Synthesis and biodistribution of 8-iodo-11-(4-methylpiperazino)-5H-dibenzo[b,e][1,4]-diazepine: Iozapine

Joshua, Alummoottil V.; Sharma, Sanjeev; Strelkov, Alicia; Scott, John R.; Martin‐Iverson, Mathew T.; Abrams, Douglas N.; Silverstone, Peter H.; McEwan, Alexander

doi:10.1016/j.bmcl.2007.04.069

Cited by 21 publications

(45 citation statements)

References 10 publications

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“…Also, NAG-1 expression is induced not only by NSAIDs but also by several antitumorigenic compounds. These include dietary compounds, peroxisome proliferatoractivated receptor- γ ligands, and phytochemicals [34, 35] as well as resveratrol, genistein, diallyl disulfide, 5F203, and retinoid 6-[3-(1-adamantyl)-4-hydroxyphenyl]-2-naphthalene carboxylic acid [17, 36, 37]. In our previous study, we also found that a novel lignin, isochaihulactone, increased NAG-1 mRNA and protein expression and inhibited cell proliferation on human lung cancer A549 cells.…”

Section: Discussionmentioning

confidence: 99%

Potential Therapeutic Role of Hispidulin in Gastric Cancer through Induction of Apoptosis via NAG-1 Signaling

Lee

et al. 2013

Evidence-Based Complementary and Alternative Medicine

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Gastric cancer is one of the most common malignant cancers due to poor prognoses and high mortality rates worldwide. However, an effective chemotherapeutic drug without side effects remains lacking. Saussurea involucrata (SI) Kar. et Kir., also known as snow lotus, grows in mountainous rocky habitats at 2600 m elevation in the Tian Shan and A'er Tai regions of China. The ethyl acetate extract of SI had been shown to inhibit proliferation and induce apoptosis in various tumor cells. In this study, we demonstrated that Hispidulin, active ingredients in SI, inhibits the growth of AGS gastric cancer cells. After Hispidulin treatment, NAG-1 remained highly expressed, whereas COX-2 expression was downregulated. Flow cytometric analysis indicated that Hispidulin induces G1/S phase arrest and apoptosis in time- and concentration-dependent manners. G1/S arrest correlated with upregulated p21/WAF1 and p16 and downregulated cyclin D1 and cyclin E, independent of p53 pathway. In addition, Hispidulin can elevate Egr-1 expression and ERK1/2 activity, whereas ERK1/2 inhibitor markedly attenuated NAG-1 mediated apoptosis. Taken together, Hispidulin can efficiently activate ERK1/2 signaling followed by NAG-1 constitutive expression and trigger cell cycle arrest as well as apoptosis in cancer cell. It can be a potential compound for combination therapy of gastric cancer in the future.

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Section: Discussionmentioning

confidence: 99%

Potential Therapeutic Role of Hispidulin in Gastric Cancer through Induction of Apoptosis via NAG-1 Signaling

Lee

et al. 2013

Evidence-Based Complementary and Alternative Medicine

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“…The traditional routes involve the preparation of lactam intermediates or amides intermediates which are often accompanied by use of harsh conditions, protecting groups and purification after each step . Synthetic pathways involving the reduction of nitro groups have also been developed . Recently Zhang et al.…”

Section: Introductionmentioning

confidence: 99%

Superparamagnetic Copper Ferrite Nanoparticles Catalyzed One Step Regioselective Synthesis of Dibenzodiazepinones via Ligand and Base Free Ullmann Type Coupling Reaction

2016

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CuFe 2 O 4 superparamagnetic nanoparticles were used as an efficient heterogeneous catalyst for the one-step synthesis of dibenzodiazepinones via Ullmann type coupling reaction. The catalyst was highly stable, efficient and easily synthesized from readily available starting materials. The prepared CuFe 2 O 4 NPs was characterized using various characterization techniques such as TEM, SEM, EDX, XRD, VSM, XPS and FT-IR analysis. The thermal stability of the catalyst was also examined by TGA analysis. The present methodology eliminates the multistep procedure for the synthesis of the said compounds. The catalyst effi-ciently catalyzed the reaction under milder condition furnishing high yield of the product within a short reaction time with higher regioselectivity. Furthermore, the CuFe 2 O 4 super paramagnetic nanoparticles could be easily separated by an external magnet and reused for four consecutive runs. The present protocol is devoid of any base or ligands and showed excellent result for reproducibility and gram scale reaction which addressing the issues of sustainability and environment friendliness.

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“…29 Several strategies consist of reduction of a nitro group to an amine, followed by formation of a lactam intermediate (like for the synthesis of iozapine). 16,30 An intramolecular amination process affording dibenzodiazepinones and pyridobenzodiazepinone was recently published, using 2-nitrobenzoyl chloride and an amine.…”

Section: 3mentioning

confidence: 99%

A catalytic route to dibenzodiazepines involving Buchwald–Hartwig coupling: reaction scope and mechanistic consideration

et al. 2015

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We report a new synthetic method for the synthesis of a family of dibenzodiazepines (DBDAs), employing Pd-catalyzed C-N coupling of o-bromoaldimine, with o-bromoaniline as the key step. Eleven DBDAs were prepared, containing electron-withdrawing groups (CN, F, NO 2 ) and electron-donating groups (OMe). The reaction conditions were optimized (catalyst, phosphine, base and solvent) and best results were obtained with Pd(OAc) 2 , SPhos, Cs 2 CO 3 in THF. Due to the ambiguity of the mechanism at hand, various mechanistic studies were performed, that included DFT calculations. The oxidative addition process was studied in detail by DFT, and these studies supported the observed reaction regioselectivity. The adducts formed between the aldimine and the Pd(0) catalyst were calculated to be more stable than the ones formed with the amine, and the barrier for the oxidative addition at the C-Br bond of the aldimine was calculated to be lower than the one at the C-Br bond of the aryl amine. The formation of DBDA over the dibenzoaminopiperidine has been explained in the final cyclization step.

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Synthesis and biodistribution of 8-iodo-11-(4-methylpiperazino)-5H-dibenzo[b,e][1,4]-diazepine: Iozapine

Cited by 21 publications

References 10 publications

Potential Therapeutic Role of Hispidulin in Gastric Cancer through Induction of Apoptosis via NAG-1 Signaling

Potential Therapeutic Role of Hispidulin in Gastric Cancer through Induction of Apoptosis via NAG-1 Signaling

Superparamagnetic Copper Ferrite Nanoparticles Catalyzed One Step Regioselective Synthesis of Dibenzodiazepinones via Ligand and Base Free Ullmann Type Coupling Reaction

A catalytic route to dibenzodiazepines involving Buchwald–Hartwig coupling: reaction scope and mechanistic consideration

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