• N. M. JAGADEESH Department of Post Graduate Studies and Research in Chemistry, School of Chemical Sciences, Kuvempu University, Shankaraghatta, Karnataka 577451, India
  • K. M. Mahadevan Department of Post Graduate Studies and Research in Chemistry, School of Chemical Sciences, Kuvempu University, Shankaraghatta, Karnataka 577451, India
  • P. Bagchi Department of Bioinformatics, Azyme Biosciences Pvt. Ltd., Bangalore 560069


Carbazole, Fluorescence, Claisen-Schmidt condensation, Stockes shift, PBR, MDM2-bind p53 receptor cancer proteins


Objective: Synthesis of novel (E)-3-(9-ethyl-9H-carbazol-3yl)-1-phenylprop-2-en-1-ones 3a-i to evaluate for their fluorescence property and anticancer activity on Murine double minutes-2(MDM2) receptor bind p53 and Pheripheral benzodiazepine receptor (PBR) proteins.

Methods: A Claisen-Schmidt condensation of 9-ethyl-9H-carbazole-3-carbaldehyde 1 with substituted acetophenones 2a-i was carried out to obtain novel class of a series of (E)-3-(9-ethyl-9H-carbazol-3yl)-1-phenylprop-2-en-1-ones 3a-i. The fluorescent behavior in ethanol and acetone as solvents, in silico docking study against MDM2 receptor bind p53 and PBR proteins was investigated.

Results: The fluorescent spectrum of (E)-3-(9-ethyl-9H-carbazol-3yl)-1-phenylprop-2-en-1-ones 3a-i shows a large red shift in acetone and ethanol. The compounds 3a-i exhibits large Stoke's shifts value ranging from 135.5 to 160.0 nm in ethanol when compared to standard rhodamine B which was 32 nm. Similarly in acetone the compounds 3a-i exhibits large Stoke's shifts value ranging from 114.5 to 141.0 nm when compared to standard rhodamine B which was 40 nm. The docking study reveals that the (E)-3-(9-ethyl-9H-carbazol-3yl)-1-phenylprop-2-en-1-ones 3a-i were shown excellent interaction with PBR receptor protein with binding energy of -2.643050e+02 to -3.104552e+02 kcal/mol. However, the same target compounds exhibited poor interaction with MDM2-bind p53 receptor cancer protein.

Conclusion: The study could further widen the scope for the development of similar new structurally distinct (E)-3-(9-ethyl-9H-carbazol-3yl)-1-phenylprop-2-en-1-ones to identify potential anticancer agents. Also since the fluorescent spectrum of (E)-3-(9-ethyl-9H-carbazol-3yl)-1-phenylprop-2-en-1-ones 3a-i exhibits a large red shift with an increase in the polarity of the solvents, these can also serve as good candidates for biological probes in medicinal field.


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Feng X, Zhenwei W, Qihuang G. Synthesis, characterization, and optical properties of two-photon-absorbing octupolar molecule with an s-triazine core. J Opt Mater 2007;29:723-7.

Jia-Xiang Y, Xu-Tang T, Chun Xue Y, Yun XY, Lei W, Zhi L, et al. A facile synthesis and properties of multicarbazole molecules containing multiple vinylene bridges. J Am Chem Soc 2005;127:3278-9.

Fitilis I, Fakis M, Polyzos I, Giannetas V, Persephonis P, Vellis P et al. A two-photon absorption study of fluorene and carbazole derivatives. The role of the central core and the solvent polarity. J Chem Phys Lett 2007;447:300-4.

Kyung-In S, Sun-Young K, Dong-Youn N. Electrochemical and fluorescent properties of ferrocenyl chalcone with N-ethyl carbazole group. J Bull Korean Chem Soc 2011;32(1):321-24.

Enrique PG, Judith PM, Víctor MC, Margarita C, José LM, Gabriel RO. Synthesis, characterization and photophysical properties of pyridine-carbazole acrylonitrile derivatives. J Materials 2011;4:562-74.

Hua-Ping Z, Fu-Zhi W, Chun-Xue Y, Xu-Tang T, Jian-Liang S, De-Chun Z et al. Indolo[3,2-b]carbazole:promising building block for highly efficient electroluminescent materials. J Org Electron 2009;10:925-31.

Addy VD, Jolanda JAMB, Nicole MMK, Bea MWL, Carsten R, Andy M et al. Carbazole compounds as host materials for triplet emitters in organic light-emitting diodes:polymer hosts for high-efficiency light-emitting diodes. J Am Chem Soc 2004;126:7718-27.

Wen-Yi H, Liang-Chen C, Wei-Jiun C, You-Ming C, Shu-Hua C, Ken-Tsung W. A new benzimidazole/carbazole hybrid bipolar material for highly efficient deep-blue electrofluorescence, yellow-green electrophosphorescence, and two-color-based white OLEDs. J Mater Chem 2010;20:10113-19.

Li JF, Guan B, Li DX, Dong C. Study on the fluorescence properties of a new intramolecular charge transfer compound 1,5-diphenyl-3-(N-ethylcarbazole-3-yl)-2-pyrazoline. J Spectrochimica Acta Part A 2007;68:404-08.

Abdullah MA, Salman AK, Muhammed SA, Kalid AA. Synthesis, characterization, absorbance, fluorescence and non linear optical properties of some donor acceptor chromophores. J Bull Korean Chem Soc 2012;33(6):1900-06.

Niziol J, Gondek E, Plucinski KJ. Azo-carbazole dye chromophore as promising materials for diffraction grating recording. J Mater Sci and Electron 2010;21:1042-5.

Ashok K, Deepa S, Yeru L, Chan TYT, Qing W, Suresh V. Architectural influence of carbazole push-pull-pull dyes on dye sensitized solar cells. J Dyes and Pigments 2013;99:787-97.

Zhiyong Y, Zhenguo C, Tao Y, Xiqi Z, Meina C, Bingjia X et al. Triphenylethylene carbazole derivatives as a new class of AIE materials with strong blue light emission and high glass transition temperature. J Mater Chem 2009;19:5541-46.

Eunhee L. Synthesis and characterization of carbazole-benzothiadiazole-based conjugated polymers for organic photovoltaic cells with triazole in the main chain. Int J Photoenergy Volume 2013;Article ID 607826, 7 pages.

Harishkumar HN, Mahadevan KM, Jagadeesh NM, Kiran Kumar HC. Synthesis and fluorescence study of phenylcoumarin/ cyanophenylbenzocoumarin-3-carboxylates. J Org Commun 2012;5(4):196-208.

Harishkumar HN, Mahadevan KM, Jagadeesh NM. Facile synthesis of 2-(1,3-benzoxazol/benzothiazol/benzoimidazole-2-yl)-3H-benzo[f]chromen-3-one as blue fluorescent brighteners. S Afr J Chem 2012;65:5-9.

Rajesha G, Kiran Kumar HC, Bhojya Naik HS, Mahadevan KM. Synthesis of new benzocoumaryl oxadiazolyls as strong blue-green fluorescent brighteners. S Afr J Chem 2011;64:88-94.

Rajesha, Bhojya Naik HS, Harishkumar HN, Hosamani KM, Mahadevan KM. Studies on the synthesis and fluorescent properties of long-chained 2-(5-alkyl-1, 3, 4-oxadiazol-2-yl)-3H-benzo[f]chromen-3-ones. J Arkivoc 2009;ii:11-9.

Siddalingamurthy E, Mahadevan KM, Jagadeesh NM, Harishkumar HN. Mild, efficient Fischer indole synthesis using 2,4,6-trichloro-1,3,5-triazine (TCT). J Tetrahedron Lett 2013;54:5591-96.

Kiran Kumar HC, Mahadevan KM, Kiran BM. High throughput one pot synthesis of 2-methylquinolines. J Tetrahedron Lett 2013;54:1368-70.

Bindu PJ, Mahadevan KM, Ravikumar Naik TR. An efficient one-pot synthesis and photo-induced DNA cleavage studies of 2-chloro-3-(5-aryl-4,5-dihydroisoxazol-3-yl) quinolines. J Bioorg Med Chem Lett 2012;22(19):6095-8.

Siddalingamurthy E, Mahadevan KM, Jagadeesh NM, Kumara MN. Synthesis and docking study of 3-(N-alkyl/aryl piperidyl) indoles with serotonin-5HT H1 and CCR2 antihistamine receptors. Int J Pharm Pharm Sci 2014;6:475-82.

Jagadeesh NM, Mahadevan KM, Kumara MN, Prashantha N. Synthesis and molecular docking study of N-alkyl/aryl-2-aryl indol-3-yl glyoxylamides as novel anticancer agents. Int J Pharm Pharm Sci 2014;6:921-26.

Sheela NL, Umesh SM, Swaminath LB, Prashant VA, Shivajirao RP, Govind BK. Synthesis and photophysical studies on 5-ethoxycarbonyl-4-cinnamyl-6-methyl-3,4-dihydropyrimidine-2(1H)-one in various solvents. J Bull Chem Soc Ethiop 2009;23(2):231-8.

Vassilev LT, Vu BT, Graves B, Carvajal D, Podlaski F, Filipovic Z et al. In vivo activation of the p53 pathway by small-molecule antagonists of MDM2. J Sci 2004;303:844-8.

Papadopoulos V, Baraldi M, Guilarte TR, Knudsen TB, Lacapere JJ, Lindemann P et al. Translocator protein (18kDa):new nomenclature for the peripheral-type benzodiazepine receptor based on its structure and molecular function. J Trends Pharmacol Sci 2006;27:402-09.

Lacapère JJ, Papadopoulos V. Peripheral-type benzodiazepine receptor:structure and function of a cholesterol-binding protein in steroid and bile acid biosynthesis. J Steroids 2003;68:569-85.

O’Hara MF, Nibbio BJ, Craig RC, Nemeth KR, Charlap JH, Knudsen TB. Mitochondrial benzodiazepine receptors regulate oxygen homeostasis in the early mouse embryo. J Reprod Toxicol 2003;17:365-75.

Galiegue S, Casellas P, Kramar A, Tinel N, Simony-Lafontaine J. Immunohistochemical assessment of the peripheral benzodiazepine receptor in breast cancer and its relationship with survival. J Clin Cancer Res 2004;10:2058-64.

Maaser K, Grabowski P, Sutter AP, Hopfner M, Foss HD, Stein H et al. Overexpression of the peripheral benzodiazepine receptor is a relevant prognostic factor in stage III colorectal cancer. J Clin Cancer Res 2002;8:3205-9.

Muegge I. PMF scoring revisited. J Med Chem 2006; 49(20): 5895-902.



How to Cite

JAGADEESH, N. M., K. M. Mahadevan, and P. Bagchi. “SYNTHESIS, MOLECULAR DOCKING AND FLUORESCENT PROPERTIES OF NOVEL (E)-3-(9-ETHYL-9H-CARBAZOL-3YL)-1-PHENYLPROP-2-EN-1-ONES”. International Journal of Pharmacy and Pharmaceutical Sciences, vol. 6, no. 10, Oct. 2014, pp. 317-25,



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