2014
DOI: 10.1039/c4nj00938j
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Homologous 1,3,5-triarylpyrazolines: synthesis, CH⋯π interactions guided self-assembly and effect of alkyloxy chain length on DNA binding properties

Abstract: The synthesis, CH⋯π interactions-driven self-assembled structure and DNA binding properties (105–106M−1binding constants) of new homologous 1,3,5-triaryl-2-pyrazolines are reported.

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Cited by 44 publications
(25 citation statements)
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“…These two features make this class of compounds more attractive than thioureas in crystal engineering. Very recently, we have highlighted these features using ferrocene-based thiosemicarbazones 53 and herein as a continuation of the previous work and our continuous research interests in the study of non-covalent interactions, [54][55][56][57] we report the synthesis of new structurally related coumarin-thiosemicarbazone hybrid molecules 3a-3c and using these molecules as a platform, demonstrate the robustness of the thioamide dimer {Á Á ÁH-N-CQS} 2 synthon of thiosemicarbazones. The purpose of introducing a freely rotatable coumarin moiety into these structures is to create a flexible environment for different possible non-covalent interactions.…”
Section: Introductionmentioning
confidence: 88%
“…These two features make this class of compounds more attractive than thioureas in crystal engineering. Very recently, we have highlighted these features using ferrocene-based thiosemicarbazones 53 and herein as a continuation of the previous work and our continuous research interests in the study of non-covalent interactions, [54][55][56][57] we report the synthesis of new structurally related coumarin-thiosemicarbazone hybrid molecules 3a-3c and using these molecules as a platform, demonstrate the robustness of the thioamide dimer {Á Á ÁH-N-CQS} 2 synthon of thiosemicarbazones. The purpose of introducing a freely rotatable coumarin moiety into these structures is to create a flexible environment for different possible non-covalent interactions.…”
Section: Introductionmentioning
confidence: 88%
“…12 DNA, an important biomacromolecule in organisms, possesses most of the hereditary information and controls the biological synthesis of proteins and enzymes through replication and transcription of this information. 14 In recent years, studies on the interactions of harmful chemicals with DNA have attracted extensive attention. In general, there are three patterns of interaction of small molecules with double helix DNA in non-covalent ways: (i) embedding in stacked base pairs, thereby distorting the DNA backbone; (ii) as groove binders, causing little distortion of the DNA backbone; and (iii) interaction with the phosphate backbone of the DNA double helix, which is the weakest binding force of the three.…”
Section: Introductionmentioning
confidence: 99%
“…Keeping this in view, we very recently reported the synthesis and solid state self-assembly of 5-fluoroisatin-based hybrid molecule 1, where no intermolecular interactions were observed for fluoro substituent in the presence of N-H···O, C-H···O, C-H···N, C-H···π, π···π, C-H···Cl interactions [32]. This observation and our continuous interest in supramolecular self-assemblies [33][34][35][36][37][38][39] increased our curiosity and prompted us to introduce 4-fluoro group as a substitute to 3-methoxy on the central N-aryl ring of the rigid core of isatin-thiazoline hybrid 1 to explore the existence of fluorine-mediated interactions in isatin-based compounds. Pleasingly, the approach remained successful and herein, we report the synthesis and methanol-encapsulated layered assembly of isatin-thiazoline hybrid 2 …”
Section: Accepted Manuscriptmentioning
confidence: 90%