- Enantioselective Synthesis of Isoflavanones and Pterocarpans through a RuII-Catalyzed ATH-DKR of Isoflavones
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Noyori-Ikariya RuII complexes promoted the one-pot C=C/C=O bonds reduction of isoflavones using sodium formate as the hydrogen source through Asymmetric Transfer Hydrogenation-Dynamic Kinetic Resolution (ATH-DKR). Due to the neutral conditions employed, isoflavones with different substituents at the 2’-position of B-ring (H, OH, OMe and Br) were successfully reduced. Ten cis-3-phenylchroman-4-ols were selectively obtained (>20 : 1 dr) in good yields (up to 86 %) and excellent enantioselectivities (up to >99 : 1 er). The synthetic applications of these chiral compounds were also demonstrated. Enantioenriched isoflavanones were obtained under mild metal-free oxidation of the cis-3-phenylchroman-4-ols while pterocarpans were synthesized by two strategies: an acid-catalyzed cyclization and a novel approach based on a Pd-catalyzed C?O intramolecular cross-coupling reaction.
- Caleffi, Guilherme S.,Costa, Paulo R. R.,Costa-Júnior, Paulo C. T.,Gaspar, Francisco V.
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p. 5097 - 5108
(2021/10/20)
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- Design, synthesis and biological evaluation of novel 3-substituted 4-anilino-coumarin derivatives as antitumor agents
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Various 3-substituted 4-anilino-coumarin derivatives have been designed, synthesized and their anti-proliferative properties have been studied. The in vitro cytotoxicity screening was performed against MCF-7, HepG2, HCT116 and Panc-1 cancer cell lines by MTT assay. Most of the synthesized compounds exhibited comparable anti-proliferative activity to the positive control 5-Fluorouracil against these four tested cancer cell lines. Among the different substituents at C-3 position of coumarin scaffold, 3-trifluoroacetyl group showed the most promising results. Especially, compounds 33d (IC50?=?16.57, 5.45, 4.42 and 5.16?μM) and 33e (IC50?=?20.14, 6.71, 4.62 and 5.62?μM) showed excellent anti-proliferative activities on MCF-7, HepG2, HCT116 and Panc-1 cell lines respectively. In addition, cell cycle analysis and apoptosis activation revealed that 33d induced G2/M phase arrest and apoptosis in MCF-7 cells in a dose-dependent manner. Low toxicity of compounds 33d and 33e was observed against human umbilical vein endothelial cells (HUVECs), suggesting their acceptable safety profiles in normal cells. Furthermore, the results of in silico ADME studies indicated that both 33d and 33e exhibited good pharmacokinetic properties.
- Luo, Guoshun,Muyaba, Moses,Lyu, Weiting,Tang, Zhichao,Zhao, Ruheng,Xu, Qian,You, Qidong,Xiang, Hua
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p. 867 - 874
(2017/02/18)
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- 3-aryl-4-arylamine-coumarin derivative and preparing method and medical application thereof
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The invention relates to the field of medicinal chemistry, in particular to a series of 3-aryl-4-arylamine-coumarin derivatives and a preparing method and medical application thereof, especially medicine applied to curing cancer like breast cancer. A structural formula of a 3-aryl-4-arylamine-coumarin derivative compound is as follow, and definitions of all radical groups in the formula are shown in instructions in details. The structural formula is shown in the specification.
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- Synthesis and structure-activity relationship study of deoxybenzoins on relaxing effects of porcine coronary artery
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Deoxybenzoins are potent antioxidants and tyrosinase inhibitors with potential to be developed as food preservatives and cosmetic ingredients. To explore the potential in cardiovascular protection, 25 polyphenolic deoxybenzoins were synthesized and evaluated for inhibitory effects on KCl-induced porcine coronary arterial contraction. The results revealed deoxybenzoins are significant inhibitors of KCl-induced arterial contraction. Among those synthesized, two-thirds of the deoxybenzoins exhibited moderate to good efficacy on relaxing contracted artery including 2,4-dihydroxydeoxybenzoin with EC50 = 3.30 μM (Emax = 100%, n = 7) and 2,4-dihydroxy-4′-methoxydeoxybenzoin EC50 = 3.70 μM (E max = 100%, n = 5). Deoxybenzoins displayed an endothelium-dependent relaxing manner on the contracted artery; the contractile responses of neither endothelium denuded nor L-NAME deactivated rings were inhibited. The structure-activity relationships of deoxybenzoin on arterial relaxing effects concluded that the 2,4-dihydroxylated deoxybenzoins presented a potential vascular relaxing pharmacophore, with favoring substitution on ring B in the order of H ≤ p-OMe > p-OH > o-OMe > m,p-diOMe ≤ m-OMe.
- Lu, Tzy-Ming,Kuo, Daih-Huang,Ko, Horng-Huey,Ng, Lean-Teik
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experimental part
p. 10027 - 10032
(2011/05/17)
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- Biocatalytic acylation studies on novel 3-aryl-3-hydroxymethyl-2, 3-dihydro-4H-1-benzopyran-4-ones
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(±)-3-Aryl-3-hydroxymethy1-2,3-dihydro-4H-1-benzopyran-4-ones have been synthesized in four steps starting with the coupling of resorcinol with corresponding phenylacetic acid leading to the formation of 2,4-dihydroxyphenyl aryl ketones, which upon monome
- Kumar, Vijayendra,Kumar, Rajesh,Raunak,Poonam,Sharma, Sunil K,Prasad, Ashok K,Cholli, Ashok L,Olsen, Carl E,Parmar, Virinder S
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p. 1501 - 1510
(2008/09/19)
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- Heteroaryl-containing isoflavones as aromatase inhibitors
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Compounds and methods useful for treating and prevention of cancer, particularly hormone-dependent breast cancer. Provided are compounds of formula I: wherein X is selected from O, N, S, SO, SO2, and S(CH2)n, wherein n=1-1
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Page/Page column 6
(2008/06/13)
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- A new series of estrogen receptor modulators: Effect of alkyl substituents on receptor-binding affinity
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New types of selective estrogen receptor modulators (SERMs) were synthesized and evaluated for their binding affinity and biological effect on reproductive cells. A proposed lead structure (B) was derivatized to provide compounds 30 and 44, which showed g
- Kamada, Atsushi,Sasaki, Atsushi,Kitazawa, Noritaka,Okabe, Tadashi,Nara, Kazumasa,Hamaoka, Shinichi,Araki, Shin,Hagiwara, Hiroaki
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- Synthesis and aromatase inhibitory activity of novel pyridine-containing isoflavones
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Aromatase, a cytochrome P450 hemoprotein that is responsible for estrogen biosynthesis by conversion of androgens into estrogens, has been an attractive target in the treatment of hormone-dependent breast cancer. As a result, a number of synthetic steroidal or nonsteroidal aromatase inhibitors have been successfully developed. In addition, there are several classes of natural products that exert potent activities in aromatase inhibition, with the flavonoids being most prominent. Previous studies have exploited flavone and flavanone scaffolds for the development of new aromatase inhibitors. In this paper, we describe the design, synthesis, and biological evaluation of a novel series of 2-(4′-pyridylmethyl)thioisoflavones as the first example of synthetic isoflavone-based aromatase inhibitors.
- Kim, Young-Woo,Hackett, John C.,Brueggemeier, Robert W.
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p. 4032 - 4040
(2007/10/03)
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- A convenient one-pot synthesis of 2-(alkylthio)isoflavones from deoxybenzoins using a phase transfer catalyst
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A convenient phase transfer catalysis procedure for the synthesis of 2-(alkylthio)isoflavones is described. A number of compounds of potential pharmaceutical interest can be prepared in a single step at ambient conditions from various, easily accessible d
- Kim, Young-Woo,Brueggemeier, Robert W
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p. 6113 - 6115
(2007/10/03)
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- An efficient 'one pot'synthesis of isoflavones
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Initial formation of deoxybenzoin 3 from phenyl acetic acid 1 and phenol 2 in the presence of BF3.Et2O followed by its treatment at room temperature with N, N'-dimethyl (chloromethylene) ammonium chloride, generated by reacting PCl5 with DMF provides a mild and efficient route for a 'one pot' synthesis of Isoflavones in high yields.
- Balasubramanian, Sreenivasan,Nair, Muraleedharan G.
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p. 469 - 484
(2007/10/03)
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- The first isolation and crystal structure of a boron difluoro complex (isoflavone yellow). Biologically active intermediates produced during isoflavone synthesis
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The yellow intermediate 4f produced during the reaction of the deoxybenzoin 3f with N,N'-dimethyl(chloromethylene)ammonium chloride in the presence of BF3*Et2O prior to the formation of the corresponding isoflavone was isolated for the first time and characterized by NMR, MS and single-crystal X-ray diffraction techniques. These yellow intermediates showed anticancer, nematicidal and mosquitocidal activities.
- Balasubramanian, Sreenivasan,Ward, Donald L.,Nair, Muraleedharan G.
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p. 567 - 570
(2007/10/03)
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