Phosphonate Derivatives of 3,5-bis(arylidene)-4-piperidone: Synthesis and Biological Evaluation

2020 ◽  
Vol 18 (3) ◽  
pp. 245-254
Author(s):  
Shweta Mishra ◽  
Debashree Das ◽  
Adarsh Sahu ◽  
Shailendra Patil ◽  
Ram Kishore Agrawal ◽  
...  
Keyword(s):  
Biological Evaluation ◽  
Cytotoxic Potential ◽  
In Series ◽  
Anti Oxidant ◽  
Potential Activity ◽  
Anti Inflammatory ◽  
Relationship Of ◽  
Biological Spectrum ◽  
Derivatives Of

Background: 3,5-Bis(arylidene)-4-piperidinones (BAP) belong to a wide class of cross conjugated dienones. The 1,5-diaryl-3-oxo-1,4-pentadienyl fragment of the BAP moiety is responsible for the molecule's anti-tumor, antioxidant, antimicrobial and anti-inflammatory manifestations. In the present study, we present combinations of phosphonate and 3,5-bis(arylidene)-4- piperidone pharmacophores. The anti-inflammatory, anti-oxidant potential, anti-proliferative, cytotoxic potential and antimicrobial of the title compounds were evaluated in in-vitro bioassay paradigms. Methods: A novel class of phosphonate linked 3,5-Bis(aryl methylene)-4-piperidone derivatives were synthesized from simple, versitalie and efficient synthetic methodology. All of the synthesized compounds were screened for their in vitro anti-inflammatory, in vitro anti-oxidant potential, in vitro anti-proliferative, in vitro cytotoxic potential and in vitro antimicrobial activity. Amongst all the synthesized compounds in series, phosphonate derivatives of 3,5-Bis(arylmethylene)-4- piperidone containing 4-hydroxy-3-methoxyphenyl curcumin like prototype were more active than phenyl substituted compounds. Results: The results of the screening revealed that compounds 5e, 5f, 5g, 5h were more active candidates as compared to 5a, 5b, 5c and 5d, however 5d can be readily endorsed as the most active compound of the series. Structure- activity relationship of the synthesized series suggested that structural resemblance of the synthesized compounds with that of curcumin was enormously accountable for the compounds anti-inflammatory, antioxidant and cytotoxic potential activity. Conclusion: The in-vitro biological spectrum indicated that the substitution of groups at third and fourth position and alkyl phosphonates substitution potentiates the activity as compared to curcumin.

scholarly journals Novel Ester and Acid Derivatives of the 1,5-Diarylpyrrole Scaffold as Anti-Inflammatory and Analgesic Agents. Synthesis and in Vitro and in Vivo Biological Evaluation

2010 ◽  
Vol 53 (2) ◽  
pp. 723-733 ◽  
Author(s):  
Mariangela Biava ◽  
Giulio C. Porretta ◽  
Giovanna Poce ◽  
Claudio Battilocchio ◽  
Fabrizio Manetti ◽  
...  
Keyword(s):  
Biological Evaluation ◽  
Analgesic Agents ◽  
Anti Inflammatory ◽  
Derivatives Of

Red Grape Polyphenol Oral Administration improves Immune Response in Women Affected by Nickel-Mediated Allergic Contact Dermatitis

2020 ◽  
Vol 20 ◽  
Author(s):  
Thea Magrone ◽  
Emilio Jirillo ◽  
Manrico Magrone ◽  
Matteo Antonio Russo ◽  
Paolo Romita ◽  
...  
Keyword(s):  
Contact Dermatitis ◽  
Oral Administration ◽  
Allergic Contact Dermatitis ◽  
Laboratory Data ◽  
Anti Oxidant ◽  
Anti Inflammatory ◽  
Red Grape ◽  
Allergic Contact ◽  
Drop Outs

Background: Our previous findings demonstrated that in vitro supplementation of polyphenols, extracted from seeds of red grape (Nero di Troia cultivar), to peripheral lymphomonocytes from patients affected by allergic contact dermatitis (ACD) to nickel (Ni) could reduce release of pro-inflammatory cytokines and nitric oxide (NO), while increasing levels of interleukin (IL)-10, an anti-inflammatory cytokine. Objective: To assess whether an intervention with oral administration of polyphenols leads to a reduction of peripheral biomarkers in ACD patients. Method: At T0, 25 patients affected by ACD to Ni were orally administered with 300 mg polyphenols prodie extracted from seeds of red grape (Nero di Troia cultivar) (NATUR-OX®) for 3 months (T1). Other 25 patients affected by ACD to Ni received placebo only for the same period of time. Serum biomarkers were analyzed at T0 and T1. In both groups seven drop outs were recorded. Result: At T1 in comparison to T0, in treated patients, values of IFN-γ, IL-4, IL-17, PTX3 and NO decreased, while IL-10 levels increased when compared with T0 values. Conversely, in placebo-treated patients no modifications of biomarkers were evaluated at T1. Conclusion: Present laboratory data rely on the anti-oxidant, anti-inflammatory and anti-allergic properties of polyphenols.

scholarly journals Hemisynthesis and Biological Evaluation of Cinnamylated, Benzylated, and Prenylated Dihydrochalcones from a Common Bio-Sourced Precursor

Antibiotics ◽  
2021 ◽  
Vol 10 (6) ◽  
pp. 620
Author(s):  
Anne Ardaillou ◽  
Jérôme Alsarraf ◽  
Jean Legault ◽  
François Simard ◽  
André Pichette
Keyword(s):  
Biological Activities ◽  
Biological Evaluation ◽  
Pharmacological Properties ◽  
Cytotoxic Potential ◽  
Naturally Occurring

Several families of naturally occurring C-alkylated dihydrochalcones display a broad range of biological activities, including antimicrobial and cytotoxic properties, depending on their alkylation sidechain. The catalytic Friedel–Crafts alkylation of the readily available aglycon moiety of neohesperidin dihydrochalcone was performed using cinnamyl, benzyl, and isoprenyl alcohols. This procedure provided a straightforward access to a series of derivatives that were structurally related to natural balsacones, uvaretin, and erioschalcones, respectively. The antibacterial and cytotoxic potential of these novel analogs was evaluated in vitro and highlighted some relations between the structure and the pharmacological properties of alkylated dihydrochalcones.

Design and synthesis of herboxidiene derivatives that potently inhibit in vitro splicing

2021 ◽  
Vol 19 (6) ◽  
pp. 1365-1377
Author(s):  
Arun K. Ghosh ◽  
Srinivasa Rao Allu ◽  
Guddeti Chandrashekar Reddy ◽  
Adriana Gamboa Lopez ◽  
Patricia Mendez ◽  
...  
Keyword(s):  
Biological Evaluation ◽  
Design And Synthesis ◽  
In Vitro Splicing ◽  
Enantioselective Syntheses ◽  
Derivatives Of

Enantioselective syntheses of C-6 modified derivatives of herboxidiene and their biological evaluation in splicing inhibitory assay.

scholarly journals Synthesis and biological evaluation of some novel pyrazolopyrimidines incorporating a benzothiazole ring system

2013 ◽  
Vol 63 (1) ◽  
pp. 19-30 ◽  
Author(s):  
Mohammed Afzal Azam ◽  
Loganathan Dharanya ◽  
Charu Chandrakant Mehta ◽  
Sumit Sachdeva
Keyword(s):  
Antimicrobial Activity ◽  
Diclofenac Sodium ◽  
Biological Evaluation ◽  
Ring System ◽  
Standard Drug ◽  
Anti Inflammatory ◽  
Pyrimidine Moiety ◽  
Synthesis And Biological Evaluation

In the present study, a series of benzothiazol derivatives 3a-l containing pyrazolo[3,4-d]pyrimidine moiety at the second position were synthesized and characterized by analytical and spectral data. The compounds were tested for their in vitro antimicrobial activity. Compounds 1-(1,3-benzothiazol-2- yl)-3-methyl-4-phenyl-1H-pyrazolo[3,4-d]pyrimidine (3a), 1- (1,3-benzothiazol-2-yl)-4-(4-chlorophenyl)-3-methyl-1H-pyrazolo[ 3,4-d]pyrimidine (3d) and 1-(1,3-benzothiazol-2-yl)- 3-methyl-4-substituted phenyl-1H-pyrazolo[3,4-d]pyrimidines (3h-j) showed significant inhibitory activity against P. aeruginosa whereas compounds 1-(1,3-benzothiazol-2-yl)-4- (2-chlorophenyl)-3-methyl-1H-pyrazolo[3,4-d]pyrimidine (3b), 2-[1-(1,3-benzothiazol-2-yl)-3-methyl-1H-pyrazolo[3,4-d]pyrimidin- 4-yl]phenol (3e), 1-(1,3-benzothiazol-2-yl)-4-(3,4-dimethoxyphenyl)- 3-methyl-1H-pyrazolo[3,4-d]pyrimidine (3h), 4-[1-(1,3-benzothiazol-2-yl)-3-methyl-1H-pyrazolo[3,4-d]pyri midin-4-yl]-N,N-dimethylaniline (3j) and 1-(1,3-benzothiazol- 2-yl)-3-methyl-4-[2-phenylvinyl]-1H-pyrazolo[3,4-d]pyrimidine (3k) were found to be active against C. albicans. Some of these synthesized compounds were evaluated for their in vivo acute toxicity, analgesic, anti-inflammatory, and ulcerogenic actions. The tested compound 4-[1-(1,3-benzothiazol- 2-yl)-3-methyl-1H-pyrazolo[3,4-d]pyrimidin-4-yl]-N, N-dimethylaniline (3j) exhibited maximum analgesic and anti-inflammatory activities. Compounds 1-(1,3-benzothiazol- -2-yl)-3-methyl-4-(3-nitrophenyl)-1H-pyrazolo[3,4-d]pyrimidine (3i) and 3j showed a significant gastrointestinal protection compared to the standard drug diclofenac sodium.

Synthesis, characterization and in vitro and in vivo anticancer activity of Pt(iv) derivatives of [Pt(1S,2S-DACH)(5,6-dimethyl-1,10-phenanthroline)]

2017 ◽  
Vol 46 (21) ◽  
pp. 7005-7019 ◽  
Author(s):  
Benjamin W. J. Harper ◽  
Emanuele Petruzzella ◽  
Roman Sirota ◽  
Fernanda Fabiola Faccioli ◽  
Janice R. Aldrich-Wright ◽  
...  
Keyword(s):  
Anticancer Activity ◽  
Biological Evaluation ◽  
Synthesis And Biological Evaluation ◽  
Derivatives Of

Synthesis and biological evaluation in vitro and in vivo of functionalized Pt(iv) derivatives of Pt56MeSS.

scholarly journals Microbial Transformations of Isophorone by Alternaria alternata and Neurospora crassa

2013 ◽  
Vol 8 (1) ◽  
pp. 1934578X1300800 ◽  
Author(s):  
Ismail Kiran ◽  
Özge Özşen ◽  
Turgay Çelik ◽  
Semra İlhan ◽  
Bükay Yenice Gürsu ◽  
...  
Keyword(s):  
Neurospora Crassa ◽  
Alternaria Alternata ◽  
Antimicrobial Agents ◽  
Antimicrobial Activities ◽  
Anti Oxidant ◽  
Agar Dilution ◽  
Important Field ◽  
Pharmacology And Toxicology ◽  
Derivatives Of

Isophorone (3,5,5-trimethyl-2-cyclohexen-1-one), a monoterpene, and the structurally related 1,8-cineole and camphor, have demonstrated a protective effect against cancer, biological activity against a variety of microorganisms, and anti-oxidant properties. The derivatization of isophorone is, therefore, an important field of xenobiochemistry, pharmacology and toxicology. The aim of this study was to obtain derivatives of isophorone through microbial biotransformation and evaluate the biotransformation metabolites as potential antimicrobial agents. Incubation of isophorone with the fungi Alternaria alternata and Neurospora crassa afforded 4α-hydroxy- and 7-hydroxy-isophorone as transformation metabolites. The antimicrobial activities of isophorone and the metabolites were evaluated in vitro both by using agar dilution and microdilution methods. However, no significant antibacterial activity was observed when compared with those of standard substances.

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