Synthesis, characterization and evaluation of antidiabetic activity of novel indoline derivatives

Series of indoline derivatives were synthesized using N-(4-aminophenyl)indoline-1-carbothiamide as a precursor. The confirmation of synthesized compounds was done by 1H-NMR, 13C-NMR, LC-MS (ESI) and FT-IR. In vitro antidiabetic activity of synthesized indoline derivatives were examined by standard α-amylase inhibition assay. The compounds 4a (IC50 = 52.1 µg/mL) and 4b (IC50 = 57.7 µg/mL) showed potent α-amylase inhibition activity. The compounds 3a (IC50 = 62.2 µg/mL) and 3b (IC50 = 60.7 µg/mL) showed moderate antidiabetic activity.Video Clip of Methodology:19 min 21 sec <a href="https://www.youtube.com/v/k5WdfpM-E8U">Full Screen</a> <a href="https://www.youtube.com/watch?v=k5WdfpM-E8U">Alternate</a>

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In SilicoMolecular Docking andIn VitroAntidiabetic Studies of Dihydropyrimido[4,5-a]acridin-2-amines

BioMed Research International ◽

10.1155/2014/971569 ◽

2014 ◽

Vol 2014 ◽

pp. 1-10 ◽

Cited By ~ 2

Author(s):

A. Bharathi ◽

Selvaraj Mohana Roopan ◽

C. S. Vasavi ◽

Punnagai Munusami ◽

G. A. Gayathri ◽

...

Keyword(s):

Molecular Docking ◽

Structural Analysis ◽

Selective Inhibition ◽

Analysis Data ◽

Antidiabetic Activity ◽

X Ray ◽

H Nmr ◽

Ft Ir ◽

C Nmr

Anin vitroantidiabetic activity onα-amylase andα–glucosidase activity of novel 10-chloro-4-(2-chlorophenyl)-12-phenyl-5,6-dihydropyrimido[4,5-a]acridin-2-amines (3a–3f) were evaluated. Structures of the synthesized molecules were studied by FT-IR,1H NMR,13C NMR, EI-MS, and single crystal X-ray structural analysis data. Anin silicomolecular docking was performed on synthesized molecules (3a–3f). Overall studies indicate that compound3eis a promising compound leading to the development of selective inhibition ofα-amylase andα-glucosidase.

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SYNTHESIS AND STRUCTURAL ELUCIDATION OF AMINO ACETYLENIC AND THIOCARBAMATES DERIVATIVES FOR 2-MERCAPTOBENZOTHIAZOLE AS ANTIMICROBIAL AGENTS

International Journal of Pharmacy and Pharmaceutical Sciences ◽

10.22159/ijpps.2017v9i2.15760 ◽

2017 ◽

Vol 9 (2) ◽

pp. 192

Author(s):

Aseel Alsarahni ◽

Zuhair Muhi Eldeen ◽

Elham Al-kaissi ◽

Ibrahim Al- Adham ◽

Najah Al-muhtaseb

Keyword(s):

Antimicrobial Activity ◽

Elemental Analysis ◽

Antimicrobial Agents ◽

Diffusion Method ◽

Benzothiazole Derivatives ◽

H Nmr ◽

Ft Ir ◽

Potential Antimicrobial Activity ◽

C Nmr

Objective: To design and synthesize amino acetylenic and thiocarbonate of 2-mercapto-1,3-benthiazoles as potential antimicrobial agents.Methods: A new series of 2-{[4-(t-amino-1-yl) but-2-yn-1-yl] sulfanyl}-1,3-benzothiazole derivatives (AZ1-AZ6), and S-1,3-benzothiazol-2-yl-O-alkyl carbonothioate derivatives were synthesised, with the aim that the target compounds show new and potential antimicrobial activity. The elemental analysis was indicated by the EuroEA elemental analyzer, and biological characterization was via IR, 1H-NMR, [13]C-NMR, DSC were determined with the aid of Bruker FT-IR and Varian 300 MHz spectrometer using DMSO-d6 as a solvent. In vitro antimicrobial activity, evaluation was done for the synthesised compounds, by agar diffusion method and broth dilution test. The minimum inhibitory concentration (MIC) and the minimum bactericidal concentration (MBC) were determined. Results: The IR, 1H-NMR, 13C-NMR, DSC and elemental analysis were consistent with the assigned structures. Compound of 2-{[4-(4-methylpiperazin-1-yl)but-2-yn-1-yl] sulfanyl}-1,3-benzothiazole (AZ1), 2-{[4-(2-methylpiperidin-1-yl)but-2-yn-1-yl]sulfanyl}-1,3-benzothiazole (AZ2), 2-{[4-(piperidin-1-yl) but-2-yn-1-yl]sulfanyl}-1, 3-benzothiazole (AZ6), S-1,3-benzothiazol-2-yl-O-ethyl carbonothioate (AZ7), and S-1,3-benzothiazol-2-yl-O-(2-methylpropyl) carbonothioate (AZ9) showed the highest antimicrobial activity against Pseudomonas aeruginosa (P. aeruginosa), AZ-9 demonstrated the highest antifungal activity against Candida albicans (C. albicans), with MIC of 31.25 µg/ml.Conclusion: These promising results promoted our interest to investigate other structural analogues for their antimicrobial activity further.

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A new class of potential antidiabetic acetohydrazides: Synthesis, in vivo antidiabetic activity and molecular docking studies

Bangladesh Journal of Pharmacology ◽

10.3329/bjp.v12i3.31428 ◽

2017 ◽

Vol 12 (3) ◽

pp. 319 ◽

Cited By ~ 1

Author(s):

Mubeen Arif ◽

Furukh Jabeen ◽

Aamer Saeed ◽

Irfan Zia Qureshi ◽

Nadia Mushtaq

Keyword(s):

Molecular Docking ◽

Video Clip ◽

Docking Studies ◽

Antidiabetic Activity ◽

Molecular Docking Studies ◽

H Nmr ◽

New Class ◽

Full Screen ◽

Pharmacologically Active

Two new pharmacologically active series of tetrazolopyridine-acetohydrazide conjugates [9 (a-n), 10 (a-n)] were synthesized by reacting a variety of suitably substituted benzaldehydes and isomeric 2-(5-(pyridin-3/4-yl)-2H-tetrazol-2-yl)acetohydrazides (7, 8). The synthesized compounds were analyzed through FTIR, 1H NMR, 13C NMR and elemental techniques. These acetohydrazides were screened for their in vivo antidiabetic activity and molecular docking studies. An excellent agreement was obtained as the best docked poses show-ed important binding features mostly based on interactions due to an oxygen atom and aromatic moieties of the series. The compounds 9a, 9c and 10l were found to be the most active in lowering blood glucose, having the potential of being good antidiabetic agents.Video Clip of Methodology:Synthesis of 3/4-(2H-tetrazole-5-yl)pyridine: 1 min 57 sec <a href="https://www.youtube.com/v/CHp8HxlEa2M">Full Screen</a> <a href="https://www.youtube.com/watch?v=CHp8HxlEa2M">Alternate</a>

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Synthesis, in vitro inhibition effect of novel phthalocyanine complexes as carbonic anhydrase and paraoxonase enzyme inhibitors

Journal of Porphyrins and Phthalocyanines ◽

10.1142/s1088424620500170 ◽

2020 ◽

Vol 24 (08) ◽

pp. 1047-1053

Author(s):

Emre Güzel ◽

Barış Seçkin Arslan ◽

Kübra Çıkrıkçı ◽

Adem Ergün ◽

Nahit Gençer ◽

...

Keyword(s):

Carbonic Anhydrase ◽

Enzyme Inhibitors ◽

Inhibition Effect ◽

H Nmr ◽

Vis Spectroscopy ◽

Ft Ir ◽

First Time ◽

Ft Ir Spectroscopy ◽

C Nmr

The preparation and assessment of carbonic anhydrase and paraoxonase enzyme inhibition properties of 3-(2-(5-amino-4-(4-bromophenyl)-3-methyl-1H-pyrazol-1-yl)ethoxy)phthalonitrile (2) and its nitrogen-containing non-peripheral phthalocyanine derivatives (3 and 4) are reported for the first time. The new phthalonitrile and its phthalocyanine derivatives have been elucidated by FT-IR spectroscopy, 1H-NMR, [Formula: see text]C-NMR, mass and UV-vis spectroscopy. The results demonstrated that all synthesized compounds moderately inhibited carbonic anhydrase and paraoxonase enzymes. Among the compounds, the most active ones were found to be compound 4 for PON (Ki : 0.14 [Formula: see text]M), compound 3 for hCA I (Ki : 22.52 [Formula: see text]M) and compound 1 for hCA II (Ki : 13.62 [Formula: see text]M).

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Design, Synthesis, and Acetylcholinesterase Inhibition Assay of Novel 9-(1-(Substituted-benzyl)piperidin-4-yl)-2-chloro-9H-purin-6-amine Derivatives

Journal of Chemistry ◽

10.1155/2013/107302 ◽

2013 ◽

Vol 2013 ◽

pp. 1-9

Author(s):

Dongwei Kang ◽

Yu'ning Song ◽

Peng Zhan ◽

Qingzhu Zhang ◽

Xinyong Liu

Keyword(s):

Mass Spectra ◽

Acetylcholinesterase Inhibition ◽

Inhibition Activity ◽

Inhibition Assay ◽

Design Synthesis ◽

H Nmr ◽

C Nmr

A new series of 9-(1-(substituted-benzyl)piperidin-4-yl)-2-chloro-9H-purin-6-amine derivatives were designed, synthesized, and characterized on the basis of1H-NMR,13C-NMR, and mass spectra. The newly synthesized compounds were evaluated for the inhibition activity against acetylcholinesterase (AChE). Biological results revealed that four compounds among them showed moderate activities against AChE with inhibitory percentage more than 10% at 100 μM. Further pharmacology investigation towards other pathological routes in AD is currently underway.

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Biological Evaluation of Noscapine analogues as Potent and Microtubule-Targeted Anticancer Agents

Scientific Reports ◽

10.1038/s41598-019-55839-8 ◽

2019 ◽

Vol 9 (1) ◽

Cited By ~ 6

Author(s):

Vartika Tomar ◽

Neeraj Kumar ◽

Ravi Tomar ◽

Damini Sood ◽

Neerupma Dhiman ◽

...

Keyword(s):

Anticancer Agents ◽

Biological Evaluation ◽

H Nmr ◽

Oxime Formation ◽

Formation Method ◽

Ft Ir ◽

U87 Cells ◽

Opium Alkaloid ◽

C Nmr

AbstractIn present investigation, an attempt was undertaken to modify the C-9 position of noscapine (Nos), an opium alkaloid to yield 9 -hydroxy methyl and 9 -carbaldehyde oxime analogues for augmenting anticancer potential. The synthesis of 9-hydroxy methyl analogue of Nos was carried out by Blanc reaction and 9-carbaldehyde oxime was engineered by oxime formation method and characterized using FT-IR, 1H NMR, 13C NMR, mass spectroscopy, and so on techniques. In silico docking techniques informed that 9-hydroxy methyl and 9-carbaldehyde oxime analogues of Nos had higher binding energy score as compared to Nos. The IC50 of Nos was estimated to be 46.8 µM signficantly (P < 0.05) higher than 8.2 µM of 9-carbaldehyde oxime and 4.6 µM of 9-hydroxy methyl analogue of Nos in U87, human glioblastoma cells. Moreover, there was significant (P < 0.05) difference between the IC50 of 9-carbaldehyde oxime and 9-hydroxy methyl analogue of Nos. Consistent to in vitro cytotoxicity data, 9-hydroxy methyl analogue of Nos induced significantly (P < 0.05) higher degree of apoptosis of 84.6% in U87 cells as compared to 78.5% and 64.3% demonstrated by 9-carbaldehyde oxime and Nos, respectively. Thus the higher therapeutic efficacy of 9-hydroxy methyl analogue of Nos may be credited to higher solubility and inhibitory constant (K).

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Studies of in vitro anti-prostate cancer potential of newer 1,2,4-triazolo-1,3,4-thiadiazines with different heteroaromatics

Bangladesh Journal of Pharmacology ◽

10.3329/bjp.v10i2.22424 ◽

2015 ◽

Vol 10 (2) ◽

pp. 308 ◽

Cited By ~ 5

Author(s):

Mao-Chuan Fan ◽

Guang-Ye Han ◽

Xin-Jun Zhang ◽

Hui-Fang Xi

Keyword(s):

Prostate Cancer ◽

Nmr Spectroscopy ◽

Cell Lines ◽

Prostate Cancer Cell ◽

Cytotoxic Agents ◽

Prostate Cancer Cell Lines ◽

H Nmr ◽

Ft Ir ◽

C Nmr

This study was aimed to evaluate anticancer potential of newer synthesize 1,2,4-triazolo[3,4-b]-1,3,4-thiadiazines and its derivatives. All newly furnished scaffolds were subjected to screening for their in vitro anticancer potential against DU-145 and PC-3 prostate cancer cell lines using SRB and MMT bioassays. The structures of final compounds were confirmed with the aid of FT-IR, 1H NMR, 13C NMR spectroscopy and CHN analysis. Bioassay studies suggested that all thiadiazines were promising cytotoxic agents with % cytotoxicity ranging from 44.39-71.24%, whereas potent GI50 level in the range 11.96-32.51 µg/mL and results were comparable to the potencies of control drugs adriamycin and doxorubicin. Variation of heterocyclic pharmacophores along with the C-5 position of 1,2,4-triazole in terms of quinoline, quinazoline, coumarin and pyridine lead to the different SAR predictions in which quinoline and benzimidazole moieties found most promising.

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Synthesis and Antimicrobial Activity of Coumarinyl Schiff Base Derivatives

International Letters of Chemistry Physics and Astronomy ◽

10.18052/www.scipress.com/ilcpa.30.193 ◽

2014 ◽

Vol 30 ◽

pp. 193-201 ◽

Cited By ~ 2

Author(s):

Arun Mishra ◽

Jaynt Rathod ◽

Dipti Namera ◽

Shailesh Thakrar ◽

Anamik Shah

Keyword(s):

Escherichia Coli ◽

Staphylococcus Aureus ◽

Antimicrobial Activity ◽

Gram Negative ◽

H Nmr ◽

Schiff Base Derivatives ◽

Test Organisms ◽

Ft Ir ◽

C Nmr

We have reported some novel N’-[(1)-ethylidene]-2-(6-methyl-2-oxo-2H-chromen-4-yl) acetohydrazide synthesized by conventional method. The reaction of 2-(6-methyl-2-oxo-2H-chromen-4-yl)acetohydrazide with substituted benzaldehyde in methanol as a solvent yielded a series of (7a-l). The structures of all synthesized compounds are well characterized by Mass, FT-IR, 1H NMR, 13C NMR and elemental analysis. Moreover, all synthesized compounds were screened for In Vitro antimicrobial activity against the gram positive (Staphylococcus aureus, Bacilluas subtilis) and gram negative (Escherichia coli, P. aeruginosa, K. pneunonae, Enterobacter) bacterial strain. In which some the compounds show potential inhibition against the test organisms.

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New bioactive triaryl triglyceride esters: Synthesis, characterization and biological activities

Bangladesh Journal of Pharmacology ◽

10.3329/bjp.v13i4.37210 ◽

2018 ◽

Vol 13 (4) ◽

pp. 302

Author(s):

Tanzila Arshad ◽

Hamdullah Khadim Sheikh ◽

Mehdi Hassan Kazmi ◽

Sadia Farheen ◽

Tehmina Sohail ◽

...

Keyword(s):

Biological Activities ◽

Video Clip ◽

Urease Inhibition ◽

Synthetic Compounds ◽

Benzoic Acid Derivatives ◽

Full Screen ◽

Ft Ir ◽

Urease Inhibition Activity ◽

Derivatives Of ◽

C Nmr

Four new bioactive aryl triester derivatives of glycerol and benzoic acids were synthesized. The synthetic compounds were studied for their antimicrobial and urease inhibition activities. Esterification was carried out by using carbonyldiimidazole to enhance the acyl elimination addition reaction with benzoic acid derivatives. The structure of triglycerides were studied by EI-MS, 1H, 13C-NMR, FT-IR and elemental analysis. All synthetic compounds showed urease inhibition activity with highest value of IC50 value 22.4 ± 0.45 μM which is nearest to standard thiourea IC50 value (21.6 ± 0.12 μM). Except compound (3d), all other compounds exhibited antimicrobial activity against Streptococcus pneumoniae, Staphylococcus epidermidis, Bacillus pumilus, Escherichia coli, Pseudomonas aeruginosa and Candida albican.Video Clip of Methodology:7 min 59 sec <a href="https://youtube.com/v/PvGTYUxO7-4">Full Screen</a> <a href="https://youtube.com/watch?v=PvGTYUxO7-4">Alternate</a>

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Ultrasound-assisted aqua-mediated synthesis of multi-substituted tetrahydropyridine-3-carboxylates using N-carboxymethyl-3-pyridinium hydrogensulfate ([N-CH2CO2H-3-pic]+HSO4−) as a new efficient ionic liquid catalyst

SN Applied Sciences ◽

10.1007/s42452-021-04671-9 ◽

2021 ◽

Vol 3 (6) ◽

Author(s):

Kobra Nikoofar ◽

Fatemeh Shahriyari

Keyword(s):

Ionic Liquid ◽

Reaction Times ◽

Aromatic Aldehydes ◽

Environmentally Benign ◽

H Nmr ◽

Sonic Waves ◽

Ft Ir ◽

High Yields ◽

Work Up ◽

C Nmr

AbstractA simple, straightforward, and ultrasound-promoted method for the preparation of some highly functionalized tetrahydropyridines reported via pseudo five-component reaction of (hetero)aromatic aldehydes, different anilines, and alkyl acetoacetates in the presence of [N-CH2CO2H-3-pic]+HSO4−, as a novel ionic liquid, in green aqueous medium. The IL was synthesized utilizing simple and easily-handled substrates and characterized by FT-IR, 1H NMR, 13C NMR, GC-MASS, FESEM, EDX, and TGA/DTG techniques. The procedure contains some highlighted aspects which are: (a) performing the MCR in the presence of aqua and sonic waves, as two main important and environmentally benign indexes in green and economic chemistry, (b) high yields of products within short reaction times, (c) convenient work-up procedure, (d) preparing the new IL via simple substrates and procedure.

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