Microwave Irradiated Synthesis of Pyrimidine Containing, Thiazolidin-4-ones: Antimicrobial, Anti-tuberculosis, Antimalarial, and Anti-protozoa evaluation

2022 ◽  
Vol 19 ◽  
Author(s):  
Hetal I. Soni ◽  
Navin B. Patel ◽  
Rahul B. Parmar ◽  
Manuel J. Chan- Bacab ◽  
Gildardo River
Keyword(s):  
Microwave Irradiation ◽  
Antimalarial Activity ◽  
Biological Activities ◽  
Biological Response ◽  
Main Concern ◽  
Synthesis Time ◽  
Time Period ◽  
Save Energy ◽  
New Compounds ◽  
Tuberculosis Activity

Aim: This study aims to synthesize thiazolidine-4-one compounds with a pyrimidine nucleus and evaluate against different species of bacteria, fungi, protozoa, and the malaria parasite. Background: Microwave irradiation was the best method for synthesizing the thiazolidin-4-one ring system. It took only 15 minutes for synthesizing thiazolidin-4-one while the conventional method required 12 hours. The rapid reaction was the main concern of this research. Objective: Pyrimidine and Thiazolidin-4-one nucleus have broad-spectrum biological activity and when it is introduced with other hetero atoms containing moiety, many types of biological activities have been found; antimicrobial, anti-tuberculosis, anti-protozoa, antimalarial are the main activities. The activity of these compounds inspired us to do extra research on Thiazolidin-4-one fused pyrimidines with different functional groups. The aim of this is to synthesize a combination of these two ring systems in less time by using a microwave irradiation method and to evaluate new compounds for different bioactivity. Method: 2-(4-Chlorophenyl)-3-(4-(substituted phenyl)-6-(substituted aryl) pyrimidin-2-yl) thiazolidin-4-ones (6A-J) were synthesized by microwave irradiation to save energy and time. The structure of all newly synthesized motifs was characterized by spectral analysis (1H NMR, 13C NMR, IR, spectroscopy) and screened for antibacterial activity against Escherichia coli, Pseudomonas aeruginosa, Staphylococcus aureus, and Streptococcus pyogenes, antifungal activity against Candida albicans, Aspergillus niger, Aspergillus clavatus, anti-tuberculosis activity against M. tuberculosis H37RV, antimalarial activity against Plasmodium falciparum and anti-protozoa activity against L. mexicana and T. cruzi. Result: Because of microwave irradiation synthesis, time period is very less for preparing the new compound. Biological response given by compounds 6B, 6C, 6D, 6E, 6G, 6H, and 6J was found excellent. Conclusion: Good yield with purity of the newly synthesized thiazolidine-4-one compounds obtained in less time by using microwave irradiation. The biological response of some of the compounds of this series was found excellent

Significance of Microwave Irradiation in Synthesis of Thiazolidin-4-one Bearing Pyrimidine Analogues: Their in vitro Antimicrobial, Antituberculosis and Antimalarial Studies

2020 ◽  
Vol 7 (3) ◽  
pp. 230-237
Author(s):  
Navin B. Patel ◽  
Hetal I. Soni ◽  
Rahul B. Parmar
Keyword(s):  
Plasmodium Falciparum ◽  
Microwave Irradiation ◽  
Antimalarial Activity ◽  
Biological Response ◽  
13C Nmr Spectroscopy ◽  
Biological Evaluation ◽  
Biologically Active ◽  
Microwave Irradiation Method ◽  
Tuberculosis Activity

Aim: To synthesise biologically active thiazolidin-4-one by microwave irradiation method and evaluate against different species of bacteria, fungi and Plasmodium falciparum. Background: Microwave irradiation method is serviceable for rapid and sustainable synthesis. In this present study, Thiazolidin-4-one bearing pyrimidine derivatives have been synthesized by microwave irradiation method. Objective: Thiazolidin-4-one is a valuable motif because of its broad-spectrum biological evaluation. It is famous for many types of biological profiles, mainly antimicrobial, anti-tuberculosis, anti- convulsant, antihypertensive, hypoglycemic agent and antimalarial. This biological response leads our attention towards the change of Thiazolidin-4-one skeleton to enhance potential. Present study aims to carry out a rapid synthesis of Thiazolidin-4-one derivative of pyrimidine by microwave- assisted heating. Methods: 4-(4-substituted phenyl)-6-(substituted aryl) pyrimidin-2-amine was the key intermediate required for the synthesis of 3-(4-(Substituted phenyl)-6-(substituted aryl) pyrimidin-2-yl)-2-(4-hydroxy phenyl) thiozolidin-4-one (5A-J), which was prepared by using microwave irradiation. The structures of all newly synthesized motifs were characterized by spectral analysis (IR, 1H NMR, 13C NMR spectroscopy) and screened for antibacterial activity against Escherichia coli, Pseudomonas aeruginosa, Staphylococcus aureus and Streptococcus pyogenes; antifungal activity against Candida albicans, Aspergillus niger, Aspergillus Clavatus; anti-tuberculosis activity against M. tuberculosis H37RV and antimalarial activity against Plasmodium falciparum. Results: Higher yield with less time-consuming method is the main advantage of Thiazolidin- 4-one bearing pyrimidine motifs synthesis. The excellent biological response of compounds 5B, 5C, 5D, 5G, 5H, 5I, and 5J was observed. Conclusion: As compared to conventional method, less time is required for the preparation of Thiazolidin- 4-one analogues by using advantageous microwave irradiation method. Thiazolidin-4-one derivatives showed improved biological activity.

A common mechanism links activities of butyrate in the colon

2017 ◽  
Author(s):  
Mohit S. Verma ◽  
Michael J. Fink ◽  
Gabriel L Salmon ◽  
Nadine Fornelos ◽  
Takahiro E. Ohara ◽  
...  
Keyword(s):  
Stem Cells ◽  
Histone Deacetylases ◽  
Biological Activities ◽  
Short Chain Fatty Acids ◽  
Common Mechanism ◽  
Epithelial Stem Cells ◽  
Degree Of Unsaturation ◽  
Structure Activity ◽  
Starting Point ◽  
New Compounds

Two biological activities of butyrate in the colon (suppression of proliferation of colonic epithelial stem cells and inflammation) correlate with inhibition of histone deacetylases. Cellular and biochemical studies of molecules similar in structure to butyrate, but different in molecular details (functional groups, chain-length, deuteration, oxidation level, fluorination, or degree of unsaturation) demonstrated that these activities were sensitive to molecular structure, and were compatible with the hypothesis that butyrate acts by binding to the Zn<sup>2+</sup> in the catalytic site of histone deacetylases. Structure-activity relationships drawn from a set of 36 compounds offer a starting point for the design of new compounds targeting the inhibition of histone deacetylases. The observation that butyrate was more potent than other short-chain fatty acids is compatible with the hypothesis that crypts evolved (at least in part), to separate stem cells at the base of crypts from butyrate produced by commensal bacteria.

Click Reactions in Chemistry of Triterpenes - Advances Towards Development of Potential Therapeutics

2018 ◽  
Vol 25 (5) ◽  
pp. 636-658 ◽  
Author(s):  
Jan Pokorny ◽  
Lucie Borkova ◽  
Milan Urban
Keyword(s):  
Biological Activities ◽  
Synthetic Approach ◽  
Clinical Use ◽  
New Approach ◽  
Click Reactions ◽  
Drug Candidates ◽  
The Past ◽  
Low Toxicity ◽  
New Compounds ◽  
Potential Therapeutics

Triterpenoids are natural compounds with a large variety of biological activities such as anticancer, antiviral, antibacterial, antifungal, antiparazitic, antiinflammatory and others. Despite their low toxicity and simple availability from the natural resources, their clinical use is still severely limited by their higher IC50 and worse pharmacological properties than in the currently used therapeutics. This fact encouraged a number of researchers to develop new terpenic derivatives more suitable for the potential clinical use. This review summarizes a new approach to improve both, the activity and ADME-Tox properties by connecting active terpenes to another modifying molecules using click reactions. Within the past few years, this synthetic approach was well explored yielding a lot of great improvements of the parent compounds along with some less successful attempts. A large quantity of the new compounds presented here are superior in both activity and ADME-Tox properties to their parents. This review should serve the researchers who need to promote their hit triterpenic structures towards their clinical use and it is intended as a guide for the chemical synthesis of better drug candidates.

Regioselective Synthesis of Potent 4,5,6,7-Tetrahydroindazole Derivatives via Microwave-assisted Vilsmeier-Haack Reaction and their Antioxidant Activity Evaluation

2019 ◽  
Vol 16 (3) ◽  
pp. 194-201 ◽  
Author(s):  
Renu Bala ◽  
Vandana Devi ◽  
Pratibha Singh ◽  
Navjot Kaur ◽  
Pawandeep Kaur ◽  
...  
Keyword(s):  
Antioxidant Activity ◽  
Microwave Irradiation ◽  
Biological Activities ◽  
Reaction Times ◽  
Conventional Heating ◽  
High Chemical ◽  
Microwave Assisted ◽  
Work Up ◽  
Active Methylene ◽  
By Products

Background: Tetrahydroindazole, a member of the fused-pyrazole system, is a least studied class of heterocyclic compounds owing to its scarcity in nature. However, a large number of synthetically prepared tetrahydroindazoles are known to show a variety of biological activities such as interleukin- 2 inducible T-Cell kinase inhibitors, AMPA receptor positive allosteric modulators, antitumor, antituberculosis, anti-inflammatory and antimicrobial activities. Vilsmeier-Haack reaction is one of the most important chemical reactions used for formylation of electron rich arenes. Even though Vilsmeier- Haack reaction was studied on a wide variety of hydrazones derived from active methylene compounds, literature lacks the examples of the use of 4-substituted cyclohexanones as a substrate for the synthesis of 4,5,6,7-tetrahydroindazoles. The study of the reaction of Vilsmeier-Haack reagent with hydrazones derived from cyclic keto compounds having active methylene has been considered the interested topic of investigation. In the present study, ethyl cyclohexanone-4-carboxylate was treated with one equivalent of various hydrazines for two hours and the resulted hydrazones were further treated with an OPC-VH reagent (Vilsmeier-Haack reagent isolated from phthaloyl dichloride and N,Ndimethylformamide) afforded 4,5,6,7-tetrahydroindazoles in excellent yields. The synthesized compounds 4a-f and 5a-f were screened for their antioxidant activities using the DPPH radical scavenging assay. The target compounds were synthesized regioselectively using 4+1 approach in excellent yields. A number of experiments using both conventional heating as well as microwave irradiation methods were tried and on comparison, microwave irradiation method was found excellent in terms of easy work up, high chemical yields, shortened reaction times, clean and, no by-products formation. Some of the synthesized compounds showed significant antioxidant activity. The microwave assisted synthesis of 4,5,6,7-tetrahydroindazoles from ethyl cyclohexanone-4-carboxylate has been reported under mild conditions in excellent yield. Easy work up, high chemical yield, shortened reaction times, clean and no by-products formation are the major advantages of this protocol. These advantages may make this method useful for chemists who are interested in developing novel 4,5,6,7-tetrahydroindazole based drugs.

scholarly journals Recent Findings in Azaphilone Pigments

2021 ◽  
Vol 7 (7) ◽  
pp. 541
Author(s):  
Lúcia P. S. Pimenta ◽  
Dhionne C. Gomes ◽  
Patrícia G. Cardoso ◽  
Jacqueline A. Takahashi
Keyword(s):  
Water Solubility ◽  
Biological Activities ◽  
Low Cost ◽  
Scale Up ◽  
Structural Diversity ◽  
Downstream Processing ◽  
Global Market ◽  
Yield Improvement ◽  
Potential Applications ◽  
New Compounds

Filamentous fungi are known to biosynthesize an extraordinary range of azaphilones pigments with structural diversity and advantages over vegetal-derived colored natural products such agile and simple cultivation in the lab, acceptance of low-cost substrates, speed yield improvement, and ease of downstream processing. Modern genetic engineering allows industrial production, providing pigments with higher thermostability, water-solubility, and promising bioactivities combined with ecological functions. This review, covering the literature from 2020 onwards, focuses on the state-of-the-art of azaphilone dyes, the global market scenario, new compounds isolated in the period with respective biological activities, and biosynthetic pathways. Furthermore, we discussed the innovations of azaphilone cultivation and extraction techniques, as well as in yield improvement and scale-up. Potential applications in the food, cosmetic, pharmaceutical, and textile industries were also explored.

What are the Potential Benefits of Including Latent Storage in Common Wallboard?

1995 ◽  
Vol 117 (4) ◽  
pp. 318-325 ◽  
Author(s):  
T. K. Stovall ◽  
J. J. Tomlinson
Keyword(s):  
Comfort Level ◽  
Load Management ◽  
Storage Device ◽  
Time Period ◽  
Payback Time ◽  
Potential Applications ◽  
Energy Penalty ◽  
Potential Benefits ◽  
Save Energy ◽  
Change Material

Previous work has shown that wallboard can be successfully manufactured to contain up to 30 percent phase-change material (PCM), or wax, thus enabling this common building material to serve as a thermal energy storage device. The PCM wallboard was analyzed for passive solar applications and found to save energy with a reasonable payback time period of five years. Further evaluations of the wallboard are reported in this paper. This analysis looks at potential applications of PCM wallboard as a load management device and as a comfort enhancer. Results show that the wallboard is ineffective in modifying the comfort level but can provide significant load management relief. In some applications the load management strategy also serves to save a small amount of energy, in others there is a small energy penalty.

scholarly journals New Benzoxazole Derivatives as Antiprotozoal Agents: In Silico Studies, Synthesis, and Biological Evaluation

2021 ◽  
Vol 2021 ◽  
pp. 1-11
Author(s):  
Mohamed A. Abdelgawad ◽  
Mohammad M. Al-Sanea ◽  
Mohamed A. Zaki ◽  
Enas I. A. Mohamed ◽  
Shabana I. Khan ◽  
...  
Keyword(s):  
Antimicrobial Agents ◽  
Antimalarial Activity ◽  
Biological Activities ◽  
Docking Study ◽  
Antimicrobial Activities ◽  
Biological Evaluation ◽  
Molecular Docking Study ◽  
Chromatographic Separations ◽  
Major Mechanism ◽  
In Silico Studies

Background. Benzoxazole derivatives have different biological activities. In pursuit of designing novel chemical entities with antiprotozoal and antimicrobial activities, benzoxazolyl aniline was utilized as a privileged scaffold of a series of (3-benzoxazole-2-yl) phenylamine derivatives, 3-benzoxazoloyl acetamide, and butyramide derivatives. Methods. These novel analogs were synthesized in straightforward simple chemistry without any quantitative chromatographic separations in reasonable yields. The biological evaluation of all target compounds as potential antimalarial, antileishmanial, antitrypanosomal, and antimicrobial agents was performed by various well-established cell-based methods. Results. Compounds 6d and 5a showed promising biological screening data. The amidation of 3-benzoxazolyl aniline 1 with the chloroacetyl functional group resulted in a good antimalarial activity and showed moderate inhibitory activities against leishmanial and trypanosomal spp. Moreover, chloroacetyl functionalization of benzoxazolyl aniline serves as a good early goal for constructing and synthesizing new antimicrobial and antiprotozoal agents. The molecular docking study rationalizes the relative inhibitory activity of compound 5a as an antimalarial agent with the deregulation of PfPNP activity which has emerged as a major mechanism of these targets.

scholarly journals Novel silver(I) compounds with 1-adamantanamine

2018 ◽  
Vol 83 (6) ◽  
pp. 699-705 ◽  
Author(s):  
Dejan Jeremic ◽  
Milena Djordjevic ◽  
Srdjan Miletic ◽  
Ljubica Andjelkovic ◽  
Dusan Sladic ◽  
...  
Keyword(s):  
Electron Donor ◽  
Aliphatic Amine ◽  
Biological Activities ◽  
Spectroscopic Characterization ◽  
Antibacterial Activities ◽  
Monodentate Ligand ◽  
Donor Ligand ◽  
Minimum Inhibitory Concentrations ◽  
New Compounds

In this work, three novel silver(I) complexes with an almost completely rigid and bulky monodentate ligand, 1-adamantanamine, were synthesized. The aliphatic amine, 1-adamantanamine, is the sole electron donor ligand in these complexes. In addition to spectroscopic characterization, the basic biological activities of the new compounds were investigated and their minimum inhibitory concentrations were determined. The antifungal and antibacterial activities indicate that these compounds could potentially be applied as new therapeutics.

scholarly journals PYRIMIDINES AS POTENT CYTOTOXIC AND ANTI-INFLAMMATORY AGENTS

2017 ◽  
Vol 10 (6) ◽  
pp. 237 ◽  
Author(s):  
Ishwar Bhat K ◽  
Abhishek Kumar
Keyword(s):  
Acetic Acid ◽  
Cytotoxic Activity ◽  
Glacial Acetic Acid ◽  
Antimalarial Activity ◽  
Biological Activities ◽  
Cytotoxic Agents ◽  
Pyrimidine Derivatives ◽  
Pharmacological Activities ◽  
Anti Inflammatory ◽  
Derivatives Of

Objective: Many derivatives of pyrimidine are known for the broad-spectrum biological activities such as antimicrobial, antitumor, antibacterial, antitubercular, anti-inflammatory, and cytotoxic activity. Chalcones with an enone group show potent pharmacological activities such as antiinflammatory, antibacterial, antifungal, and antimalarial activity. A series of pyrimidines from chalcones have been synthesized and screened for anti-inflammatory and cytotoxic activity studies.Methods: Chalcones [1-(4-nitrophenyl)-3-substituted-phenylprop-2-en-1-one] were synthesized from various substituted aldehydes with 4-nitroacetophenone and cyclized with urea and glacial acetic acid to give pyrimidine derivatives [4-(4-nitrophenyl)-6-substituted-phenylpyrimidin-2-ol].Results: Anti-inflammatory and cytotoxic activity studies revealed that some of the synthesized compounds have shown significant activity.Conclusion: The observed results proved that pyrimidines are found to be interesting lead molecules for the synthesis of anti-inflammatory and cytotoxic agents

scholarly journals Synthesis and Antimalarial Activity of 1,4-Disubstituted Piperidine Derivatives

Molecules ◽  
2020 ◽  
Vol 25 (2) ◽  
pp. 299 ◽  
Author(s):  
Rokhyatou Seck ◽  
Abdoulaye Gassama ◽  
Sandrine Cojean ◽  
Christian Cavé
Keyword(s):  
Plasmodium Falciparum ◽  
Side Effects ◽  
Antimalarial Activity ◽  
Low Cost ◽  
Compound Library ◽  
New Compounds

In order to prepare, at low cost, new compounds active against Plasmodium falciparum, and with a less side-effects, we have designed and synthesized a library of 1,4-disubstituted piperidine derivatives from 4-aminopiperidine derivatives 6. The resulting compound library has been evaluated against chloroquine-sensitive (3D7) and chloroquine-resistant (W2) strains of P. falciparum. The most active molecules—compounds 12d (13.64 nM (3D7)), 13b (4.19 nM (3D7) and 13.30 nM (W2)), and 12a (11.6 nM (W2))—were comparable to chloroquine (22.38 nM (3D7) and 134.12 nM (W2)).

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