Benzimidazole Derivatives as Potential Antimicrobial and Antiulcer Agents: A Mini Review

2019 ◽  
Vol 19 (16) ◽  
pp. 1292-1297 ◽  
Author(s):  
Ali Mohd Ganie ◽  
Ayaz Mahmood Dar ◽  
Fairooz Ahmad Khan ◽  
Bashir Ahmad Dar
Keyword(s):  
Cell Lines ◽  
Cancer Cell ◽  
1H Nmr ◽  
13C Nmr ◽  
Benzimidazole Derivatives ◽  
Spectroscopic Techniques ◽  
One Pot ◽  
Biological Screening ◽  
Elemental Analyses ◽  
Characterization Studies

:Here in we report the number of strategies for the synthesis of differently substituted benzimidazole derivatives. The protocols involved in the syntheses of these derivatives were one-pot or multi-component. The characterization studies of these derivatives were carried by using different spectroscopic techniques (1H NMR, 13C NMR and MS) and elemental analyses. The biological screening studies revealed that these benzimidazole derivatives show potential antibacterial as well as antifungal behavior. These benzimidazole derivatives not only depicted potential antiulcer properties but also showed moderate to good anticancer/cytotoxic behavior against different cancer cell lines.

scholarly journals An efficient, microwave-assisted, one-pot synthesis of novel 5,6,7,8-tetrahydroquinoline-3-carbonitriles

2011 ◽  
Vol 76 (6) ◽  
pp. 823-830 ◽  
Author(s):  
Dipti Dodiya ◽  
Haresh Ram ◽  
Amit Trivedi ◽  
Viresh Shah
Keyword(s):  
1H Nmr ◽  
13C Nmr ◽  
Microwave Assisted Synthesis ◽  
Spectroscopic Techniques ◽  
One Pot ◽  
Antifungal Activities ◽  
Microwave Assisted ◽  
Antibacterial And Antifungal Activities ◽  
Elemental Analyses ◽  
Antibacterial And Antifungal

An efficient, microwave-assisted synthesis of novel 2-alkoxy- 5,6,7,8-tetrahydroquinoline-3-carbonitriles, which have not hitherto been reported, via reactions of cyclohexanone and arylidene malononitriles in the corresponding alcohols in presence of sodium is described. All the newly synthesized compounds were characterized by the IR, 1H-NMR, 13C-NMR and mass spectroscopic techniques and by elemental analyses. The newly synthesized compounds were evaluated for their antibacterial and antifungal activities.

scholarly journals Synthesis of new 3-(substituted-phenyl)-N-(2-hydroxy-2-(substituted-phenyl)ethyl)-N-methylthiophene-2-sulfonamide derivatives as antiproliferative agents

2018 ◽  
Vol 9 (1) ◽  
pp. 13-21 ◽  
Author(s):  
Chandrakant Pawar ◽  
Dattatraya Pansare ◽  
Devanand Shinde
Keyword(s):  
Cell Lines ◽  
Cancer Cell ◽  
1H Nmr ◽  
13C Nmr ◽  
Antiproliferative Activity ◽  
Positive Control ◽  
Antiproliferative Agents ◽  
Ic50 Values ◽  
Mcf 7

In the present work, we report the synthesis of a series of 3-(substituted phenyl)-N-(2-hydroxy-2-(substituted-phenyl)ethyl)-N-methylthiophene-2-sulfonamide derivatives through Suzuki and Buchwald reaction. We have optimized methodology for targets from milligram to multi-gram scale. The newly synthesized compounds were characterized by 1H NMR, 19F NMR, 13C NMR, LC-MS techniques and purity was further checked by HPLC. The compounds were evaluated for their in-vitro antiproliferative activity against MCF-7, HeLa, A-549 and Du-145 cancer cell lines by CCK-8 assay. The preliminary bioassay suggests that most of the compounds show antiproliferation with different degrees and 5-fluorouracil was used as positive control. Among these compounds 2d, 2g, 2i, 4e, 4h and 4k are most active compared to the standard. All the synthesized compounds show IC50 values from 1.82-9.52 µM in different cell lines. Amongst these, compounds 2d, 2g, 2i, 4e, 4h and 4k were most potent, with IC50 values ranging from 1.82-4.28 µM in different cell lines.

scholarly journals Dipeptides of S-Substituted Dehydrocysteine as Artzyme Building Blocks: Synthesis, Complexing Abilities and Antiproliferative Properties

2021 ◽  
Vol 22 (4) ◽  
pp. 2168
Author(s):  
Paweł Lenartowicz ◽  
Mateusz Psurski ◽  
Aleksandra Kotynia ◽  
Aleksandra Pieniężna ◽  
Monika Cuprych ◽  
...  
Keyword(s):  
Cell Lines ◽  
Cancer Cell ◽  
Triazole Ring ◽  
Building Blocks ◽  
Cancer Cell Lines ◽  
Spectroscopic Techniques ◽  
Reaction Centre ◽  
One Pot ◽  
Synthetic Strategy ◽  
Artificial Metalloenzymes

Background: Dehydropeptides are analogs of peptides containing at least one conjugate double bond between α,β-carbon atoms. Its presence provides unique structural properties and reaction centre for chemical modification. In this study, the series of new class of dipeptides containing S-substituted dehydrocysteine with variety of heterocyclic moieties was prepared. The compounds were designed as the building blocks for the construction of artificial metalloenzymes (artzymes). Therefore, the complexing properties of representative compounds were also evaluated. Furthermore, the acknowledged biological activity of natural dehydropeptides was the reason to extend the study for antiproliferative action of against several cancer cell lines. Methods: The synthetic strategy involves glycyl and phenylalanyl-(Z)-β-bromodehydroalanine as a substrate in one pot addition/elimination reaction of thiols. After deprotection of N-terminal amino group the compounds with triazole ring were tested as complexones for copper(II) ions using potentiometric titration and spectroscopic techniques (UV-Vis, CD, EPR). Finally, the antiproliferative activity was evaluated by sulforhodamine B assay. Results and Conclusions: A simple and efficient procedure for preparation of dipeptides containing S-substituded dehydrocysteine was provided. The peptides containing triazole appeared to be strong complexones of copper(II) ions. Some of the peptides exhibited promising antiproliferative activities against number of cancer cell lines, including cell lines resistant to widely used anticancer agent.

scholarly journals One pot synthesis of Biginelli 3,4-dihydro-1H-pyrimidin-2-ones and 1,2,3,4-tetrahydro pyrimidines

2020 ◽  
Vol 55 (3) ◽  
pp. 173-180
Author(s):  
Md E Halim ◽  
K Akhter ◽  
SM Ahmed ◽  
Md Al Amin Hossain ◽  
UKR Romman
Keyword(s):  
1H Nmr ◽  
13C Nmr ◽  
Ethyl Acetoacetate ◽  
Nmr Spectra ◽  
13C Nmr Spectra ◽  
One Pot ◽  
One Pot Synthesis ◽  
Elemental Analyses ◽  
Cyclocondensation Reaction ◽  
Anhydrous Zncl2

A simple and practical route for the Biginelli cyclocondensation reaction using anhydrous ZnCl2 as a catalyst in n-heptane-toluene medium by reaction of substituted benzaldehydes,1a-d (1a=2-ClC6H4-, 1b=2-BrC6H4- and 1c=4-ClC6H4-,1d=2-H3CC6H4-) with 1, 3-dicarbonyl compounds, 2a-b (2a= ethyl acetoacetate and 2b= acetylacetone) and urea or thiourea, 3a-b to give the corresponding Biginelli 3,4-dihydro- 1H-pyrimidin-2-ones and 1,2,3,4-tetrahydro pyrimidines, 4a-d. The structures of the compounds 4a-d were confirmed by their ultraviolet, infrared, 1H NMR, 13C NMR spectra and elemental analyses. Bangladesh J. Sci. Ind. Res.55(3), 173-180, 2020

5-Aminouracil as a Building Block in Heterocyclic Synthesis, Part II. One-pot Synthesis of Pyrido[3,2-d:6,5-dʹ]dipyrimidines under Microwave Irradiation without Catalyst

2009 ◽  
Vol 64 (10) ◽  
pp. 1193-1198 ◽  
Author(s):  
Raafat M. Shaker ◽  
Mohamed A. Ameen ◽  
Afaf M. Abdel Hameed ◽  
Mohamed Abd Elrady
Keyword(s):  
Microwave Irradiation ◽  
1H Nmr ◽  
13C Nmr ◽  
Building Block ◽  
Heterocyclic Synthesis ◽  
One Pot ◽  
Microwave Assisted ◽  
One Pot Synthesis ◽  
Elemental Analyses

An efficient and direct procedure for the synthesis of pyrido[3,2-d:6,5-dʹ]dipyrimidine derivatives under microwave-assisted conditions is been described. The structures of the products were characterized by elemental analyses, and their IR, 1H NMR, 13C NMR, and MS spectra.

Synthesis of Highly Functionalized Quinazoline-2,4(1H,3H)-diones from Isocyanides, Aniline and Isocyanate via Cu-Catalyzed Intermolecular C-H Activation Reactions

2020 ◽  
Vol 17 (11) ◽  
pp. 832-836
Author(s):  
Manijeh Nematpour ◽  
Hossein Fasihi Dastjerdi ◽  
Mehdi Jahani ◽  
Sayyed Abbas Tabatabai
Keyword(s):  
13C Nmr ◽  
Reaction Times ◽  
High Yield ◽  
One Pot ◽  
1H And 13C Nmr ◽  
Activation Reaction ◽  
Elemental Analyses

A simple and appropriate procedure for the synthesis of quinazoline-2,4(1H,3H)-dione derivatives from isocyanides, aniline and isocyanate via the Cu-catalyzed intramolecular C-H activation reaction is reported. The advantages of this method are one-pot conditions, accessible starting materials- catalyst, high yield of products, and short reaction times. The structures are confirmed spectroscopically (1H- and 13C-NMR, IR and EI-MS) and by elemental analyses.

scholarly journals Synthesis and Cytotoxic Activity of Several Novel N-Alkyl-Plinabulin Derivatives With Aryl Group Moieties

2021 ◽  
Vol 16 (4) ◽  
pp. 1934578X2110100
Author(s):  
Pham The Chinh ◽  
Pham Thi Tham ◽  
Duong Huong Quynh ◽  
Nguyen Van Tuyen ◽  
Dinh Thuy Van ◽  
...  
Keyword(s):  
Cytotoxic Activity ◽  
Cancer Cells ◽  
Cell Lines ◽  
Cancer Cell ◽  
Aldol Condensation ◽  
One Pot ◽  
Aryl Group ◽  
Vascular Disrupting Agents ◽  
Benzaldehyde Derivatives ◽  
Vascular Disrupting

Seven novel N-alkyl-plinabulin derivatives with aryl groups moieties (nitroquinoline, 1,4-dihydroquinoline, 4-methoxybenzene, and 4-chlorobenzene) have been synthesized via aldol condensation and alkylation in one-pot, and tested for their cytotoxicity against 4 cancer cell lines (KB, HepG2, Lu, and MCF7). Compounds ( Z)−3-((6,8-dimethyl-4-oxo-1,4-dihydroquinolin-2-yl)methylene)−6-(( Z)−4-methoxybenzylidene)−1-(prop-2-yn-1-yl)piperazine-2,5-dione (5a), ( Z)−6-(( Z)−4-methoxybenzylidene)−1-(prop-2-yn-1-yl)−3-((1,6,8-trimethyl-4-oxo-1,4-dihydroquinolin-2-yl)methylene)piperazine-2,5-dione (5b), and ( Z)−3-(( Z)−4-chlorobenzylidene)−1,4-dimethyl-6-((8-methyl-4-nitroquinolin-2-yl)methylene)piperazine-2,5-dione (8) showed strong cytotoxicity against 3 of the cancer cells lines (KB, HepG2 and Lu) with IC50 values ranging from 3.04 to 10.62 µM. The quinoline-derived compounds had higher cytotoxic activity than the benzaldehyde derivatives. The successful synthesis of these derivatives offers useful information for the development of more potent vascular disrupting agents based on plinabulin.

scholarly journals Stereoselective Synthesis of the Di-Spirooxindole Analogs Based Oxindole and Cyclohexanone Moieties as Potential Anticancer Agents

Molecules ◽  
2021 ◽  
Vol 26 (20) ◽  
pp. 6305
Author(s):  
Abdullah Mohammed Al-Majid ◽  
M. Ali ◽  
Mohammad Shahidul Islam ◽  
Saeed Alshahrani ◽  
Abdullah Saleh Alamary ◽  
...  
Keyword(s):  
Anticancer Activity ◽  
Cell Line ◽  
Cell Lines ◽  
Cancer Cell ◽  
Anticancer Agents ◽  
Stereoselective Synthesis ◽  
Cancer Cell Lines ◽  
Azomethine Ylides ◽  
Active Member ◽  
One Pot

A new series of di-spirooxindole analogs, engrafted with oxindole and cyclohexanone moieties, were synthesized. Initially, azomethine ylides were generated via reaction of the substituted isatins 3a–f (isatin, 3a, 6-chloroisatin, 3b, 5-fluoroisatin, 3c, 5-nitroisatin, 3d, 5-methoxyisatin, 3e, and 5-methylisatin, 3f, and (2S)-octahydro-1H-indole-2-carboxylic acid 2, in situ azomethine ylides reacted with the cyclohexanone based-chalcone 1a–f to afford the target di-spirooxindole compounds 4a–n. This one-pot method provided diverse structurally complex molecules, with biologically relevant spirocycles in a good yields. All synthesized di-spirooxindole analogs, engrafted with oxindole and cyclohexanone moieties, were evaluated for their anticancer activity against four cancer cell lines, including prostate PC3, cervical HeLa, and breast (MCF-7, and MDA-MB231) cancer cell lines. The cytotoxicity of these di-spirooxindole analogs was also examined against human fibroblast BJ cell lines, and they appeared to be non-cytotoxic. Compound 4b was identified as the most active member of this series against prostate cancer cell line PC3 (IC50 = 3.7 ± 1.0 µM). The cyclohexanone engrafted di-spirooxindole analogs 4a and 4l (IC50 = 7.1 ± 0.2, and 7.2 ± 0.5 µM, respectively) were active against HeLa cancer cells, whereas NO2 substituted isatin ring and meta-fluoro-substituted (2E,6E)-2,6-dibenzylidenecyclohexanone containing 4i (IC50 = 7.63 ± 0.08 µM) appeared to be a promising agent against the triple negative breast cancer MDA-MB231 cell line. To explore the plausible mechanism of anticancer activity of di-spirooxindole analogs, molecular docking studies were investigated which suggested that spirooxindole analogs potentially inhibit the activity of MDM2.

Synthesis of urease inhibitory 2, 4-bis (4-cyanobenzyl)glycoluril using sandmeyer reaction and density functional theory investigation

2021 ◽  
Vol 18 ◽  
Author(s):  
Mirza Arfan Yawer ◽  
Shehar Bano ◽  
Muhammad Saleem ◽  
Affiefa Yawer ◽  
Riaz Hussain ◽  
...  
Keyword(s):  
Mass Spectrometry ◽  
Density Functional Theory ◽  
1H Nmr ◽  
13C Nmr ◽  
Density Functional ◽  
Spectroscopic Techniques ◽  
Pure Compound ◽  
Functional Theory ◽  
Sandmeyer Reaction ◽  
Urease Enzyme

Aims: The aim of present research was to synthesize glycoluril derivative 2,4-Bis(4-cyanobenzyl)glycoluril through convergent scheme. Background: For this purpose Sandmeyer reaction procedure was employed for the synthesis of said compound. The structure of the pure compound was confirmed by using different spectroscopic techniques such as 1H-NMR, 13C-NMR and (HR-MS) Mass spectrometry. Objective: Convergent synthesis of 2,4-BIS (4-CYANOBENZYL)GLYCOLURIL USING SANDMEYER REACTION and urease inhibition study. Methods: The structure of the pure compound was confirmed by using different spectroscopic techniques such as 1H-NMR, 13C-NMR and (HR-MS) Mass spectrometry. The electronic properties of newly synthesized compound and thiourea were determined by using density functional theory. Results: Furthermore compound was evaluated against urease enzyme and was found to be potent inhibitors with IC50 value of 11.5 ± 1.50 µM when compared with standard inhibitor thiourea (IC50 = 21.0 ± 1.90 µM). Compound may serve as lead compound for the synthesis of new cyano based bambusuril in future with enhanced biological properties. Conclusion: We have synthesized a new glycoluril derivative 2,4-Bis(4-cyanobenzyl)glycoluril by the sandmeyer reaction. It has obtained in the form of light yellowish powder in good yield (96%). Glycoluril based macrocycles have been used in various fields. Starting from the 2,4-Bis(4-nitrobenzyl)glycoluril (already reported compound) which has undergone reduction (CH3OH,Pt/C) , diazotization (NaNO2/HCl), cyanation (CuCl/KCN) respectively in order to synthesize the desired new glycoluril derivative. The obtained product will be used as a building block for the synthesis of the cyano based bambusuril marcocycle in future. The yield of the obtained product has been monitored by using different amount of cyanating reagent but the best results shown by the use of 4 mmol of CuCl/KCN. KCN with CuCl assisted the conversion of diazo group into cyano group with enhanced yield when used in excess amount. It act as a catalyst. Solubility characteristic of 2,4-Bis(4-cyanobenzyl)glycoluril has determined also in different organic solvents. 1H NMR technique proved to be very helpful for the structure determination of our desired product. Benzylic protons give signals at 7.5 ppm and 7.8 ppm respectively. The downfield peaks confirm about the presence of CN group near the benzylic protons. Methine protons show signal at 5.2 ppm which ensures about the basic skeleton of glycoluril. Ureidyl protons also confirm the synthesis of the heterocyclic 2,4-Bis(4-cyanobenzyl)glycoluril compound. The negative and positive electrostatic potential sites, molecular descriptors, and charge density distribution of frontier molecular orbitals are revealing that 4a with promising sites for electrophilic and nucleophilic attacks would result to enhance the urease inhbition which is in good agreement with the experimental data.

Sign in / Sign up

Export Citation Format

Share Document