Design and synthesis of novel 2,4-diaryl-5H-indeno[1,2-b]pyridine derivatives, and their evaluation of topoisomerase inhibitory activity and cytotoxicity

Kadayat, Tara Man; Park, Chanmi; Jun, Kyu‐Yeon; Magar, Til Bahadur Thapa; Bist, Ganesh; Yoo, Han Young; Kwon, Young Joo; Lee, Eung-Seok

doi:10.1016/j.bmc.2014.11.010

Cited by 24 publications

(17 citation statements)

References 35 publications

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“…We systematically designed eighteen compounds (1)(2)(3)(4)(5)(6)(7)(8)(9)(10)(11)(12)(13)(14)(15)(16)(17)(18) in six different series introducing hydroxyl and chlorine groups at phenyl, thienyl or furyl ring of 2,4-diaryl-5H-indeno [1,2-b]pyridines (Fig. 2).…”

Section: Design and Synthesismentioning

confidence: 99%

“…Adriamycin, etoposide and camptothecin, widely used anticancer drugs, were used as positive controls. The inhibitory activity (IC 50 ) of the synthesized compounds (7)(8)(9)(10)(11)(12)(13)(14)(15)(16)(17)(18) is expressed as micromolar concentration as shown in Table 3 and 4.…”

Section: Cytotoxicity Of the Compoundsmentioning

confidence: 99%

“…Structure-activity relationship (SAR) was studied based on results of topo I and II inhibitory activity and cytotoxicity with respect to the non-substituted 2,4-diaryl-5H-indeno[1,2-b]pyridines (A, B, C), one hydroxylated 2,4-diaryl-5H-indeno [1,2-b]pyridines (1)(2)(3)(4)(5)(6)(7)(8)(9), and one chlorinated 2,4-diaryl-5H-indeno [1,2-b]pyridines containing one hydroxyl moiety (10)(11)(12)(13)(14)(15)(16)(17)(18). Figure 5 illustrates the overall SAR study.…”

Section: Structure-activity Relationship Studymentioning

confidence: 99%

“…Compounds A and C were reported to have strong and moderate topo I inhibitory activity, respectively, whereas compound B showed very weak topo I activity at 100 µM. Compounds (4-6) with one hydroxyl group at 2-phenyl ring and thienyl ring on 4-position exhibited strong topo I inhibitory activity, however further substitution of one chlorine group at 4-thienyl ring (13)(14)(15) decreased the topo I inhibitory activity. Similarly, compounds 1-3, and 7-9 containing one hydroxyl group at phenyl ring exhibited moderate or strong topo I inhibitory activity.…”

Section: Structure-activity Relationship Studymentioning

confidence: 99%

“…1). Among them, several compounds with meta or para-hydroxyl group at phenyl ring in combination with furyl or thieny moiety exhibited considerable topo inhibitory activity and cytotoxicity [13,14].…”

Section: Introductionmentioning

confidence: 99%

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Modified 2,4-diaryl-5H-indeno[1,2-b]pyridines with hydroxyl and chlorine moiety: Synthesis, anticancer activity, and structure–activity relationship study

Kadayat

Song

Kwon

et al. 2015

Bioorganic Chemistry

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Section: Design and Synthesismentioning

confidence: 99%

Section: Cytotoxicity Of the Compoundsmentioning

confidence: 99%

Section: Structure-activity Relationship Studymentioning

confidence: 99%

Section: Structure-activity Relationship Studymentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Modified 2,4-diaryl-5H-indeno[1,2-b]pyridines with hydroxyl and chlorine moiety: Synthesis, anticancer activity, and structure–activity relationship study

Kadayat

Song

Kwon

et al. 2015

Bioorganic Chemistry

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Diversified Photo/Electronic Functions Based on a Simple Chalcone Skeleton: Effects of Substitution Pattern and Molecular Packing

Cheng

Wang

Tang

et al. 2018

Adv Funct Materials

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Structurally simple chalcone derivatives 1–2 are prepared and their diversified emission behaviors are deeply investigated. Two polymorphs (1G: λem = 536 nm, Φf = 0.08, τ = 1.81 ns; 1O: λem = 573 nm, Φf = 0.19, τ = 10.82 ns) with distinctively different emission behaviors are constructed by finely controlling the crystallization conditions of compound 1. 1G exhibits typical amplified spontaneous emission while 1O shows an interesting blue shift under smashing process (1O‐S: λem = 562 nm, Φf = 0.23, τ = 6.42 ns), which is ascribed to their different molecular packing structures and intermolecular interactions. Notably, simply introducing a fluorine substituent effectively endows the crystal with red emission (crystal 2: λem = 598 nm, Φf = 0.16, τ = 18.77 ns). Thus multicolor emissions including green, yellow, orange, and red emissions are obtained based on this simple chalcone skeleton.

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Self‐Assembly of Chiral‐at‐End Diketopyrrolopyrroles: Symmetry Dependent Solution and Film Optical Activity and Photovoltaic Performance

Hume

Monks

Pop

et al. 2018

Chemistry A European J

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Chiral thiophene-diketopyrrolopyrrole derivatives have been synthesised to investigate the potential of stereochemistry and symmetry as a means of modulating properties by influencing self-assembly of these purely organic materials. In particular, derivatives of diketopyrrolopyrrole were employed because of their proven interest as dyes, especially for organic solar cells. The natural product myrtenal was used as the source of stereochemistry, introduced through a Kröhnke reaction of a thiophene-bearing pyridinium salt and diketopyrrolopyrroles were prepared through Suzuki coupling with this chiral moiety at one end only as well as at both ends. Absorption spectroscopy and electrochemistry confirmed the potential suitability of the compounds for photovoltaic devices. The nanostructures formed by the compounds have been probed with circular dichroism spectroscopy in solution and in films. It is shown that a chiral C symmetric molecule assembles in solution giving a strong circular dichroic signal while as a film this optical activity is nulled, whereas an asymmetric homologue is most optically active as a thin film. The X-ray crystal structure of the asymmetric compound shows a polar order of the molecules that might explain this observation. The lack of optical activity in solution is very likely a result of the high solubility of the compound. The results reaffirm the sensitivity of circular dichroism spectroscopy to inter-chromophore organisation, whereas absorption spectroscopy in the visible region reveals only slight changes to the bands. The differing order in the compounds also affects their performance in bulk heterojunction photovoltaic devices. Atomic force microscopy of the blended thin films with the fullerene derivative usually employed (PC BM) showed that smooth and well mixed films were achieved, with the conditions required during spin coating depending greatly on the derivative, because of their differing solubility. The apparently better performance of the symmetrical compound (although with very low efficiency) is probably a result of the alignment of the molecules inferred by the circular dichroism experiments, whereas the asymmetric compound presumably adopts a twisted supramolecular organisation.

show abstract

Design and synthesis of novel 2,4-diaryl-5H-indeno[1,2-b]pyridine derivatives, and their evaluation of topoisomerase inhibitory activity and cytotoxicity

Cited by 24 publications

References 35 publications

Modified 2,4-diaryl-5H-indeno[1,2-b]pyridines with hydroxyl and chlorine moiety: Synthesis, anticancer activity, and structure–activity relationship study

Modified 2,4-diaryl-5H-indeno[1,2-b]pyridines with hydroxyl and chlorine moiety: Synthesis, anticancer activity, and structure–activity relationship study

Diversified Photo/Electronic Functions Based on a Simple Chalcone Skeleton: Effects of Substitution Pattern and Molecular Packing

Self‐Assembly of Chiral‐at‐End Diketopyrrolopyrroles: Symmetry Dependent Solution and Film Optical Activity and Photovoltaic Performance

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