scholarly journals Synthesis of Polycyclic Ether-Benzopyrans and In Vitro Inhibitory Activity against Leishmania tarentolae

Molecules ◽  
2020 ◽  
Vol 25 (22) ◽  
pp. 5461
Author(s):  
Sarita Singh ◽  
Jacob P. Grabowski ◽  
Shilpa Pohani ◽  
C. Fiore Apuzzo ◽  
David C. Platt ◽  
...  
Keyword(s):  
Boronic Acid ◽  
Cross Coupling ◽  
Nitric Oxide Production ◽  
Aryl Bromide ◽  
Leishmania Tarentolae ◽  
Concentration Time ◽  
Polycyclic Ether ◽  
Boronic Acid Derivatives ◽  
Therapeutic Compounds

Construction of a focused library of polycyclic ether-benzopyrans was undertaken in order to discover new therapeutic compounds that affect Leishmania growth and infectivity. This is especially of interest since there are few drug therapies for leishmaniasis that do not have serious drawbacks such high cost, side effects, and emerging drug resistance. The construction of these polycyclic ether-benzopyrans utilized an acetoxypyranone-alkene [5+2] cycloaddition and the Suzuki-Miyaura cross-coupling. The multi-gram quantity of the requisite aryl bromide was obtained followed by effective Pd-catalyzed coupling with boronic acid derivatives. Compounds were tested in vitro using the parasitic protozoan, Leishmania tarentolae. Effects of concentration, time, and exposure to light were evaluated. In addition, the effects on secreted acid phosphatase activity and nitric oxide production were investigated, since both have been implicated in parasite infectivity. The data presented herein are indicative of disruption of the Leishmania tarentolae and thus provide impetus for the development and testing of a more extensive library.

Ultrasound Assisted Synthesis of 3-(het)aryl Isocoumarin Derivatives and their in vitro Pharmacological Evaluation

2019 ◽  
Vol 19 (10) ◽  
pp. 842-850 ◽  
Author(s):  
Gutta Lakshmi Prasanna ◽  
V.D. Nagendra Kumar Abbaraju ◽  
Yarlagadda Bharath ◽  
Mandava V. Basaveswara Rao ◽  
Manojit Pal
Keyword(s):  
Boronic Acid ◽  
Biological Activities ◽  
Ultrasound Irradiation ◽  
Bond Forming ◽  
Pharmacological Evaluation ◽  
Tnf Α ◽  
Ic50 Value ◽  
Ultrasound Assisted ◽  
Boronic Acid Derivatives

Background: In view of numerous biological activities of 3-substituted isocoumarins a number of analogues based on this scaffold were synthesized for their in vitro pharmacological evaluation. Methods: The syntheses of 3-substituted isocoumarins were carried out via a Pd/C-catalyzed Suzuki- Miyaura coupling of 3-chloroisochromen-1-one with a range of boronic acid derivatives. This C-C bond forming reaction was facilitated by ultrasound irradiation to afford the desired products in good yields. A number of 3-(het)aryl isocoumarin derivatives were prepared by using this methodology and subsequently tested for their TNF-α inhibitory properties in vitro followed by cytotoxicities via the MTT assay. Results: Several compounds showed inhibition of TNF-α with one compound showing an IC50 value of 9.01±1.25 µM. Three compounds also showed promising cytotoxic properties against two cancer cell lines with IC50 ~ 0.9-2.7 µM. Conclusion: The isocoumarin framework could be an effective template for the design and discovery of new inhibitor of TNF-α for the potential treatment of related diseases.

scholarly journals Development of an Antibiotic Resistance Breaker to Resensitize Drug-Resistant Staphylococcus aureus: In Silico and In Vitro Approach

2021 ◽  
Vol 11 ◽  
Author(s):  
Gopalakrishnan Thamilselvan ◽  
Hema Bhagavathi Sarveswari ◽  
Sahana Vasudevan ◽  
Alex Stanley ◽  
Karthi Shanmugam ◽  
...  
Keyword(s):  
Staphylococcus Aureus ◽  
Boronic Acid ◽  
Bacterial Resistance ◽  
Efflux Pump ◽  
Parent Compound ◽  
Efflux Pumps ◽  
Online Tool ◽  
Efflux Pump Inhibition ◽  
Boronic Acid Derivatives

Efflux pumps are one of the predominant microbial resistant mechanisms leading to the development of multidrug resistance. In Staphylococcus aureus, overexpression of NorA protein enables the efflux of antibiotics belonging to the class of fluoroquinolones and, thus, makes S. aureus resistant. Hence, NorA efflux pumps are being extensively exploited as the potential drug target to evade bacterial resistance and resensitize bacteria to the existing antibiotics. Although several molecules are reported to inhibit NorA efflux pump effectively, boronic acid derivatives were shown to have promising NorA efflux pump inhibition. In this regard, the current study exploits 6-(3-phenylpropoxy)pyridine-3-boronic acid to further improve the activity and reduce cytotoxicity using the bioisostere approach, a classical medicinal chemistry concept. Using the SWISS-Bioisostere online tool, from the parent compound, 42 compounds were obtained upon the replacement of the boronic acid. The 42 compounds were docked with modeled NorA protein, and key molecular interactions of the prominent compounds were assessed. The top hit compounds were further analyzed for their drug-like properties using ADMET studies. The identified potent lead, 5-nitro-2-(3-phenylpropoxy)pyridine (5-NPPP), was synthesized, and in vitro efficacy studies have been proven to show enhanced efflux inhibition, thus acting as a potent antibiotic breaker to resensitize S. aureus without elucidating any cytotoxic effect to the host Hep-G2 cell lines.

502: Pressure Induces Nitric Oxide Production by Human Ureteral Cells in Vitro

2005 ◽  
Vol 173 (4S) ◽  
pp. 137-137
Author(s):  
Michael M. Ohebshalom ◽  
Stella K. Maeng ◽  
Jie Chen ◽  
Dix P. Poppas ◽  
Diane Felsen
Keyword(s):  
Nitric Oxide ◽  
Nitric Oxide Production ◽  
Oxide Production

Structural characterization of naphthalene sulfonamides and a sulfonate ester and their in vitro efficacy against Leishmania tarentolae promastigotes

2021 ◽  
Vol 45 (10) ◽  
pp. 4791-4801
Author(s):  
Edward W. Li ◽  
Jade Katinas ◽  
Marjorie A. Jones ◽  
Christopher G. Hamaker
Keyword(s):  
Biological Activity ◽  
Structural Characterization ◽  
Leishmania Tarentolae ◽  
Sulfonate Ester

Structural and biological activity analyses of two naphthalene sulfonamides and a naphthalene sulfonate ester.

Resveratrol and grape juice: Effects on redox status and nitric oxide production of endothelial cells in in vitro preeclampsia model

2021 ◽  
Vol 23 ◽  
pp. 205-210
Author(s):  
Mayara Caldeira-Dias ◽  
Sarah Viana-Mattioli ◽  
Jackeline de Souza Rangel Machado ◽  
Mattias Carlström ◽  
Ricardo de Carvalho Cavalli ◽  
...  
Keyword(s):  
Nitric Oxide ◽  
Endothelial Cells ◽  
Grape Juice ◽  
Redox Status ◽  
Nitric Oxide Production ◽  
Oxide Production

Base-Free Synthesis and Synthetic Application of Novel 3-(organochalcogenyl)prop-2-yn-1-yl Esters: Promising Anticancer Agents

Synthesis ◽  
2021 ◽  
Author(s):  
Fabiane Gritzenco ◽  
Jean Carlo Kazmierczak ◽  
Thiago Anjos ◽  
Adriane Sperança ◽  
Maura Luise Bruckchem Peixoto ◽  
...  
Keyword(s):  
Anticancer Agents ◽  
Cross Coupling ◽  
Coupling Reactions ◽  
Chalcogen Bond ◽  
Cross Coupling Reactions ◽  
Air Atmosphere ◽  
Carbon Carbon Bonds ◽  
Palladium Catalyzed ◽  
Synthetic Application

This manuscript portrays the CuI-catalyzed Csp-chalcogen bond formation through cross-coupling reactions of propynyl esters and diorganyl dichalcogenides by using DMSO as solvent, at room temperature, under base-free and open-to-air atmosphere. Generally, the reactions have proceeded very smoothly, being tolerant to range of substituents present in both substrates, affording the novel 3-(organochalcogenyl)prop-2-yn-1-yl esters in moderate to good yields. Noteworthy, the 3-(butylselanyl)prop-2-yn-1-yl benzoate proved to be useful as synthetic precursor in palladium-catalyzed Suzuki and Sonogashira type cross-coupling reactions by replacing the carbon-chalcogen bond by new carbon-carbon bonds. Moreover, the 3-(phenylselanyl)prop-2-yn-1-yl benzoate has shown promising in vitro activity against glioblastoma cancer cells.

Synthesis of Sugar–Boronic Acid Derivatives: A Class of Potential Agents for Boron Neutron Capture Therapy

2017 ◽  
Vol 19 (7) ◽  
pp. 1678-1681 ◽  
Author(s):  
Daniela Imperio ◽  
Erika Del Grosso ◽  
Silvia Fallarini ◽  
Grazia Lombardi ◽  
Luigi Panza
Keyword(s):  
Boron Neutron Capture Therapy ◽  
Neutron Capture ◽  
Boronic Acid ◽  
Neutron Capture Therapy ◽  
Boron Neutron Capture ◽  
Boronic Acid Derivatives

Effects of Periodic Body Acceleration on the In Vivo Vasoactive Response to N-w-nitro–L-arginine and the In Vitro Nitric Oxide Production

2003 ◽  
Vol 31 (11) ◽  
pp. 1337-1346 ◽  
Author(s):  
Jose A. Adams ◽  
James E. Moore, Jr. ◽  
Michael R. Moreno ◽  
Jaqueline Coelho ◽  
Jorge Bassuk ◽  
...  
Keyword(s):  
Nitric Oxide ◽  
Nitric Oxide Production ◽  
Body Acceleration ◽  
Oxide Production
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