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

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, characterization and evaluation of antidiabetic activity of novel indoline derivatives

Bangladesh Journal of Pharmacology ◽

10.3329/bjp.v12i2.30872 ◽

2017 ◽

Vol 12 (2) ◽

pp. 20 ◽

Cited By ~ 1

Author(s):

Dhineshkumar Manoharan ◽

Kannan Kulanthai ◽

Gnanavel Sadhasivam ◽

Vijayan Raji ◽

Paalvannan Thayumanavan

Keyword(s):

Video Clip ◽

Antidiabetic Activity ◽

Inhibition Activity ◽

Inhibition Assay ◽

H Nmr ◽

Full Screen ◽

Ft Ir ◽

C Nmr

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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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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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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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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In VitroLarvicidal and Antioxidant Activity of Dihydrophenanthroline-3-carbonitriles

BioMed Research International ◽

10.1155/2014/915797 ◽

2014 ◽

Vol 2014 ◽

pp. 1-8 ◽

Cited By ~ 1

Author(s):

A. Bharathi ◽

Selvaraj Mohana Roopan ◽

Abdul Abdul Rahuman ◽

Govindasamy Rajakumar

Keyword(s):

Antioxidant Activity ◽

Analysis Data ◽

Antioxidant Potential ◽

Assay Method ◽

Mass Analysis ◽

Dpph Assay ◽

H Nmr ◽

Naturally Occurring ◽

Ft Ir ◽

C Nmr

Many naturally occurring and synthetic compounds containing dihydrocyanopyridine and cyanopyran moiety show pharmacological properties. The aim of this study is to investigate the larvicidal and antioxidant potential of dihydrophenanthroline-3-carbonitrile derivatives4a–f. A novel series of 2-amino-10-chloro-4,12-diphenyl-1,4,5,6-tetrahydrobenzo[j][1,7]phenanthroline-3-carbonitrile derivatives were synthesized by reacting different substituted acridine chalcones through Michel addition. The compounds were synthesized in excellent yields and the structures were corroborated on the basis of FT-IR,1H NMR,13C NMR, and ESI Mass analysis data. All the synthesized compounds were evaluated for larvicidal activity againstAedes aegyptiandCulex quinquefasciatuslarvae. Furthermore, the antioxidant activity was studied by the 1,1-diphenyl-2-picrylhydrazyl (DPPH) assay method. From the antioxidant assay, the compound4cwas reported with profound antioxidant potential.

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Synthesis, biological evaluation, and molecular docking of ((4-([1,2,4]triazolo[4,3-b][1,2,4,5]tetrazin-6-yl) piperazin-1-yl)methyl) benzohydrazide derivatives

Journal of Chemical Research ◽

10.1177/1747519820911278 ◽

2020 ◽

Vol 44 (9-10) ◽

pp. 543-550

Author(s):

Xiaoyu Wu ◽

Feng Xu ◽

Zhenzhen Yang ◽

Zhonglu Ke ◽

Lei Shi ◽

...

Keyword(s):

Molecular Docking ◽

Antitumor Activity ◽

Tumor Cells ◽

Elemental Analysis ◽

Biological Evaluation ◽

Significant Inhibition ◽

Antitumor Activities ◽

H Nmr ◽

C Nmr

A series of ((4-([1,2,4]triazolo[4,3- b][1,2,4,5] methyl) benzo-hydrazide derivatives was designed, synthesized, and evaluated for their inhibition activities against five tumor cells and c-Met kinase in vitro. These compounds were fully characterized by 1H NMR, 13C NMR, MS, and elemental analysis. Antitumor experiments indicated that some compounds exhibited significant inhibition activities against A549 and Bewo. Especially, the IC50 values of 5f (12 μM), 5h (7.1 μM), 6a (8.4 μM), and 6d (9.2 μM) demonstrated better antitumor activities against A549 than the positive agent cisplatin (13.3 μM), and the IC50 value of 6a (5.2 μM) exhibited better antitumor activity against Bewo than cisplatin (7.7 μM).

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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, structure and in vitro cytotoxicity testing of some 2-aroylbenzofuran-3-ols

Acta Crystallographica Section C Structural Chemistry ◽

10.1107/s2053229620011018 ◽

2020 ◽

Vol 76 (9) ◽

pp. 874-882

Author(s):

Nguyen Tien Cong ◽

Huynh Thi Xuan Trang ◽

Pham Duc Dung ◽

Tran Hoang Phuong ◽

Vu Quoc Trung ◽

...

Keyword(s):

Human Cancer ◽

In Vitro Cytotoxicity ◽

X Ray Diffraction ◽

Hep G2 ◽

Hep G2 Cells ◽

X Ray ◽

Human Cancer Cell Lines ◽

H Nmr ◽

C Nmr

Five 2-aroyl-5-bromobenzo[b]furan-3-ol compounds (two of which are new) and four new 2-aroyl-5-iodobenzo[b]furan-3-ol compounds were synthesized starting from salicylic acid. The compounds were characterized by mass spectrometry and 1H NMR and 13C NMR spectroscopy. Single-crystal X-ray diffraction studies of four compounds, namely, (5-bromo-3-hydroxybenzofuran-2-yl)(4-fluorophenyl)methanone, C15H8BrFO3, (5-bromo-3-hydroxybenzofuran-2-yl)(4-chlorophenyl)methanone, C15H8BrClO3, (5-bromo-3-hydroxybenzofuran-2-yl)(4-bromophenyl)methanone, C15H8Br2O3, and (4-bromophenyl)(3-hydroxy-5-iodobenzofuran-2-yl)methanone, C15H8BrIO3, were also carried out. The compounds were tested for their in vitro cytotoxicity on the four human cancer cell lines KB, Hep-G2, Lu-1 and MCF7. Six compounds show good inhibiting abilities on Hep-G2 cells, with IC50 values of 1.39–8.03 µM.

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Synthesis, structure and in vitro cytotoxicity testing of some 1,3,4-oxadiazoline derivatives from 2-hydroxy-5-iodobenzoic acid

Acta Crystallographica Section C Structural Chemistry ◽

10.1107/s2053229618008719 ◽

2018 ◽

Vol 74 (7) ◽

pp. 839-846 ◽

Cited By ~ 2

Author(s):

Cong Nguyen Tien ◽

Thin Nguyen Van ◽

Giang Le Duc ◽

Manh Vu Quoc ◽

Trung Vu Quoc ◽

...

Keyword(s):

Human Cancer ◽

In Vitro Cytotoxicity ◽

X Ray Diffraction ◽

Hep G2 ◽

X Ray ◽

Human Cancer Cell Lines ◽

Π Interactions ◽

H Nmr ◽

C Nmr

The syntheses of nine new 5-iodosalicylic acid-based 1,3,4-oxadiazoline derivatives starting from methyl salicylate are described. These compounds are 2-[4-acetyl-5-methyl-5-(3-nitrophenyl)-4,5-dihydro-1,3,4-oxadiazol-2-yl]-4-iodophenyl acetate (6a), 2-[4-acetyl-5-methyl-5-(4-nitrophenyl)-4,5-dihydro-1,3,4-oxadiazol-2-yl]-4-iodophenyl acetate (6b), 2-(4-acetyl-5-methyl-5-phenyl-4,5-dihydro-1,3,4-oxadiazol-2-yl)-4-iodophenyl acetate, C19H17IN2O4 (6c), 2-[4-acetyl-5-(4-fluorophenyl)-5-methyl-4,5-dihydro-1,3,4-oxadiazol-2-yl]-4-iodophenyl acetate, C19H16FIN2O4 (6d), 2-[4-acetyl-5-(4-chlorophenyl)-5-methyl-4,5-dihydro-1,3,4-oxadiazol-2-yl]-4-iodophenyl acetate, C19H16ClIN2O4 (6e), 2-[4-acetyl-5-(3-bromophenyl)-5-methyl-4,5-dihydro-1,3,4-oxadiazol-2-yl]-4-iodophenyl acetate (6f), 2-[4-acetyl-5-(4-bromophenyl)-5-methyl-4,5-dihydro-1,3,4-oxadiazol-2-yl]-4-iodophenyl acetate (6g), 2-[4-acetyl-5-methyl-5-(4-methylphenyl)-4,5-dihydro-1,3,4-oxadiazol-2-yl]-4-iodophenyl acetate (6h) and 2-[5-(4-acetamidophenyl)-4-acetyl-5-methyl-4,5-dihydro-1,3,4-oxadiazol-2-yl]-4-iodophenyl acetate (6i). The compounds were characterized by mass, 1H NMR and 13C NMR spectroscopies. Single-crystal X-ray diffraction studies were also carried out for 6c, 6d and 6e. Compounds 6c and 6d are isomorphous, with the 1,3,4-oxadiazoline ring having an envelope conformation, where the disubstituted C atom is the flap. The packing is determined by C—H...O, C—H...π and I...π interactions. For 6e, the 1,3,4-oxadiazoline ring is almost planar. In the packing, Cl...π interactions are observed, while the I atom is not involved in short interactions. Compounds 6d, 6e, 6f and 6h show good inhibiting abilities on the human cancer cell lines KB and Hep-G2, with IC50 values of 0.9–4.5 µM.

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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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