocyanates serves as a transformable transient directing group in a Ru(II)-catalyzed ortho olefination leading to o-alkenylanilines. In alcoholic solvents, aryl isocyanates are transformed into carbamates, which initiate the insertion of acrylates via o-C–H activation. In particular, t AmOH serves the dual role of solvent-cum transient directing mediator. The o-alkenylanilines are converted into azacoumarins and subsequently into C-4 aryl-substituted azacoumarins using aryl iodides as coupling partners via Pd(II)-catalyzed C–H functionalizations.

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Cytotoxic 1,5-diaryl-3-oxo-1,5-pentadienes: An assessment and comparison of membrane permeability using Caco-2 and MDCK monolayers

Cited by 14 publications

References 15 publications

Pyridine C(sp²)–H bond functionalization under transition-metal and rare earth metal catalysis

Pyridine C(sp²)–H bond functionalization under transition-metal and rare earth metal catalysis

Cytotoxic Tumour-Selective 1,5-Diaryl-3-Oxo-1,4-Pentadienes Mounted on a Piperidine Ring

Transformable Transient Directing Group-Assisted C(sp²)–H Activation: Synthesis and Late-Stage Functionalizations of o-Alkenylanilines

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Cytotoxic 1,5-diaryl-3-oxo-1,5-pentadienes: An assessment and comparison of membrane permeability using Caco-2 and MDCK monolayers

Cited by 14 publications

References 15 publications

Pyridine C(sp2)–H bond functionalization under transition-metal and rare earth metal catalysis

Pyridine C(sp2)–H bond functionalization under transition-metal and rare earth metal catalysis

Cytotoxic Tumour-Selective 1,5-Diaryl-3-Oxo-1,4-Pentadienes Mounted on a Piperidine Ring

Transformable Transient Directing Group-Assisted C(sp2)–H Activation: Synthesis and Late-Stage Functionalizations of o-Alkenylanilines

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Product

Resources

About

Pyridine C(sp²)–H bond functionalization under transition-metal and rare earth metal catalysis

Pyridine C(sp²)–H bond functionalization under transition-metal and rare earth metal catalysis

Transformable Transient Directing Group-Assisted C(sp²)–H Activation: Synthesis and Late-Stage Functionalizations of o-Alkenylanilines