Facile syntheses of Mannich bases of 3-[p-(5'-aryl-pyrazolin-3'-yl)]-phenylsydnones, as anti-tubercular and anti-microbial agents, under ionic liquid/TBAB catalytic conditions

% MIC % antitubercular activity KR nema Novel methylene bridged Mannich bases 2(a-j) were synthesized in good to excellent yields from the pyrazoline derivative (1) using various primary/secondary amines, 37 % formalin in presence of ionic liquids/TBas catalyst. The structures of the newly synthesized compounds were confirmed by IR, 1H- and 13C-NMR and GC-MS spectroscopy, as well as elemental analysis. The title compounds were screened for their anti-tubercular and antimicrobial activities. Some of the compounds exhibited very good anti-tubercular, antifungal and antibacterial activities.

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Synthesis and Biological Evaluation of Aminonaphthols Incorporated Indole Derivatives

International Journal of Medicinal Chemistry ◽

10.1155/2014/673206 ◽

2014 ◽

Vol 2014 ◽

pp. 1-12 ◽

Cited By ~ 3

Author(s):

Saundane Anand Raghunath ◽

Kirankumar Nandibeoor Mathada

Keyword(s):

Radical Scavenging ◽

Antitubercular Activity ◽

Antimicrobial Activities ◽

Biological Evaluation ◽

Secondary Amines ◽

Anticancer Activities ◽

One Pot ◽

Antioxidant Power ◽

Mic Value

An efficient one pot condensation of naphthols (1), 2,5-disubstituted indole-3-carboxaldehydes (2), and secondary amines (3) has been achieved using dichloromethane as a solvent, stirring at room temperature. Some of the new [(disubstituted amino)(5-substituted 2-phenyl-1H-indol-3-yl)methyl]naphthalene-ols (4) derivatives were prepared in good yields. The significant features of this method are simple work-up procedure, inexpensive nontoxic solvent, shorter reaction times, and excellent product yields. The structures of newly synthesized compounds (4a–r) are confirmed by their elemental analysis, FTIR, 1H and 13C NMR, and mass spectral data. These compounds were screened for their in vitro antioxidant, antimicrobial, antitubercular, and anticancer activities. Among the synthesized compounds (4a–r), the compound 4e exhibited highest activity for radical scavenging and ferric ions reducing antioxidant power activities; compounds 4b, 4h, and 4k showed good metal chelating activity. Compounds 4n and 4q showed excellent antimicrobial activities with MIC value 08 µg/mL against tested strains. Compounds 4h, 4k, 4n, and 4q exhibited promising antitubercular activity with MIC value 12.5 µg/mL. Compounds 4k and 4q exhibited 100% cell lysis at concentration 10 µg/mL against MDA-MB-231 (human adenocarcinoma mammary gland) cell lines.

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PRAVADOLINE SYNTHESIS USING AN IMIDAZOLIUM-BASED IONIC LIQUID AS A GREEN SOLVENT

Science and Technology Development Journal ◽

10.32508/stdj.v14i3.1967 ◽

2011 ◽

Vol 14 (3) ◽

pp. 79-86

Author(s):

Nam Thanh Son Phan ◽

Ha Vu Le

Keyword(s):

Ionic Liquid ◽

Ionic Liquids ◽

Acid Catalyst ◽

High Yield ◽

Viet Nam ◽

Pharmaceutical Chemical ◽

Green Solvents ◽

Green Solvent ◽

1H And 13C Nmr ◽

Lewis Acid Catalyst

An easily accessible ionic liquid, 1-butyl-3-methylimidazolium hexafluorophosphate ([BMIM][PF6]) was synthesized, and characterized using 1H and 13C NMR, and MS. The ionic liquid was demonstrated to be an efficient green solvent for the synthesis of pravadoline, one of non-steroidal drugs. High yield was achieved without the presence of an anhydrous Lewis acid catalyst. The reaction was also successfully carried out using other imidazolium-based ionic liquids, including 1-hexyl-3-methylimidazolium hexafluorophosphate ([HMIM][PF6]), and 1-octyl-3- methylimidazolium hexafluorophosphate ([OMIM][PF6]). To our best knowledge, this is the first report in Viet Nam on the synthesis of a pharmaceutical chemical in ionic liquids as green solvents.

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Synthesis and Antimicrobial, Antiproliferative Evaluation of Novel Quinolone and Conazole Analogues via Conventional and Microwave Techniques

10.21203/rs.3.rs-505744/v1 ◽

2021 ◽

Author(s):

Şule Ceylan ◽

Yıldız Uygun Cebeci ◽

Neslihan Demirbaş ◽

Şengül Alpay Karaoğlu ◽

Muhammed Altun

Keyword(s):

Antitubercular Activity ◽

Antimicrobial Activities ◽

Mannich Bases ◽

Ring Closure ◽

Anticancer Activities ◽

Standard Drug ◽

Antiproliferative Effects ◽

Benzyl Chlorides ◽

Cervical Cancer Cells ◽

Microwave Techniques

Abstract 1,2,4-Triazole-3-one (3), acquired from cinnemaldehyde was converted to the corresponding carbox(thio)amides via several steps (6a-c). Their reaction with sodium hydroxide gave the 1,2,4-triazole derivatives (7a-c). Compound 3 treatment with 2-bromo-1-(4-chlorophenyl) ethanone or 2-chloro-1-(2,4-dichlorophenyl)ethanone afforded the compounds 8a,b and by reducing these compounds reduction products were obtained (9a,b). The synthesis of (10a-e) was carried out by the reaction compounds 9a,b with different benzyl chlorides. Then oxadiazol derivative (12) was obtained by ring closure from hydrazide compound 5. Subsequently compounds 3, 7a-c and 12 were treated with various amines in the presence of formaldehyde to yield Mannich bases (11a-e, 14a-e, 13a,b). Microwave-assisted and conventional techniques were utilized for the syntheses. The structures of newly synthesized compounds were illuminated by spectroscopic methods. Their antimicrobial (MIC method), and anticancer activities (Abay’s method) were examined. Results showed that most of the compounds exhibited good antimicrobial activities. Especially compounds 14a-e which is a mannich base showed very good antitubercular activity against Mycobacterium smegmatis compared with Streptomycin standard drug. Also compounds 8a and 9b have been found to have strong antiproliferative effects on the HeLa cervical cancer cells and also these compounds did not have cytotoxic effect on normal cell.

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Mapping the “Extra Solvent Power, ESP” of Ionic Liquids for Monomers, Polymers and Globular Nanoparticles

10.26434/chemrxiv.5384293.v1 ◽

2017 ◽

Author(s):

Jose A. Pomposo

Keyword(s):

Ionic Liquid ◽

Ionic Liquids ◽

Linear Polymers ◽

Green Solvents ◽

Ionic Polymers ◽

First Time ◽

Solvent Power

Understanding the miscibility behavior of ionic liquid (IL) / monomer, IL / polymer and IL / nanoparticle mixtures is critical for the use of ILs as green solvents in polymerization processes, and to rationalize recent observations concerning the superior solubility of some proteins in ILs when compared to standard solvents. In this work, the most relevant results obtained in terms of a three-component Flory-Huggins theory concerning the “Extra Solvent Power, ESP” of ILs when compared to traditional non-ionic solvents for monomeric solutes (case I), linear polymers (case II) and globular nanoparticles (case III) are presented. Moreover, useful ESP maps are drawn for the first time for IL mixtures corresponding to case I, II and III. Finally, a potential pathway to improve the miscibility of non-ionic polymers in ILs is also proposed.

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Dynamics of Ion Locking in Doubly Polymerized Ionic Liquids

10.26434/chemrxiv.13239059.v1 ◽

2020 ◽

Author(s):

Swati Arora ◽

Julisa Rozon ◽

Jennifer Laaser

Keyword(s):

Dielectric Constant ◽

Ionic Liquid ◽

Ionic Liquids ◽

Ion Pairs ◽

Polymer Chains ◽

Ion Motion ◽

Charged Species ◽

Broadband Dielectric Spectroscopy ◽

Covalently Linked ◽

Insight Into

<div>In this work, we investigate the dynamics of ion motion in “doubly-polymerized” ionic liquids (DPILs) in which both charged species of an ionic liquid are covalently linked to the same polymer chains. Broadband dielectric spectroscopy is used to characterize these materials over a broad frequency and temperature range, and their behavior is compared to that of conventional “singly-polymerized” ionic liquids (SPILs) in which only one of the charged species is attached to the polymer chains. Polymerization of the DPIL decreases the bulk ionic conductivity by four orders of magnitude relative to both SPILs. The timescales for local ionic rearrangement are similarly found to be approximately four orders of magnitude slower in the DPILs than in the SPILs, and the DPILs also have a lower static dielectric constant. These results suggest that copolymerization of the ionic monomers affects ion motion on both the bulk and the local scales, with ion pairs serving to form strong physical crosslinks between the polymer chains. This study provides quantitative insight into the energetics and timescales of ion motion that drive the phenomenon of “ion locking” currently under investigation for new classes of organic electronics.</div>

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Ionic Liquid Assisted Synthesis of Some 2-Aminobenzenethiols

Letters in Organic Chemistry ◽

10.2174/1570178615666181011114454 ◽

2019 ◽

Vol 16 (7) ◽

pp. 550-555

Author(s):

Dinesh K. Jangid ◽

Keshav L. Ameta ◽

Surbhi Dhadda ◽

Anjali Guleria ◽

Prakash G. Goswami ◽

...

Keyword(s):

Ionic Liquid ◽

Ionic Liquids ◽

Comparative Study ◽

Maximum Yield ◽

Efficient Synthesis ◽

Target Molecules ◽

Presence And Absence

Ionic Liquid assisted efficient synthesis of some 2-aminobenzenethiols has been reported using three different Ionic Liquids (ILs) namely methylimidazolium tetrafluoroborate [MIM]+[BF4]−, methylimidazolium chloride [MIM]+[Cl]− and methylimidazolium nitrate [MIM]+[NO3]−. A comparative study has been carried out for the synthesis of target molecules in the presence and absence of IL, leading to conclusion that maximum yield has been observed with [MIM]+[BF4]−.

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Synthesis and Antimicrobial activities of Some Polyphenol compounds by Nano ZnO-TBAB as a Heterogeneous Catalytic Media

Letters in Organic Chemistry ◽

10.2174/1570178617999200517131353 ◽

2020 ◽

Vol 17 ◽

Author(s):

Rahele Bargebid ◽

Ali Khalafi-Nezhad ◽

Kamiar Zomorodian ◽

Leila Zamani ◽

Ali Ahmadinejad ◽

...

Keyword(s):

Antibacterial Activities ◽

Antimicrobial Activities ◽

Reusable Catalyst ◽

Nano Zno ◽

Antifungal Activities ◽

Chemical Structures ◽

Heterogeneous Catalytic ◽

Solvent Free Conditions ◽

New Compounds ◽

Derivatives Of

Introduction: Mannich reaction is a typical example of a three-component condensation reaction and the chemistry of Mannich bases has been the matter of search by researchers. Here an efficient procedure for the synthesis of some new Mannich derivatives of simple phenols is described. Methods: In this procedure a microwave-assisted and solvent less condensation were done between different phenols, secondary amines and paraformaldehyde. The reactions proceed in the presence of catalytic amount of nano ZnO and tetrabutylammonium bromide (TBAB) in excellent yields. 10 new compounds were synthesized (A1-A10). Chemical structures of all new compounds were confirmed by different spectroscopic methods. We optimized the chemical reactions in different conditions. Optimization reactions were done in the presence of different mineral oxides, different amount of TBAB and also different solvents. Nano ZnO and TBAB in catalytic amounts and solvent free conditions were the best conditions. All the synthesized compounds were screened for their antimicrobial activities. Antifungal and antibacterial activities of the synthesized compounds were evaluated against some Candida, filaments fungi, gram positive and gram negative bacteria by broth micro dilution method as recommended by CLSI. Results: The result showed that compounds A2, A3 and A4 against most of the tested Candida species and compounds A5 and A7 against C. parapsilosis and C. tropicalis, exhibited considerable antifungal activities. Also Compounds A8 and A10 showed desirable antifungal activities against C. neoformance and C. parapsilosis, respectively. The antibacterial activities of the synthesized compounds were also evaluated. Compounds A6 - A10 against E. Fecalis and compounds A5, A7, A9 and A10 against P. aeruginosa showed desirable antibacterial activities. Discussion: We have synthesized some new Mannich adducts of poly-hydroxyl phenols in the presence of nano-ZnO as a reusable catalyst, with the hope of discovering new lead compounds serving as potent antimicrobial agents. The advantages of this method are generality, high yields with short reaction times, simplicity, low cost and matching with green chemistry protocols. The antimicriobial studies of Mannich derivatives of phenols showed desirable results in vitro.

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The Development of Tyrosyl-DNA Phosphodyesterase 1 (TDP1) Inhibitors Based on the Amines Combining Aromatic/Heteroaromatic and Monoterpenoid Moieties

Letters in Drug Design & Discovery ◽

10.2174/1570180816666181220121042 ◽

2019 ◽

Vol 16 (5) ◽

pp. 597-605 ◽

Cited By ~ 1

Author(s):

Evgenii Mozhaitsev ◽

Evgenii Suslov ◽

Yuliya Demidova ◽

Dina Korchagina ◽

Konstantin Volcho ◽

...

Keyword(s):

Dna Repair ◽

Tumor Cell ◽

13C Nmr ◽

Inhibitory Activity ◽

Secondary Amines ◽

Repair Enzyme ◽

1H And 13C Nmr ◽

Chemical Structures ◽

Natural Substances ◽

Micromolar Range

Background: Inhibition of the DNA repair enzyme, tyrosyl-DNA phosphodiesterase 1 (TDP1), may increase the efficacy of cancer drugs that cause damage to tumor cell DNA. Among the known TDP1 inhibitors, there are compounds containing moieties of natural substances, e.g., monoterpenoids. In this work, we synthesized several compounds containing aromatic/ heteroaromatic amines and monoterpenoid groups and assessed their TDP1 inhibition potential. Methods: Structures of all the synthesized compounds were confirmed by 1H and 13C NMR as well as HRMS. The TDP1 inhibitory activity of the amines was determined by real-time fluorescence oligonucleotide biosensor. Results: The synthesized secondary amines had TDP1 inhibitory activity IC50 in the range of 0.79-9.2 µM. The highest activity was found for (–)-myrtenal derivatives containing p-bromoaniline or m-(trifluoromethyl)aniline residue. Conclusion: We synthesized 22 secondary amines; of these, 17 amines are novel chemical structures. Many of the amines inhibit TDP1 activity in the low micromolar range. Therefore, these compounds are promising for further study of their antiproliferative activity in conjunction with DNA damaging drugs.

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Dispersive Liquid-Liquid Microextraction Based on Ionic Liquid and Spectrophotometric Determination of Bilirubin in Biological Samples

Current Analytical Chemistry ◽

10.2174/1573411015666190212123437 ◽

2020 ◽

Vol 16 (5) ◽

pp. 652-659

Author(s):

Asiye A. Avan ◽

Hayati Filik

Keyword(s):

Ionic Liquid ◽

Ionic Liquids ◽

Biological Samples ◽

Urine Samples ◽

Spectrophotometric Detection ◽

Full Color ◽

Dispersive Liquid Liquid Microextraction ◽

Urine And Serum ◽

Liquid Microextraction

Background: An Ionic Liquid-based based Dispersive Liquid-Liquid Microextraction (IL-DLLME) method was not applied to preconcentration and determination of bilirubin. Ionic Liquids (ILs) are new chemical compounds. In recent years, Ionic Liquids (ILs) have been employed as alternative solvents to toxic organic solvents. Due to these perfect properties, ILs have already been applied in many analytical extraction processes, presenting high extraction yield and selectivity for analytes. Methods: In this study, IL-DLLME was applied to biological samples (urine and serum) for the spectrophotometric detection of bilirubin. For bilirubin analysis, the full-color development was based on the reaction with periodate in the presence of hydrochloric acid. The high affinity of bilirubin for the ionic liquid phase gave extraction percentages above 98% in 0.3 M HCl solution. Results: Several IL-extraction parameters were optimized and room temperature ionic liquid 1-butyl- 1-methylpyrrolidinium bis(trifluoromethylsulfonyl)imide and ethanol were used as extraction and disperser solution. The linear range was found in the range of 0.5-6.0 μM (0.3-3.5 μg mL-1) and the limits of detection of the proposed method was 0.5 μM (0.3 μg mL-1). The proposed method was applied for the preconcentration and separation of trace bilirubin in real urine samples. Also, the recoveries for bilirubin in spiked biological samples (urine and serum) were found to be acceptable, between 95-102%. Conclusion: The proposed IL-DLLMEapproach was employed for the enrichment and determination of trace levels of bilirubin in urine samples using NaIO4 as an oxidizing agent and Uv-vis spectrophotometric detection. The periodate oxidation of bilirubin is rapid, effective, selective, and simple to perform. The method contains only HCl, NaOI4, and an anionic surfactant. The method may be useful for economizing in the consumption of reagents in bilirubin determining. The IL-DLLMEmethod ensures a high yield and has a low toxicity no skin sensitization, no mutagenicity and no ecotoxicity in an aquatic environment since only very low quantities of an IL is required. For full-color formation, no any extra auxiliary reagents are required. Besides, the IL-DLLME technique uses a low-cost instrument such as Uv-vis which is present in most of the medical laboratories.

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