50402-83-0Relevant academic research and scientific papers
Regiospecific inverse electron demand Diels-Alder reactions of 7-methylcoumarin-4-azadienes
Sanap, Kailas K.,Samant, Shriniwas D.
, p. 36696 - 36706 (2015)
Condensation of 7-methylcoumarin-4-carbaldehyde with different anilines affords 7-methylcoumarin-4-azadienes. The 7-methylcoumarin-4-azadienes do not undergo normal electron demand Diels-Alder reaction with N-phenylmaleimide, but react with dihydropyran, dihydrofuran, and styrene via inverse electron demand Diels-Alder reaction in the presence of anhydrous ZnCl2. The diene involves the azomethine group and the aniline ring. The product is a mixture of two diastereomers in which the major diastereomer has all the hydrogens at the ring junction in cis configuration. This journal is
Synthesis and PASS-assisted evaluation of coumarin–benzimidazole derivatives as potential anti-inflammatory and anthelmintic agents
Sethi, Purva,Bansal, Yogita,Bansal, Gulshan
, p. 61 - 71 (2018/04/17)
Two series of novel derivatives have been designed by coupling medicinally important coumarin and benzimidazole nuclei through different linkers. These compounds have been predicted to be potent anti-inflammatory and anthelmintic by in silico studies using PASS (prediction of activity spectra for substances) software. The compounds are synthesized and evaluated for the predicted activities as well as for their in vitro antioxidant potential. Compounds of first series (4a–4f) are found good to moderate anti-inflammatory agents. Among these, compounds 4b and 4f exhibited maximum anti-inflammatory activity (45% inhibition), which is equivalent to the activity of indomethacin (48% inhibition) after 3 h (peak inflammatory response time). Compounds of second series (5a–5f) exhibit anthelmintic activity. Amongst these, compound 5f has mortality activity marginally higher than albendazole (10–11 s). Compound 5e is found to be the most potent antioxidant with remarkable EC50 value (0.08 μM/mL), which is though a little less than that of ascorbic acid (0.03 μM/mL). In addition, a comparative analysis of calculated Lipinski’s parameters reveals that all test compounds have the propensity to be orally bioavailable. Based on these findings, compounds 4b, 4f, 5e, and 5f are identified as new leads to develop potent anti-inflammatory, anthelmintic, and antioxidant compounds.
Synthesis and photophysical study of novel coumarin based styryl dyes
Sanap, Anita K.,Sanap, Kailas K.,Shankarling, Ganapati S.
, p. 190 - 199 (2015/05/13)
New organic dyes comprising phenothiazine, carbazole, indole, diphenylamine moieties, as the electron donors, and coumarin ring as the electron acceptor through ethylenic π bridge were synthesized and characterized. The reaction of different coumarin-4-acetic acids with phenothiazine-3-carbaldehyde in the presence of piperidine in methanol gives highly fluorescent styryl derivatives having cis configuration of ethylenic double bond. Under similar conditions 7-methylcoumarin-4-acetic acid was condensed with indole-3-carbaldehyde, carbazole-3-carbaldehyde, and diphenyl amine aldehyde to give different styryl derivatives with trans configuration of ethylenic double bond. Synthesized compounds were also studied for photophysical properties and show solvatochromism.
Synthetic and Structural Studies on Novel 4,3′-Bicoumarins
Pujar, Kiran K.,Kulkarni, Manohar V.,Alawandi, Ganesh N.,Anilkumar,Basanagouda, Mahantesha
, p. 2043 - 2052 (2015/08/18)
A series of directly linked 4-3′ bicoumarins have been synthesized by both Knoevenagel and Perkin reactions. This single-step transformation was accomplished by the reaction of coumarin-4-acetates with substituted salicylaldehydes in presence of piperidin
Facile intramolecular Diels-Alder reaction of 4-(o-propargyloxy) styrylcoumarins leading to highly fluorescent coumarin-containing polycyclic compounds
Khatri, Adil I.,Samant, Shriniwas D.
, p. 2362 - 2365 (2014/05/06)
The 4-(o-propargyloxy)styrylcoumarins are prepared by the condensation of O-propargylated salicylaldehyde with substituted coumarin-4-acetic acids. The intramolecular Diels-Alder reaction of 4-(o-propargyloxy)styrylcoumarins, without any catalyst gives fu
Regiospecific normal Diels-Alder reaction of trans -1,2- biscoumarinylethenes
Sanap, Kailas K.,Samant, Shriniwas D.
, p. 2189 - 2194 (2012/10/30)
The reaction of different 7,8-substituted coumarin 4-acetic acids with 7-diethylaminocoumarin-3-carbaldehyde in the presence of piperidine in methanol gives 1,2-biscoumarinylethenes. These compounds undergo regiospecific Diels-Alder reactions at their electron-rich diene components CCCC with electron-deficient dienophiles. The feasibility of normal electron-demand Diels-Alder reactions could be explained on the basis of the HOMO-LUMO gap. All the compounds are new and are intensely colored. Georg Thieme Verlag Stuttgart ? New York.
Synthesis and in vitro anti-HIV activity of N-1,3-benzo[d]thiazol-2-yl-2- (2-oxo-2H-chromen-4-yl)acetamide derivatives using MTT method
Bhavsar, Dhairya,Trivedi, Jalpa,Parekh, Shrey,Savant, Mahesh,Thakrar, Shailesh,Bavishi, Abhay,Radadiya, Ashish,Vala, Hardevsinh,Lunagariya, Jignesh,Parmar, Manisha,Paresh, Ladwa,Loddo, Roberta,Shah, Anamik
scheme or table, p. 3443 - 3446 (2011/06/24)
A series of novel N-1,3-benzo[d]thiazol-2-yl-2-(2-oxo-2H-chromen-4-yl) acetamide derivatives has been synthesized. All the newly synthesized compounds were evaluated for their anti-HIV activity using MTT method. Most of these compounds showed moderate to potent activity against wild-type HIV-1 with an EC50 ranging from >7 EC50 [μg/ml] to 50 [μg/ml]. Among them, N-1,3-benzo[d]thiazol-2-yl-2-(2-oxo-2H- chromen-4-yl)acetamide 6v was identified as the most promising compound (EC 50 = 7 μg/ml). Among all the compounds, three compounds 6m, 6v and 6u have been exhibits potent anti-HIV activity against MT-4 cells.
Bernthsen synthesis, antimicrobial activities and cytotoxicity of acridine derivatives
Patel, Mehul M.,Mali, Mimansha D.,Patel, Saurabh K.
scheme or table, p. 6324 - 6326 (2010/12/18)
The condensation reaction of diphenylamine with 2-oxo-2H-(substituted chromen)-4-yl acetic acid in presence of anhydrous zinc chloride afford 4-(acridine-9-ylmethyl)-2H-(substituted chromen)-2-one. The synthesized compounds were characterized by spectral studies and elemental analysis and screened for their in vitro antibacterial activity against Staphylococcus aureus, Staphylococcus pyogenes (gram +ve), Escherichia coli, Pseudomonas aeruginosa (gram -ve) and antifungal activity against Aspergillus niger and anticancer activity (HL-60, Hep-2 & HEK293T) by MTT assay. Chloro substituted compounds showed antimicrobial and anticancer activity with IC 50 values in the low micromolar range.
Synthesis of some novel 4-substituted coumarins having potential biological activity (Part II)
Mashelkar,Audi
, p. 967 - 971 (2007/10/03)
Coumarin 4-methyl acetates are oxidized to coumarin-4-methyl glyoxalate using SeO2. Unlike the oxidative decarboxylation observed in the case of coumarin-4-acetic acid, here the oxidation is very selective for the active methylene group, without affecting the COOH group protected with ester function. The product thus obtained is analogous to the phenyl glyoxalic acid methyl ester i.e., coumarin-4-methyl glyoxalate and can be a useful moiety for the various synthetic manipulations of heterocycles substituted at 4-position of the coumarin.
