New styryl sulfones as anticancer agents (original) (raw)
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Journal of advanced Biomedical and Pharmaceutical Sciences, 2020
A novel series of benzimidazole-hydrazone derivatives was designed and synthesized as a potential anti-cancer agents. The structure of the target compounds was assured using different spectroscopic methods such as IR, 1 H NMR, 13 C NMR and elemental analysis. These new compounds were examined and evaluated for their antiproliferative activities against 60 different cell lines. Combination of benzimidazole scaffold with hydrazone group exhibited promising anti-cancer activity. Compounds 3a and 3b showed significant activity against different cancer cells lines between 50-84 % of growth inhibition. A molecular modeling study for compounds 3a and 3b into VEGFR-2 active site was performed with reasonable docking scores.
Benzimidazole scaffolds as promising antiproliferative agents: a review
BMC Chemistry
Cancer is one of the most serious medical problem and second leading cause of death in the world, characterized by a deregulation of the cell cycle which mainly results in a progressive loss of cellular differentiation and uncontrolled cellular growth. The benzimidazole is a heterocyclic moiety found in extensive number of natural and biological active molecules. Benzimidazole derivatives might be considered as auxiliary isosters of nucleotides having attached heterocyclic cores in their structures, cooperate effortlessly with biopolymers and have potential action for chemotherapeutic applications. Benzimidazole and its derivatives displayed a wide range of biological activity because of its structural similarity with the naturally occurring nucleotides. Benzimidazole has established huge alertness in current time and is extremely significant heterocyclic pharmacophore in recent drug innovation and medicinal chemistry. The present review summarizes the chemistry of various substituted benzimidazole derivatives with their antiproliferative significance towards the various cancer cell lines such as HCT116, MCF7, HeLa, HepG2, A549 and A431.
Importance of Fluorine in Benzazole Compounds
Molecules
Fluorine-containing heterocycles continue to receive considerable attention due to their unique properties. In medicinal chemistry, the incorporation of fluorine in small molecules imparts a significant enhancement their biological activities compared to non-fluorinated molecules. In this short review, we will highlight the importance of incorporating fluorine as a basic appendage in benzothiazole and benzimidazole skeletons. The chemistry and pharmacological activities of heterocycles containing fluorine during the past years are compiled and discussed.
Frontiers in Pharmacology, 2021
Nowadays, nitrogenous heterocyclic molecules have attracted a great deal of interest among medicinal chemists. Among these potential heterocyclic drugs, benzimidazole scaffolds are considerably prevalent. Due to their isostructural pharmacophore of naturally occurring active biomolecules, benzimidazole derivatives have significant importance as chemotherapeutic agents in diverse clinical conditions. Researchers have synthesized plenty of benzimidazole derivatives in the last decades, amidst a large share of these compounds exerted excellent bioactivity against many ailments with outstanding bioavailability, safety, and stability profiles. In this comprehensive review, we have summarized the bioactivity of the benzimidazole derivatives reported in recent literature (2012-2021) with their available structure-activity relationship. Compounds bearing benzimidazole nucleus possess broad-spectrum pharmacological properties ranging from common antibacterial effects to the world's most virulent diseases. Several promising therapeutic candidates are undergoing human trials, and some of these are going to be approved for clinical use. However, notable challenges, such as drug resistance, costly and tedious synthetic methods, little structural information of receptors, lack of advanced software, and so on, are still viable to be overcome for further research.
International Journal of Scientific Research in Science and Technology, 2020
A series of novel N-(1H-benzimidazole-2-yl-carbamothioyl)benzamide derivatives were synthesized under microwave irradiation and evaluated for anticancer activity. The synthesized compounds were characterized by IR, 1H-NMR, and mass spectral data. Complexity associated with cancer disease and prevalence of diversified cell populations vindicates highly specific treatment options for treatment of cancer. Resistance to these anticancer agents has posed a great hindrance in successful treatment of cancer. Pondering this ongoing situation, it was speculated to develop novel compounds targeting cancer. All the newly synthesized compounds 3a-f were further evaluated for anticancer activity against MCF-7 cell lines using MTT assay. Molecular docking studies were performed using VLife MDS 4.3 software. The compounds 3c exhibited good docking scores of -60.37. The anticancer and docking results highlight the fact that the synthesized compounds 3c could be considered as possible hit as therapeutic agents. A significant correlation was observed between the in silico and the in vitro studies.
Novel benzimidazole derivatives as expected anticancer agents
Acta poloniae pharmaceutica
A series of 1-(1H-benzimidazol-2-yl)-3-(substituted)-2-propen-1-one and its 1-methyl analogues 2c-h were synthesized and cyclized with different reagents such as ethyl cyanoacetate, thiourea, hydroxylamine hydrochloride, guanidinium sulfate, methylhydrazine, phenylhydrazine and/or hydrogen peroxide in different reactions to produce pyridones 3a,b, pyrimidinethione 4a,b, isoxazole 5a,b, aminopyrimidine 6a,b, pyrazoline 7i-k and epoxy derivative 8, respectively. Acetohydrazide 10 reacted with formic acid, acetic anhydride, carbon disulfide and/or thiosemicarbazide to yield compounds 11-19. Also compound 21a,b was condensed with different monosaccharides to yield the corresponding N-glycoside Schiff's bases derivatives 22a-h, which upon treatment with acetic anhydride afforded 23a-h derivatives. The anticancer activity of some of the newly synthesized compounds was evaluated against HEPG2 (human liver carcinoma cell line) and PC12 (pheochromocytoma of the rat adrenal medulla) cells...
Chemistry Central Journal
Background: The emergence of bacterial resistance is a major public health problem. It is essential to develop and synthesize new therapeutic agents with better activity. The mode of actions of certain newly developed antimicrobial agents, however, exhibited very limited effect in treating life threatening systemic infections. Therefore, the advancement of multi-potent and efficient antimicrobial agents is crucial to overcome the increased multi-drug resistance of bacteria and fungi. Cancer, which remains as one of the primary causes of deaths and is commonly treated by chemotherapeutic agents, is also in need of novel and efficacious agents to treat resistant cases. As such, a sequence of novel substituted benzamides was designed, synthesized and evaluated for their antimicrobial and anticancer activities. Methodology: All synthesized compounds were characterized by IR, NMR, Mass and elemental analysis followed by in vitro antimicrobial studies against Gram-positive (Staphylococcus aureus), Gram-negative (Salmonella typhi and Klebsiella pneumoniae) bacterial and fungal (Candida albicans and Aspergillus niger) strains by the tube dilution method. The in vitro anticancer evaluation was carried out against the human colorectal carcinoma cell line (HCT116), using the Sulforhodamine B assay. Results, discussion and conclusion: Compound W6 (MIC sa, st, kp = 5.19 µM) emerged as a significant antibacterial agent against all tested bacterial strains i.e. Gram-positive (S. aureus), Gram-negative (S. typhi, K. pneumoniae) while compound W1 (MIC ca, an = 5.08 µM) was most potent against fungal strains (A. niger and C. albicans) and comparable to fluconazole (MIC = 8.16 µM). The anticancer screening demonstrated that compound W17 (IC 50 = 4.12 µM) was most potent amongst the synthesized compounds and also more potent than the standard drug 5-FU (IC 50 = 7.69 µM).
1-(1H-Benzimidazol-2-yl)-3-[5-(trichloromethyl)-1,3,4-oxadiazol-2-yl]propan-1-one
Molbank, 2012
The title compound, 1-(1H-benzimidazol-2-yl)-3-[5-(trichloromethyl)-1,3,4oxadiazol-2-yl]propan-1-one (2) was synthesized successfully from 4-(1H-benzimidazol-2yl)-4-oxobutanehydrazide (1) under microwave irradiation in good yield by reacting with trichloroacetic acid, and the structure of title compound was confirmed on the basis of IR, 1 H-NMR, 13 C-NMR, MS and CHN analyses results.
European Journal of Medicinal Chemistry, 2011
The syntheses of 1,3-diarylpyrazino[1,2-a]benzimidazole derivatives and the investigation of their anticancer activities were studied. For this, 2-aryloylbenzimidazole derivatives were reacted with 2-bromoacetophenones in acetone to give 1-(2-aryl-2-oxoethyl)-2-aryloylbenzimidazoles. The resulting materials were reacted with ammonium acetate in acetic acid to obtain the aimed compound. In this reaction, microwave irradiation method was applied as the reaction conditions. Anticancer activities of the compounds obtained were investigated. It was observed that some of the compounds showed remarkable anticancer activities.
Benzimidazole: a medicinally important heterocyclic moiety
Medicinal Chemistry Research
Benzimidazole nucleus is a constituent of many bioactive heterocyclic compounds that are of wide interest because of their diverse biological and clinical applications. Moreover, benzimidazole derivatives are structural isosters of naturally occurring nucleotides, which allows them to interact easily with the biopolymers of the living system. This created interest in researchers who have synthesized variety of benzimidazole derivatives and screened them for their various biological activities, viz., anticancer, hormone antagonist, antiviral, anti-HIV, anthelmintic, antiprotozoal, antimycobacterial, antihypertensive, anti-inflammatory, analgesic, anxiolytic, antiallergic, coagulant, anticoagulant, antioxidant as well antidiabetic activities.