Dataset Information

A New Pathway for the Synthesis of a New Class of Blue Fluorescent Benzofuran Derivatives.

ABSTRACT: In this study an efficient and straightforward method for obtaining a new class of blue fluorescent bezofuran derivatives, under microwave irradiation, as well as under conventional thermal heating, is presented. Under conventional TH the reactions occur selectively, and a single type of benzofuran ester derivative was obtained. The synthesis under MW irradiation also led to benzofuran derivatives, but in a time-dependent manner. Irradiation for a short period of time led to a mixture of two types of benzofuran derivatives (3a?c and 4a?c), while MW irradiation for a longer period of time led to a single type of benzofuran (3-methylbenzofuran), the reaction becoming highly selective. Taking into consideration the advantages offered by MW irradiation in terms of a substantial decrease of solvent consumed, a substantial reduction in reaction time (from days to hours), and a consequent diminution in energy consumption, these methods could be considered environmentally friendly. Here, feasible reaction mechanisms for the benzofuran derivatives formation are described. The absorption and fluorescence emission of the obtained benzofuran derivatives were studied, with part of these compounds being intense blue emitters. A certain influence of the benzofuran substituents concerning absorption and fluorescent properties was observed. Only compounds anchored with a carbomethoxy group of furan ring have shown good quantum yields.

SUBMITTER: Moldoveanu C

PROVIDER: S-EPMC6222448 | biostudies-literature | 2018 Aug

REPOSITORIES: biostudies-literature

ACCESS DATA

Publications

A New Pathway for the Synthesis of a New Class of Blue Fluorescent Benzofuran Derivatives.

Moldoveanu Costel C Mangalagiu Ionel I Isac Dragos Lucian DL Airinei Anton A Zbancioc Gheorghita G

Molecules (Basel, Switzerland) 20180806 8

In this study an efficient and straightforward method for obtaining a new class of blue fluorescent bezofuran derivatives, under microwave irradiation, as well as under conventional thermal heating, is presented. Under conventional TH the reactions occur selectively, and a single type of benzofuran ester derivative was obtained. The synthesis under MW irradiation also led to benzofuran derivatives, but in a time-dependent manner. Irradiation for a short period of time led to a mixture of two typ ...[more]

PMID: 30082667

Similar Datasets

Project description:A new series of benzofuran derivatives has been designed and synthesized. The structures of the synthesized compounds have been confirmed by the use of 1H NMR, 13C NMR, 2D 1H-1H NOESY NMR, and IR. Anticancer activity is evaluated against Hepatocellular carcinoma (HePG2), mammary gland breast cancer (MCF-7), Epitheliod carcinoma cervix cancer (Hela) and human prostate cancer (PC3). Compounds 8, 9, and 11 showed the highest activity towards the four cell lines with an IC50 range of 8.49-16.72 µM, 6.55-13.14 µM and 4-8.99 µM respectively in comparison to DOX (4.17-8.87 µM). Phosphatidylinositol-3-kinases (PI3K) inhibition was evaluated against the most active anticancer compounds 8, 9 and 11. Compounds 8, 9 and 11 showed good inhibitory activity against PI3Kα with IC50 values 4.1, 7.8, and 20.5 µM, respectively in comparison to 6.18 µM for the reference compound LY294002. In addition, activity of compounds 8 and 9 on cell cycle arrest and induction of apoptosis in different phases of MCF-7 cells were assessed and detected pre-G1 apoptosis and cell growth arrest at G2/M. Also, both extrinsic and intrinsic apoptosis in MCF-7 cells induced by compounds 8 and 9. Molecular docking, binding affinity surface mapping, and contact preference of the synthesized compounds 8, 9 and 11 against PI3K were estimated and studied computationally using molecular operating environment software (MOE) and showed good interaction with essential residues for inhibition Val851. In addition, antimicrobial activity was evaluated against gram positive isolates as Staphylococcus aureus and Bacillus cereus, gram negative isolate as Escherichia coli, Pseudomonas aeruginosa and antifungal potential against Candida albicans. Compound 17 showed outstanding anti Gram-positive activity with MIC values 8 and 256 µg/mL in Staphylococcus aureus and Bacillus cereus respectively. Also, compounds 15, 17, 18 and 21 showed good anti Gram-negative activity with MIC value 512 µg/mL for all compounds. In addition, the state-of-art quorum sensing (QS) inhibiting effects were detected using Chromobacterium violaceum and compounds 7, 9, 10, 11, and 12 showed good QS inhibition (3, 3, 5, 2, and 7 mm).

Project description:Ectonucleotidases inhibitors (ENPPs, e5'NT (CD73) and h-TNAP) are potential therapeutic candidates for the treatment of cancer. Adenosine, the cancer-developing, and growth moiety is the resultant product of these enzymes. The synthesis of small molecules that can increase the acidic and ionizable structure of adenosine 5-monophosphate (AMP) has been used in traditional attempts to inhibit ENPPs, ecto-5'-nucleotidase and h-TNAP. In this article, we present a short and interesting method for developing substituted indole acetic acid sulfonate derivatives (5a-5o), which are non-nucleotide based small molecules, and investigated their inhibitory potential against recombinant h-ENPP1, h-ENPP3, h-TNAP, h-e5'NT and r-e5'NT. Their overexpression in the tumor environment leads to high adenosine level that results in tumor development as well as immune evasion. Therefore, selective, and potent inhibitors of these enzymes would be expected to decrease adenosine levels and manage tumor development and progression. Our intended outcome led to the discovery of new potent inhibitors like' 5e (IC50 against h-ENPP1 = 0.32 ± 0.01 μM, 58 folds increased with respect to suramin), 5j (IC50 against h-ENPP3 = 0.62 ± 0.003 μM, 21 folds increase with respect to suramin), 5c (IC50 against h-e5'NT = 0.37 ± 0.03 μM, 115 folds increase with respect to sulfamic acid), 5i (IC50 against r-e5'NT = 0.81 ± 0.05 μM, 95 folds increase with respect to sulfamic acid), and 5g (IC50 against h-TNAP = 0.59 ± 0.08 μM, 36 folds increase with respect to Levamisole). Molecular docking studies revealed that inhibitors of these selected target enzymes induced favorable interactions with the key amino acids of the active site, including Lys255, Lys278, Asn277, Gly533, Lys528, Tyr451, Phe257, Tyr340, Gln465, Gln434, Lys437, Glu830, Cys818, Asn499, Arg40, Phe417, Phe500, Asn503, Asn599, Tyr281, Arg397, Asp526, Phe419 and Tyr502. Enzyme kinetic studies revealed that potent compounds such as 5j and 5e blocked these ectonucleotidases competitively while compounds 5e and 5c presented an un-competitive binding mode. 5g revealed a non-competitive mode of inhibition.

Dataset Information

A New Pathway for the Synthesis of a New Class of Blue Fluorescent Benzofuran Derivatives.

Publications

A New Pathway for the Synthesis of a New Class of Blue Fluorescent Benzofuran Derivatives.

Similar Datasets

OmicsDI is part of the ELIXIR infrastructure

Tweets