The Experts below are selected from a list of 171 Experts worldwide ranked by ideXlab platform
Klaus Harms - One of the best experts on this subject based on the ideXlab platform.
-
a modular approach for the synthesis of Dibenzoazepine derivatives
Synthesis, 2006Co-Authors: Gerhard Hilt, Fabrizio Galbiati, Klaus HarmsAbstract:A straightforward reaction sequence consisting of a Sonogashira coupling of protected propargylic amines, a cobalt-catalysed neutral Diels-Alder reaction, DDQ oxidation of the dihydroaromatic intermediate, a sodium borohydride reduction and an acid induced Friedel-Crafts-type cyclisation approach incorporating four simple starting materials leads to polyfunctionalised polycyclic products. Based on the electronic, steric and structural preconditions either seven-membered Dibenzoazepine derivatives or alternatively six- or eight-membered isoindoline derivatives are formed.
Yun Liang - One of the best experts on this subject based on the ideXlab platform.
-
palladium catalyzed double n arylation to synthesize multisubstituted Dibenzoazepine derivatives
ChemInform, 2013Co-Authors: Xiaoyun Zhang, Yuan Yang, Yun LiangAbstract:Various bis(2-bromophenyl)ethenes are treated with primary aromatic and aliphatic amines to produce medicinally interesting functionalized systems.
-
palladium catalyzed double n arylation to synthesize multisubstituted Dibenzoazepine derivatives
Tetrahedron Letters, 2012Co-Authors: Xiaoyun Zhang, Yuan Yang, Yun LiangAbstract:Palladium-catalyzed double N-arylation of primary amines with (Z)-1,2-bis(2-bromophenyl)ethenes was investigated. A variety of Dibenzoazepine derivatives were synthesized in good to excellent yields.
Joanna Wiśniewska - One of the best experts on this subject based on the ideXlab platform.
-
Mechanism of the oxidative degradation of Dibenzoazepine derivatives via manganese(III) complexes in acidic phosphate media
Reaction Kinetics Mechanisms and Catalysis, 2013Co-Authors: Joanna Wiśniewska, Paweł RześnickiAbstract:The oxidative degradation of tricyclic antidepressants (TCA) was studied in the presence of a large excess of the oxidizing agents, manganese(III)-pyrophosphate (P_2O_7 ^4−), phosphate (PO_4 ^3–), in acidic media. The products were detected and identified using UV–Vis, ESI–MS and IR methods. The reaction between dibenz[b,f]azepines and manganese(III) ions proceeded via two consecutive reactions: first, acridine analogues were formed, and then a dealkylation process resulted in the formation of unsubstituted acridine. The kinetics of the first degradation step of the TCAs was investigated independently of the slower dealkylation step. The pseudo-first order rate constants ( k _obs) were determined for the first degradation process. The reaction between 10,11-dihydro-5H-dibenz[b,f]azepines and the manganese(III) ion resulted in oxidative dehydrogenation, which proceeded via the formation of two intermediates: a free organic radical and a dimeric dication. Further oxidation of the second intermediate led to a positively charged radical dimer as a single final product. Simultaneously, two other substituent cleavage degradation processes occurred, which led to two dimeric derivatives. The kinetic traces were determined to be zeroth order.
-
The oxidative degradation and C–C coupling reaction of Dibenzoazepine derivatives by peroxydisulfate ion and sulfate radical in aqueous media
Reaction Kinetics Mechanisms and Catalysis, 2012Co-Authors: Joanna Wiśniewska, Grzegorz Wrzeszcz, Stanisław Koter, Tomasz LigorAbstract:The kinetics of the oxidation of imipramine and opipramol using peroxydisulfate salts in the presence of a large excess of Dibenzoazepine derivative (TCA) in acidic sulfate media was studied using UV–vis spectroscopy. The reaction between imipramine and S_2O_8 ^2− proceeds via the formation of two intermediates: a free organic radical and a dimeric dication. Further reaction of the intermediate dimeric dication leads to a positively charged radical dimer as one final product. Simultaneously, two other substituent cleavage degradation processes occur, leading to two dimeric derivatives. The first product, the positively charged radical dimer, and the next main product, a radical dimer without one alkyl substituent, were identified by EPR measurements. The measured kinetic trace is not first order and revealed a sigmoid shape with a characteristic induction time. The rate constants were determined by numerical analysis based on ordinary differential equations (ODEs). The reaction between opipramol and S_2O_8 ^2− proceeds by a two consecutive reaction scheme. The kinetics of the first degradation step were studied independently of the slower degradation reactions. Linear dependences, with zero intercept, of the pseudo-first-order rate constants ( k _obs) on [TCA] were determined for the first degradation process of opipramol.
-
the oxidative degradation of Dibenzoazepine derivatives by cerium iv complexes in acidic sulfate media
Dalton Transactions, 2012Co-Authors: Joanna Wiśniewska, Grzegorz Wrzeszcz, Marzanna Kurzawa, Rudi Van EldikAbstract:The kinetics of the oxidation of imipramine and desipramine using cerium(IV) complexes were studied in the presence of a large excess of azepine derivative (TCA) in acidic sulfate media using UV-Vis spectroscopy. The reaction proceeds viaDibenzoazepine radical formation, identified by EPR measurements. The kinetics of the first degradation step were studied independently of the further slower degradation reactions. Linear dependences, with zero intercept, of the pseudo-first-order rate constants (kobs) on [TCA] were established for both Dibenzoazepine radical formation processes. Rates of reactions decreased with increasing concentration of the H+ ion indicating that cerium(IV) as well as both reductants exist in an equilibrium with their protolytic forms. The activation parameters for the degradation of Dibenzoazepine derivatives in the first oxidation stage were as follows: ΔH≠ = 39 ± 2 kJ mol−1, ΔS≠ = −28 ± 8 J K−1 mol−1 for imipramine and ΔH≠ = 39 ± 2 kJ mol−1, ΔS≠ = −28 ± 6 J K−1 mol−1 for desipramine, respectively. Imipramine and desipramine radicals dimerized leading to an intermediate radical dimer, which decayed in a first-order consecutive decay process. These two further reactions proceed with rates which are characterized by non-linear dependences of the pseudo-first-order rate constants (kobs) on [TCA]. The degradation reaction of the intermediate radical dimer leads to an uncharged dimer as a final product. Mechanistic consequences of all the results are discussed.
Gerhard Hilt - One of the best experts on this subject based on the ideXlab platform.
-
a modular approach for the synthesis of Dibenzoazepine derivatives
Synthesis, 2006Co-Authors: Gerhard Hilt, Fabrizio Galbiati, Klaus HarmsAbstract:A straightforward reaction sequence consisting of a Sonogashira coupling of protected propargylic amines, a cobalt-catalysed neutral Diels-Alder reaction, DDQ oxidation of the dihydroaromatic intermediate, a sodium borohydride reduction and an acid induced Friedel-Crafts-type cyclisation approach incorporating four simple starting materials leads to polyfunctionalised polycyclic products. Based on the electronic, steric and structural preconditions either seven-membered Dibenzoazepine derivatives or alternatively six- or eight-membered isoindoline derivatives are formed.
M. P. Sadashiva - One of the best experts on this subject based on the ideXlab platform.
-
Anti-cancer activity of novel dibenzob,fazepine tethered isoxazoline derivatives
2020Co-Authors: M. P. Sadashiva, Basappa, Shivananju Nanjundaswamy, Feng Li, Kanjoormana Aryan Manu, Murugan Sengottuvelan, D. S. Prasanna, Nirvanappa C. Anilkumar, Gautam Sethi, Kazuyuki SugaharaAbstract:Background: Dibenzoazepine (DB) derivatives are important and valuable compounds in medicinal chemistry. The synthesis and chemotherapeutic properties of naturally occurring DBs and different heterocyclic moiety tethered DBs are reported. Herein, we report the DB-fused hybrid structure that containing isoxazolines (DBIs) and their anti-cancer activity, which could throw light on the structural and functional features of new molecules. Results and Conclusion. The synthesis and characterization of novel ring DB tethered isoxazoline derivatives (DBIs) were carried out. After the detailed structural characterization using 2D-NMR experiments, the compounds were identified as 5-substituted isoxazolines. The effect of newly synthesized DBIs against the invasion of murine osteosarcoma (LM8G7) cells was studied. Among the tested molecules, compound 4g (5--3-(4-chlorophenyl)-4,5-dihydroisoxazol-5-yl-methyl- 5 H-dibenzob,fazepine), was found to inhibit the invasion of LM8G7 cells strongly, when compared to other structurally related compounds. Cumulatively, the compound 4g inhibited the invasion MDA-MB-231 cells completely at 10 I¼M. In addition to anti-invasion property the compound 4g also inhibited the migration of LM8G7 and human ovarian cancer cells (OVSAHO) dose-dependently. Compound 4g inhibited the proliferation of LM8G7, OVSAHO, human breast cancer cells (MCF-7) and human melphalan-resistant multiple myeloma (RPMI8226-LR5) cells that are comparable to cisplatin and suramin. © 2012 Sadashiva et al.; licensee BioMed Central Ltd.
-
5-{[1-(2,4-Dichlorophenyl)-1H-1,2,3-triazol-4-yl]methyl}-5H-dibenz[b,f]azepine
IUCrData, 2016Co-Authors: K.s. Vinay Kumar, Chandra, B.m. Rajesh, Madegowda Mahendra, M. P. SadashivaAbstract:In the molecule of the title compound, C23H16Cl2N4, the dihedral angle between the benzene rings fused to the azepine ring is 52.00 (6)°. The plane of the triazole ring makes dihedral angles of 74.40 (5), 25.56 (8) and 44.78 (6)° with the planes of the benzene rings of the Dibenzoazepine moiety and the dichlorophenyl ring, respectively. The azepine ring adopts a boat conformation. There are no classical hydrogen bonds in the crystal.
-
Anti-cancer activity of novel dibenzo[b,f]azepine tethered isoxazoline derivatives
BMC Chemical Biology, 2012Co-Authors: M. P. Sadashiva, Basappa, Shivananju Nanjundaswamy, Feng Li, Kanjoormana Aryan Manu, Murugan Sengottuvelan, D. S. Prasanna, Nirvanappa C. Anilkumar, Gautam Sethi, Kazuyuki SugaharaAbstract:Background Dibenzoazepine (DB) derivatives are important and valuable compounds in medicinal chemistry. The synthesis and chemotherapeutic properties of naturally occurring DBs and different heterocyclic moiety tethered DBs are reported. Herein, we report the DB-fused hybrid structure that containing isoxazolines (DBIs) and their anti-cancer activity, which could throw light on the structural and functional features of new molecules.
-
Anti-cancer activity of novel dibenzo[b,f]azepine tethered isoxazoline derivatives
BMC Chemical Biology, 2012Co-Authors: M. P. Sadashiva, Shivananju Nanjundaswamy, Feng Li, Kanjoormana Aryan Manu, Murugan Sengottuvelan, D. S. Prasanna, Nirvanappa C. Anilkumar, Gautam Sethi, Kazuyuki Sugahara, Kanchugarakoppal Subbegowda RangappaAbstract:Background Dibenzoazepine (DB) derivatives are important and valuable compounds in medicinal chemistry. The synthesis and chemotherapeutic properties of naturally occurring DBs and different heterocyclic moiety tethered DBs are reported. Herein, we report the DB-fused hybrid structure that containing isoxazolines (DBIs) and their anti-cancer activity, which could throw light on the structural and functional features of new molecules. Results and Conclusion The synthesis and characterization of novel ring DB tethered isoxazoline derivatives (DBIs) were carried out. After the detailed structural characterization using 2D-NMR experiments, the compounds were identified as 5-substituted isoxazolines. The effect of newly synthesized DBIs against the invasion of murine osteosarcoma (LM8G7) cells was studied. Among the tested molecules, compound 4g (5-[−3-(4-chlorophenyl)-4,5-dihydroisoxazol-5-yl-methyl]-5 H- dibenzo[b,f]azepine), was found to inhibit the invasion of LM8G7 cells strongly, when compared to other structurally related compounds. Cumulatively, the compound 4g inhibited the invasion MDA-MB-231 cells completely at 10 μM. In addition to anti-invasion property the compound 4g also inhibited the migration of LM8G7 and human ovarian cancer cells (OVSAHO) dose-dependently. Compound 4g inhibited the proliferation of LM8G7, OVSAHO, human breast cancer cells (MCF-7) and human melphalan-resistant multiple myeloma (RPMI8226-LR5) cells that are comparable to cisplatin and suramin.