734-88-3Relevant academic research and scientific papers
Development of Novel Imaging Fluorescent Agents Bearing Anti-Inflammatory Drugs: Synthesis, Structural Characterization and Evaluation of Biological Activity
Adnan, Shaimaa,Jaber, Qassim A. H.,Nabeel, A. Abdul-Rida
, p. 620 - 626 (2020)
Abstract: A new series of 5,6-benzocoumarin derivatives carrying anti-inflammatory drugs were synthesized via alkylamide spacers, the target to develop novel imaging fluorescent agents as useful technique to cancer early discovery. Experimentally, treatment of N-Boc-1,3-propanediamine with ethyl 5,6-benzocoumarin-3-carboxlate (III) under reflux conditions followed by hydrolyzed with CF3COOH to the corresponding primary amine (V), then treatment of derivative (V) with anti-inflammatory drugs have carboxylic group in presence of DCC (N,N'-dicyclohexylcarbodiimide) as catalyst and MeCN as solvent. The structure of the synthesized compounds was confirmed by FT-IR, NMR (1H,13C) spectral data as well as elemental analysis. The fluorescence properties study was investigated spectrophotometrically in methanol and maximum emission (λem) exhibited within range 411–436 nm, meanwhile, the quantum yields were calculated comparison to Rhodamine 6G as reference. Interestingly, the compound (III) gave a higher quantum yield (ΦF = 0.96), meanwhile, compounds (VII, VIII, IX and XI) gave reasonable quantum yields (ΦF) 0.60, 0.65, 0.78 and 0.84, respectively. All synthesized compounds were screened for their anti-AChE and antimicrobial activity. Based on the results, some of the compounds showed good activity in compared to the standard drugs.
A coumarin embedded highly sensitive nitric oxide fluorescent sensor: Kinetic assay and bio-imaging applications
Ali, Mahammad,Dutta, Ananya,Islam, Abu Saleh Musha,Katarkar, Atul,Maiti, Debjani,Sasmal, Mihir
, p. 8450 - 8458 (2020)
Fluorescence spectroscopy is a significant bio-analytical technique for specific detection of nitric oxide (NO) and for broadcasting the in vitro and in vivo biological activities of this gasotransmitter. Herein, a benzo-coumarin embedded smart molecular probe (BCM) is employed for NO sensing through detailed fluorescence studies in purely aqueous medium. All the spectroscopic analysis and literature reports clearly validate the mechanistic insight of this sensing strategy i.e., the initial formation of 1,2,3,4-oxatriazole on treatment of the probe with NO which finally converted to its carboxylic acid derivative. This oxatriazole formation results in a drastic enhancement in fluoroscence intensity due to the photoinduced electron transfer (PET) effect. The kinetic investigation unveils the second and first-order dependency on [NO] and [BCM] respectively. The very low detection limit (16 nM), high fluorescence enhancement (123 fold) in aqueous medium and good formation constant (Kf = (4.33 ± 0.48) × 104 M-1) along with pH invariability, non-cytotoxicity, biocompatibility and cell permeability make this probe a very effective one for tracking NO intracellularly. This journal is
Synthesis, cytotoxicity and in silico study of some novel benzocoumarin-chalcone-bearing aryl ester derivatives and benzocoumarin-derived arylamide analogs
Abdul-Ridha, Nabeel A.,Salmaan, Afraah D.,Sabah, Rita,Saeed, Bahjat,Al-Masoudi, Najim A.
, p. 201 - 210 (2021/04/26)
The development of new prostate cancer protein receptor cytochrome P450 17A1 inhibitors offers the possibility of generating structures of increased potency. To this end, the chalcone analogs 7 and 8 were prepared from treatment of methyl 3-oxo-3H-benzocoumarin-2-carboxylate (4) with aryl aldehydes. Treatment of 7 and 8 with three anti-inflammatory drugs, flurbiprofen, ketoprofen and ibuprofen, in the presence of POCl3/DMAP gave the ester analogs 9-12. Analogously, treatment of ethyl 3-oxo-3H-benzocoumarin-2-carboxylate (15), prepared previously from 2-hydroxy-1-naphthaldehyde (13) and dimethylmalonate (14), with various arylamines: 4-bromoaniline, 2-amino-6-methylpyridine, amino-antipyrine and 2-amino-5-nitrothiazole, in the presence of potassium tert-butoxide gave the benzocoumarine-3-arylamide analogs. The in vitro cytotoxic activities of 9-12 and 16-19 were evaluated against human prostate cancer cell lines (PC-3) and normal human liver epithelia (WRL-68) by MTT assay. Compounds 10 and 17 were the most active cytotoxic agents among the series against PC-3 cells with IC50 values of 71.35 and 78.25 μg mL-1 with SI values of 3.0 and 4.2, respectively (calculated from the cytotoxicity effects of 10 and 17 on the normal human liver epithelia [WRL-68]). Furthermore, compounds 11 and 12 were tested against breast cancer (HER2 cell lines), prostate cancer (DU-135 cell lines) and MCF-7 but were inactive. Molecular docking studies between the protein receptor CYPP450 17A1 and compounds 10 and 17 revealed that these compounds primarily form hydrophobic interactions with the receptor.
A two-photon benzocoumarin-NBD dyad for highly selective and sensitive ratiometric detection of H2S in biological samples
Chen, Guofeng,Gao, Jingshuo,Guo, Zhenbo,Jia, Xu,Li, Xiaoliu,Wei, Chao,Wei, Lingyu,Yang, Shuhan,Zhang, Pingzhu
, (2020/10/09)
Hydrogen sulfide (H2S), the third endogenous gas signaling transmitter, plays an important role in the basic signal conduction process of human physiology and pathology. It is critical to monitor the dynamic change of H2S in living organisms. In this article, a two-photon ratiometric fluorescent probe (BCD) based on the benzocoumarin-NBD framework was first designed and synthesized. The probe showed large emission separation (about 115 nm), excellent selectivity, and high sensitivity. Moreover, it could be applied to ratiometric image endogenous H2S biosynthesis in the living cells and zebrafish.
Enantioselective Construction of Spirooxindole-Fused Cyclopentanes
Do?ekal, Vojtěch,Vopálenská, Andrea,Měrka, Pavel,Kone?ná, Klára,Jand'Ourek, Ond?ej,Pour, Milan,Císa?ová, Ivana,Vesely, Jan
, p. 12623 - 12643 (2021/07/31)
The present study reports an asymmetric organocatalytic cascade reaction of oxindole derivates with α,β-unsaturated aldehydes efficiently catalyzed by simple chiral secondary amine. Spirooxindole-fused cyclopentanes were produced in excellent isolated yields (up to 98%) with excellent enantiopurities (up to 99% ee) and moderate to high diastereoselectivities. The synthetic utility of the protocol was exemplified on a set of additional transformations of the corresponding spiro compounds. In addition, a study showing the promising biological activity of selected enantioenriched products was accomplished.
Au(I)-Catalyzed Domino Cyclization of 1,6-Diynes Incorporated with Indole
Chen, Guzhou,Liu, Peng-Yu,Zou, Huanhuan,Hu, Jiadong,Fang, Xiaowu,Xu, Dongyang,He, Yu-Peng,Wei, Hongbo,Xie, Weiqing
supporting information, p. 2279 - 2284 (2021/04/05)
We disclose herein a Au(I)-catalyzed domino cyclization of 1,6-diynes incorporated with indole. This protocol enabled the diastereoselective buildup of indole-fused azabicyclo[3.3.1]nonanes from linear precursors. Density functional theory calculations showed that the reaction proceeded via an unprecedented cascade dearomatization/rearomatization/dearomatization process. Independent gradient model analysis revealed that a noncovalent attractive interaction between the distal alkyne and the Au/proximal complex was responsible for the chemoselectivity of the first spirocyclization step.
Zirconium(IV) oxychloride: A simple and efficient catalyst for the synthesis of chromen-2-one derivatives
TASQEERUDDIN,ASIRI, YAHYA I.,SHAHEEN
, p. 2611 - 2616 (2020/10/22)
The present work explores a highly efficient, environmental friendly, green protocol for the synthesis of chromen-2-one derivatives (3a-m) by the condensation of salicylaldehydes with various active methylene compounds using zirconium (IV) oxychloride as catalyst. This is a convenient and rapid method for Knoevenagel condensation and this methodology offers several advantages including shorter reaction time, milder conditions, inexpensive catalyst, simple operational procedure and allowed to achieve the desired products in excellent yields. The structures of all the synthesized compounds were confirmed by spectral data.
Fluorescent probe, preparation method thereof, fluorescent probe test paper, and application of fluorescent probe test paper
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Paragraph 0065-0068, (2020/02/19)
The invention belongs to the technical field of biological mercaptan detection, and particularly relates to a fluorescent probe, a preparation method thereof, a fluorescent probe test paper, and an application of the fluorescent probe test paper. The fluorescent probe can specifically recognize biological mercaptan (Cys, Hcy and GSH), and has the advantages of easiness in preparation, low price, strong specificity, high sensitivity, and suitableness for the physiological pH; and the fluorescent probe test paper prepared by using the fluorescent probe can be used to quantitatively detect biological mercaptan in a urine sample through naked eyes, and has great application values in the fields of biomedicines and the like.
Tandem Olefin Isomerization/Cyclization Catalyzed by Complex Nickel Hydride and Br?nsted Acid
Kathe, Prasad M.,Caciuleanu, Alexandru,Berkefeld, Andreas,Fleischer, Ivana
, p. 15183 - 15196 (2020/11/30)
We disclose a nickel/Br?nsted acid-catalyzed tandem process consisting of double bond isomerization of allyl ethers and amines and subsequent intramolecular reaction with nucleophiles. The process is accomplished by [(Me3P)4NiH]N(SO2CF3)2 in the presence of triflic acid. The methodology provides rapid access to tetrahydropyran-fused indoles and other oxacyclic scaffolds under very low catalyst loadings.
AZEPINO-INDOLES AND OTHER HETEROCYCLES FOR TREATING BRAIN DISORDERS
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Paragraph 0204, (2020/09/12)
The present invention provides azepino-indoles and other heterocycles and methods of using the compounds for treating brain disorders.
