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A comprehensive and facile method for the synthesis of new functionalized bis-heterocyclic compounds containing a thieno[2,3-b]thiophene motif is described. The hitherto unknown bis-pyrazolothieno[2,3-b]thiophene derivatives 2a-c, bis-pyridazin othieno[2,3-b]thiophene derivatives 4, bis-pyridinothieno[2,3-b]thiophene derivatives 6a,b, and to an ana...
Citations
... Significant consideration has been made on thienothiophene derivatives owing to their impressive biological movements. They are using as the potential antiviral, antitumor, antibiotic and as inhibitors of platelet gathering or antiglaucoma drugs [1][2][3][4][5]. Thienothiophene derivatives are also of plausible interest as p electron donors and have possible utilization in a broad diversity of optical and electronic classification [6][7][8][9][10][11][12]. ...
In this approach, diethyl thieno [2,3-b] thiophene-2,5-dicarboxylate-2 (DETTDC2) was prepared in one-pot synthesis by using pentan-2,4-dione (P24D), carbon disulfide, and ethyl bromoacetate (EBA) precursors and finally the characterization was carried out systematically with proton-Nuclear Magnetic Resonance (H-NMR), Impedance spectroscopy (EIS), Fourier-transform infrared spectroscopy (FTIR) and carbon hydrogen and nitrogen (CHN) analyzer. An ultra-thin sheet of DETTDC2 was retained on a glassy carbon electrode (GCE) with managing binder to evolve the expected working electrode of Hg(II) cationic sensors. The calibration plot was determined based on the current vs. amount of Hg(II) ion and the final calibration curve was appeared to be linear (r2: 0.9979) over the low to high range (LDR: 0.1 nM ∼ 0.01M). The sensor performance in term of sensitivity (0.74367 µAµM−1cm−2) was predicted from the slope of calibration plot. It was also measured the detection limit (DL: 12.80 ±0.64 pM) of the sensor at signal to noise ratio of 3. This sensor was applied to sensitive detection of Hg(II) ions in phosphate buffer condition. Therefore, this novel electrochemical approach is the suitable method for designing the toxic heavy-metal detection to safe-guard the public health and environment remediation.
... The recent efforts have been made towards the investigation of more potential anti-microbial agents [35]. Further, the synthesis of a variety of bis-heterocyclic compounds has received great attention [36] not only as main chain polymers but also because of many biologically active natural [37] and synthetic products have molecular symmetry [38]. Thus, bis-heterocyclic compounds may avoid the microbial resistance. ...
A series of novel 3-4-[2-hydroxy-5-(4-hydroxy-3-2-[2-(aryl)-4-oxo-1,3-thiazolan-3-yl]-6-phenyl-4-pyrimidinylbenzyl)phenyl]-6-phenyl-2-pyrimidinyl-2-(aryl)-1,3-thiazolan-4-ones 5(a-j) have been synthesized and assayed for their antibacterial activity against B. subtilis, B. sphaericus, S. aureus, P. aeruginosa, K. Aerogenes and C. violaceum. The inhibition zones and minimal inhibitory concentrations were measured and compared with the streptomycin. The antibacterial screening data reveal that the compounds containing 4-nitrophenyl (5c), 3-nitrophenyl (5d), 4-dimethylaminophenyl (5g) and 1,3-benzodioxole (5j) moiety at 2-position of the thiazolidin-4-one ring exhibited potent inhibitory activity towards all the tested microorganism, which is higher than streptomycin. The other compounds also showed moderate to good activity.
... Naproxeni is widelyi used initherapeutics asianalgesic andiantipyretic andi it isialso used forirelief ofisymptoms of rheumatoidiarthritis and osteoarthritis in addition to treatment ofidysmenorrheal, among otheriindications (2) . Oxadiazole is one of heterocyclic compounds that are found as construction unitsithrough severalibiological molecules (8) ,imostly are moleculesiwhich contain five and siximembered ring (9) . The synthesis of heterocyclic compounds is due to potential biological and industrial applications (10)(11)(12)(13)(14) . ...
Some new oxadiazole compounds were prepared by the reaction of some hydrazidesi of different carboxylic acides (aliphatic and aromatic acids) with Naproxen in presence of phosphorous oxy chloride (POCl 3 ). There are several methods are available for the synthesis of hydrazide derivatives, the most important one is based on the reaction of esters with hydrazine monohydrate that has been applicated in this research for preparation hydrazide derivatives. These synthezied oxadiazole compounds were identified by melting points, FT-IR, and H-NMR, spectroscopy.
... The solid products were filtered and recrystallized from ethanol to afford the desired compounds in pure forms. Reaction of compound 5 with malonitrile in ethanol, under reflux, afforded compound 6 [26,27] (Scheme 3). Structures of these two compounds were confirmed by spectroscopic methods. ...
Background
The thiophene nucleus has been recognized as an important entity in the synthesis of heterocyclic compounds with promising pharmacological characteristics. ResultsA number of new heterocyclic compounds incorporating thiophene species have been prepared from the titled enaminone via the reaction with different nucleophiles and electrophiles. The structure elucidation of the designed compounds was derived from their spectral information. The results of antimicrobial activity of the prepared compounds revealed that derivatives 7b and 8 exhibited activity comparable to the standard drugs ampicillin and gentamicin for all tested bacteria species. Additionally, compound 3 displayed potent activity against Aspergillus fumigates, whereas compounds 5, 6, and 7a showed good activity against Syncephalastrum racemosum. Conclusions
We have synthesized a number of new thiophene-containing compounds. The results of antimicrobial activity of the prepared compounds revealed that changing the substituents at position-2 of thiophene ring significantly affect their biological activity. The pyridine side chain derivatives in compounds 7a, 7b and 8 showed excellent antimicrobial activity.
... Many reports claimed that the condensation of activated methylene compounds with alkyl or aryl isothiocyanates in a basic medium, followed by the addition of a-haloester or a-haloketones is an efficient method for the preparation of the thiophenes. [13][14][15][16] In light of the above-mentioned ndings and as part of our interest in the synthesis of potent biologically active thiophenes, [16][17][18][19][20] we decided to synthesize new thiophene derivatives utilizing this reported method in order to test their biological activities. ...
... Many reports claimed that the condensation of activated methylene compounds with alkyl or aryl isothiocyanates in a basic medium, followed by the addition of a-haloester or a-haloketones is an efficient method for the preparation of the thiophenes. [13][14][15][16] In light of the above-mentioned ndings and as part of our interest in the synthesis of potent biologically active thiophenes, [16][17][18][19][20] we decided to synthesize new thiophene derivatives utilizing this reported method in order to test their biological activities. ...
One pot synthesis of two novel hitherto unreported thiophenes was achieved by a facile and selective
synthetic method. The crystal structures of the synthesized compounds were determined using an X-ray
single crystal technique. The synthesized thiophenes were evaluated for their anti-cancer and
antimicrobial activities. Molecular docking studies of the synthesized compounds were performed by
(MOE). The predicted results from the molecular docking studies were in complete agreement with the
experimental data for antimicrobial evaluation.
... Thieno[2,3-b]thiophene sca old represents the key pharmacophore of several pharmaceutically agents. Thus, several thieno [2,3-b] thiophene were reported to exhibit marked chemotherapeutic activities such as antibacterial, antiviral, antitumor, anti-glaucoma drugs, β-glucuronidase, αglucosidase inhibition, and anti-oxidant potential [2][3][4][5][6][7][8][9][10][11][12][13]. In continues of our research program we report her crystal structure of title compound elucidated by X-ray di raction analysis. ...
C19H17.75O4.13S2, monoclinic, P21/n (no. 14), a = 7.1921(6) Å, b = 18.6304(14) Å, c = 13.3739(11) Å, β = 92.681(4)°, V = 1790.0(2) Å3, Z = 4, Rgt(F) = 0.0478, wRref(F2) = 0.0913, T = 100 K.
... [4][5][6][7][8][9] Thienothiophenes have also been reported as potential antitumour, antiviral, antibiotic and antiglaucoma drugs and as inhibitors of platelet aggregation. [10][11][12][13][14][15][16][17][18] Moreover, other interesting heterocyclic systems including thiazoles and thiadiazoles have been synthesised 19 and tested for several pharmacological properties such as anti-HIV-1 NNRTIs 20 and for the treatment of allergies, 21 hypertension, inflammation, schizophrenia and bacterial infections. [22][23][24][25] Here we utilised 2,5-diacetylthieno [2,3-b]thiophene derivatives 1a,b as key precursors for constructing interesting bis-heterocycles linked to the thienothiophene moiety. ...
In this paper, the synthesis of bis-thiazoles and bis-1,3,4-thiadiazoles linked to a thienothiophene nucleus is described. The synthesis was achieved through interaction between 2,5-diacetylthieno[2,3-b]thiophene bis-thiosemicarbazones with a variety of hydrazonyl halides in a basic medium. All the synthesised compounds were characterised by IR, 1H NMR, 13C NMR and mass spectroscopic analyses. The newly synthesised compounds represent a variety of novel polyheteroatomic moieties containing nitrogen and sulfur. Most of the synthesised compounds were evaluated for their antitumour activity against the breast cancer MCF-7 cell line. The results revealed that four compounds are equipotent to tamoxifen (IC50 = 8.04 μg mL-1) with IC50 = 8.23, 8.26, 8.68 and 9.12 μg mL-1 respectively.
... They have been tested as potential antitumor, antiviral, antibiotic and antiglaucoma drugs or as inhibitors of platelet aggregation. [1][2][3][4][5] In addition, thienothiophenes are of potential interest as π -electron donors and have potential applications in a wide variety of optical and electronic systems. [6][7][8][9][10][11][12] Moreover, thiazole derivatives have attracted increasing attention due to their numerous pharmacological applications and biological activities, such as anti-inflammatory, analgesic, antimicrobial, anti-HIV , antihypertensive and herbicidal activity. ...
Synthesis of novel bis(thiazoles) 19–22, 24, 25, 30 and 31 is reported. Thus, reaction of the bis(α-bromoketones) 14 and 15 with the corresponding thioamide derivatives 16–18 in refluxing EtOH in the presence of triethylamine afforded 19–22 in good yields. On the other hand, the novel bis(thiazoles) 24 and 25 can be synthesized by the reaction of 14 and 15 with the corresponding p-chlorobenzaldehyde thiosemicarbazones 23 in refluxing EtOH. The novel isomeric bis(thiazoles) 30 and 31 can also be synthesized by a reaction of the corresponding bis(benzaldehyde thiosemicarbazones) 27 and 28 with p-chlorophenacyl bromide 29. Compounds 27 and 28 were obtained by condensation of the corresponding bis(aldehydes) 12 and 13 with thiosemicarbazide 26.
... Recently, Mabkhot and co-workers have been involved in a research program aimed to development of new synthetic strategies for novel bioactive molecules and evaluation of their biological activity [22][23][24][25][26][27][28]. ...
In this work, synthesis, antimicrobial activities and molecular docking studies of some new series of substituted quinazolinone 2a–h and 3a–d were described. Starting form 2-aminobenzamide derivatives 1, a new series of quinazolinone derivatives has been synthesized, in high yields, assisted by microwave and classical methods. Some of these substituted quinazolinones were tested for their antimicrobial activity against Gram-negative bacteria (Pseudomonas aeruginosa and Esherichia coli) and Gram-positive bacteria (Staphylococcus aureus, and Bacillus subtilis), and anti-fungal activity against (Aspergillus fumigatus, Saccharomyces cervevisiae, and Candida albicans) using agar well diffusion method. Among the prepared products, 3-benzyl-2-(4-chlorophenyl)quinazolin-4(3H)-one (3a) was found to exhibits the most potent in vitro anti-microbial activity with MICs of 25.6 ± 0.5, 24.3 ± 0.4, 30.1 ± 0.6, and 25.1 ± 0.5 µg/mL against Staphylococcus aureus, Bacillus subtilis, Pseudomonas aeruginosa and Esherichia coli, respectively. Compound 3a was found to exhibits the most potent in vitro anti-fungal activity with MICs of 18.3 ± 0.6, 23.1 ± 0.4, and 26.1 ± 0. 5 µg/mL against Aspergillus fumigatus, Saccharomyces cervevisiae, and Candidaal bicans, respectively.
