- Microwave-assisted efficient and convenient one-pot synthesis of novel 3-(4-aminothieno[2,3-d]pyrimidin-5-yl)coumarins under solvent-free conditions
-
[Figure not available: see fulltext.] An efficient green synthesis of novel 3-(4-aminothieno[2,3-d]pyrimidin-5-yl)coumarins has been developed. One-pot reaction of 3-acetylcoumarin, malononitrile, and elemental sulfur, catalyzed by L-proline, resulted in the formation of thiophene derivatives, which were used as precursors for the synthesis of 3-(4-aminothieno[2,3-d]pyrimidin-5-yl)coumarins. Target compounds were prepared by a one-pot method or stepwise, and NH4OAc was exploited as a reagent and molten salt. Microwave irradiation method was successfully applied to afford the products in excellent yields.
- Srikrishna, Devulapally,Dubey, Pramod Kumar
-
-
Read Online
- Synthesis and characterisation of novel 3-(4-benzoyl-5-phenylfuran-2-yl) coumarins
-
Novel 3-(4-benzoyl-5-phenylfuran-2-yl)coumarin derivates were synthesised via a simple three-step reaction from salicylic aldehydes, ethyl 3-oxobutanoate and 1,3-diphenylpropane-1,3-dione. The synthesised compounds were characterised by NMR, MS and elemental analyses and single-crystal X-ray diffraction analysis.
- Weidong, Wang,Fang, Zhao,Yang, Hu,Qiao, Li,Shengli, Hu
-
-
Read Online
- A facile one pot multi component synthesis of alkyl 4-oxo-coumarinyl ethylidene hydrazono-thiazolidin-5-ylidene acetates and their antiviral activity
-
An efficient one-pot synthesis of alkyl 4-oxo-coumarinyl ethylidene hydrazono-thiazolidin-5-ylidene acetate derivatives has successfully been achieved via a three component cyclization reaction of various substituted 3-acetyl coumarins, thiosemicarbazide and dialkyl acetylenedicarboxylates, in presence of acetic acid. The isolated products were obtained in pure form with high yields through simple workup. The newly synthesised compounds structure was established on the basis of spectral (IR, 1H NMR, 13C NMR, ESI- mass) elemental analysis and single crystal X-ray data. All synthesised compounds were screened for their antiviral activity against a broad spectrum of human viruses in different cell cultures. Of the novel synthesised compounds, thirteen compounds exerted activity against Punta Toro virus, including compound IV-19, for which an antiviral potency was noted against a broad panel of DNA and RNA viruses as well.
- Kulkarni, Chandrashekhar V.,Vaarla, Krishnaiah,Vedula, Rajeswar Rao,Vermeire, Kurt,Vishwapathi, Vinod
-
-
- Novel thiazoline-coumarin hybrid compounds containing sugar moieties: synthesis, biological evaluation and molecular docking study as antiproliferative agents
-
A new series of 2,3-thiazoline-coumarin hybrid compounds that containedd-glucose andd-galactose moieties (4a-g) were synthesized and their cytotoxic activity was evaluated against breast adenocarcinoma (MCF-7), human liver cancer (HepG2), human cervical cancer (HeLa), human melanoma cancer (SK-Mel-2), and human lung cancer (LU-1) cells. To reveal their selectivity toward cancer cells, the compounds were also tested against the human fibroblast cell line MRC-5. The synthesized compounds exhibited potent cytotoxic activity against the tested cell lines with IC50values of 1.18-11.32, 1.91-9.81, 1.96-13.16, 1.35-16.12, and 2.12-15.92 μM (against MCF-7, HepG2, HeLa, SK-Mel-2, and LU-1 cells, respectively) compared with Sorafenib, doxorubicin, and 5-fluorouracil. Interestingly, compounds4a-gdisplayed selectivity toward cancer cell lines over MRC-5 (IC503.97-25.75 μM). The most active compounds, including4d,4e, and4f, also displayed potent inhibitory activity against EGFR and HER2 kinases (IC500.15-0.31 and 0.15-0.25 μM, respectively) compared with the standard drug Sorafenib (IC50= 0.11 and 0.13 μM, respectively). Molecular docking also showed that the hydrogen binding interactions often occurred between the CO lactone of the coumarin ring and appropriate amino acid residues, which played a key role in enhancing its potency against both enzymes.
- Ngoc Toan, Vu,Dinh Thanh, Nguyen
-
p. 10636 - 10653
(2021/06/27)
-
- Synthesis and anti-acetylcholinesterase activities of novel glycosyl coumarylthiazole derivatives
-
Eleven glycosyl coumarylthiazole derivatives are synthesized by cyclization and condensation of glycosyl thiourea with 3-bromoacetyl coumarins in ethanol. The reaction conditions are optimized and good yields of products (80%–95%) are obtained. The structures of all new products were confirmed by IR, 1H and 13C NMR, and by HRMS (electrospray ionization). The in vitro acetylcholinesterase (AChE) inhibitory activities of these new compounds are tested by Ellman’s method. Among them, N-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl)-4-(6-nitrocoumarinyl)-1,3-thiazole-2-amine showed the best activity with an in vitro AChE inhibitory rate of 58% and an IC50 value of 12 ± 0.38 μg/mL.
- Cao, Lian-Gong,Cao, Zhi-Ling,Jiang, Kai-Jun,Liu, Shu-Hao,Liu, Wei-Wei,Lu, Xing,Shao, Zhong-Bai,Shi, Da-Hua,Wang, Lei,Wang, You-Xian
-
p. 359 - 364
(2020/12/28)
-
- Synthesis and antiproliferative activity of hybrid thiosemicarbazone derivatives bearing coumarin and d-galactose moieties with EGFR inhibitory activity and molecular docking study
-
A series of substituted N-(2,3,4,6-tetra-O-acetyl-β-d-galactopyranosyl)thiosemicarbazones 5a–5j of substituted 3-acetylcoumarins were synthesized with yields of 45–68%. All synthesized thiosemicarbazones were evaluated for cytotoxic activity against several cancer cell lines, such as human breast adenocarcinoma cells MCF7, human liver cancer cells HepG2, human cervical cancer cells HeLa, human melanoma cancer cells SK-Mel-2, and human lung cancer cells LU-1 by using the standard MTT assay. The IC50 values for these cancer cell lines were 1.28–11.81 μM (for MCF-7), 1.53–22.12 μM (for HepG2), 1.43–48.16 μM (for HeLa), 1.82–14.62 μM (for SK-Mel-2), and 1.74–14.62 μM (for LU-1). Most of the compounds were noncytotoxic against human WI-38 normal cell line (IC50 > 16.9 μM). The antiproliferative mechanisms were studied via EGFR inhibition and molecular docking. Docking studies revealed that there are strong interactions between a typical compound with the receptor of the EGFR tyrosine kinase domain with Erlotinib. [Figure not available: see fulltext.]
- Toan, Vu Ngoc,Thanh, Nguyen Dinh
-
p. 1868 - 1885
(2021/08/23)
-
- Synthesis and biological screening of thiosemicarbazones of substituted 3-acetylcoumarins having D-glucose moiety
-
Thiosemicarbazones 5a-j were synthesized with yields of 45–68% by condensation of 3-acetylcoumarins 3a-j and tetra-O-acetyl-β-D-thiosemicarbazide 4. All obtained thiosemicarbazones were screened for anti-microorganic activities against bacteria (B. subtilis, S. aureus, S. epidermidis, E. coli, P. aeruginosa, K. pneumoniae, S. typhimurium) and fungi (A. niger, C. albicans, S. cerevisiae, and A. flavus). Some compounds had significant inhibitory activity with MICs of 0.78–3.125 μM in comparison with 5a, including 5e,h,i for S. aureus, and 5c,f,i for S. epidermidis (Gram-(+) bacteria), 5c,f,g for E.coli, 5f for K. pneumoniae, 5b,c,g for P. aeruginosa, and 5i for S. typhimurium (Gram-(?) bacteria), 5d,h,i for A. niger, 5i for A. flavus, 5b,d,e,h for C. albicans, and 5i for S. cerevisiae. Compounds exhibited excellent activity against tested microorganism with MIC = 0.78 μM, including 5h,i (against S. aureus), 5h (against C. albicans), and 5i (against S. cerevisiae).
- Ngoc Toan, Vu,Dinh Thanh, Nguyen,Minh Tri, Nguyen,Thi Thu Huong, Nguyen
-
supporting information
(2020/11/20)
-
- Ros inhibitory activity and cytotoxicity evaluation of benzoyl, acetyl, alkyl ester, and sulfonate ester substituted coumarin derivatives
-
Background: A number of non-steroidal anti-inflammatory drugs (NSAIDs) including aspirin, indomethacin, ibuprofen, flufenamic acid, and phenylbutazone are being clinically used to treat inflammatory disorders. These NSAIDs are associated with serious side
- Salar, Uzma,Mohammed Khan, Khalid,Jabeen, Almas,Faheem, Aisha,Naqvi, Farwa,Ahmed, Shakil,Iqbal, Erum,Ali, Farman,Kanwal,Perveen, Shahnaz
-
p. 1099 - 1111
(2020/11/09)
-
- Synthesis and antiproliferative evaluation of novel biheterocycles based on coumarin and 2-aminoselenophene-3-carbonitrile unit
-
A series of novel coumarins with 2-amino-3-cyanoselenophen-5-yl unit on C-3 have been synthesized. These compounds prepared easily at room temperature, in a short time and in high yield. The importance of biheterocyclic units as dominant structural motif of coumarin derivatives has been well recognized. Anti-cancer activity screening on MCF-7 cell line allowed identification of 2-amino-5-(6-bromo-2-oxo-2H-chromen-3-yl)selenophene-3-carbonitrile with the highest level of cytotoxic activity with mean IC50 and cLogP (partition co-efficient) values 10.84 μM and 3.18, respectively. The most radical scavenging compound was also recognized. Graphic abstract: [Figure not available: see fulltext.].
- Er?at?r, Mehmet,Giray, Elife Sultan,Y?ld?r?m, Metin,Yal?n, Serap
-
p. 625 - 636
(2020/05/05)
-
- Pyrazole–coumarin and pyrazole–quinoline chalcones as potential antitubercular agents
-
Pyrazole, coumarin, and quinoline are medicinally important moieties. In this study, two series of novel pyrazole–coumarin chalcones and pyrazole–quinoline chalcones were synthesized using multiple-step reactions. All the synthesized compounds were well c
- Kumar, Gautam,Siva Krishna, Vagolu,Sriram, Dharmarajan,Jachak, Sanjay M.
-
-
- Improved one-pot synthetic conditions for synthesis of functionalized fluorescent coumarin-thiophene hybrids: Syntheses, DFT studies, photophysical and thermal properties
-
We have synthesized coumarin-thiophene hybrids using stepwise and one-pot methods under MWI and CM conditions, and then report the findings and conclusions: one-pot is better than stepwise in terms of high yields and fastness of getting products, and MWI is better than CM in terms of purity of compounds, better yields, and reaction period. Even though both protocols were found to be efficient, the microwave-assisted irradiation reactions were identified to be better, environmentally friendly, cost-effective, mild, more efficient, less time consuming but with high purity. The two protocols were employed for the synthesis of the target coumarin-thiophene hybrids via the Gewald reaction in stepwise and in one-pot three-component. The dyes 3a-j were prepared in good to excellent yields. Although, we recorded better yields via the stepwise protocol (80–96%), for the synthesis of the target molecules, as compared to the one-pot (82–90%), the stepwise condition is fraught with many changes such as long reaction conditions, extra use of solvents for purification of intermediates, and long reaction durations. Photophysical activities of all the target derivatives were investigated using a combination of UV–vis and fluorescence spectroscopies in different solvents. The umbelliferon-like derivative 3g was further investigated for possible use as a pH sensor via deprotonation (using TBAOH) and reverse protonation (using TFA), and was found to be applicable as pH sensor both in organic medium (DMSO) and partial aqueous binary (DMSO/H2O, v/v, 9:1) medium. Again, the ground and the excited state properties of the umbelliferon-like derivative 3g and its deprotonated form were also studied using the quantum chemical calculations. Finally, the thermal properties of all the target compounds were investigated using TGA in order to test their potency and applicability as optical dyes. All the dyes 3a-j have high thermal stability therefore they can be applicable as optical dyes.
- Yahaya, Issah,Sefero?lu, Nurgül,Sefero?lu, Zeynel
-
supporting information
p. 2143 - 2154
(2019/02/28)
-
- Anti-MRSA (Multidrug resistant Staphylococcus aureus) activity of 3-substituted coumarins
-
Background: Infectious pathogenic bacteria are the key virulence in our daily life. Especially diseases produced by multidrug resistant Staphylococcus aureus (MRSA) still contributing in morbidity and mortality in humans. Discovery of new and safer antibi
- Salar, Uzma,Khan, Khalid Mohammed,Muhammad, Humaira,Fakhri, Muhammed Imran,Sanaullah,Perveen, Shahnaz,Choudhary, Muhammed Iqbal
-
p. 353 - 362
(2018/04/20)
-
- Design, synthesis, DFT, docking studies and ADME prediction of some new coumarinyl linked pyrazolylthiazoles: Potential standalone or adjuvant antimicrobial agents
-
The control of antimicrobial resistance (AMR) seems to have come to a dead end. The major consequences of the use and abuse of antibacterial drugs are the development of resistant strains due to genetic mutability of both pathogenic and nonpathogenic microorganisms. We, herein, report the synthesis, characterization and biological activities of coumarin-thiazole-pyrazole (CTP) molecular hybrids with an effort to explore and overcome the increasing antimicrobial resistance. The compounds were characterized by analyzing their IR, Mass, 1H and13C NMR spectral data and elemental analysis. The in vitro antimicrobial activity of the synthesized compounds was investigated against various pathogenic strains; the results obtained were further explained with the help of DFT and molecular orbital calculations. Compound 1b and 1f displayed good antimicrobial activity and synergistic effects when used with kanamycin and amphotericin B. Furthermore, in vitro cytotoxicity of compounds 1b and 1f were studied against HeLa cells (cervical cancer cell) and Hek-293 cells. The results of molecular docking study were used to better rationalize the action and prediction of the binding modes of these compounds.
- Kumar, Sunil,Saini, Vikram,Maurya, Indresh K.,Sindhu, Jayant,Kumari, Mukesh,Kataria, Ramesh,Kumar, Vinod
-
-
- Synthesis and antimicrobial activity of some novel quinoline-pyrazoline-based coumarinyl thiazole derivatives
-
A series of novel 3-(2-(5-(2-chloroquinolin-3-yl)-3-substituted phenyl-4,5-dihydro-1H-pyrazol-1-yl)thiazol-4-yl)-6-H/halo-2H-chromen-2-ones (9a–9y) was prepared as antimicrobial agents by the condensation of 3-(2-bromoacetyl)-6-H/halo-2H-chromen-2-ones (4
- Ansari, Mohd. Imran,Khan, Suroor Ahmad
-
p. 1481 - 1496
(2017/06/05)
-
- Development of hydrogelator-based gel-entrapped base catalysts (GEBCs) as heterogeneous basic catalysts for the synthesis of 3-acetylcoumarins
-
New gel entrapped base catalysts (GEBCs) have been prepared by entrapping some organic and inorganic bases into a solid aqueous gel matrix. Sodium alginate, gelrite and carboxymethyl chitosan were studied for the preparation of GEBCs. The phase behaviour of binary systems (gelator + water) is well studied, but ternary systems (gelator + water + base) are not much studied. Addition of a base to a (gelator + water) system drastically affected the behaviour of the gel. The phase behaviour of ternary systems (gelator + water + base) was studied by developing the corresponding ternary phase diagrams. From this study, the promising homogeneous viscous phases were converted into hard, irreversible gel beads by cross-linking the gelator with divalent cations Ca2+, Ba2+ and Sr2+. These gel beads were studied for base entrapment efficiency and leaching of the base. The GEBCs were used for the condensation of salicylaldehydes and methyl/ethyl acetoacetate to obtain 3-acetylcoumarins.
- Korgavkar, Nilesh N.,Samant, Shriniwas D.
-
p. 12422 - 12428
(2017/11/06)
-
- Application of iron-based metal-organic frameworks in catalysis: Oxidant-promoted formation of coumarins using Fe3O(BPDC)3 as an efficient heterogeneous catalyst
-
An iron-based metal-organic framework, Fe3O(BPDC)3, was synthesized, and was characterized by X-ray powder diffraction (XRD), scanning electron microscopy (SEM), transmission electron microscopy (TEM), thermogravimetric analysis (TGA), Fourier transform infrared (FT-IR) spectroscopy, atomic absorption spectrophotometry (AAS), and nitrogen physisorption measurements. The Fe-MOF could be used as an efficient heterogeneous catalyst for the synthesis of coumarins from salicylaldehydes and activated methylene compounds in the presence of tert-butyl hydroperoxide as the oxidant under base-free conditions. The Fe3O(BPDC)3 was more catalytically active for the synthesis of coumarins than other MOFs such as Cu2(BDC)2(BPY), Cu3(BTC)2, Cu2(BDC)2(DABCO), Ni2(BDC)2(DABCO), and Fe3O(BDC)3. This Fe-MOF also offered significantly higher catalytic activity for the transformation than that of common metal salts such as FeCl3, Fe(NO3)3, FeSO4, CuCl2, CuCl, Cu(NO3)2, and Ni(NO3)2. The Fe3O(BPDC)3 catalyst could be recovered and reused several times without significant degradation in catalytic activity. To the best of our knowledge, the oxidant-promoted formation of coumarins under heterogeneous catalysis conditions was not previously mentioned in the literature.
- Lieu, Thien N.,Nguyen, Khoa D.,Le, Dung T.,Truong, Thanh,Phan, Nam T. S.
-
p. 5916 - 5926
(2016/08/05)
-
- New two-photon absorption benzotriazole-coumarin dyads: The evidence of internal proton transfer in the excited state
-
New near-infrared two-photon absorption π-extended benzotriazole-coumarin dyads as target molecules were synthesized. The corresponding coumarin derivatives and esterified dyads were also prepared as the references. The experimental evidence of internal p
- Gong, Yulong,Lu, Yao,Wang, Zhenqiang,Zhang, Shengtao,Luo, Ziping,Li, Hongru,Gao, Fang
-
p. 236 - 242
(2015/02/19)
-
- Copper(I)-promoted cycloalkylation-peroxidation of unactivated alkenes via sp3 C-H functionalisation
-
A copper(i)-promoted cycloalkylation-peroxidation strategy has been developed via a three-component reaction involving cycloalkanes, tert-butyl hydroperoxide (TBHP) and internal conjugated alkenes possessing electron-withdrawing groups (EWGs). This process installs C-O and C-C bonds via sp3 C-H functionalisation with concomitant generation of two stereocentres. This regioselective radical addition of coumarin system is opposite to that of styrene.
- Banerjee, Arghya,Santra, Sourav Kumar,Mishra, Aniket,Khatun, Nilufa,Patel, Bhisma K.
-
supporting information
p. 1307 - 1312
(2015/01/30)
-
- One-pot multicomponent synthesis of indole incorporated thiazolylcoumarins and their antibacterial, anticancer and DNA cleavage studies
-
A series of indole incorporated thiazolylcoumarins (7a-q) have been synthesized and evaluated for their antibacterial, anticancer and DNA cleavage studies. Analysis of antibacterial studies indicated that all the synthesized compounds possess promising activity towards the screened bacterial strains. In vitro anticancerous action was studied for compound 7a (NSC: 768621/1) against the full panel of 60 human tumor cell lines. The five dose level activity results revealed that, the compound 7a was active against all the cell lines among them it has shown potent activity against Leukemia: CCRF-CEM (GI50: 0.33 μM), Non-Small Cell Lung Cancer: NCI-H522 (GI50: 1.03 μM), Colon Cancer: HCT-116 (GI50: 1.60 μM), CNS Cancer: SF-539 (GI50: 1.58 μM), Melanoma MALME-3M (GI50: 1.59 μM), Ovarian Cancer: OVCAR-3 (GI50: 1.16 μM), Renal Cancer: UO-31 (GI50: 0.76 μM), Prostate Cancer: PC-3 (GI50: 0.82 μM) and Breast Cancer: BT-549 (GI50: 1.13 μM). DNA cleavage studies revealed that even at 50 μg/mL concentration complete DNA digestion was observed for all the compounds, except for compound (7o) where partial DNA digestion was observed even at 100 μg/mL.
- Gali, Rajitha,Banothu, Janardhan,Gondru, Ramesh,Bavantula, Rajitha,Velivela, Yashodhara,Crooks, Peter A.
-
p. 106 - 112
(2015/02/19)
-
- Some new indole-coumarin hybrids; Synthesis, anticancer and Bcl-2 docking studies
-
Hybrid molecules have attracted attention for their improved biological activity, selectivity and lesser side effects profile, distinct from their individual components. In the quest for novel anticancer drug entities, three series of indole-coumarin hybrids - 3-(1-benzyl-1H-indol-2-yl)-2H-chromen-2-ones, 2-(2-oxo-2H-chromen-3-yl)-1H-indole-3-carbaldehydes and 2-(2-oxo-2H-chromen-3-yl)-1H-indole-3-carboxylic acids were synthesized. All the synthesized compounds were characterized by spectral techniques like IR, 1H NMR, 13C NMR, mass spectrometry and elemental analysis. In silico docking studies of synthesized molecules with apoptosis related gene Bcl-2 that is recognized to play an important role in tumerogenesis were carried out. Dose-dependent cytotoxic effect of the compounds in human breast adenocarcinoma (MCF-7) and normal cell lines were assessed using MTT assay and compared with that of the standard marketed drug, Vincristine. Compound 4c had a highly lipophilic bromine substituent capable of forming halogen bond and was identified as a potent molecule both in docking as well as cytotoxicity studies. Flow cytometric cell cycle analysis of 4c exhibited apoptotic mode of cell death due to cell cycle arrest in G2/M phase. Structure activity relationship of these hybrid molecules was also studied to determine the effect of steric and electronic properties of the substituents on cell viability.
- Kamath, Pooja R.,Sunil, Dhanya,Ajees, A. Abdul,Pai,Das, Shubhankar
-
p. 101 - 109
(2015/10/28)
-
- The indium(iii) chloride catalyzed synthesis of sulfur incorporated 3-acylcoumarins; Their photochromic and acetate sensing properties
-
The synthesis and evaluation of the photochromic properties of 3-acylcoumarins are very important as they exhibit selective sensing properties. We found that InCl3 efficiently catalyzes the condensation of 2-hydroxybenzaldehydes and β-keto este
- Surya Prakash Rao,Desai, Avinash
-
p. 63642 - 63649
(2015/02/19)
-
- Synthesis of 3-Substituted coumarins: An efficient green approach using l-Proline as catalyst in triethanolamine medium
-
3-Substituted coumarins were synthesized very efficiently, using Knoevenagel method from salicylaldehydes 1 and active methylene compounds 2 under green conditions. The effect of catalyst and solvent on this condensation was studied. L-Proline was found t
- Srikrishna, Devulapally,Tasqeeruddin, .Syed,Dubey, Pramod Kumar
-
p. 556 - 563
(2014/07/21)
-
- Synthesis, biological evaluation and docking analysis of 3-methyl-1-phenylchromeno[4,3-c]pyrazol-4(1H)-ones as potential cyclooxygenase-2 (COX-2) inhibitors
-
As a part of our continued efforts to discover new COX inhibitors, a series of 3-methyl-1-phenylchromeno[4,3-c]pyrazol-4(1H)-ones were synthesized and evaluated for in vitro COX inhibitory potential. Within this series, seven compounds (3a-d, 3h, 3k and 3
- Grover, Jagdeep,Kumar, Vivek,Sobhia, M. Elizabeth,Jachak, Sanjay M.
-
supporting information
p. 4638 - 4642
(2015/01/09)
-
- Synthesis and antibacterial activity of some novel coumarinyl oxadiazole derivatives
-
A novel series of 3-[2-(5-pyridin-4-yl)-1,3,4-oxadiazol-2-yl thio] acetyl-2H-chromen- 2-ones IV(a-h) were synthesized by the reaction of 2-pyridyl-1,3,4-oxadiazol-2-thiol (III) and substituted 3-bromo acetyl coumarins II(a-h) in presence of sodium ethoxide. The purity of the synthesized compounds was confirmed by their physical constants and TLC. The structures of the synthesized compounds were further confirmed by IR, NMR and mass spectral data. All the synthesized compounds were screened for antibacterial activity using broth microdilution method and gentamycin as standard drug. Among the series IVb, IVc, IVg and IVh compounds showed good antibacterial activity.
- Kumar, M.R. Pradeep,Honnalli,Ashalatha
-
p. 189 - 192
(2019/01/21)
-
- Amino-grafted SBA-15 material as dual acid-base catalyst for the synthesis of coumarin derivatives
-
We report herein an experimental and theoretical study concerning the preparation of the coumarins (2) from 2-hydroxybenzaldehydes (3) and ethyl acetoacetate (4) promoted by amino-grafted SBA-15 materials. The reaction takes places by Knoevenagel condensation between reagents, in the absence of any solvent and under mild conditions, followed by a non catalytic lactonization step. Amino-grafted SBA-15 loaded with secondary amine groups, MAP/SBA-15, was found to be the most efficient and totally recyclable catalyst as compared with its analog containing tertiary amine groups, DEAP/SBA-15 (where MAP and DEA are methyl aminopropyl and diethyl aminopropyl groups, respectively). Our theoretical analysis confirms that the steric congestion and the absence of NH protons as the catalytic active sites are determining factors for the increasing of the activation barrier and, therefore, for the lower catalytic activity and reactivity to the formation of the coumarin. The computational study herein reported demonstrates that MAP/SBA-15, a traditional basic mesoporous silica having NH protons, shows a dual acid-base catalytic behavior when used in the synthesis of coumarins via Knoevenagel condensation. Otherwise, the substitution in 2-hydroxybenzaldehydes (3) at 5-position clearly influences the acceptor and acidity capacities of the CHO and the OH groups as experimentally and theoretically demonstrated.
- Aider, Nadia,Smuszkiewicz, Agata,Pérez-Mayoral, Elena,Soriano, Elena,Martín-Aranda, Rosa M.,Halliche, Djamila,Menad, Saliha
-
p. 215 - 222
(2014/03/21)
-
- An organocatalyst from renewable materials for the synthesis of coumarins and chromenes: Three-component reaction and multigram scale synthesis
-
A new concept of catalysts which are prepared from renewable materials is demonstrated. It is known that amino acids (e.g., proline and hydroxyproline) are robust organocatalysts for several reactions. Bovine tendons which are proteins rich in hydroxyproline and proline were used as a source of amino acids. An acid hydrolysate of tendons (a TH catalyst) could catalyze two reactions: (i) the synthesis of coumarins and chromenes under solvent-free conditions and (ii) the synthesis of densely functionalized 4H-chromenes via a three-component reaction. Moreover, an economical and easily accessible TH catalyst is applicable in a multigram scale synthesis of coumarins and chromenes, as well as in the three-component reaction for chromene synthesis. A catalytic activity of hydroxyproline for the synthesis of 4H-chromenes via the three-component reaction was also discovered. The present work demonstrates not only the green catalysts from renewable materials, but also an environmentally benign preparation of coumarins and chromenes. This journal is the Partner Organisations 2014.
- Sangsuwan, Rapeepat,Sangher, Sasithorn,Aree, Thammarat,Mahidol, Chulabhorn,Ruchirawat, Somsak,Kittakoop, Prasat
-
p. 13708 - 13718
(2014/04/03)
-
- Synthesis and pharmacological evaluation of some novel 2-(5-hydroxy-5- trifluoromethyl-4,5-dihydropyrazol-1-yl)-4-(coumarin-3-yl)thiazoles
-
A series of novel 2-(5-hydroxy-5-trifluoromethyl-4,5-dihydropyrazol-1-yl)- 4-(coumarin-3-yl)thiazoles (6) were synthesized by condensing 3-(2-bromoacetyl)coumarins (4) with various 5-hydroxy-5-trifluoromethyl-4,5- dihydropyrazol-1-thiocarboxamides (5), obtained by the reaction of thiosemicarbazide with trifluoromethyl-β-diketones. All the tested compounds displayed significant to moderate in vivo anti-inflammatory activity when compared to the standard drug indomethacin, and good broad spectrum in vitro antibacterial activity against three Gram-positive and four Gram-negative bacteria when compared with cefixime.
- Aggarwal, Ranjana,Kumar, Sunil,Kaushik, Pawan,Kaushik, Dhirender,Gupta, Girish Kumar
-
p. 508 - 514
(2013/05/09)
-
- An approach to the synthesis of 2-Acylchromeno[3,4- c ]pyrrol-4(2 H)-one derivatives via a sequential three-component reaction
-
An efficient synthesis of 2-acylchromeno[3,4-c]pyrrol-4(2H)-one derivatives by a three-component reaction of salicylaldehydes, β-keto esters, and p-toluenesulfonylmethyl isocyanide is reported. Georg Thieme Verlag Stuttgart, New York.
- Alizadeh, Abdolali,Ghanbaripour, Rashid,Zhu, Long-Guan
-
supporting information
p. 2124 - 2126
(2013/10/21)
-
- Biological evaluation of coumarin derivatives as mushroom tyrosinase inhibitors
-
A series of coumarin derivatives were synthesised and their inhibitory effects on the diphenolase activity of mushroom tyrosinase were evaluated. The results showed that some of the synthesised compounds exhibited significant inhibitory activities. Especially, 2-(1-(coumarin-3-yl)ethylidene) hydrazinecarbothioamide bearing thiose-micarbazide group exhibited the most potent tyrosinase inhibitory activity with IC50 value of 3.44 μM. The inhibition mechanism analysis of 2-(1-(coumarin-3-yl)-ethylidene) hydrazinecarbothioamide and 2-(1-(6-chlorocoumarin-3-yl)ethylidene)- hydrazinecarbothioamide demonstrated that the inhibitory effects of the compounds on the tyrosinase were irreversible. Preliminary structure activity relationships' (SARs) analysis suggested that further development of such compounds might be of interest.
- Liu, Jinbing,Wu, Fengyan,Chen, Lingjuan,Zhao, Liangzhong,Zhao, Zibing,Wang, Min,Lei, Sulan
-
p. 2872 - 2878
(2012/10/30)
-
- Identification of novel molecular scaffolds for the design of MMP-13 inhibitors: A first round of lead optimization
-
Osteoarthritis (OA) is the leading cause of joint pain and disability in middle-aged and elderly patients, and is characterized by progressive loss of articular cartilage. Among the various matrix metalloproteinases (MMPs), MMP-13 is specifically expresse
- La Pietra, Valeria,Marinelli, Luciana,Cosconati, Sandro,Di Leva, Francesco Saverio,Nuti, Elisa,Santamaria, Salvatore,Pugliesi, Isabella,Morelli, Matteo,Casalini, Francesca,Rossello, Armando,La Motta, Concettina,Taliani, Sabrina,Visse, Robert,Nagase, Hideaki,Da Settimo, Federico,Novellino, Ettore
-
experimental part
p. 143 - 152
(2012/03/09)
-
- Synthesis and antibacterial activity of some 4-(coumarin-3-yl)/Aryl 2 (3,5-dimethylpyrazol-1-yl)thiazoles
-
Reaction of 3-(2-bromoacetyl) coumarins (4) with 3,5-dimethylpyrazol-1- thiocarboxamide (5) results in the formation of title compounds 6. 4-Aryl-2-(3,5-dimethylpyrazol-1-yl) thiazoles (8) which could not be synthesized earlier through this method, were obtained by performing the reaction in presence of a base. All the synthesized compounds have shown moderate to significant antibacterial activity against Gram-positive bacteria namely S. aureus and B. subtilis.
- Aggarwal, Ranjana,Kumar, Sunil,Sharma, Chetan,Aneja, Kamal R.,Singh, Shiv P.
-
p. 331 - 336
(2013/09/24)
-
- Diastereoselective three-step route to o-(6-nitrocyclohex-3-en-1-yl)phenol and tetrahydro-6h-benzo[c]chromen-6-ol derivatives from salicylaldehydes
-
This work was aimed at preparing o-(6′-nitrocyclohex-3′-en- 1′-yl)phenol and tetrahydro-6H-benzo[c]chromen-6-ol derivatives in three steps starting from salicylaldehydes. Initially 3-acetylcoumarins were prepared in the absence of solvent using a solid base catalyst such as PS-TBD. In the second step, the Diels-Alder reactions of 3-nitrocoumarins and 3-acetylcoumarins under thermal conditions or in the presence of hafnium chloride yielded the corresponding tetrahydrobenzo[c]chromenones. The final part of the work was dedicated to the transformation of nitro-tetrahydrobenzo[c]chromenones into o-(6′-nitrocyclohex-3′-en-1′-yl)phenol derivatives in aqueous medium and to the conversion of acetyl tetrahydrobenzo[c]chromenones into the corresponding tetrahydro-6H-benzo[c]chromen-6-ol derivatives in tetrahydrofuran (THF), in the presence of tetrabutylammonium fluoride (TBAF) on silica. In every case the diastereoselectivity was complete and the reaction yields were high.
- Lanari, Daniela,Ballini, Roberto,Palmieri, Alessandro,Pizzo, Ferdinando,Vaccaro, Luigi
-
experimental part
p. 2874 - 2884
(2011/06/28)
-
- ZnO nanoparticle as catalyst for efficient green one-pot synthesis of coumarins through Knoevenagel condensation
-
Green chemistry protocols with the reusability of the nano particle as catalyst in the synthesis of coumarins is described. The zinc oxide (ZnO) nanoparticles functions as highly effective catalyst for the reactions of various o-hydroxy benzaldehydes with 1,3-dicarbonyl compounds under microwave and thermal conditions to afford the corresponding coumarins in moderate to good yields. The catalyst is inexpensive, stable, can be easily recycled and reused for several cycles with consistent activity. Indian Academy of Sciences.
- Kumar, B Vinay,Naik, Halehatty S. Bhojya,Girija,Kumar, B Vijaya
-
experimental part
p. 615 - 621
(2012/07/03)
-
- Biocatalytic domino reaction: Synthesis of 2H-1-benzopyran-2-one derivatives using alkaline protease from Bacillus licheniformis
-
A novel BLAP (alkaline protease from Bacillus licheniformis) catalyzed synthesis of 2H-1-benzopyran-2-one derivatives was achieved by domino Knoevenagel/intramolecular transesterification reaction. The control of enzymatic chemoselectivity between Knoevenagel/intramolecular transesterification and Knoevenagel/intramolecular hemiketalization could be realized by adjusting parameters including solvent, water content and temperature. The products were obtained in acceptable yields. This BLAP catalyzed selective domino reaction provided an alternative synthetic method for 2H-1-benzopyran-2-one derivatives.
- Wang, Chang-Heng,Guan, Zhi,He, Yan-Hong
-
experimental part
p. 2048 - 2054
(2011/10/03)
-
- Synthesis and selective human monoamine oxidase inhibition of 3-carbonyl, 3-acyl, and 3-carboxyhydrazido coumarin derivatives
-
Several 3-carbonyl (1-26), 3-acyl (27-52), and 3-carboxyhydrazido (53-58) coumarins have been synthesized in high yields (72-99%) and tested in vitro for their human monoamine oxidase A and B (hMAO-A and hMAO-B) inhibitory activity. Different substituents on the coumarin nucleus were evaluated for their effect on biological activity and isoform selectivity. Substitution at position C7 of the 3-ethyl ester coumarin ring, or the introduction of a hydrazido substituent at C3, were important to obtain highly potent and selective hMAO-B inhibitors with IC50 values in the nanomolar range. Some derivatives were also submitted to a stability test and showed no chemical cleavage in vitro.
- Secci, Daniela,Carradori, Simone,Bolasco, Adriana,Chimenti, Paola,Yá?ez, Matilde,Ortuso, Francesco,Alcaro, Stefano
-
experimental part
p. 4846 - 4852
(2011/11/13)
-
- Unexpected hydrobromic acid-catalyzed C-C bond-forming reactions and facile synthesis of coumarins and benzofurans based on ketene dithioacetals
-
Hydrobromic acid was found to be a unique catalyst in C-C bond-forming reactions with ketene dithioacetals. Distinctly different from other acids (including Lewis and Bronsted acids), the remarkable catalytic performance of hydrobromic acid in catalytic a
- Yuan, Hongjuan,Wang, Mang,Liu, Yingjie,Wang, Lili,Liu, Jun,Liu, Qun
-
experimental part
p. 13450 - 13457
(2011/02/27)
-
- Thermal [4 + 2] cycloadditions of 3-acetyl-, 3-carbamoyl-, and 3-ethoxycarbonyl-coumarins with 2,3-dimethyl-1,3-butadiene under solventless conditions: A structural study
-
The thermal [4+2] cycloadditions of 3-acetyl-, 3-carbamoyl, and 3-ethoxycarbonylcoumarins with 2,3-dimethyl-1,3-butadiene under solvent free conditions are reported, as well as the epoxidation reactions of some adducts. Discussion is focused on the struct
- Flores-Larios, Irma Y.,Lopez-Garrido, Lizbeth,Martinez-Martinez, Francisco J.,Gonzalez, Jorge,Garcia-Baez, Efren V.,Cruz, Alejandro,Padilla-Martinez, Itzia I.
-
experimental part
p. 1513 - 1530
(2010/09/08)
-
- Titanium tetraisopropoxide promoted rreactions for the synthesis of substituted coumarins
-
Substituted coumarins are synthesized by the reaction of salicylaldehyde derivatives with malonitrile, isopropyl cyanoacetate or diisopropyl malonate promoted by Ti(O-i-Pr)4. When i-PrOH is used as a solvent, these reactions proceeded by the catalytic amount of Ti(O-i-Pr)4 (~0.1 equivalent).
- Tanaka, Takanori,Yamashita, Kohei,Hayashi, Masahiko
-
scheme or table
p. 631 - 636
(2010/04/27)
-
- Copper(II)-catalyzed C-C bond-forming reactions of α-electron- withdrawing group-substituted ketene S,S-acetals with carbonyl compounds and a facile synthesis of coumarins
-
A new catalytic C-C bond-forming reaction has been developed. Catalyzed by cheap and commercially available copper(II) bromide (CuBr2; 10 mol%), the reactions of α-electron-withdrawing group (EWG)-substituted ketene S,S-acetals with aldehydes or ketones in acetonitrile at room temperature gave a variety of densely functionalized coupling products in excellent yields (80-98%). Based on this catalytic process, coumarin derivatives were efficiently synthesized when salicylaldehydes were selected as the carbonyl components.
- Yuan, Hong-Juan,Wang, Mang,Liu, Ying-Jie,Liu, Qun
-
supporting information; experimental part
p. 112 - 116
(2009/08/07)
-
- Coumarin synthesis via Knoevenagel condesation in moisture stable room temperature ionic liquids
-
Several coumarins have been synthesised by Knoevenagel condesation in the piperidine/HOAc/moisture stable room temperature ionic liquid ([Emim] +BF4- referring to structure) system at room temperature; the yield of the reaction is good and the reaction medium can be recycled.
- Bao, Weiliang,Wang, Zhiming,Li, Yuxia
-
p. 294 - 295
(2007/10/03)
-
- Samarium (III) triiodide catalysed reaction of salicylaldehydes with active methylene compounds
-
The unambiguous synthesis and isolation of 2-oxo-2H-1-benzopyran derivatives are described. The Knoevenagel condensation of 2-hydroxy benzaldehydes with active methylene compounds catalysed by samarium triiodide resulted in coumarium derivatives in fair yields under refluxing conditions.
- Chen,Zhang
-
p. 394 - 395
(2007/10/03)
-
- 2-Hydroxy-2-methyl-2H-1-benzopyran-3-carboxamide Derivatives
-
The reaction of 2-hydroxybenzaldehydes with 3-oxobutanamide affords 2,4-dihydroxy-2-methyl-2H-3,4-dihydro-1-benzopyran-3-carboxamides and 2-hydroxy-2-methyl-2H-1-benzopyran-3-carboxamides, depending on the particular aldehyde and the experimental conditions used.
- O'Callaghan, Conor N.,McMurry, T. Brian H.
-
p. 643 - 649
(2007/10/03)
-
- A Novel Pentacyclic Pyridine Dilactone. 7-Methylbenzopyranobenzoxacinopyridine-6,16-dione
-
When equimolar quantities of salicylaldehyde 2 and ethyl 3-amino-2-butenoate 3 or its constituents (ethyl 3-oxobutanoate and ammonia) were refluxed on a steam-bath for 6 hours with a trace of acetic acid, two products, a pentacyclic pyridine dilactone 4 and 3-acetyl coumarin 5, resulted in 15percent and 45percent yields, respectively.The structure of 4 was elucidated as 7-methylbenzopyranobenzoxacinopyridine-6,16-dione on the basis of its spectral data.The mechanism of its formation has been discussed.The reaction has been extended to three more substituted salicylaldehydes.
- Rajyalakshmi, K.,Srinivasan, V. R.
-
p. 1737 - 1739
(2007/10/02)
-