Literature DB >> 32524218

Production of benzazepine derivatives via four-component reaction of isatins: study of antioxidant activity.

Fathali Gholami Orimi1, Behrooz Mirza2, Zinatossadat Hossaini1.   

Abstract

In current research, benzazepine derivative is synthesized via a new process of four-component reaction of isatin or its derivatives, α-haloketones, activated acetylenic compounds, isoquinoline and potassium fluoride/clinoptilolite nanoparticles (KF/CP NPs) in acidic solution of H2O2 in water at room temperature. Also, antioxidation property of some prepared benzazepines is investigated by employing trapping diphenyl-picrylhydrazine (DPPH) radical and ability of ferric reduction experiment. Among investigated compounds, compounds 5c have good results relative to BHT and TBHQ as standard antioxidant. Also, the Gram-positive and Gram-negative bacteria disk diffusion research is used for the confirmation of antimicrobial power of some prepared benzazepines. The achieved outcomes of disk diffusion experiment showed that these compounds avoided the growth of bacteria. Our procedure has a few benefits relative to reported method such as good rate of reaction, product with high efficiency, simple removal of catalyst from mixture of reaction. In the yield of the product, KF/clinoptilolite nanoparticles show a satisfactory recyclable activity.
© 2020. Springer Nature Switzerland AG.

Entities:  

Keywords:  Alkyl bromide; Antioxidant property; Benzazepine derivatives; Four-component reaction; PG-KF/CP NPs

Mesh:

Substances:

Year:  2020        PMID: 32524218     DOI: 10.1007/s11030-020-10110-5

Source DB:  PubMed          Journal:  Mol Divers        ISSN: 1381-1991            Impact factor:   2.943


  32 in total

1.  Recent developments in the utilization of green solvents in polymer chemistry.

Authors:  Tina Erdmenger; Carlos Guerrero-Sanchez; Juergen Vitz; Richard Hoogenboom; Ulrich S Schubert
Journal:  Chem Soc Rev       Date:  2010-07-05       Impact factor: 54.564

Review 2.  Recent developments in isocyanide based multicomponent reactions in applied chemistry.

Authors:  Alexander Dömling
Journal:  Chem Rev       Date:  2006-01       Impact factor: 60.622

3.  Discovery and SAR of new benzazepines as potent and selective 5-HT(2C) receptor agonists for the treatment of obesity.

Authors:  Brian M Smith; Jeffrey M Smith; James H Tsai; Jeffrey A Schultz; Charles A Gilson; Scott A Estrada; Rita R Chen; Douglas M Park; Emily B Prieto; Charlemagne S Gallardo; Dipanjan Sengupta; William J Thomsen; Hazel R Saldana; Kevin T Whelan; Frederique Menzaghi; Robert R Webb; Nigel R A Beeley
Journal:  Bioorg Med Chem Lett       Date:  2005-03-01       Impact factor: 2.823

4.  Orally active CCR5 antagonists as anti-HIV-1 agents. Part 3: Synthesis and biological activities of 1-benzazepine derivatives containing a sulfoxide moiety.

Authors:  Masaki Seto; Naoki Miyamoto; Katsuji Aikawa; Yoshio Aramaki; Naoyuki Kanzaki; Yuji Iizawa; Masanori Baba; Mitsuru Shiraishi
Journal:  Bioorg Med Chem       Date:  2005-01-17       Impact factor: 3.641

Review 5.  Chemistry and biological activity of new 3-benzazepines.

Authors:  M Kawase; S Saito; N Motohashi
Journal:  Int J Antimicrob Agents       Date:  2000-04       Impact factor: 5.283

6.  Multicomponent synthesis of 2-imidazolines.

Authors:  Robin S Bon; Bart van Vliet; Nanda E Sprenkels; Rob F Schmitz; Frans J J de Kanter; Christian V Stevens; Marcel Swart; F Matthias Bickelhaupt; Marinus B Groen; Romano V A Orru
Journal:  J Org Chem       Date:  2005-04-29       Impact factor: 4.354

7.  Ugi multicomponent reaction followed by an intramolecular nucleophilic substitution: convergent multicomponent synthesis of 1-sulfonyl 1,4-diazepan-5-ones and of their benzo-fused derivatives.

Authors:  Luca Banfi; Andrea Basso; Giuseppe Guanti; Nicola Kielland; Claudio Repetto; Renata Riva
Journal:  J Org Chem       Date:  2007-02-20       Impact factor: 4.354

8.  Characterization of orally active nonpeptide vasopressin V(2) receptor agonist. Synthesis and biological evaluation of both the (5R)- and (5S)-enantioisomers of 2-[1-(2-Chloro-4-pyrrolidin-1-yl-benzoyl)-2,3,4,5-tetrahydro-1H-1-benzazepin- 5-yl]-N-isopropylacetamide.

Authors:  Kazumi Kondo; Keizo Kan; Yoshihisa Tanada; Masahiko Bando; Tomoichi Shinohara; Muneaki Kurimura; Hidenori Ogawa; Shigeki Nakamura; Takahiro Hirano; Yoshitaka Yamamura; Masaru Kido; Toyoki Mori; Michiaki Tominaga
Journal:  J Med Chem       Date:  2002-08-15       Impact factor: 7.446

9.  New MCRs: the first 4-component reaction leading to 2,4-disubstituted thiazoles.

Authors:  Jürgen Kolb; Barbara Beck; Michael Almstetter; Stefan Heck; Eberhardt Herdtweck; Alexander Dömling
Journal:  Mol Divers       Date:  2003       Impact factor: 2.943

10.  Discovery of a novel class of benzazepinone Na(v)1.7 blockers: potential treatments for neuropathic pain.

Authors:  Scott B Hoyt; Clare London; David Gorin; Matthew J Wyvratt; Michael H Fisher; Catherine Abbadie; John P Felix; Maria L Garcia; Xiaohua Li; Kathryn A Lyons; Erin McGowan; D Euan MacIntyre; William J Martin; Birgit T Priest; Amy Ritter; McHardy M Smith; Vivien A Warren; Brande S Williams; Gregory J Kaczorowski; William H Parsons
Journal:  Bioorg Med Chem Lett       Date:  2007-05-27       Impact factor: 2.823

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