Eco-Friendly Synthesis, Characterization and Biological Evaluation of Some Novel Pyrazolines Containing Thiazole Moiety as Potential Anticancer and Antimicrobial Agents

The one-pot synthesis of a series of pyrazoline derivatives containing the bioactive thiazole ring has been performed through a 1,3-dipolar cycloaddition reaction of N-thiocarbamoylpyrazoline and different hydrazonoyl halides or α-haloketones in the presence of DABCO (1,4-diazabicyclo[2.2.2] octane) as an eco-friendly catalyst using the solvent-drop grinding method. The structure of the synthesized compounds was elucidated using elemental and spectroscopic analyses (IR, NMR, and Mass). The activity of these compounds against human hepatocellular carcinoma cell line (HepG2) was tested and the results showed that the pyrazoline 11f, which has a fluorine substituent, is the most active. The antimicrobial activities of the newly synthesized compounds were determined against two fungi and four bacterial strains, and the results indicated that some of the newly synthesized pyrazolines are more potent than the standard drugs against test organisms.

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Novel Substituted Indazoles towards Potential Antimicrobial Agents

Oriental Journal Of Chemistry ◽

10.13005/ojc/370234 ◽

2021 ◽

Vol 37 (2) ◽

pp. 508-512

Author(s):

Jaganmohana Rao Saketi ◽

S N Murthy Boddapati ◽

Raghuram M ◽

Geetha Bhavani Koduru ◽

Haribabu Bollikolla

Keyword(s):

Escherichia Coli ◽

Antimicrobial Activity ◽

Candida Albicans ◽

Xanthomonas Campestris ◽

Antimicrobial Agents ◽

Evaluation Studies ◽

Antimicrobial Activities ◽

Biological Evaluation ◽

Fungal Strain ◽

Bacterial Strains

The in vitroantimicrobial properties of a series of N-methyl-3-aryl indazoles (5a-5j) were screened. In this present work, we describe our efforts towards the development of potent antimicrobial activity of synthesized indazole derivatives. The antimicrobial activities of the prepared compounds were investigated against four bacterial strains: Xanthomonas campestris, Escherichia coli, Bacillus cereus, Bacillus megaterium, and a fungal strain Candida albicans. The biological evaluation studies of these indazole derivatives revealed that some of these tested compounds have shown moderate to goodin vitroantimicrobial activities.

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Design, Synthesis and Antimicrobial Study of Novel 1-(1,3-benzothiazol-2- yl)-3-chloro-4H-spiro[azetidine-2,3'-indole]-2',4(1'H)-diones Through Ketene– imine Cycloaddition Reaction

Letters in Organic Chemistry ◽

10.2174/1570178616666190705153224 ◽

2020 ◽

Vol 17 (2) ◽

pp. 141-148

Author(s):

Divyani Gandhi ◽

Ayushi Sethiya ◽

Dinesh Kr. Agarwal ◽

Prakash Prajapat ◽

Shikha Agarwal

Keyword(s):

Candida Albicans ◽

Antimicrobial Agents ◽

Cycloaddition Reaction ◽

Antimicrobial Activities ◽

Dilution Method ◽

Bacterial Strains ◽

Design Synthesis ◽

E Coli ◽

Excellent Activity ◽

Broth Dilution

: The present study deals with the synthesis of novel 1-(1,3-benzothiazol-2-yl)-3-chloro-4Hspiro[ azetidine-2,3'-indole]-2',4(1'H)-dione derivatives from the reaction of 3-(1,3-benzothiazol-2- ylimino)-1,3-dihydro-2H-indol-2-one derivatives with chloroacetyl chloride in the presence of triethylamine (TEA). The mechanism involved simple acid or base catalysed reaction through the formation of Schiff base followed by cyclisation via ketene–imine cycloaddition reaction. All synthesized compounds were characterized by FT-IR, 1H-NMR, 13C-NMR, and elemental analysis. The antimicrobial activities of the synthesized derivatives 5a-5g were examined via Micro Broth Dilution method against bacterial strains Bacillius subtilis, Staphylcoccus aureus, E. coli, P. aeruginosa, and fungal strain Candida albicans for determining MIC values. Ampicillin, chloramphenicol, and griseofulvin were used as standard drugs. : The MIC values for antimicrobial activity of synthesized compounds were examined using Micro Broth Dilution method. Compounds 5a, 5b, and 5c were found effective against E. coli (MTCC 442) and P.aeruginosa (MTCC 441) and all compounds showed moderate to excellent activity against Streptococcus aureus (MTCC 96) and Bacillius subtilis (MTCC 441). Regarding the antifungal screening, compounds 5a, 5b, and 5c exhibited excellent activity against Candida albicans MTCC 227. 1-(1,3-benzothiazol-2-yl)-3-chloro-4H-spiro[azetidine-2,3'-indole]-2',4(1'H)-dione derivatives may be used as potential lead molecules as effective antimicrobial agents.

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Synthesis and biological evaluation of (3-arylisoxazol-5-yl) methyl 6-fluoro-4-oxo-4H-chromene-2-carboxylates as antioxidant and antimicrobial agents

Journal of the Serbian Chemical Society ◽

10.2298/jsc151222088b ◽

2017 ◽

Vol 82 (1) ◽

pp. 1-12 ◽

Cited By ~ 14

Author(s):

Kumaraswamy Battula ◽

Sirassu Narsimha ◽

Vasudeva Nagavelli ◽

Rao Srinivasa

Keyword(s):

Antioxidant Activity ◽

Antimicrobial Agents ◽

Antimicrobial Activities ◽

Biological Evaluation ◽

Bacterial Strains ◽

Standard Drug ◽

Gram Negative ◽

Synthesis And Biological Evaluation ◽

Antioxidant And Antimicrobial Activities

A series of novel (3-aryl-1,2-oxazol-5-yl) methyl 6-fluoro-4-oxo-4H- -chromene-2-carboxylate derivatives (C1-C12) were synthesized by Cu (I) catalyzed reaction of in situ generated nitrile oxides with prop-2-yn-1-yl 6-fluoro-4-oxo-4H-chromene-2-carboxylate in good yields and investigated their antioxidant and antimicrobial activities. Among all the synthesized compounds, C1 (IC50: 16.43 ? 0.57 ?M) and C12 (IC50:15.98 ? 0.72 ?M) have registered good antioxidant activity as compared to the standard drug Trolox. Compound-C1, C3, and C6 have registered very good inhibition against all gram-positive and gram-negative bacterial strains with MIC values ranging from 9.375 to 37.5 (?g mL-1). Compound-C7, C8, C9, C10, and C11 have registered good inhibition against B. subtilis and S. aureus with MIC values ranging from 18.75 to 37.5 (?g mL-1). Compound-C10 and C11 against P. aero-ginosa have shown prominent activity than the standard drug Penicillin (MIC: 12.5 ?g mL-1) with MIC 9.375 ?g mL-1 (~ 1.33 fold potent than Penicillin). Compound-C7, C8, and C9 have registered good to moderate antifungal activity against four tested fungal strains with MIC values ranging from 18.75 and 37.5 ?g mL-1

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SYNTHESIS, CHARACTERIZATION AND BIOLOGICAL EVALUATION OF 3-FORMYL INDOLE BASED SCHIFF BASES

Journal of Biomedical and Pharmaceutical Research ◽

10.32553/jbpr.v7i6.561 ◽

2018 ◽

Vol 7 (6) ◽

Author(s):

Singh Gurvinder ◽

Singh Prabhsimran ◽

Dhawan R. K.

Keyword(s):

Antimicrobial Activity ◽

Spectral Analysis ◽

Schiff Bases ◽

Antimicrobial Agents ◽

Biological Evaluation ◽

Fungal Strain ◽

Bacterial Strains ◽

Standard Drug ◽

Gram Negative ◽

E Coli

In order to develop new antimicrobial agents, a series of 3-formyl indole based Schiff bases were synthesized by reacting 3-formyl indole(indole-3-carboxaldehyde) with substituted aniline taking ethanol as solvent. The reaction was carried in the presence of small amount of p-toluene sulphonic acid as catalyst.All the synthesized compounds were characterized by IR, 1H-NMR spectral analysis. All the synthesized compounds were evaluated for antimicrobial activity against two gram positive bacterial strains (B. subtilisand S. aureus) and two gram negative bacterial strains (P. aeruginosaand E. coli) and one fungal strain (C. albicans). All the synthesized compounds were found to have moderate to good antimicrobial activity. The standard drug amoxicillin, fluconazole were used for antimicrobial activity. Among the synthesized compounds, the maximum antimicrobial activity was shown by compounds GS04, GS07, GS08 and GS10.

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Copper-catalyzed Convenient Synthesis and SAR Studies of Substituted-1,2,3-triazole as Antimicrobial Agents

Letters in Drug Design & Discovery ◽

10.2174/1570180815666180326153322 ◽

2018 ◽

Vol 16 (1) ◽

pp. 3-10

Author(s):

Aniket P. Sarkate ◽

Kshipra S. Karnik ◽

Pravin S. Wakte ◽

Ajinkya P. Sarkate ◽

Ashwini V. Izankar ◽

...

Keyword(s):

Antimicrobial Activity ◽

Antifungal Activity ◽

Antimicrobial Agents ◽

Cycloaddition Reaction ◽

Dipolar Cycloaddition ◽

One Pot ◽

Triazole Derivatives ◽

Sar Studies ◽

Convenient Synthesis ◽

Antibacterial And Antifungal

Background:A novel copper-catalyzed synthesis of substituted-1,2,3-triazole derivatives has been developed and performed by Huisgen 1,3-dipolar cycloaddition reaction of azides with alkynes. The reaction is one-pot multicomponent.Objective:We state the advancement and execution of a methodology allowing for the synthesis of some new substituted 1,2,3-triazole analogues with antimicrobial activity.Methods:A series of triazole derivatives was synthesized by Huisgen 1,3-dipolar cycloaddition reaction of azides with alkynes. The structures of the synthesized compounds were elucidated and confirmed by 1H NMR, IR, MS and elemental analysis. All the synthesized compounds were tested for their antimicrobial activity against a series of strains of Bacillus subtilis, Staphylococcus aureus and Escherichia coli for antibacterial activity and against the strains of Candida albicans, Aspergillus flavus and Aspergillus nigar for antifungal activity, respectively.Results and Conclusion:From the antimicrobial data, it was observed that all the newly synthesized compounds showed good to moderate level of antibacterial and antifungal activity.

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A New Supported Manganese-Based Coordination Complex as a Nano-Catalyst for the Synthesis of Indazolophthalazinetriones and Investigation of Its Antibacterial Activity

Chemistry ◽

10.3390/chemistry3030056 ◽

2021 ◽

Vol 3 (3) ◽

pp. 783-799

Author(s):

Maryam Ariannezhad ◽

Davood Habibi ◽

Somayyeh Heydari ◽

Vahideh Khorramabadi

Keyword(s):

Antibacterial Activity ◽

Simple Procedure ◽

Condensation Reaction ◽

Antibacterial Properties ◽

Coordination Complex ◽

Bacterial Strains ◽

One Pot ◽

Nano Catalyst ◽

Ft Ir ◽

The One

A new magnetic supported manganese-based coordination complex (Fe3O4@SiO2@CPTMS@MBOL@ Mn) was prepared in consecutive stages and characterized via various techniques (VSM, SEM, TEM, XRD, FT-IR, EDX, TG-DTA, and ICP). To evaluate its application, it was used for synthesis of divers Indazolophthalazinetriones in a simple procedure via the one-pot three-component condensation reaction of aldehydes, dimedone, and phthalhydrazide in ethanol under reflux conditions. The Mn catalyst can be recycled without any noticeable loss in catalytic activity. Additionally, the antibacterial properties of the nano-catalyst were studied against some bacterial strains.

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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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DPPH-Scavenging and Antimicrobial Activities of Asteraceae Medicinal Plants on Uropathogenic Bacteria

Evidence-based Complementary and Alternative Medicine ◽

10.1155/2020/7807026 ◽

2020 ◽

Vol 2020 ◽

pp. 1-9 ◽

Cited By ~ 2

Author(s):

Phan-Canh Trinh ◽

Le-Thi-Thanh Thao ◽

Hoang-Tran-Viet Ha ◽

TuAnh Nguyen

Keyword(s):

Antimicrobial Agents ◽

Natural Antioxidants ◽

Ethyl Acetate Fraction ◽

Antimicrobial Activities ◽

Chrysanthemum Morifolium ◽

Bacterial Strains ◽

Ageratum Conyzoides ◽

Potent Effect ◽

E Coli ◽

Dpph Scavenging

Asteraceae species were widely applied in traditional medicines in Asian countries as sources of natural antioxidants and antimicrobial agents. This study aimed to evaluate DPPH-scavenging capacities and antimicrobial activities of nine Asteraceae species collected from Southern Vietnam. Antioxidant and antimicrobial activities were determined by standard protocols. Essential oils from Ageratum conyzoides, Helianthus annuus, and Artemisia vulgaris indicated significant inhibitory effects on Staphylococcus aureus and Candida spp. Crude extracts and fractions from Taraxacum officinale, Chrysanthemum morifolium, A. conyzoides, and Tagetes erecta showed inhibitory ability on at least one testing bacterial strains including S. aureus, Escherichia coli, Klebsiella pneumoniae, and Pseudomonas aeruginosa. In a study on clinical isolates, ethyl acetate fraction from A. conyzoides flower displayed the most potent effect on uropathogenic E. coli and K. pneumoniae with MIC at 1.25–10 mg/ml and 5–12.5 mg/ml, respectively. DPPH-scavenging assay indicated that T. erecta extract had the lowest IC50 (17.280 μg/ml) and is 2.4 times higher than vitamin C (7.321 μg/ml). This study revealed that A. conyzoides has good potential against uropathogenic E. coli and K. pneumoniae, and therefore could be applied for prophylactic treatment of urinary infection.

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

Journal of Chemistry ◽

10.1155/2021/6631868 ◽

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.

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N-(Hydroxyalkyl) Derivatives of tris(1H-indol-3-yl)methylium Salts as Promising Antibacterial Agents: Synthesis and Biological Evaluation

Pharmaceuticals ◽

10.3390/ph13120469 ◽

2020 ◽

Vol 13 (12) ◽

pp. 469

Author(s):

Sergey N. Lavrenov ◽

Elena B. Isakova ◽

Alexey A. Panov ◽

Alexander Y. Simonov ◽

Viktor V. Tatarskiy ◽

...

Keyword(s):

Antibacterial Activity ◽

Antimicrobial Agents ◽

Carbon Chain ◽

Biological Evaluation ◽

Carbon Chain Length ◽

Klebsiella Pneumonia ◽

Moderate Activity ◽

Bacterial Strains ◽

Reference Drug

The wide spread of pathogens resistance requires the development of new antimicrobial agents capable of overcoming drug resistance. The main objective of the study is to elucidate the effect of substitutions in tris(1H-indol-3-yl)methylium derivatives on their antibacterial activity and toxicity to human cells. A series of new compounds were synthesized and tested. Their antibacterial activity in vitro was performed on 12 bacterial strains, including drug resistant strains, that were clinical isolates or collection strains. The cytotoxic effect of the compounds was determined using an test with HPF-hTERT (human postnatal fibroblasts, immortalized with hTERT) cells. The activity of the obtained compounds depended on the carbon chain length. Derivatives with C5–C6 chains were more active. The minimum inhibitory concentration (MIC) of the most active compound on Gram-positive bacteria, including MRSA, was 0.5 μg/mL. Compounds with C5–C6 chains also revealed high activity against Staphylococcus epidermidis (1.0 and 0.5 μg/mL, respectively) and moderate activity against Gram-negative bacteria Escherichia coli (8 μg/mL) and Klebsiella pneumonia (2 and 8 μg/mL, respectively). However, they have no activity against Salmonella cholerasuis and Pseudomonas aeruginosa. The most active compounds revealed higher antibacterial activity on MRSA than the reference drug levofloxacin, and their ratio between antibacterial and cytotoxic activity exceeded 10 times. The data obtained provide a basis for further study of this promising group of substances.

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