scholarly journals One-Pot Synthesis of Phosphinylphosphonate Derivatives and Their Anti-Tumor Evaluations

Molecules ◽  
2021 ◽  
Vol 26 (24) ◽  
pp. 7609
Author(s):  
Jade Dussart-Gautheret ◽  
Julia Deschamp ◽  
Thibaut Legigan ◽  
Maelle Monteil ◽  
Evelyne Migianu-Griffoni ◽  
...  
Keyword(s):  
Human Cancer ◽  
Bone Matrix ◽  
Effective Control ◽  
31P Nmr Spectroscopy ◽  
Experimental Conditions ◽  
One Pot ◽  
Human Cancer Cell Lines ◽  
One Pot Synthesis ◽  
The One

This paper reports on the synthesis of new hydroxymethylene-(phosphinyl)phosphonates (HMPPs). A methodology has been developed to propose an optimized one-pot procedure without any intermediate purifications. Various aliphatic and (hetero)aromatic HMPPs were synthesized in good to excellent yields (53–98%) and the influence of electron withdrawing/donating group substitution on aromatic substrates was studied. In addition, the one-pot synthesis of HMPP was monitored by 31P NMR spectroscopy, allowing effective control of the end of the reaction and identification of all phosphorylated intermediate species, which enabled us to propose a reaction mechanism. Optimized experimental conditions were applied to the preparation of biological relevant aminoalkyl-HMPPs. A preliminary study of the complexation to hydroxyapatite (bone matrix) was carried out in order to verify its lower affinity towards bone compared to bisphosphonate molecules. Moreover, in vitro anti-tumor activity study revealed encouraging antiproliferative activities on three human cancer cell lines (breast, pancreas and lung).

scholarly journals Microwave Assisted One Pot Synthesis of Tetrazole Based 3-hydroxy-4H-chromen-4-ones by modified Algar-Flynn-Oyamada reaction and their Antimicrobial activity

2019 ◽  
Vol 63 (4) ◽  
Author(s):  
ASHOK DONGAMANTI ◽  
Nagaraju Nalaparaju ◽  
Sarasija Madderla ◽  
Vijaya Lakshmi Bommidi
Keyword(s):  
Escherichia Coli ◽  
Antimicrobial Activity ◽  
Klebsiella Pneumonia ◽  
Good Activity ◽  
One Pot ◽  
Microwave Assisted ◽  
One Pot Synthesis ◽  
Antimicrobial Studies ◽  
The One

In the present work, we report the one pot synthesis of tetrazole based 3-hydroxy-4H-chromen-4-ones 3(a-g) from  4-(1H-tetrazol-5-yl)benzaldehyde and 2-hydroxy acetophenone using KOH and H2O2 by modified Algar-Flynn-Oyamada reaction under conventional and microwave irradiation conditions. In this technique, flavonols are synthesized without isolating chalcones, in good yields. All the synthesized compounds were characterized by IR, NMR, MS and elemental. All newly synthesized compounds were screened for their in-vitro antimicrobial activity against strains such as Staphylococcus aurous, Bacillus subtilis, Klebsiella pneumonia, Escherichia coli, Aspergillus Niger, Aspergillus flavus, and Fusarium oxysporum. The results of antimicrobial studies revealed that most of the compounds exhibit good activity.

scholarly journals An Efficient, Three-Component Synthesis of Isoindolin-1-One-3-Phosphonates Under Mild and Solvent-Free Conditions and Their Biological Activities

2021 ◽  
Author(s):  
Hamida Jelali ◽  
Ibrahim S. Al Nasr ◽  
Waleed S. Koko ◽  
Tariq A. Khan ◽  
Eric Deniau ◽  
...  
Keyword(s):  
Leishmania Major ◽  
Human Cancer ◽  
Biological Activities ◽  
Antimicrobial Activities ◽  
Primary Amines ◽  
One Pot ◽  
Human Cancer Cell Lines ◽  
Solvent Free Conditions ◽  
Three Component Reaction

Abstract In this work, the synthesis of isoindolin-1-one-3-phosphonates by a ‘one-pot’ three-component reaction of 2-formylbenzoic acid with primary amines and dimethyl phosphite under solvent and catalyst free-conditions was reported. 1H NMR, 13C NMR, FT-IR and elemental analysis techniques, characterized the obtained compounds. The isoindolin-1-one-3-phosphonates were screened for their antimicrobial activities against bacteria and a fungus (Candida albicans). They were additionally also investigated for their anti-parasitical activities against Leishmania major promastigotes and amastigotes and Toxoplasma gondii in vitro. Cytotoxicity investigations of the isoindolin-1-one-3-phosphonates were led conducted in two human cancer cell lines, MDA-MB-231 and MCF-7and vero cells.

One-Pot Synthesis of New (1,3-Thiazolo[5,4-b]pyridin-2-yl)benzenediols and Their Antiproliferative Activities against Human Cancer Cell Lines

2012 ◽  
Vol 9 (1) ◽  
pp. 48-57 ◽  
Author(s):  
Joanna Matysiak ◽  
Monika M. Karpińska ◽  
Andrzej Niewiadomy ◽  
Joanna Wietrzyk ◽  
Dagmara Kłopotowska
Keyword(s):  
Cell Lines ◽  
Cancer Cell ◽  
Human Cancer ◽  
Cancer Cell Lines ◽  
Human Cancer Cell ◽  
One Pot ◽  
Human Cancer Cell Lines ◽  
One Pot Synthesis ◽  
Antiproliferative Activities

One-pot synthesis of fused benzoxazino[1,2,3]triazolyl[4,5-c]quinolinone derivatives and their anticancer activity

RSC Advances ◽  
2016 ◽  
Vol 6 (78) ◽  
pp. 74332-74339 ◽  
Author(s):  
Sirassu Narsimha ◽  
Kumara Swamy Battula ◽  
Satheesh Kumar Nukala ◽  
Ramesh Gondru ◽  
Yellu Narasimha Reddy ◽  
...  
Keyword(s):  
Cytotoxic Activity ◽  
Anticancer Activity ◽  
Cell Lines ◽  
Cancer Cell ◽  
Human Cancer ◽  
Human Cancer Cell ◽  
One Pot ◽  
Human Cancer Cell Lines ◽  
One Pot Synthesis ◽  
Mcf 7

Cu/Pd catalyzed one pot synthesis of fused benzoxazino[1,2,3]triazolyl[4,5-c]quinolinone hybrids and their cytotoxic activity against human cancer cell lines MCF-7, HeLa and A-549 is described.

Mild and efficient 64Cu labeling of perhydro-1, 4-diazepine derivatives for potential use with large peptides, proteins and antibodies

2020 ◽  
Vol 108 (7) ◽  
pp. 555-563 ◽  
Author(s):  
Lukas Greifenstein ◽  
Denise Späth ◽  
Jean Phillip Sinnes ◽  
Tilmann Grus ◽  
Frank Rösch
Keyword(s):  
Energy Barrier ◽  
Radioactive Isotope ◽  
One Pot ◽  
One Pot Synthesis ◽  
Novel Approach ◽  
The One ◽  
Cyclic Part ◽  
Potential Use

AbstractDATA (6-Amino-1,4-diazapine-triacetate) and AAZTA (6-Amino-1,4-diazapine-tetracetate) chelators represent a novel approach representing hybrid-chelates: possessing significant cyclic and acyclic character. It is believed that flexibility of the acyclic part facilitates rapid complexation, whilst the preorganized cyclic part minimizes the energy barrier to complexation and inhibits decomplexation processes. So far, these chelators have been used exclusively with 44Sc and 68Ga only. Recent results with natCu predict high stabilities for Cu-AAZTA, yet no radioactive labeling of AAZTA or DATA with 64Cu or any additional radioactive isotope has been reported. We present the one pot synthesis of the bifunctional derivatives AAZTA5OMe and DATA5mOMe and their labeling with 64Cu. In addition, in vitro stability of the respective complexes are presented.

An Overview of the One-pot Synthesis of Imidazolines

2020 ◽  
Vol 24 (20) ◽  
pp. 2341-2355
Author(s):  
Thaipparambil Aneeja ◽  
Sankaran Radhika ◽  
Mohan Neetha ◽  
Gopinathan Anilkumar
Keyword(s):  
Asymmetric Catalysis ◽  
Organic Compounds ◽  
Ring Opening ◽  
Ecological Impact ◽  
Chiral Auxiliary ◽  
One Pot ◽  
One Pot Synthesis ◽  
The One ◽  
Synthetic Intermediate ◽  
Heterocyclic Moiety

One-pot syntheses are a simple, efficient and easy methodology, which are widely used for the synthesis of organic compounds. Imidazoline is a valuable heterocyclic moiety used as a synthetic intermediate, chiral auxiliary, chiral catalyst and a ligand for asymmetric catalysis. Imidazole is a fundamental unit of biomolecules that can be easily prepared from imidazolines. The one-pot method is an impressive approach to synthesize organic compounds as it minimizes the reaction time, separation procedures, and ecological impact. Many significant one-pot methods such as N-bromosuccinimide mediated reaction, ring-opening of tetrahydrofuran, triflic anhydrate mediated reaction, etc. were reported for imidazoline synthesis. This review describes an overview of the one-pot synthesis of imidazolines and covers literature up to 2020.

Synthesis and Cytotoxicity Assessment of Novel 7-O- and 14-O-Derivatives of Glaucocalyxin A

2020 ◽  
Vol 20 (10) ◽  
pp. 1241-1249
Author(s):  
Hong-Chuan Liu ◽  
Li-Ming Qiao ◽  
Wei Zheng ◽  
Zhao-Bao Xiang ◽  
Hai-Sheng Chen ◽  
...  
Keyword(s):  
Acute Toxicity ◽  
Cell Lines ◽  
Cancer Cell ◽  
Human Cancer ◽  
Folk Medicine ◽  
A549 Cells ◽  
Cancer Cell Lines ◽  
Human Cancer Cell Lines ◽  
Derivatives Of

Background: Rabdosia japonica has been historically used in China as a popular folk medicine for the treatment of cancer, hepatitis, and gastricism. Glaucocalyxin A (GLA), an ent-kaurene diterpene isolated from Rabdosia japonica, is one of the main active ingredients showing potent inhibitory effects against several types of tumor cells. To the best of our knowledge, studies regarding the structural modification and Structure- Activity Relations (SAR) of this compound have not yet been reported. Objective: The aim of this study was to discover more potent derivatives of GLA and investigate their SAR and cytotoxicity mechanisms. Methods: Novel 7-O- and 14-O-derivatives of GLA were synthesized by condensation of acids or acyl chloride. The anti-tumor activities of these derivatives against various human cancer cell lines were evaluated in vitro by MTT assays. Apoptosis assays of compound 17 (7,14-diacylation product) were performed on A549 and HL-60 cells by flow cytometry and TUNNEL. The acute toxicity of this compound was tested on mice, at the dose of 300mg per kg body weight. Results: Seventeen novel 7-O- and 14-O-derivatives of GLA (1-17) were synthesized. These compounds showed potent cytotoxicity against the tested cancer cell lines, and almost all of them were found to be more cytotoxic than GLA and oridonin. Of the synthesized derivatives, compound 17 presented the greatest cytotoxicity, with IC50 values of 0.26μM and 1.10μM in HL-60 and CCRF-CEM cells, respectively. Furthermore, this compound induced weak apoptosis of A549 cells but showed great potential in stimulating the apoptosis of HL- 60 cells. Acute toxicity assays indicated that compound 17 is relatively safer. Conclusion: The results reported herein indicate that the synthesized GLA derivatives exhibited greater cytotoxicity against leukemia cells than against other types of tumors. In particular, 7,14-diacylation product of GLA was found to be an effective anti-tumor agent. However, the cytotoxicity mechanism of this product in A549 cells is expected to be different than that in other tumor cell lines. Further research is needed to confirm this hypothesis.

Evaluation of Pyrano[3,2 C] Quinoline Analogues as Anticancer Agents

2019 ◽  
Vol 19 (10) ◽  
pp. 1285-1292 ◽  
Author(s):  
Kuldip D. Upadhyay ◽  
Anamik K. Shah
Keyword(s):  
Anticancer Agents ◽  
Human Cancer ◽  
Biological Activities ◽  
Cytotoxic Agents ◽  
Tumor Growth Inhibition ◽  
Mice Model ◽  
One Pot ◽  
Aryl Ring ◽  
Hct 116

Background: Quinoline analogues exhibited diversified biological activities depending on the structure type. A number of natural products with pyrano[3,2-c]quinolone structural motifs and patented chromenes were reported as promising cytotoxic agents. Objective: The present study is aimed to evaluate a new series of pyrano[3,2-c]quinoline scaffolds derived from the fusion of bioactive quinolone pharmacophore with structurally diverse aryl substituted chromene for its cytotoxicity. Methods: A library of pyrano[3,2-c]quinoline analogues was prepared from one-pot multi component synthesis using various aromatic aldehydes, malononitrile and 2,4-dihydroxy-1-methylquinoline. The new synthetics were primarily screened for its cytotoxicity (IC50) against different human cancer cell lines in vitro. The promising synthetics were further evaluated in vitro for their potency against different kinase activity. The promising compounds were finally tested for their in vivo efficacy in SCID type mice HCT-116 tumor model. Results: The screening results revealed that compounds 4c, 4f, 4i and 4j showed promising activity in in vitro study. However, compound 4c was found to be the most potent candidate with 23% tumor growth inhibition in HCT-116 tumor mice model. Conclusion: The structure activity relationship suggested that 3-substitution on the aryl ring at C4 position of the pyrano[3,2 c]quinolone moiety seems to have an important position for cytotoxicity activity. However, 3- chloro substitution at C4 aryl ring showed a significant alteration of the bioactive conformer of the parent scaffold and outcome with compound 4c as the most potent candidate of the series.

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