scholarly journals Synthesis, Computational Analysis, and Antiproliferative Activity of Novel Benzimidazole Acrylonitriles as Tubulin Polymerization Inhibitors: Part 2

2021 ◽  
Vol 14 (10) ◽  
pp. 1052
Author(s):  
Anja Beč ◽  
Lucija Hok ◽  
Leentje Persoons ◽  
Els Vanstreels ◽  
Dirk Daelemans ◽  
...  
Keyword(s):  
Antiproliferative Activity ◽  
Phenyl Group ◽  
Biological Action ◽  
Microwave Assisted Synthesis ◽  
Synthesis Methods ◽  
Tubulin Polymerization ◽  
Lead Compounds ◽  
Dynamics Simulations ◽  
Tubulin Polymerization Inhibitors

We used classical linear and microwave-assisted synthesis methods to prepare novel N-substituted, benzimidazole-derived acrylonitriles with antiproliferative activity against several cancer cells in vitro. The most potent systems showed pronounced activity against all tested hematological cancer cell lines, with favorable selectivity towards normal cells. The selection of lead compounds was also tested in vitro for tubulin polymerization inhibition as a possible mechanism of biological action. A combination of docking and molecular dynamics simulations confirmed the suitability of the employed organic skeleton for the design of antitumor drugs and demonstrated that their biological activity relies on binding to the colchicine binding site in tubulin. In addition, it also underlined that higher tubulin affinities are linked with (i) bulkier alkyl and aryl moieties on the benzimidazole nitrogen and (ii) electron-donating substituents on the phenyl group that allow deeper entrance into the hydrophobic pocket within the tubulin’s β-subunit, consisting of Leu255, Leu248, Met259, Ala354, and Ile378 residues.

scholarly journals Microwave-Assisted Synthesis of Some Potential Bioactive Imidazolium-Based Room-Temperature Ionic Liquids

Molecules ◽  
2018 ◽  
Vol 23 (7) ◽  
pp. 1727 ◽  
Author(s):  
Ahmed Albalawi ◽  
Wael El-Sayed ◽  
Ateyatallah Aljuhani ◽  
Saud Almutairi ◽  
Nadjet Rezki ◽  
...  
Keyword(s):  
Ionic Liquids ◽  
Room Temperature ◽  
Inhibitory Concentration ◽  
Minimum Bactericidal Concentration ◽  
Alkyl Chain ◽  
Phenyl Group ◽  
Room Temperature Ionic Liquids ◽  
Microwave Assisted Synthesis ◽  
Conventional Procedure

An environmentally-friendly and easy synthesis of a series of novel functionalized imidazolium-based ionic liquids (ILs) is described under both the conventional procedure and microwave irradiation. The structures of newly synthesized room-temperature ionic liquids (RTILs) were established by different spectral analyses. All ILs (1–14) were screened for their in vitro antimicrobial activity against a panel of clinically isolated bacteria. The results of the minimum inhibitory concentration (MIC) and the minimum bactericidal concentration (MBC) showed that some of the tested ILs are very promising anti-bacterial agents especially those containing an alkyl chain with a phenyl group (most notably 1, 2, 12, and 13).

Synthesis, in vitro and in vivo evaluation of new hybrids of millepachine and phenstatin as potent tubulin polymerization inhibitors

2017 ◽  
Vol 15 (4) ◽  
pp. 852-862 ◽  
Author(s):  
Baijiao An ◽  
Shun Zhang ◽  
Jun Yan ◽  
Ling Huang ◽  
Xingshu Li
Keyword(s):  
Tubulin Polymerization ◽  
In Vivo Evaluation ◽  
Tubulin Polymerization Inhibitors

In this paper, a series of millepachine derivatives were synthesized and evaluated as tubulin polymerization inhibitors.

Design, synthesis and antiproliferative activity of the new conjugates of E7010 and resveratrol as tubulin polymerization inhibitors

2016 ◽  
Vol 14 (4) ◽  
pp. 1382-1394 ◽  
Author(s):  
Ahmed Kamal ◽  
Md. Ashraf ◽  
Shaik Thokhir Basha ◽  
S. M. Ali Hussaini ◽  
Shamshair Singh ◽  
...  
Keyword(s):  
Antiproliferative Activity ◽  
Tubulin Polymerization ◽  
Design Synthesis ◽  
New Class ◽  
Tubulin Polymerization Inhibitors ◽  
Amine Conjugates

A new class of (E)-N-phenyl-3-styrylpyridin-2-amine conjugates were designed and synthesized on the basis of E7010 and resveratrol scaffolds.

scholarly journals Design, Synthesis and Antifungal Activity of New Schiff Bases Bearing 2-Aminothiophene Derivatives Obtained by Molecular Simplification

2021 ◽  
Author(s):  
Isadora Luna ◽  
Wendell Neves ◽  
Reginaldo de Lima-Neto ◽  
Amanda Albuquerque ◽  
Maíra Pitta ◽  
...  
Keyword(s):  
Antifungal Activity ◽  
Schiff Bases ◽  
Antifungal Drugs ◽  
Microwave Assisted Synthesis ◽  
Design Synthesis ◽  
Reference Drug ◽  
Lead Compounds ◽  
Pharmacokinetic Properties ◽  
In Vitro Antifungal Activity

Seventeen Schiff bases bearing 2-aminothiophene derivatives were designed and synthesized using molecular simplification. The resulting compounds (4a-4q) were evaluated for their in vitro antifungal activity against dermatophytes. Prediction of their druglikeness and pharmacokinetic properties, establishment of their structure-activity relationships (SAR), and cytotoxic evaluation of the most active compounds were performed. Using an eco-friendly procedure, microwave assisted synthesis resulted in compounds in good yields (35-85%). Compounds 4a-4q presented good druglikeness and pharmacokinetic profiles and no cytotoxicity for any cell line tested up to 100 μM. The compounds presenting the best antifungal profiles were 4e, 4f, 4g, 4k, 4l, 4m, 4o and 4p with more than one minimum inhibitory concentration (MIC) value occurring between 16‑64 μg mL-1, thus, in some cases better than the reference drug (fluconazole). SAR testing indicated that the presence of halogens and nitro substituents increases antifungal activity. Taken together, the results demonstrate that 2-aminothiophene derivatives are promising lead compounds for the development of antifungal drugs.

Antimycobacterial assessment and Microwave-assisted synthesis of 2-aryl-3-(4-methylphenylamino)thiazolidin-4-one derivatives

2021 ◽  
Vol 18 ◽  
Author(s):  
Saad Alghamdi ◽  
Mehnaz Kamal ◽  
Mohammad Asif
Keyword(s):  
Inhibitory Concentration ◽  
Aromatic Aldehydes ◽  
Microwave Assisted Synthesis ◽  
Alamar Blue ◽  
Mycobacterium Tuberculosis H37rv ◽  
Lead Compounds ◽  
Microwave Assisted ◽  
H37rv Strain ◽  
Antimycobacterial Agents

: This article reports the microwave-assisted synthesis, characterization, and evaluation of some -4-one derivatives (2a-2h) for their in-vitro antimycobacterial activities against Mycobacterium tuberculosis H37Rv strain by microplate Alamar blue assay (MABA) method. All these final compounds (2a-2h) were synthesized from Schiff’s bases, 1-arylidene-2-(4-methylphenyl)hydrazines (1a-1h), and thioglycolic acid by using zinc chloride as a catalyst. Compounds (1a-1h) were synthesized from the reaction of 4-methylhydrazine and appropriate aromatic aldehydes by Schiff’s reaction. Among the target compounds, 2-(4-ethoxyphenyl)-3-(4-methylarylamino)thiazolidin-4-one (2f) and 2-(4-ethylphenyl)-3-(4-methylarylamino)thiazolidin-4-one (2g) were promising with a minimum inhibitory concentration (MIC) of 12.5 μg/mL against M. tuberculosisH37Rv. Based on the preliminary results, compounds 2f and 2g were considered as lead compounds for the advanced design and development of antimycobacterial agents.

Design, Synthesis, and in vitro and in vivo Evaluations of (Z)-3,4,5-Trimethoxystyrylbenzenesulfonamides/sulfonates as Highly Potent Tubulin Polymerization Inhibitors

ChemMedChem ◽  
2017 ◽  
Vol 12 (9) ◽  
pp. 678-700 ◽  
Author(s):  
Rasala Mahesh ◽  
Vadithe Lakshma Nayak ◽  
Korrapati Suresh Babu ◽  
Syed Riyaz ◽  
Thokhir Basha Shaik ◽  
...  
Keyword(s):  
Tubulin Polymerization ◽  
Design Synthesis ◽  
Tubulin Polymerization Inhibitors

Microwave-assisted synthesis and in vitro antiproliferative activity of some novel 1,2,3-triazole-based pyrazole aldehydes and their benzimidazole derivatives

2020 ◽  
Vol 29 (4) ◽  
pp. 699-706 ◽  
Author(s):  
Dongamanti Ashok ◽  
M. Ram Reddy ◽  
Nalaparaju Nagaraju ◽  
Ravinder Dharavath ◽  
Katta Ramakrishna ◽  
...  
Keyword(s):  
Antiproliferative Activity ◽  
Benzimidazole Derivatives ◽  
Microwave Assisted Synthesis ◽  
Microwave Assisted
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