Synthesis, Characterization and in Vitro Cytotoxic Evaluation of Some Novel Heterocyclic Compounds Bearing Indole Ring

Asmaa S. Salman

Authors

Asmaa S. Salman

thiosemicarbazone, 13-thiazole, 1, 3 thia-zoldinone, pyrazolo[3, 4-d][1, 3]thiazole, cytotoxic activity, MTT assay

Abstract

Reaction 1H-indole-3-carboxaldhyde 1 with thiosemicarbazide derivatives to give thiosemicarbazone derivatives 2a,b. Cyclization of thiosemicarbazone 2a with HCl, Ac 2 O, phenacyl bromides and chloroacetic acid afforded the corresponding 1,2,4-triazole-3-thiol derivative 3, diacetyl derivative 4 and 1,3-thiazole derivative 5 and 1,3-thiazolidin-4-ones derivative 6 respectively. Compound 6 undergoes a series of heterocyclization reactions to give new heterocyclic compounds. The structure of the newly synthesized compounds had been confirmed by elemental analysis and spectra data. The some newly synthesized compounds were evaluated for in vitro cytotoxic activity against three human cancer cell lines, including human liver cancer (HepG2), human colon cancer (HT-29) and human breast cancer (MCF-7) using MTT assay.

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Synthesis, Characterization and in Vitro Cytotoxic Evaluation of Some Novel Heterocyclic Compounds Bearing Indole Ring. (2016). Global Journal of Science Frontier Research, 16(B1), 1-16. https://journalofscience.org/index.php/GJSFR/article/view/1722

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References

Dimitra Kovala-Demertzi, Paras Yadav, Mavroudis Demertzis, Mauro Coluccia (2000) Synthesis, crystal structure, spectral properties and cytotoxic activity of platinum(II) complexes of 2-acetyl pyridine and pyridine-2-carbaldehyde N(4)-ethyl-thiosemicarbazones. 78(4), 347-354.

S Singh, K Ashok, M Galal, C Amit (2015) Synthesis and antibacterial studies of some semicarbazones of some carbonyl compounds. 4(3), 389-392.

V Rao, M Rao, N Jain, J Panwar, A Kumar (2011) Silver triflate catalyzed synthesis of 3aminoalkylated indoles and evaluation of their antibacterial activities. 1(10), 1-7.

M Ismail, M Kamel, L Mohamed, S Faggal (2012) Synthesis of new indole derivatives structurally related to donepezil and their biological evaluation as acetylcholinesterase inhibitors. 17, 4811-4823.

R Chavan, H S ; More, A Bhosale (2010) Synthesis and evaluation of analgesic and antiinflammatory activities of a novel series of 3-(4, 5dihydropyrazolyl)-indoles. 1(4), 135-143.

Sunil Kumar, Samir Mehndiratta, Kunal Nepali, Manish Gupta, Surrinder Koul, Parduman Sharma, Ajit Saxena, Kanaya Dhar (2013) Novel indole-bearing combretastatin analogues as tubulin polymerization inhibitors. 3(1), 3.

Afshin Zarghi, A Tahghighi, Z Soleimani, B Daraie, G Dadrass, M Hedayati (2008) Design and Synthesis of Some 5-Substituted-2-(4-(azido or methylsulfonyl) phenyl)-1H-indole Derivatives as Selective Cyclooxygenase (COX-2) Inhibitors. 76(3), 361-376.

Ö Güze, N ; Karali, A Salman (2008) Synthesis and antituberculosis activity of 5-methyl/ trifluoromethoxy-1H-indole-2,3-dione 3thiosemicarbazone derivatives. 16, 8976-8987.

Sadek Abdou, Salah El-Qusy, Sami Ghabrial, Mahmoud Haggag (2011) Reactions with Visnaginone: Synthesis, Cyclisation and Microbial Evaluation of Some Visnaginone Thiosemicarbazone Derivatives. 5(5), 140-149.

M Shih, Ling Wu, C (2005) Efficient syntheses of thiadiazoline and thiadiazole derivatives by the cyclization of 3-aryl-4-formylsydnone thiosemicarbazones with acetic anhydride and ferric chloride. 61, 10917-10925.

Adel Abdel‐rahman, Wael El‐sayed, El‐sayed Zaki, Asem Mohamed, Ahmed Fadda (2012) Synthesis and antimicrobial activity of substituted [(pyrazol‐4‐yl)methylene]hydrazono‐2,3‐dihydrothiazoles and their sugar derivatives. 49(1), 93-101.

O Ahmed, P Sharma, I Singhvi (2014) Synthesis and investigation of antimicrobial activity of novel Thiazolidinone derivatives. 7(3), 1008-1014.

K Prakasha, G Channe (2011) Synthesis of 5arylidine2-(3,4,5,trimethoxyphenyl)-3-(4-phenyl-thiazol-2-yl)thiazolidin-4-one derivatives as a novel class of antimicrobial agents. 2(3), 10-14.

M Rao, J Sreeramulu, L Ravindranath, G Naga-Rajareddy, K Hanumanthurayudu, G Nageswara Reddy, A Jayaraju1, P Madhusudhan Synthesis and biological screening of some Pyridine and Pyrrole derivatives of Pyrazolo. 3, 4.

Pyrazoles (2012) Unknown Title. 4(1), 272-278.

B Sailu, S Mahantia, A Satya Srinivas, B Balram, B Ram, B Taara, B Vasudh (2012) Synthesis and antibacterial activity of novel isoxazoline derivatives. 4(5), 2036-2041.

Nilesh Thumar, Manish Patel (2012) ChemInform Abstract: Synthesis, Characterization, and in vitro Microbial Evaluation of Some New 4H‐Chromene and Quinoline Derivatives of 1H‐Pyrazole.. 44(17), 1169.

E El-Rady (2008) A convenient and facile synthesis of new thiazole derivatives. 183, 1659-1671.

Samir Bondock, Wesam Khalifa, Ahmed Fadda (2007) Synthesis and antimicrobial evaluation of some new thiazole, thiazolidinone and thiazoline derivatives starting from 1-chloro-3,4-dihydronaphthalene-2-carboxaldehyde. 42(7), 948-954.

K El-Gaml (2015) Synthesis and antimicrobial evaluation of new polyfunctionally substituted heterocyclic compounds derived from 2-cyano-n-(3cyanoquinolin-2-yl)acetamide. 5(1), 1-9.

H Abdel-Aziz, A Gamal-Eldeen, N Hamdy, I Fakhr (2009) Immunomodulatory and a nticancer activity of some novel 2-substituted-6bromo-3-methylthiazolo[3,2-a]benzimidazole derivatives. 342, 230-237.

Tim Mosmann (1983) Rapid colorimetric assay for cellular growth and survival: Application to proliferation and cytotoxicity assays. 65(1-2), 55-63.

A Monks, D Scudiero, P Skehan, R Shoemaker, K Paull, D Vistica, C Hose, J Langley, P Cronise, A Vaigro-Wolff, M Gray-Goodrich, H Campbell, J Mayo, M Boyd (1991) Feasibility of a High-Flux Anticancer Drug Screen Using a Diverse Panel of Cultured Human Tumor Cell Lines. 83(11), 757-766.

N Marshall, C Goodwin, S Holt (1995) A critical assessment of the use of microculture tetrazolium assays to measure cell growth and function. 5, 69-84.