Synthesis and cytotoxicity evaluation of (tetrahydro-β-carboline)-1,3,5-triazine hybrids as anticancer agents

Kumar, Ravi; Gupta, Leena; Pal, Pooja; Khan, Shahnawaz; Singh, Neetu; Katiyar, Sanjay Babu; Meena, Sanjeev; Sarkar, Jayanta; Sinha, Sudhir; Kanaujiya, Jitendra Kumar; Lochab, Savita; Trivedi, Arun Kumar; Chauhan, Prem M. S.

doi:10.1016/j.ejmech.2010.02.001

Cited by 65 publications

(23 citation statements)

References 36 publications

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“…Dimerization between two intermediates TAZs (5g and 2g) occurred in the reaction of TCTAZ with a nucleophile (gH) at a high reaction temperature, resulting in the formation of dimeric triazine (Ag), which had a bridged structure with two TAZ rings (Entry 13, see Experimental for details). The reaction mechanism for formation of the dimerized compound Ag via triamino-TAZ (2g) 22) is shown in Chart 1.…”

Section: Resultsmentioning

confidence: 99%

Synthesis and Biological Evaluation of Symmetrical 2,4,6-Trisubstituted 1,3,5-Triazine Derivatives

Mibu

Yokomizo

Takemura

et al. 2013

CHEMICAL & PHARMACEUTICAL BULLETIN

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We describe the synthesis and biological evaluation of newly designed 2,4,6-trisubstituted symmetrical 1,3,5-triazine (TAZ) derivatives. Among the tested trisubstituted symmetrical TAZ derivatives, various C 3 -or C S -symmetrical alkoxy-amino-substituted TAZ derivatives showed significant antiviral activity against herpes simplex virus type 1 (HSV-1) and/or cytotoxic activity against Vero cells. The structure-activity relationships for anti-HSV-1 activity of these symmetrical 2,4,6-trisubstituted TAZ derivatives are also described. Experimental results indicated that a C S -symmetrical TAZ structure with introduction of two alkoxy groups and one amine moiety seems to be the minimally required structure for anti-HSV-1 activity.Key words 1,3,5-triazine; anti-herpes simplex virus type 1; cytotoxic activity; C 3 symmetry; C S symmetry; plaque reduction assay Molecular recognition of two-fold (C 2 ) or three-fold (C 3 ) symmetrical geometry macromolecules is one of the common features in many important biological responses, 1,2) and we have therefore already designed a few symmetrical target molecules for the purpose of finding biologically active new leads or candidates.3-5) With reference to the molecular symmetry, small molecules having C 3 -, C S -, or C 2 -symmetrical geometry frequently appear in various biologically active compounds. [6][7][8] Such small symmetrical molecules are usually constructed on a corresponding symmetrical template.From this point of view, we have recently reported some molecular modifications of tris(2-aminoethyl) amine (TAEA) derivatives to C 3 -or C S -symmetrical tripodal receptor type molecules and the results of biological evaluation of these symmetrical compounds.3) We have also reported an interesting lectin-like property for sugar recognition of some of these tripodal receptor type TAEA molecules. 4)In order to achieve a suprafacial three-dimensional interaction of a bioactive symmetrical molecule for its binding site, the nature of substituents in the molecule is thought to be very important for preferential interactions. Such interactions are dictated largely by van der Waals interactions or formation of hydrogen bonds. The introduction of amine (basic nitrogen atom) and/or a bivalent oxygen group such as a hydroxy or alkoxy group into a C 3 -symmetrical 1,3,5-triazine (TAZ) template seems to be interesting, because it is well known that amine functionalities behave as both hydrogen acceptors and hydrogen donors in appropriate circumstances. These facts may indicate that molecules with some amine and/or bivalent oxygen functionalities on a heterocyclic C 3 -symmetrical TAZ template can produce a property for suprafacial hydrogenbonding interaction.For an extension of our studies, we planned to investigate the synthesis of 2,4,6-trisubstituted symmetrical TAZ derivatives [9][10][11][12][13][14][15][16] as well as to evaluate their biological properties. In this paper, we report the results of new synthetic routes for C 3 -or C S -symmetrical 2,4,6-trisubstituted TAZ derivativ...

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Section: Resultsmentioning

confidence: 99%

Synthesis and Biological Evaluation of Symmetrical 2,4,6-Trisubstituted 1,3,5-Triazine Derivatives

Mibu

Yokomizo

Takemura

et al. 2013

CHEMICAL & PHARMACEUTICAL BULLETIN

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“…Irsogladine ( Figure 22) has been shown to have anti-tumor activity in murine xenograft models of epidermoid cancer and glioma [152]. More recently, the effect of compound 64 was also investigated in a human breast cancer athymic nude mouse system and the results suggested that irsogladine can be useful in the breast cancer adjuvant setting [153]. R. Kumar et al described a series of (tetrahydro-β-carboline)-1, 3, 5-triazine hybrid molecules showed cytotoxicity against human cancer cell lines and considered as important lead compounds for potential application in anticancer chemotherapy [154].…”

Section: 3 5-triazine Derivatives As Cytotoxic Agentsmentioning

confidence: 95%

A Systematic Review on Antitumor Agents with 1, 3, 5-triazines

Liu¹

2015

Med chem

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“…Considering enzyme inhibition as an intrinsic property of the complete melamine structure, still remains vast potential of decoration of triazine scaffold by introducing "address" fragment increasing selectivity, components facilitating transport through the cell membranes, and last but not least, components of classic anticancer drugs with well-documented therapeutic competence. Therefore recent approaches involve development of hybrid cancer drugs 18 or application of 1,3,5-triazine as inductor of new specific molecular targets 19 . In these studies it has been attempted to introduce into 1,3,5-triazine scaffold one, two or three fragments bearing 2-chloroethylamine moiety characteristic for nitrogen mustards 20,21 and to confirm anti-proliferative activity of the obtained hybrids.…”

Section: Research Articlementioning

confidence: 99%

Synthesis and cytotoxicity studies of bifunctional hybrids of nitrogen mustards with potential enzymes inhibitors based on melamine framework

Kolesińska

Barszcz

Kamiński

et al. 2011

Journal of Enzyme Inhibition and Medicinal Chemistry

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Synthesis and cytotoxicity evaluation of (tetrahydro-β-carboline)-1,3,5-triazine hybrids as anticancer agents

Cited by 65 publications

References 36 publications

Synthesis and Biological Evaluation of Symmetrical 2,4,6-Trisubstituted 1,3,5-Triazine Derivatives

Synthesis and Biological Evaluation of Symmetrical 2,4,6-Trisubstituted 1,3,5-Triazine Derivatives

A Systematic Review on Antitumor Agents with 1, 3, 5-triazines

Synthesis and cytotoxicity studies of bifunctional hybrids of nitrogen mustards with potential enzymes inhibitors based on melamine framework

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