Oxazepine Derivatives Research Articles

Ferrocenyl conjugated oxazepines/quinolines: multiyne coupling and ring-expanding or rearrangement.

Ferrocenyl conjugated oxazepine/quinoline derivatives were presented through the reaction of hexadehydro-Diels-Alder (HDDA) generated arynes with ferrocenyl oxazolines under mild conditions via ring-expanding or rearrangement processes. Water molecule participated in this unexpected rearrangement process to produce quinoline skeletons, and DFT calculations supported a ring-expanding and intramolecular hydrogen migration process for the formation of oxazepine derivatives. Two variants of this chemistry, expanded the reactivity between ferrocenyl conjugated substances and arynes, further providing an innovative approach for the synthesis of ferrocene derivatives.

Synthesis, characterization and Antibacterial Evaluation of Novel 1,3-Oxazepine Derivatives Using A Cycloaddition Approach

This study demonstrated the synthesis and characterization of novel heterocyclic compounds, particularly oxazepine derivatives, using a cycloaddition procedure. The synthesis involved the reaction of chloroacetohydrazide with various aromatic aldehydes under acidic conditions in ethanol solvent to produce hydrazone compounds. These hydrazones subsequently underwent pericyclic synthesis with phthalic anhydride to yield oxazepine derivatives. The physicochemical properties of the synthesized compounds (F1 to F13) were characterized using FT-IR and H-NMR spectroscopy. The antibacterial activity of the synthesized oxazepine derivatives (F8, F9, F10, F11, F12, and F13) was evaluated against both Gram-positive (Staphylococcus aureus) and Gram-negative (Escherichia coli) bacterial strains using the cup plate agar diffusion technique. Notably, compounds F8, F9, and F10 exhibited potent antibacterial activity against both Gram-positive and Gram-negative bacteria, suggesting their potential as effective antibacterial agents. Molecular docking studies were also conducted to investigate the binding interactions of selected compounds with bacterial protein receptors, specifically Escherichia coli K-12 (PDB ID: 4QGS) and Staphylococcus aureus (PDB ID: 7PQ1). The results demonstrate the potential of these novel oxazepine derivatives as antibacterial agents, highlighting their promising biological activities and molecular interactions with bacterial proteins.

Discovery of Novel Oxazepine Derivatives as Akt/ROCK Inhibitors for Growth Arrest and Differentiation Induction in Neuroblastoma Treatment.

Patients with high-risk neuroblastoma face limited treatment choices, typically involving a combination of cytotoxic and differentiation maintenance therapies due to a scarcity of drugs. Evidence suggests that targeted inhibitors may provide opportunities for inducing neuroblastoma differentiation while inhibiting proliferation. Here, we demonstrate the synergistic effect of inhibiting Akt and ROCK in antineuroblastoma and present the design and discovery of a new Akt/ROCK inhibitor, B12. It displays strong antiproliferative effects and excellent differentiation inducing activity against Neuro2a cells. Treatment with B12 results in the arrest of G0/G1 cell cycles, a significant decrease in N-myc protein level, and an increase in differentiation markers. The administration of B12 effectively suppresses xenograft tumor growth and promotes differentiation. Overall, the discovery of B12 based on the Akt/ROCK dual inhibition strategy may provide hope for the development of more effective and targeted therapies for this challenging disease.

Design and synthesis of oxazepine derivatives from sulfonamide Schiff bases as antimicrobial and antioxidant agents with low cytotoxicity and hemolytic prospective

The eco-friendly sonication and microwave irradiation techniques were used for the straight forward synthesis of the Schiff base platform from sulfathiazole. Herein, Schiff bases were developed and converted to oxazepane derivatives. Compounds were tested for their antimicrobial, antioxidant, in vivo cytotoxicity activity. Moreover, density functional theory (DFT) and molecular docking studies were also carried out to explore the structural prpoperties and interaction of compounds with the receptor molecules. In vitro antimicrobial activity was determined against Gram-positive and Gram-negative strains via microdilution technique, which showed that the synthesized derivatives exhibit significant antimicrobial activity. Furthermore, in vivo cytotoxicity activity of the compounds were carried out via intravenous injection in rats. The results were compared with negative controls and it was observed that most of the synthesized compounds displayed excellent antimicrobial activity and low toxicity in comparison to references and negative controls, respectively. Hemolysis test was carried out for bioactive compounds, and results showed higher hemolysis values of the Schiff bases than the correponding oxazepines and lower hemolytic effects. The free radical inhibittion and antioxidant activity was carried out by using 2,2′-diphenyl-1-picrylhydrazyl radical (DPPH) and ferric reducing antioxidant power (FRAP) methods which suggested that the free radical scavenging activity increases with the presence of hydroxyl group. The Spectral measurements fourier-transform infrared spectroscopy (FT-IR), nuclear magnetic resonance (NMR), and high resolution electrospray ionization mass spectrometry (HRESIMS) confirmed the structure of the compounds.

Synthesis, Characterization and Study the Biological Activity ofnew Derivatives of 1,3- orazepine containing 1,2,4-Triazoloe ring

Compound [1] is prepared from Esterificition of 4-Nitro benzoic acid. It has been reacted with hydrazine to get compound [2]. 3,5-bis (4-Nitro phenyl)-4-amino -1,2,4-triazole [3] has been synthesized by melting of 4-Nitro benzoic acid hydrizide to cretin temperature. The new series of Schiff bases [4a-f] have been syntheised by reacting compound [3] with different benzaldehydes., These derivatives shows ring closer reaction with phathalic anhydride to obtain 1.3- Oxazepine derivatives [Sa-f]. The syntheised compound were characterized by (IR.UV) spectra, melting points the above reaction were followed by TLC. The biological activities are studied against four different kinds of bacteria .

Synthesis and Characterization of New Oxazepines Compounds Derived From D- Galactose

New Schiff bases derived from D-galactose were synthesized by condensation of aldehyde (1,2:3,4-Di-O-isopropylidene-6-carboxaldehyde-α-D-galactopyranose) with different aromatic amines such as (4-bromo, 3-hydroxy, 4-iodo, 4-methoxy) aniline in dry benzene using glacial acetic acid as a catalyst. These compounds were converted to oxazepine derivatives by addition
 reaction with maleic anhydride in dry benzene as a solvent. The structures of the synthesized compounds have been characterized by elemental analysis, FTIR spectra, some of them by using 1HNMR spectra and measurement of its physical properties.

Study the effect of oxazepine derivatives of alkaline phosphatase in normal persons sera

تم دراسة تأثير مركب 2 ( p-toyl) 3 – (2- traizole ) -2,3 dihydro {1,3} – oxazepine – 4,7 dione وهو من مشتقات مركب oxazepine في فعالية انزيم الفوسفاتيز القاعدي في مصول الاشخاص الاصحاء مختبريا . اعطى مشتق oxazepine نسبة تثبيط بين (22.5 - 69) % . 3 درس نوع التثبيط من خلال تثبيت تركيز الماده العضوية وتغير تركيز الماده الاساس m mol/L (10¯3 × 6 10¯3 ×7 , 10¯3 × 8, 10¯3 ×9 , 10¯3 × 10) وعند رسم معادلة line weaver – burk plot وجد ان التثبيط من نوع تنافسي حيث بقيت السرعه القصوى vmax ثابتة بمقدار U/L 6.66 بينما حصل تغير في قيمة ثابت السرعه لمايكل Km وقد كان للتفاعل بدون وجود المثبط mol/L m 10 m mol/L بينما في حالة وجوده mol/L m 9 . تحضير مشتقات جديدة من 1,3 oxazepine 4-7 dion من المتوقع ان تكون لها فعالية بايولوجية في معالجة التشنجات العصبية .

Synthesis and Biological Activity of New Derivatives of Thiazolidine and Oxazepine-Linked to Pyridine Moieties

This research includes reaction and condensation between substituted 4-aminopyridine and 4-(N, N-dimethyl amino benzaldehyde) to produce Schiff base derivative (3), the compound (3) was selected to react with a different compound such as Thioglycolic acid, Phthalic anhydride, and maleic anhydride, to produced new ring of Thiazolidine derivatives and oxazepine derivatives structures (4,5,6,7,8,9,10,11,12), respectively. The final compound was characterized the structure by Fourier transform-infrared spectroscopy, H-Nuclear magnetic resonance (H-NMR) in addition to the Carbon, Hydrogen, Nitrogen (CHN) analyzer. Biological activity has been considered for the final structures and achievements of multi drugs.

Synthesis And Characterization ( Oxazepine , Thiazine and Quinazoline ) Derivatives And Study The Biological Activity As Antibacterial

This research. Included the preparation. and characterization some novel. Six and seven membered Heterocyclic. Compounds ( oxazepine , thiazine , quinazoline ) The first step in clode react 2-amino-6- methoxybenzothiazole with 4- amino acetophenone to get Schiff base derivative (1). The second step react (1) with 4 -hydroxy acetophenone to get schiff base derivative (2) the last step involve react (2) with ( Phthalic , Maleic , Succinic) anhydride to .get oxazepine derivatives (3,4and 5) also react (2) with(2-amino benzoic acid) and (2-mercaptobenzoic acid ) to get quinazoline (6)and thiazine (7) derivatives respectively .the physical; properties of the prepared; These Compounds. Were Identification (FT-IR) ,(1H-NMR) and (13C-NMR) by spectroscopy thene study their biological effect on two types of bacteria Staphylococcus aureuses (Gram positive) and Escherichia coli (Gram Negative)

Construction of dibenzo[d,f][1,3]oxazepine skeleton from 2′-amino-2-hydroxybiphenyl and isothiocyanates via iodine-mediated cyclodesulfurization

1,3-Oxazepines are of interest because of their application as biologically active substances. Herein, 2′-amino-2-hydroxybiphenyl was reacted with isothiocyanate-derived thioureas and treated in situ with iodine in the presence of triethylamine to afford dibenzo[d,f][1,3]oxazepine derivatives in good-to-excellent yields. X-ray analysis revealed that the obtained product comprises a 7-membered heterocycle and has a Z-configuration imine moiety in its solid state. All oxazepine derivatives obtained by this reaction are novel compounds.

Synthesis, Characterization, Biological Evaluation of Some Heterocyclic Oxazepine Derivatives

Synthesis, Characterization, Biological Evaluation of Some Heterocyclic Oxazepine Derivatives

Synthesis and Estimation of Biological Activity of New Oxazepine Derivatives

Synthesis and Estimation of Biological Activity of New Oxazepine Derivatives

A simple model for the assessment of the agonistic activity of dibenzazepine derivatives by molecular moieties

A simple approach is introduced to assess the agonistic activity of dibenzazepine derivatives including 11H-dibenz[b,e]azepine and the dibenz[b,f][1,4]oxazepine derivatives. Dibenzazepine derivatives show extremely potent activators of the human transient receptor potential ankyrin 1 receptor, which has a key role as a biological sensor. This new approach is based on molecular moieties for desk calculation of these compounds with more reliance on their answers as one could expect from available quantitative structure–activity relationship models. The measured agonistic activities of 31 diverse compounds in terms of pEC50 = −log (EC50), where EC50 is half-maximal effective concentration, are used as training (26 compounds) and test (5 compounds) sets. For the internal cross-validation, the calculated values of leave-one-out (Q2LOO) and the leave-more-out (Q2LMO) cross-validations are the same (0.99550) and very close to the coefficient of determination (R2 = 0.9965), which confirms that the new model is robust, well-behaved, and not over-fitted. The values of mean absolute percent error (MAPE) for training and test sets are 0.5943 and 0.8846, respectively, which are much lower than the outputs of two available complex comparative molecular field analysis (CoMFA) and comparative molecular similarity indices analysis (CoMSIA), i.e., the values of MAPE for training sets of CoMFA and CoMSIA are 0.8799 and 1.0412, while MAPE values for test sets of CoMFA and CoMSIA are 2.1591 and 1.7711, respectively.

Synthesis of New Oxazepine and Thaizolidine Compounds derived from Pyrimidine-2(2H)-one

In this paper the compounds (11-20) (methyl pyrimidine - 2(1H)-one and others phenyl pyrimidine -2(1H)- one) that will prepared from α, β unsaturated carbonyl compounds they are called chalcones, that compounds prepared from reaction of different aldehyde (4-methoxy benzaldehyde, 2-nitro benzaldehyde, 3-nitrobenzaldehyde, 4-N,N—dimethyle amino benzaldehyde, benzaldehyde, 4-nitro-benzaldehyde) with different ketones (acetone, acetophenone, 2-nitro acetophenone, 3-nitro acetophenone) after prepared this compounds and purified it and mesurment for physical, chemical and spectroscopy that we can do to get chalcones that reacted with urea under known chemical conditions to get pyrimidinone compounds we needed. pyrimidine compounds were reacted with two aromatic amines (2,4-dinitro aniline and 4- amino acetophenone) using glacial acetic acid as catalyst in absolute ethanol giving a new compounds of schiff's bases (21-40). New thiazolidine 4-one (41-50) were synthesized from reactions of Schiff's bases (21-30) with thioglycolic acid in absolute ethanol. 1,3- oxazepine derivatives. (51-60) are prepared from reaction between Schiff's bases (31-40) with malic anhydrid in absolut ethanol. The structures of the Synthesized compounds were estimated by IR, 1H- NMR and some physical data.

Synthesis of substituted benzo[b][1,4]oxazepine derivatives by the reaction of 2-aminophenols with alkynones

We have developed a novel synthetic method accessing benzo[b][1,4]oxazepines that are one of the rare classes of benzoxazepine derivatives by reaction of 2-aminophenols with alkynones in 1,4-dioxane at 100 °C. A series of benzo[b][1,4]oxazepine derivatives can be prepared by using this synthetic protocol. Mechanistic experiments indicated that the hydroxy proton of the aminophenol could play a crucial role in the formation of an alkynylketimine intermediate that undergoes 7-endo-dig cyclization.

Switchable solvent-controlled divergent synthesis: an efficient and regioselective approach to pyrimidine and dibenzo[b,f][1,4]oxazepine derivatives

An efficient solvent-controlled regioselective reaction has been developed. The reaction represents a novel protocol for the divergent one-pot synthesis of pyrimidine and dihydrodibenzo[b,f][1,4]oxazepine derivatives.

Unexpected regio- and stereoselective [4 + 3] cycloaddition reaction of azomethine ylides with benzylidene thiazolidinediones: synthesis of pharmacologically active spiroindoline oxazepine derivatives and theoretical study.

An unexpected regio- and stereoselective [4 + 3] cycloaddition reaction of azomethine ylides with 5-benzylidenethiazolidine-2,4-diones has been successfully developed for the synthesis of the novel pharmacologically active 4',5'-dihydro-3'H-spiro[indoline-3,2'-[1, 3] oxazepin]-2-one derivatives in basic condition. Easy purification, high yield, short experimental time and operational simplicity are specific advantages of this protocol. Furthermore, all the synthesized compounds have been evaluated for antioxidant and antibacterial activities. According to the results, most of the synthesized compounds exhibited DPPH radical scavenging activity and nine of them showed antibacterial properties. The reaction mechanism and 1H NMR spectrum have been evaluated by B3LYP/6311G method.

Cascade CN and CO bond constructions for the synthesis of dibenzoimidazo[1,4]oxazepines catalyzed by CuI/o‐phen

AbstractA novel method for the synthesis of dibenzo[b,f]imidazo[1,2‐d][1,4]oxazepine derivatives was described via cascade Csp2N and Csp2O bond constructions. It was a crossed double Ullmann reactions using 4,5‐diaryl‐2‐(2‐hydroxylphenyl)‐1H‐imidazole as the double nucleophilic centers in the presence of Cs2CO3, while 1‐bromo‐2‐iodobenzene was used as a substrate catalyzed by CuI and o‐phenanthroline in good yields.

Synthesis and characterization Some of heterocyclic compounds from Nitrogen derivative

This paper involves the synthesis of new oxazepine derivatives by multi-reaction steps. The first step synthesis azo derivative from 2-naphthol with 3-aminoacetophenone. The second step was the condensation reaction between ketone group of the azo compound and different primary aromatic amines (4-amino phenol, 3-nitro aniline and 4-methyl aniline) to yiled new azo Schiff base compounds (S1-S3) respectively. In the final step, Oxazepine compounds (L1-L3)and (L4-L6)were prepared from reaction imine compounds (S1-S3) with maleic and phthalic anhydride in toluene as solvent. All these derivatives were characterized by melting point, FTIR, HNMR and 13CNMR.

Concise design and synthesis of pyridine-fused heterocycles via 6π-Azaelectrocyclization process of iminoalkyne derivatives

A concise and regioselective approach to the synthesis of pyridine-fused heterocycles and benzoxazepine derivatives was developed. Propargyl imines derived from aromatic aldehydes and propargyl amine underwent 6π-electrocyclization reactions at high temperatures in high yields to form pyridine-fused heterocycles. Application of the same methodology to aromatic imines having a hydroxyl group in the ortho position resulted in the formation of (benz)oxazepine derivatives. The formation mechanism of the products was discussed.