3158-85-8Relevant academic research and scientific papers
Oxidative Synthesis of Quinazolinones under Metal-free Conditions
Feng, Jian-Bo,Wu, Xiao-Feng
, p. 794 - 798 (2017)
A metal-free procedure for the synthesis of quinazolinones under oxidative conditions has been developed. In the presence of DABCO and TBHP, the desired products can be obtained in moderate yields with 2-fluorobenzaldehydes and 2-aminopyridines as the substrates.
An Alternative Approach to the Hydrated Imidazoline Ring Expansion (HIRE) of Diarene-Fused [1.4]Oxazepines
Grintsevich, Sergey,Sapegin, Alexander,Reutskaya, Elena,Peintner, Stefan,Erdélyi, Máté,Krasavin, Mikhail
, p. 5664 - 5676 (2020/07/21)
A four-step approach to the “hydrated imidazoline ring expansion” (HIRE) is presented. In most cases, the ring expansion was the sole process. However, for the first time, an alternative course of the hydrated imidazoline evolution was discovered which gave N-aminoethyl derivatives. These can, in principle, be converted into the target HIRE products under sufficiently forcing conditions. The approach offers improved flexibility with respect to the peripheral substituents and is also applicable to the synthesis of eleven-membered lactams. We observed that the latter can exist in two stable isomeric forms due to lactam–amide bond isomerization. The latter finding further demonstrates the value of medium-sized rings as multiple-conformer probes for biological target interrogation.
One-pot synthesis of substituted dibenzoxazepinones and pyridobenzoxazepinones using octacarbonyldicobalt as an effective CO source
Anchan, Kavitha,Baburajan, Poongavanam,Puttappa, Nagaswarupa H.,Kumar Sarkar, Sujit
supporting information, p. 348 - 360 (2019/12/03)
A facile one-pot protocol for the synthesis of substituted dibenzoxazepinones and pyridobenzoxazepinones from commercially available aryl/heteroaryl halides and amino phenols using octacarbonyldicobalt (Co2(CO)8) as an effective metal carbonyl source has been demonstrated. This method proceeds via the sequential coupling of aryl/heteroaryl halides with aminophenol by amidation and intramolecular cyclization to give dibenzoxazepinones/pyridobenzoxazepinones.
Palladium-Catalyzed Carbonylative Synthesis of N-Heterocycles from 1-Chloro-2-fluorobenzenes
Yuan, Yang,Wu, Xiao-Feng
supporting information, p. 2172 - 2175 (2019/03/17)
A simple and efficient synthesis of pyrido-fused quinazolinones and dibenzoxazepinones by palladium-catalyzed annulation of commercially available substituted 1-chloro-2-fluorobenzenes and 2-aminopyridines or 2-aminophenols has been developed. The reaction involves carbonylation/aromatic nucleophilic substitution sequential in a one-pot manner.
Design of Conjugated Molecules Presenting Short-Wavelength Luminescence by Utilizing Heavier Atoms of the Same Element Group
Yamaguchi, Madoka,Tanaka, Kazuo,Chujo, Yoshiki
, p. 1342 - 1347 (2018/04/30)
The introduction of heavy atoms into conjugated molecules often induces a redshift in the emission spectra. Conversely, we report here a blueshifting effect in the absorption and emission bands of a conjugated organic dye by employing a heavier atom from the same element group. Boron complexes having oxygen- and sulfur-bridged structures in the ligand moiety were synthesized, and their optical properties were compared. Significant optical bands in the absorption and luminescence spectra of the sulfur-bridged complex were observed in a shorter wavelength region than those of the oxygen-bridged complex. Theoretical calculations suggest that replacement of the bridging atom by a heavier one should reduce molecular planarity because of the larger atom size. As a result, the degree of electronic conjugation decreases, and this is followed by a blueshift in the optical bands. Finally, a blue-emissive crystal is demonstrated.
Dibenzo[b,f][1,4]oxazepines and dibenzo[b,e]oxepines: Influence of the chlorine substitution pattern on the pharmacology at the H1R, H4R, 5-HT2AR and other selected GPCRs
Naporra, Franziska,Gobleder, Susanne,Wittmann, Hans-Joachim,Spindler, Julia,Bodensteiner, Michael,Bernhardt, Günther,Hübner, Harald,Gmeiner, Peter,Elz, Sigurd,Strasser, Andrea
, p. 610 - 625 (2016/10/12)
Inspired by VUF6884 (7-Chloro-11-(4-methylpiperazin-1-yl)dibenzo[b,f][1,4]oxazepine), reported as a dual H1/H4 receptor ligand (pKi: 8.11 (human H1R (hH1R)), 7.55 (human H4R (hH4R))), four known and 28 new oxazepine and related oxepine derivatives were synthesised and pharmacologically characterized at histamine receptors and selected aminergic GPCRs. In contrast to the oxazepine series, within the oxepine series, the new compounds showed high affinity to the hH1R (pKi: 6.8–8.7), but no or moderate affinity to the hH4R (pKi: ≤ 5.3). For one oxepine derivative (1-(2-Chloro-6,11-dihydrodibenzo[b,e]oxepin-11-yl)-4-methylpiperazine), the enantiomers were separated and the R-enantiomer was identified as the eutomer at the hH1R (pKi: 8.83 (R), 7.63 (S)) and the guinea-pig H1R (gpH1R) (pKi: 8.82 (R), 7.41 (S)). Molecular dynamic studies suggest that the tricyclic core of the compounds is bound in a similar mode into the binding pocket, as described for doxepine in the hH1R crystal structure. Moreover, docking studies of all oxepine derivatives at the hH1R indicate that the oxygen and the position of the chlorine in the tricyclic core determines, if the R- or the S-enantiomer is the eutomer. For some of the oxazepines and oxepines the affinity to other aminergic GPCRs is in the same range as to hH1R or hH4R, thus, those compounds have to be classified as dirty drugs. However, one oxazepine derivative (3,7-Dichloro-11-(4-methylpiperazin-1-yl)dibenzo[b,f][1,4]oxazepine was identified as dual hH1/h5-HT2A receptor ligand (pKi: 9.23 (hH1R), 8.74 (h5-HT2AR), ≤7 at other analysed GPCRs), whereas one oxepine derivative (1-(3,8-Dichloro-6,11-dihydrodibenzo[b,e]oxepin-11-yl)-4-methylpiperazine) was identified as selective hH1R antagonist (pKi: 8.44 (hH1R), ≤6.7 at other analyzed GPCRs). Thus, the pharmacological results suggest that the oxazepine/oxepine moiety and additionally the chlorine substitution pattern toggles receptor selectivity and specificity.
MeOTf- and TBD-Mediated Carbonylation of ortho-Arylanilines with CO2 Leading to Phenanthridinones
Wang, Sheng,Shao, Peng,Du, Gaixia,Xi, Chanjuan
, p. 6672 - 6676 (2016/08/16)
Carbonylation of o-arylanilines utilizing CO2 as a carbonyl source for the synthesis of important phenanthridinones with a free (NH)-lactam motif has been described under metal-free condition. A range of o-arylanilines were transformed to the corresponding phenanthridinones in high yields.
Synthesis method of diaryloxazepine ketone compound
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Paragraph 0014, (2018/02/04)
The invention relates to a synthesis method of a diaryloxazepine ketone compound. The synthesis method specifically includes the steps that ortho-hydroxy aryl methyl alcohol, ortho-haloaromaticamine, a ruthenium catalyst, copper salt, a phosphine ligand and alkali are taken and added into an organic solvent, heating is conducted, extraction, drying by distillation and recrystallization are conducted after the reaction is over, and the diaryloxazepine ketone product is obtained. The diaryl and ox-azepine ketone compound is synthesized through one step, the method is easy to operate, economical and efficient, the range of a reaction substrate is wide, the yield is high, and application prospects are wide.
Tricyclic dihydrobenzoxazepine and tetracyclic indole derivatives can specifically target bacterial DNA ligases and can distinguish them from human DNA ligase I
Yadav, Nisha,Khanam, Taran,Shukla, Ankita,Rai, Niyati,Hajela, Kanchan,Ramachandran, Ravishankar
, p. 5475 - 5487 (2015/05/20)
DNA ligases are critical components for DNA metabolism in all organisms. NAD+-dependent DNA ligases (LigA) found exclusively in bacteria and certain entomopoxviruses are drawing increasing attention as therapeutic targets as they differ in their cofactor requirement from ATP-dependent eukaryotic homologs. Due to the similarities in the cofactor binding sites of the two classes of DNA ligases, it is necessary to find determinants that can distinguish between them for the exploitation of LigA as an anti-bacterial target. In the present endeavour, we have synthesized and evaluated a series of tricyclic dihydrobenzoxazepine and tetracyclic indole derivatives for their ability to distinguish between bacterial and human DNA ligases. The in vivo inhibition assays that employed LigA deficient E. coli GR501 and S. typhimurium LT2 bacterial strains, rescued by ATP-dependent T4 DNA ligase or Mycobacterium tuberculosis NAD+-dependent DNA ligase (Mtb LigA), respectively, showed that the compounds can specifically inhibit bacterial LigA. The in vitro enzyme inhibition assays using purified MtbLigA, human DNA ligase I & T4 DNA ligase showed specific inhibition of MtbLigA at low micromolar range. Our results demonstrate that tricyclic dihydrobenzoxazepine and tetracyclic indole derivatives can distinguish between bacterial and human DNA ligases by ～5-folds. In silico docking and enzyme inhibition assays identified that the compounds bind to the cofactor binding site and compete with the cofactor. Ethidium bromide displacement and gel-shift assays showed that the inhibitors do not exhibit any unwanted general interactions with the substrate DNA. These results set the stage for the detailed exploration of this compound class for development as antibacterials.
[bipy.H] hosted by Al-MCM-41: An efficient dibenzo[b,f][1,4]oxazepine (CR) decontamination nano-reactor
Khorshidi, Alireza,Heidari, Sirous
, p. 32804 - 32812 (2015/04/27)
Encapsulation of [Fe(bipy)Cl4][bipy.H] (1) (where bipy is 2,2′-bipyridine) in the Al-MCM-41 molecular sieve by using a "ship in a bottle synthesis" approach was achieved and the product characterized by X-ray diffraction, FTIR, DRS, TG, EDS and BET analysis. Encapsulation of the complex into the channels of Al-MCM-41, did not affect the morphology of the host as is evident from SEM and TEM micrographs. The obtained nanocatalyst in combination with K2S2O8 as the oxidant, was successfully used in selective catalytic conversion of dibenzo[b,f][1,4]oxazepine (CR, riot control agent) to dibenzo[b,f][1,4]oxazepin-11(10H)-one as a potential decontamination route. Good selectivity was also obtained toward formation of benzil in the oxidation of trans-stilbene. This journal is
