Synthesis and anticancer activity of new pyrrolocarbazoles and pyrrolo-β-carbolines

Laronze, Marie; Boisbrun, Michel; Léonce, Stéphane; Pfeiffer, Bruno; Renard, Pierre; Lozach, Olivier; Meijer, Laurent; Lansiaux, Amélie; Bailly, Christian; Sápi, János; Laronze, Jean‐Yves

doi:10.1016/j.bmc.2004.12.045

Cited by 81 publications

(43 citation statements)

References 55 publications

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“…The preliminary research had conducted by Stanford Medicine, they conclude that the compounds present in food called phytochemicals; (carbazole and indole class of phytochemicals) which can decrease the risk of developing diseases such as hypertension, diabetes, and cancer [2]. Carbazole and indole have received significant attention in compounds which are active against cancer, and cardiovascular disorders [3,4], that exhibit antioxidant, antidiabetic, antimitotic, and antimicrobial activities [5][6][7][8]. Furthermore, carbazole derivatives also play a significant role as an active material in the organic light emitting diodes for blue light emission and organic field-effect transistors (OFET) [9,10].…”

Section: Introductionmentioning

confidence: 99%

Physical and Structural Characterization of Biofield Energy Treated Carbazole

Trivedi¹,

Branton²,

Trivedi³

et al. 2015

Pharm Anal Acta

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Carbazole is a class of phytochemical associated with cancer prevention. It attracted a significant interest in recent time for their usefulness in synthetic heterocyclic chemistry, analytical chemistry and pharmacology. The aim of the study was to evaluate the impact of biofield energy treatment on carbazole by various analytical methods. The study was performed in two groups i.e. control and treatment. The treatment group was subjected to Mr. Trivedi's biofield treatment. Subsequently, both the samples were characterized with respect to physical and structural properties using X-ray diffraction (XRD), differential scanning calorimetry (DSC), thermogravimetric analysis (TGA), Fourier transform infrared (FT-IR), gas chromatography-mass spectrometry (GC-MS), laser particle size analyzer, and surface area analyzer. The XRD study revealed that the crystallite size of treated carbazole was decreased significantly with 37.5% as compared to the control. In addition, the intensity of XRD peaks was slightly decreased as compared to the control. The latent heat of fusion (ΔH) of treated carbazole was substantially increased by 253.6% as compared to the control. Maximum degradation temperature (T max ) of treated carbazole was increased by 41.46°C as compared to the control (211.93°C to 253.39°C). FT-IR spectra showed similar stretching frequencies in both control and treated carbazole samples. GC-MS data revealed that isotopic abundance ratio of either 13 C/ 12 C or 15 N/ 14 N or 2 H/ 1 H (PM+1/PM) of treated carbazole was significantly increased up to 278.59%. Particle size analysis showed substantial decrease in average particle size (d 50 ) and d 90 of the treated carbazole by 25.24% and 4.31%, respectively as compared to the control. The surface area analysis exhibited an increase in the surface area of treated sample by 4.8% as compared to the control. Overall, the experimental results suggest that biofield energy treatment has significant effect on physical, spectral and thermal properties of carbazole.

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Section: Introductionmentioning

confidence: 99%

Physical and Structural Characterization of Biofield Energy Treated Carbazole

Trivedi¹,

Branton²,

Trivedi³

et al. 2015

Pharm Anal Acta

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“…FTIR spectra showing the absorption at 3420 cm -1 for νN-H and at 1370 cm H-NMR spectra data of compound (3,7) [17] δppm in DMSO-d6 solvent:2.47 (S, 6H, -CH 3 ); 7.4-7.6 (S, 5H, p-Ar-H); 7.5-7.9 (m, 6H, p-Ar-H);12.9 (broad, 1H,NH) for compound(3] while compound(7) δppm in DMSO-d6 solvent:3.4-3.6 (S, 9H, -OCH 3 ); 7.2-7.7 (m, 6H, C-Carbazole);13.1 (broad, 1H,NH). 13 C-NMR spectra for compounds (3, 7) showed results were listed in Table ( The conversion to the intermediate could be effected in five minutes at room temperature in dry ether and dry THF, but incubation of the reaction mixture in refrigerator for 24 hrs. FTIR Spectra of compound (9)(10)(11)(12)(13)(14) are shown absorption in Table (2).…”

Section: Resultsmentioning

confidence: 99%

“…Carbazoles are a large and an interesting group of organic compounds which one can find pharmaceutical activity [2] , dyestuffs, plastics [3][4][5] , and known to possess mutagenic and toxice activities and also to be arecalcitrant molecule [6] . Carbazole derivatives showed anticancer [7] , antifungal [8] , anti malarial [9] , anti tumor (leuckemia, renal, colon), anti inflammatory, antiallergic antiviral, and anti hypertensive properties [10][11][12] .Due to their extensive biological activity carbazole derivatives and their chemistry have been studies at length. Keeping the above facts, we aimed to synthesize new carbazole derivatives to thus obtain new hetero cyclic system which is expected to possess characteristic of biological activites.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Evaluation of the Biological Activity for Some of Carbazole Derivatives

Sultani¹

2010

JNUS

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This research includes preparing of some carbazole derivatives .The (3,6-Disulfonylchloride-9H-carbazole (1) was achieved by the reaction of carbazole with chloro sulfonic acid in cold condition, reaction of compound (1) with sodium azide in acetone as a solvent to give (3,6-Disulfonyl azide-9H-carbazole) (2), then reaction of compound (2) with different phosphine and phosphate compounds(1mole and 2 mole) yielded the (3,6-Disulfonyl -6-azide-3-(phosphine or phosphate imine)-9H-carbazole) derivatives (3-8) and (3,6-Disulfonyl (phosphine or phosphate imine)-

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“…β-carbolines are indole alkaloids that interact with DNA, [8][9][10][11][12] and induce crossingover and conversion of mitotic genes. 13 Other effects on cells and organs include modulating the extrinsic or death receptor pathway and the intrinsic or mitochondrial pathway, 14 interfering with Ras-related signaling pathways, 15 inhibiting tumor-related enzymes, [16][17][18][19] and limiting thrombosis and inflammation.…”

Section: Introductionmentioning

confidence: 99%

Small molecule PZL318: forming fluorescent nanoparticles capable of tracing their interactions with cancer cells and activated platelets, slowing tumor growth and inhibiting thrombosis

Wang

et al. 2015

IJN

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Low selectivity of chemotherapy correlates with poor outcomes of cancer patients. To improve this issue, a novel agent, N-(1-[3-methoxycarbonyl-4-hydroxyphenyl]-β-carboline-3-carbonyl)-Trp-Lys-OBzl (PZL318), was reported here. The transmission electron microscopy, scanning electron microscopy, and atomic force microscopy images demonstrated that PZL318 can form nanoparticles. Fluorescent and confocal images visualized that PZL318 formed fluorescent nanoparticles capable of targeting cancer cells and tracing their interactions with cancer cells. In vitro, 40 μM of PZL318 inhibited the proliferation of tumorigenic cells, but not nontumorigenic cells. In vivo, 10 nmol/kg of PZL318 slowed the tumor growth of S180 mice and alleviated the thrombosis of ferric chloride-treated ICR mice, while 100 μmol/kg of PZL318 did not injure healthy mice and they exhibited no liver toxicity. By analyzing Fourier transform–mass spectrometry and rotating-frame Overhauser spectroscopy (ROESY) two-dimensional nuclear magnetic resonance spectra, the chemical mechanism of PZL318-forming trimers and nanoparticles was explored. By using mesoscale simulation, a nanoparticle of 3.01 nm in diameter was predicted containing 13 trimers. Scavenging free radicals, downregulating sP-selectin expression and intercalating toward DNA were correlated with the antitumor mechanism of PZL318.

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Synthesis and anticancer activity of new pyrrolocarbazoles and pyrrolo-β-carbolines

Cited by 81 publications

References 55 publications

Physical and Structural Characterization of Biofield Energy Treated Carbazole

Physical and Structural Characterization of Biofield Energy Treated Carbazole

Synthesis and Evaluation of the Biological Activity for Some of Carbazole Derivatives

Small molecule PZL318: forming fluorescent nanoparticles capable of tracing their interactions with cancer cells and activated platelets, slowing tumor growth and inhibiting thrombosis

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