scholarly journals ChCl: Gly (DESs) Promote Environmentally Benign Synthesis of Xanthene Derivatives and Their Antitubercular Activity

Molecules ◽  
2021 ◽  
Vol 26 (12) ◽  
pp. 3667
Author(s):  
Mashooq A. Bhat ◽  
Ahmed M. Naglah ◽  
Siddique Akber Ansari ◽  
Hanaa M. Al-Tuwajiria ◽  
Abdullah Al-Dhfyan
Keyword(s):  
Reaction Times ◽  
Antitubercular Activity ◽  
Antimycobacterial Activity ◽  
Environmentally Benign ◽  
Reaction Yield ◽  
Benign Synthesis ◽  
Xanthene Derivatives ◽  
Wide Range ◽  
Major Application

A ChCl: Gly (DESs) promoted environmentally benign method was developed for the first time using the reaction of aryl aldehydes and dimedone to give excellent yields of xanthene analogues. The major application of this present protocol is the use of green solvent, a wide range of substrate, short reaction times, ease of recovery, the recyclability of the catalyst, high reaction yield, and ChCl: Gly as an alternative catalyst and solvent. In addition to this, all the synthesized compounds were evaluated for their in vitro antimycobacterial activity against M. tuberculosis H37Ra (MTB) and M. bovis BCG strains. The compounds 3d, 3e, 3f, and 3j showed significant antitubercular activity against MTB and M. bovis strains with minimum inhibitory concentration (MIC) values of 2.5−15.10 µg/mL and 0.26–14.92 µg/mL, respectively. The compounds 3e, 3f, and 3j were found to be nontoxic against MCF-7, A549, HCT 116, and THP-1 cell lines. All the prepared compounds were confirmed by 1H NMR and 13C NMR analysis.

scholarly journals Synthesis of Novel Sulfamethaoxazole 4-Thiazolidinone Hybrids and Their Biological Evaluation

Molecules ◽  
2020 ◽  
Vol 25 (16) ◽  
pp. 3570 ◽  
Author(s):  
Mashooq A. Bhat ◽  
Mohamed A. Al-Omar ◽  
Ahmed M. Naglah ◽  
Azmat Ali Khan
Keyword(s):  
Antitubercular Activity ◽  
Antimycobacterial Activity ◽  
Biological Evaluation ◽  
Oral Drug ◽  
Drug Candidates ◽  
Cyclocondensation Reaction ◽  
Aryl Aldehyde ◽  
Hct 116 ◽  
Mcf 7

A search for potent antitubercular agents prompted us to design and synthesize sulfamethaoxazole incorporated 4-thiazolidinone hybrids (7a–l) by using a cyclocondensation reaction between 4-amino-N-(5-methylisoxazol-3-yl)benzenesulfonamide (4), aryl aldehyde (5a–l), and mercapto acetic acid (6) resulting in good to excellent yields. All the newly synthesized 4-thiazolidinone derivatives were screened for their in vitro antitubercular activity against M. Bovis BCG and M. tuberculosis H37Ra (MTB) strains. The compounds 7d, 7g, 7i, 7k, and 7l revealed promising antimycobacterial activity against M. Bovis and MTB strains with IC90 values in the range of 0.058–0.22 and 0.43–5.31 µg/mL, respectively. The most active compounds were also evaluated for their cytotoxicity against MCF-7, HCT 116, and A549 cell lines and were found to be non-cytotoxic. Moreover, the synthesized compounds were also analyzed for ADME (absorption, distribution, metabolism, and excretion) properties and showed potential as good oral drug candidates.

Advances in the Synthesis of Xanthenes: An Overview

2018 ◽  
Vol 15 (3) ◽  
pp. 341-369 ◽  
Author(s):  
Ankita Chaudhary ◽  
Jitender M. Khurana
Keyword(s):  
Heterogeneous Catalysts ◽  
Biological Activities ◽  
Reaction Times ◽  
Environmentally Benign ◽  
Central Nucleus ◽  
Diversity Oriented Synthesis ◽  
Wide Range ◽  
Privileged Scaffold ◽  
Synthetic Methodologies ◽  
Reaction Media

Background: Xanthene is pharmacologically important oxygen containing heterocyclic moeity exhibiting an array of potent biological activities like antibacterial, antiviral, antiinflammatory, antitumor, antioxidant, antiplasmodial etc. Other useful applications of these heterocycles are as fluorescent materials for the visualization of biomolecules and in laser technology. Objective: This review gives an insight of the literature available on the methods for the construction of xanthene nucleus. This review article can be reasonably encouraging for those involved in the synthesis of molecules exhibiting a wide range of biological activities involving xanthene as central nucleus and would provide them assistance in developing new eco-friendly, efficient and economical viable methods. Conclusion: Owing to diverse applications of xanthenes, various synthetic methodologies have been developed, whether to construct this privileged scaffold. Many of the reported methods involve the use of various harsh catalysts/reagents that are not environmentally benign, produce a large amount of waste and need longer reaction times. The sustainable and diversity oriented synthesis of xanthene scaffold which incorporates Green Chemistry tools like multicomponent reaction approach, heterogeneous catalysts, alternate reaction media such as water, ionic liquids, polyethylene glycol etc. has also been developed.

Benzoylthioureas: Design, Synthesis and Antimycobacterial Evaluation

2020 ◽  
Vol 16 (1) ◽  
pp. 93-103
Author(s):  
Tiago O. Brito ◽  
Lethícia O. Abreu ◽  
Karen M. Gomes ◽  
Maria C.S. Lourenço ◽  
Patricia M.L. Pereira ◽  
...  
Keyword(s):  
Benzene Ring ◽  
Biological Activities ◽  
Antitubercular Activity ◽  
Antimycobacterial Activity ◽  
New Drugs ◽  
Design Synthesis ◽  
Thiourea Derivatives ◽  
Structural Modifications ◽  
General Series ◽  
Wide Range

Background: New drugs and strategies to treat tuberculosis (TB) are urgently needed. In this context, thiourea derivatives have a wide range of biological activities, including anti-TB. This fact can be illustrated with the structure of isoxyl, an old anti-TB drug, which has a thiourea as a pharmacophore group. Objective: The aim of this study is to describe the synthesis and the antimycobacterial activity of fifty-nine benzoylthioureas derivatives. Methods: Benzoylthiourea derivatives have been synthesized and evaluated for their activity against Mycobacterium tuberculosis using the MABA assay. After that, a structure-activity relationship study of this series of compounds has been performed. Results and Discussion: Nineteen compounds exhibited antimycobacterial activity between 423.1 and 9.6 μM. In general, we observed that the presence of bromine, chlorine and t-Bu group at the para-position in benzene ring plays an important role in the antitubercular activity of Series A. These substituents were fixed at this position in benzene ring and other groups such as Cl, Br, NO2 and OMe were introduced in the benzoyl ring, leading to the derivatives of Series B. In general, Series B was less cytotoxic than Series A, which indicates that the presence of a substituent at benzoyl ring contributes to an improvement in both antimycobacterial activity and toxicity profiles. Conclusion: Compound 4c could be considered a good prototype to be submitted to further structural modifications in the search for new anti-TB drugs, since it is 1.8 times more active than the first line anti-TB drug ethambutol and 0.65 times less active than isoxyl.

scholarly journals SYNTHESIS AND ANTITUBERCULAR ACTIVITY OF PIPERIDINE AND MORPHOLINE 1, 8 NAPHTHYRIDINE ANALOGUES

2016 ◽  
Vol 8 (12) ◽  
pp. 252 ◽  
Author(s):  
Muwaffag Badawneh ◽  
Jalal Aljamal
Keyword(s):  
Mycobacterium Tuberculosis ◽  
Inhibitory Concentration ◽  
Antitubercular Activity ◽  
Antimycobacterial Activity ◽  
Significant Activity ◽  
Reference Drug ◽  
Novel Drugs ◽  
Elemental Analyses ◽  
Antimycobacterial Agents

<p><strong>Objective: </strong>The search for new, potentially useful antimycobacterial agents. In continuation with our previous screening for the discovery of novel drugs for tuberculosis, a new series of 1,8-naphthyridines derivatives were synthesized and evaluated <em>in vitro </em>for antimycobacterial activity against <em>Mycobacterium tuberculosis </em>H37Rv.</p><p><strong>Methods: </strong>Several 4-morpholinomethyl-1.8-naphthyridine derivatives have been synthesized in excellent yields. The synthesized compounds were characterized by spectroscopic methods as well as elemental analyses. They were screened for their antimycobacterial activity. The growth was monitored radiometrically in 7H12 broth with the BACTEC 460 TB system. The minimum inhibitory concentration (MIC) was determined for compounds that demonstrated ≥ 90% growth inhibition in the primary screening.</p><p><strong>Results: </strong>The obtained data suggested that all compounds showed significant activity against <em>Mycobacterium tuberculosis </em>H37Rv<em> </em>compared to the standard reference drug. Analogues (6-11) having heterocyclic groups in position 7 were the most potent of those we tested.</p><p><strong>Conclusion: </strong>These findings clearly identify the 1,8-naphthyridine analogue (10) with a 6-amino-2-(4'-methoxy benzylamine-4-morpholinomethyl-7-morpholino-substituent as promising anti-tubercular agents possessing significant activity against <em>Mycobacterium tuberculosis </em>H37Rv</p>

scholarly journals Synthesis of Tetrahydro-2H-[1,3,5]thiadiazine-5-(4-pyridylcarboxamido)-2-thione with antitubercular activity

2004 ◽  
Vol 72 (1) ◽  
pp. 35-41 ◽  
Author(s):  
D. Sriram ◽  
K. Jyothi Mallika ◽  
P. Yogeeswari
Keyword(s):  
Mycobacterium Tuberculosis ◽  
Antitubercular Activity ◽  
Antimycobacterial Activity ◽  
Therapeutic Use ◽  
Tuberculosis H37rv ◽  
Mycobacterium Tuberculosis H37rv ◽  
Radiometric System ◽  
Elemental Analyses ◽  
Derivatives Of

3-Substituted-5-(4-pyridylcarboxamide)tetrahydro-2H-[1,3,5]thiadizine-2-thione derivatives (1-9) were synthesized as derivatives of isoniazid (INH) to overcome the resistance developed with its therapeutic use. The structures were confirmed by their spectral and elemental analyses data. These derivatives revealed higher lipophilicity compared with INH. The antimycobacterial activity of the synthesized compounds and INH was evaluated in vitro against Mycobacterium tuberculosis H37Rv at 6.25 µg/ml in BACTEC 12B medium using the BACTEC 460 radiometric system. The derivatives exhibited antitubercular activity.

scholarly journals Isoxazoles-A Biocompatible Radical Scavenging Agents: Citrus Juice Mediated Environmentally Benign Synthesis and Characterization

2020 ◽  
Vol 32 (12) ◽  
pp. 2997-3001
Author(s):  
K.R. Raghavendra ◽  
M.G. Prabhudeva ◽  
A. Dileep Kumar ◽  
K. Ajay Kumar ◽  
H.P. Jayadevappa
Keyword(s):  
Hydroxyl Radical ◽  
Radical Scavenging Activity ◽  
Radical Scavenging ◽  
Environmentally Benign ◽  
Citrus Juice ◽  
Hydroxyl Radical Scavenging Activity ◽  
Benign Synthesis ◽  
Antioxidant Agents ◽  
Isoxazole Derivatives

This study demonstrates the efficient eco-friendly synthesis of a series of isoxazole derivatives 5a-h through (3+2) annulation of chalcones 3a-h and hydroxylamine (4) in citrus juice medium. The synthesized compounds were characterized by spectroscopic and CHN analysis, and assessed in vitro for their antioxidant susceptibilities by DPPH and hydroxyl radical scavenging assays. The result shows that compounds 5a, 5b, 5d and 5h have excellent DPPH and hydroxyl radical scavenging activity in both assays and therefore these molecule could serve as potent antioxidant agents.

scholarly journals One-Pot Solvent Free, Green Route to Novel Substituted Spiro[oxindole-isoxazolidine] Derivatives: Novel Candidates as Antimicrobial Agents

2021 ◽  
Vol 33 (6) ◽  
pp. 1299-1303
Author(s):  
Manpreet Kaur ◽  
Sumeet Kaur Bhatia ◽  
Baldev Singh
Keyword(s):  
Antimicrobial Agents ◽  
Reaction Times ◽  
Solvent Free ◽  
Environmentally Benign ◽  
Dipolar Cycloaddition ◽  
One Pot ◽  
Green Route ◽  
High Yields ◽  
Solvent Free Synthesis

The environmentally benign catalyst and solvent-free synthesis of ketonitrones may not always be accomplished by simple condensation reactions. The occasional reports of green synthetic routes toward these compounds have been reported. The key features of this 1,3-dipolar cycloaddition reactions of N-[4-(-carboxycyclohexylmethyl)]maleimide with substituted isatin ketonitrone under microwave conditions resulted in the green synthesis of series of novel fluoro-substituted spiro[oxindole-isoxazolidine] derivatives in high yields, improved purity and short reaction times. All the synthesized compounds have been identified as potent in vitro antimicrobial agents. These results promoted the greener route to synthesize spiro[oxindole-isoxazolidine] derivatives with immense pharmacological importance in eco-friendly manner.

Clofazimine: an old drug for never-ending diseases

2020 ◽  
Vol 15 (7) ◽  
pp. 557-566 ◽  
Author(s):  
Niccolò Riccardi ◽  
Andrea Giacomelli ◽  
Diana Canetti ◽  
Agnese Comelli ◽  
Enrica Intini ◽  
...  
Keyword(s):  
Side Effects ◽  
Antimycobacterial Activity ◽  
Pharmacokinetic Profile ◽  
Clinical Development ◽  
Drug Resistant ◽  
Resistant Tuberculosis ◽  
Wide Range ◽  
Mycobacterial Diseases ◽  
Dose Dependent

Clofazimine (CFZ), an old hydrophobic riminophenazine, has a wide range of antimycobacterial activity ranging from leprosy to nontuberculous mycobacterial diseases. CFZ has several advantages such as a favorable pharmacokinetic profile, dose-dependent side effects as well as low price. In this narrative review, we have assessed the clinical development of CFZ, starting from the potential in vitro mechanism of actions, to the spectrum of side effects and potential drug–drug interactions, highlighting its current place in therapy and future possible use in leprosy, nontuberculous mycobacterial diseases and drug-resistant tuberculosis.

scholarly journals In vitro bactericidal activities of two novel dihydropyridine derivatives against Mycobacterium tuberculosis

2017 ◽  
Vol 11 (06) ◽  
pp. 453-458 ◽  
Author(s):  
Mehdi Zandhaghighi ◽  
Farzin Hadizadeh ◽  
Saman Soleimanpour ◽  
Zahra Meshkat ◽  
Seyed Abdolrahim Rezaee ◽  
...  
Keyword(s):  
Mycobacterium Tuberculosis ◽  
Growth Inhibition ◽  
Antitubercular Activity ◽  
Antimycobacterial Activity ◽  
Cross Resistance ◽  
Control Programs ◽  
Resistant Strains ◽  
Different Strains ◽  
Dihydropyridine Derivatives

Introduction: Introducing new and effective antitubercular agents is important in tuberculosis control programs. In this study, the in vitro antitubercular activity of two novel 1,4-dihydropyridine derivatives (F-27, Cl-33) were screened against a total of 113 different strains of Mycobacterium tuberculosis (77 susceptible and 36 resistant clinical isolates). Methodology: The in vitro activities of these compounds were evaluated based on the modified broth macro-dilution assay. Results: Compound F-27 showed more than 90% growth inhibition at the range of 2 to 8 μg/mL (minimum inhibitory concentration [MIC]90: 4.13 ± 0.45 µg/mL; p  < 0.01), and complete growth inhibition was observed at the range of 8 to 32 μg/mL (minimum bactericidal concentration [MBC]: 11.2 ± 1.65 µg/mL; p < 0.01) against susceptible strains. However, 92% of the resistant strains showed some degree of susceptibility against this compound (MIC90 range: 16 to 64 µg/mL; mean: 40.4 ± 8 µg/mL; p < 0.01). It was found that although there is a linear relationship between the inhibitory activity of F-27 and isoniazid against resistant strains at low concentrations (r = 0.484, p < 0.001), there was no relationship between resistance to isoniazid and F-27 at higher concentrations (r = 0.019, p > 0.1). This may emphasize no cross-resistance between F-27 and isoniazid. Conclusions: Considering the sufficient sample size of the study and based on the excellent antimycobacterial activity of F-27, it could be concluded that F-27 is a potent candidate as a lead compound, and may be considered for development of a new antitubercular agent.

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