Synthesis and characterization of 2-substituted 6-(methylthio)bicyclo[2.2.1]heptanes (original) (raw)
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Turkish Journal of Pharmaceutical Sciences, 2009
In this study, synthesis and structural illumination of eight compounds that are expected to display antifungal and antibacterial activity in addition to interaction with DnA has been conducted. The syntheses were performed by heating o-phenylendiamine and derivatives with succinic acid and maIonic acid in 4N HCl. It has been observed that, the reactions with succinic acid formed bisbenzimidazole derivatives. On the other hand, the reactions with the malonic acid under the same conditions resulted in formation of benzimidazole derivatives instead of bisbenzimidazole derivatives. The structures of all synthesized compounds were analysed with spectroscopic methods (UV, IR, 1H NMR, MS). Among the synthesized compounds, 1 and 5 which are nonsubstitue compounds, were selected so as to dispose the roles of electron acceptor or donor atoms in the activity and their interaction with DNA has been examined with respect to concentration and time. When these two compounds were compared, it '...
2018
Benzimidazole scaffolds are structural isosteres of naturally occurring nucleotides which allows them to interact with the biopolymers and enzymatic sites of living systems. The aim of this present work is to synthesize selected 2-alkanamino-benzimidazole derivatives in order to investigate their antimicrobial efficiency for possible future drug development. The series of targeted compounds were conventionally synthesized in good to excellent yields via [4+1]-cyclo-addition of o-phenylenediamine with some L-amino acid and purified by recrystallization or column chromatography where necessary. The chemical structures were confirmed by physico-chemical and spectral data which include UV, IR, 1Hand 13C-NMR. In addition, the antimicrobial properties of the synthesized benzimidazole derivatives were determined on six bacteria isolates alongside with gentamycin standard drug using agar diffusion method. The synthesized compounds showed broader activities spectrum than gentamycin and (1H-b...
SYNTHESIS AND ANTIMICROBIAL ACTIVITIES OF NOVEL BENZIMIDAZOLE DERIVATIVES
Benzimidazole is a heterocyclic aromatic organic compound. Benzimidazole derivatives are of wide interest because of their diverse biological activity and clinical applications, they are remarkably effective compounds both with respect to their inhibitory activity and their favorable selectivity ratio. Looking at the importance of benzimidazole and oxadiazole nucleus, it was thought that it would be worthwhile to design and synthesize new benzimidazole derivatives. In recent years, attention has increasingly been given to the synthesis of benzimidazole derivatives. Hence, there will always be a vital need to discover new chemotherapeutic agents to overcome the emergence of resistance and ideally shorten the duration of therapy. Due to the structural similarity to purine, antibacterial ability of benzimidazoles is explained by their competition with purines resulting in inhibition of the synthesis of bacterial nucleic acids and proteins. Thus, from the present study it can be concluded that cyclohexyl derivatives of benzimidazole ring have significant antibacterial activity.
Research on Chemical Intermediates, 2012
In recent years the synthesis of benzimidazole and its derivatives has attracted the attention of many organic chemists because of the compounds' interesting biological activity and the crucial importance of the benzimidazole unit in the function of these biologically important molecules. Benzimidazole-based polyheterocyclic compounds have several interesting biological properties. Simple synthetic strategies leading to benzimidazole-based fused polyheterocyclic systems and the antiviral and anticancer biological activity of the compounds are surveyed in this review article.
A series of new 1-(1H-benzo[d] imidazol-2-yl)-3-methyl-4-(substituted phenylhydrazono)-1H-pyrazol-5(4H)-ones (4a-i) were synthesized by the condensation of 2-hydrazinyl-1H-benzo[d]imidazole (2) with ethyl-2-arylhydrazono-3-oxobutyrates (3a-i) in glacial acetic acid. Also, 3-(1H-benzo[d]imidazol-2-ylamino)-2-(7-hydroxy-substituted-2-oxo-2H-chromen/quinolin -3-yl)thiazolidin-4-one)s (7a-d) were prepared via the cyclisation of Schiff bases 3-((2-(1H-benzo[d]imidazol-2-yl)hydrazono)substituted)-7-hydroxy-4-methyl-2H-chromen/quinolin-2-one (6a-d) with thioglycolic acid in refluxing benzene. Structural assignments of these synthesized compounds were based on IR, 1HNMR, and Mass spectral data. The newly synthesized compounds (4a-i), (6a-d) and (7a-d) which possess a variety of heterocycles with benzimidazole as core nucleus were evaluated for their antimicrobial and anti-inflammatory activities by cup-plate method and formalin induced rat hind paw oedema method respectively.
Benzimidazole and its derivatives are regarded as an important heterocyclic motif that exhibits a wide range of pharmaceutical applications including anticancers, antihypertensives, antivirals, antifungals, anti-HIVs, anti-convulsants, and anti-diabetics. In view of their wide ranging activities, the synthesis of benzimidazoles and its derivatives remain a primary focus for synthetic chemistry communities. Till date numerous reports especially on the synthesis of 2-arylbenzimidazoles have been published but lack of knowledge on the detailed synthetic reports of two important derivatives such as 2-aminobenzimidazoles, and 2-(alkyl/aryl)thio benzimidazoles still persists. However, owing to fast developing benzimidazole containing new drugs numerous reports have appeared on the synthesis of this privileged scaffold. In this review, efforts have been taken to shed light on the latest informations available on the syntheses and applications of different benzimidazole derivatives. We have also tried to summarize the chemistry involved in the synthesis of various derivatives of benzimidazole for medicinal applications.
BMC Chemistry
Background: Nitrogen containing heterocycles are widely used and investigated by pharmaceutical industry, as they are important in discovery and designing of new drug molecules. Drugs with a benzimidazole nucleus possess exclusive structural features and electron-rich atmosphere, which enable them to bind to a number of biologically important targets and result in a wide range of activities. This has served as the basis of the present study whereby new scaffolds with benzimidazole moiety were designed and synthesized. Methods: The structures of synthesized compounds were confirmed by physicochemical and spectral means. The synthesized compounds were screened for their antimicrobial and antiproliferative activities by tube dilution and Sulforhodamine B (SRB) assays, respectively. Results and conclusion: The in vitro biological screening results revealed that compound Z24 exhibited promising antimicrobial and anticancer activities which are comparable to standards.
2015
2-Anthryl benzimidazole derivatives (5–7) with hydrogen, carboxyl and benzoyl substituents at the 5th position have been synthesized using a silica supported periodic acid catalyst. The DNA cleavage activity of 5–7 was studied in the presence of light using pBR322 plasmid DNA and was shown to vary with substitution at the 5th position of benzimidazole derivatives. DNA binding studies using ethidium bromide displacement assay demonstrated the non-intercalative binding mode of 5–7. The anticancer activity of these target molecules was tested against MCF-7 and HL-60 cell lines, and they exhibited remarkable activity in the micromolar range. Cellular uptake and morphological changes were confirmed by fluorescence and confocal microscopy. A molecular docking study was carried out to explore the DNA binding mechanism of 5–7.
Journal of enzyme inhibition and medicinal chemistry, 2015
A novel series of 5-nitro-1H-benzimidazole derivatives substituted at position 1 by heterocyclic rings was synthesized. Cytotoxicity and antiviral activity of the new compounds were tested. Compound 3 was more active than doxorubicin against A-549, HCT-116 and MCF-7. However, compound 3 showed no activity against human liver carcinoma Hep G-2 cell line. Compounds 9 and 17b (E) showed potency near to doxorubicin against the four cell lines. The acute toxicity of compound 9 on liver cancer induced in rats was determined in vivo. Interestingly, it showed restoration activity of liver function and pathology towards normal as compared to the cancer-bearing rats induced by DENA. Compounds 17a (Z), 17b (E) and 18a (Z) were the most promising compounds for their antiviral activity against rotavirus Wa strain.