Structure-based design of flavone-based inhibitors of wild-type and T315I mutant of ABL

Choe, Hyeonjeong; Kim, Jieun; Hong, Sungwoo

doi:10.1016/j.bmcl.2013.05.095

Cited by 13 publications

(15 citation statements)

References 19 publications

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“…The first task was the selective O-alkylation of chrysin (1) at position 7 with various N-phenylchloroacetamides, such as 2-chloro-N-phenylacetamide (2), 2-chloro-N-o-tolylacetamide (3), 2-chloro-N-(2-methoxyphenyl)acetamide (4), 2-chloro-N-(3,5-dimethoxyphenyl)acetamide (5), as well as 2-chloro-N-(2-(trifluoromethyl)phenyl)acetamide (6). The "driving force" of this work was that compounds with a similar structure had previously been shown to have antitumor activity on a resistant ABL (T315I) cell line [18]. The alkylation reactions were performed in DMF using potassium carbonate as the base at room temperature (Scheme 1).…”

Section: Chemistrymentioning

confidence: 97%

“…The first task was the selective O-alkylation of chrysin (1) (6). The "driving force" of this work was that compounds with a similar structure had previously been shown to have antitumor activity on a resistant ABL (T315I) cell line [18]. The alkylation reactions were performed in DMF using potassium carbonate as the base at room temperature (Scheme 1).…”

Section: Chemistrymentioning

confidence: 99%

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Synthesis and In Vitro Anticancer Evaluation of Novel Chrysin and 7-Aminochrysin Derivatives

et al. 2020

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Chrysin is a naturally occurring flavonoid with mild anticancer activity. In this paper we report the synthesis of new chrysin derivatives alkylated with N-phenylchloroacetamides in position 7. A novel method was developed for the preparation of 7-aminochrysin derivatives via the Smiles rearrangement, resulting in diphenylamine-type compounds. In silico studies of the Smiles rearrangement were performed. We also present the in vitro antiproliferative activity of the synthesized compounds against 60 human tumor cell lines (NCI60). The most potent derivative exhibited nanomolar antitumor activity on the MCF7 cell line of breast cancer (GI50 = 30 nM) and on the HCT-15 cell line of colon cancer (GI50 = 60 nM).

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Section: Chemistrymentioning

confidence: 97%

Section: Chemistrymentioning

confidence: 99%

Synthesis and In Vitro Anticancer Evaluation of Novel Chrysin and 7-Aminochrysin Derivatives

et al. 2020

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“…Like several flavonoids, it has a number of biologic effects, of which it is important to mention its anticancer activity both as a chemopreventive and as a chemotherapeutic agent [46]. The driving force of our work was that several 7-O-modified derivatives had been found to be effective against different malignant tumor cells [47,48]. Therefore, we synthesized several new aryloxy acetamide derivatives (45)(46)(47)(48) (Figure 13).…”

Section: -Oh and 7-nh Modified Flavonoid Derivativesmentioning

confidence: 99%

“…The driving force of our work was that several 7-O-modified derivatives had been found to be effective against different malignant tumor cells [47,48]. Therefore, we synthesized several new aryloxy acetamide derivatives (45)(46)(47)(48) (Figure 13). These products were rearranged to a biphenyl amine structure via Smiles rearrangement and hydrolysis to obtain a new series of 7-aminoflavone derivatives (49-52) ( Figure 14) [49].…”

Section: -Oh and 7-nh Modified Flavonoid Derivativesmentioning

confidence: 99%

Results in Chemistry of Natural Organic Compounds. Synthesis of New Anticancer Vinca Alkaloids and Flavone Alkaloids

et al. 2020

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The antitumor indole–indoline alkaloids of the evergreen Catharanthus roseus—namely vinblastine and vincristine—are widely used in chemotherapy of cancer. Many efforts were made to synthesize more efficient derivatives with less side-effect. The 14,15-cyclopropane derivative of vinblastine was synthesized successfully by a five-step procedure starting from vindoline. Vincristine, vinorelbine and several derivatives condensed with a cyclopropane ring were synthesized. Various hybrid molecules were prepared by the coupling reaction of vindoline and methyl ester of tryptophan, which were conjugated by carrier peptides of octaarginine. Studying the halogenation reactions of vindoline and catharanthine some fluorine derivatives were obtained which showed promising antitumor activity on various tumor types. The synthesis of the Aspidospermane alkaloid bannucine and 5′-epibannucine were carried out using N-acyliminium intermediates. The same intermediate was also applied in the first synthesis of sessiline. The research group have synthesized of flavonoid alkaloids: dracocephins A and B. Further three flavonoid alkaloids, namely 8-(2”-pyrrolidinon-5′′-yl)quercetin, 6-(2′′-pyrrolidinon-5′′-yl)-(−)- and 8-(2′′-pyrrolidinon-5′′-yl)-(−)-epicatechin were prepared by acid-catalyzed regioselective Mannich reaction starting from the corresponding flavonoid precursor. Vindoline was also coupled to synthetic pharmacophores, such as triphenylphosphine and various N-heterocycles. Some of these hybrid molecules showed significant antitumor activity. Furthermore, 7-OH and 7-NH modified flavonoid derivatives were synthesized by a regioselective alkylation followed by Smiles rearrangement and hydrolysis.

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“…Atom-precise, ligand-protected metal clusters, especially those comprising Au and Ag atoms, are receiving signicant research attention owing to their excellent physicochemical properties which in turn enable their wide application in catalysis, [1][2][3][4][5][6][7] biosensing, 8,9 drug delivery, 10,11 and biological imaging. 12 While the term monolayer-protected clusters (MPCs) was used ubiquitously in the past for all thiolate-stabilized systems regardless of particle size, in this review we dene atom-precise clusters as systems that typically have discrete electronic structures that vary with size, have well dened atom counts, and contain less than several hundred metal atoms and are below 2 nm in size.…”

Section: Introductionmentioning

confidence: 99%

Activation of atom-precise clusters for catalysis

2020

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Structure-based design of flavone-based inhibitors of wild-type and T315I mutant of ABL

Cited by 13 publications

References 19 publications

Synthesis and In Vitro Anticancer Evaluation of Novel Chrysin and 7-Aminochrysin Derivatives

Synthesis and In Vitro Anticancer Evaluation of Novel Chrysin and 7-Aminochrysin Derivatives

Results in Chemistry of Natural Organic Compounds. Synthesis of New Anticancer Vinca Alkaloids and Flavone Alkaloids

Activation of atom-precise clusters for catalysis

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