A One-Pot Synthesis of Oxazepine-Quinazolinone bis-Heterocyclic Scaffolds via Isocyanide-Based Three-Component Reactions

Shaabani, Shabnam; Shaabani, Ahmad; Kučeraková, Monika; Dušek, Michal

doi:10.3389/fchem.2019.00623

Cited by 21 publications

(7 citation statements)

References 63 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…In 2019, Shaabani et al reported an efficient and eco-friendly protocol for the synthesis of biologically important fused oxazepine-quinazolinone BHCs 2. [34] The products were prepared through a one-pot reaction of 2-(2formylphenoxy) acetic acid and 2-aminobenzamide as bifunctional reactants with an isocyanide unit (Scheme 3). Notably, this is the first report to use two bifunctional starting materials in Ugi-reaction to obtain fused BHCs.…”

Section: One-pot Synthesis Of Fused Bhcsmentioning

confidence: 99%

One‐Pot Construction of Bis‐Heterocycles through Isocyanide Based Multicomponent Reactions

Bhat

2020

ChemistrySelect

View full text Add to dashboard Cite

Bis‐heterocycles (BHCs) are hybrid molecules comprising two linked, bound, spacer, or fused heterocyclic skeletons. In recent years, these compounds have attracted increased attention of scientific communities because of their improved potential applications than their discrete units. The emergence of numerous synthetic protocols utilizing Isocyanide as one of the components in multicomponent reactions has unleashed innumerable openings to design and synthesize diverse heterocyclic scaffolds and thus Isocyanide based multicomponent reactions (IMCRs) are leading today's MCR chemistry. To date, there has not been any exclusive review on the construction of BHCs via direct IMCRs or its combination with other reaction sequences in one‐pot. This article presents the first overview of IMCRs such as Ugi, Groebke‐Blackburn‐Bienaymé (GBBR), their sequential combination with other reactions, and new IMCRs established for the one‐pot synthesis of BHCs in the last two decades.

show abstract

Section: One-pot Synthesis Of Fused Bhcsmentioning

confidence: 99%

One‐Pot Construction of Bis‐Heterocycles through Isocyanide Based Multicomponent Reactions

Bhat

2020

ChemistrySelect

View full text Add to dashboard Cite

show abstract

“…Oxazepine and its derivatives have many important biological pharmacological activities 14 such as enzyme inhibitors 15 , anti-depressant and psychoactive drug 16 . Amoxapine is a group of drugs was called tricyclic antidepressants 17 , which are used for treating symptoms of depression, anxiety, and agitation. Xin-Hua Liu et al synthesized eight novel oxazepine derivatives to be screened for anticancer activity.…”

Section: Introductionmentioning

confidence: 99%

Molecular Docking, Synthesis and Evaluation for Antioxidant and Antibacterial Activity of New Oxazepane and Benzoxazepine Derivatives

Sager,

Abaies,

Katoof

2024

Baghdad Sci.J

View full text Add to dashboard Cite

In the field of molecular simulations, molecular docking is a method that can determine the optimal and preferred orientation of a certain molecule related to another when they are coupled to create a stable complex. The strength of the association, or binding affinity, between two molecules can be predicted using knowledge of their preferred orientation. In this study, a series of prepared compounds were evaluated for their binding modes, potential interactions, and target binding locations. Some derivatives 1,3-oxazepane, and 1,3-benzoxazepine were prepared from three Schiff bases compounds (1S-3S). The compounds (1S-3S) were reacted with succinic anhydride and phthalic anhydride to obtain derivatives of 1,3- oxazepane and 1,3-benzoxazepine (1B-3C). The characterization of prepared compounds was achieved by methods of elemental analysis, FT-IR, 1H, and 13C-NMR spectral analysis. The antibacterial activity of the compounds (1B-3C) was recorded against some isolated bacteria including gram-negative (Staphylococcus aureus), and gram-positive (E.coli) in parallel with Amoxicillin as a regular drug. Compounds (1B-3C) exhibited good values as antibacterial spreading from middling to perfect against the bacteria strains. Moreover, the antioxidant activity of the synthesized compounds (1B-3C) was evaluated using 2,2-diphenyl-1-picrylhydrazyl. The results showed that compounds have the highest values as radical scavenging.

show abstract

“…Their chemical structure has a distinctive feature in pharmacological chemotherapy drugs: antimicrobial (5), anti-cancer and anti-tuberculosis (6,7), anti-inflammatory (8), antioxidant (9), antifungal (10), and antibacterial. As auxiliary agents and in the manufacture of dyes as coloring materials, inhibitors of metal corrosion (11), and has a varied biological activity, its effectiveness used as an anticoagulant (12), treatment of mental disorders (13,14), anti-tumor (15), (16). Based on the great importance of these compounds, the research aimed to prepare two compounds from Schiff bases with the derivation of the oxazepine ring and study their biological effectiveness on MDA breast cancer to know the extent of the toxicity of the compounds on healthy cells Ref.…”

Section: Introductionmentioning

confidence: 99%

Synthesis, identification, and cytotoxicity effect of Oxazapine scaffolding

Azzawi

Hussein

2022

ijhs

View full text Add to dashboard Cite

The research includes the preparation of two Schiff bases MA (2-1) and some of their derivatives from the reaction of para-bromobenzaldehyde or para-methoxy benzaldehyde with stoichiometric 5-methyl pyrazole-3-amino in the presence of glacial acetic acid. Then the corresponding oxazepine rings MA (6-3) were prepared from each MA (2-1) with maleic anhydride or phthalic anhydride. The prepared chemical formulas were spectroscopically confirmed using FTIR and 1HNMR spectroscopy. The biological activity of MA5 had tested against MDA breast cancer and REF healthy cells at seven concentrations (500,250,125,62.5,31.5,15.5,7.5) µg / ml. The compound showed a high inhibition against cancer cells, so this makes it a candidate as a drug for future cytotoxicity.

show abstract

A One-Pot Synthesis of Oxazepine-Quinazolinone bis-Heterocyclic Scaffolds via Isocyanide-Based Three-Component Reactions

Cited by 21 publications

References 63 publications

One‐Pot Construction of Bis‐Heterocycles through Isocyanide Based Multicomponent Reactions

One‐Pot Construction of Bis‐Heterocycles through Isocyanide Based Multicomponent Reactions

Molecular Docking, Synthesis and Evaluation for Antioxidant and Antibacterial Activity of New Oxazepane and Benzoxazepine Derivatives

Synthesis, identification, and cytotoxicity effect of Oxazapine scaffolding

Contact Info

Product

Resources

About