153000-44-3Relevant articles and documents
Catalytic asymmetric alkylation of substituted isoflavanones
Nibbs, Antoinette E.,Baize, Amanda-Lauren,Herter, Rachel M.,Scheidt, Karl A.
supporting information; experimental part, p. 4010 - 4013 (2009/12/05)
The asymmetric alkylation of isoflavanones (3-aryl-chroman-4-ones) and protected 3-phenyl-2,3-dihydroquinolin-4(1H)-ones catalyzed by a novel cinchonidine-derived phase transfer catalyst E is reported. This functionalization occurs at the unactivated C3 methine to afford novel products that can easily be functionalized to generate more complex fused ring systems. The process accommodates a variety of isoflavanones and activated electrophiles and installs a stereogenic quaternary center in high yield and with good-to-excellent selectivity. Isoflavanones are a privileged class of natural products with a broad spectrum of biological activities including insecticidal, antimicrobial, antibacterial, estrogenic, antitumor, and anti-HIV activity. 1 Isoflavanones are also precursors for more complex natural products such as pterocarpans and rotenones.1 Given their therapeutic promise, selective strategies to access new classes of isoflavanones and related structures has high value.2 The functionalization of the C3 position could promote beneficial interactions with biological targets of interest. Specifically, an alkylation at C3 can rapidly access new members of the general class of biologically active homoisoflavanones.3
Pd-Catalyzed efficient cross-couplings of 3-iodochromones with triarylbismuths as substoichiometric multicoupling organometallic nucleophiles
Rao, Maddali L. N.,Venkatesh, Varadhachari,Jadhav, Deepak N.
experimental part, p. 2597 - 2600 (2010/01/16)
An efficient cross-coupling of 3-iodochromones with triarylbismuths under catalytic palladium conditions is reported. Triarylbismuths were employed as substoichiometric multicoupling nucleophiles for the synthesis of a variety of substituted isoflavones.
Synthesis and biological evaluation of novel 2,4,5-substituted pyrimidine derivatives for anticancer activity
Xie, Fuchun,Zhao, Hongbing,Zhao, Lizhi,Lou, Liguang,Hu, Youhong
scheme or table, p. 275 - 278 (2009/05/07)
A series of novel 2,4,5-substituted pyrimidine derivatives were synthesized and evaluated for inhibition against the human hepatocellular carcinoma BEL-7402 cancer cell line. Several compounds showed potent inhibition with an IC50 value less than 0.10 μM. Structure-activity relationships for this class of compounds at the 2- and 5-position of the pyrimidine scaffold have been elucidated. The most active compound 7gc showed good inhibition of several different human cancer cell lines with IC50 values from 0.024 to 0.55 μM.
Structural studies on bioactive compounds. 40.1 synthesis and biological properties of fluoro-, methoxyl-, and amino-substituted 3-phenyl-4H-1-benzopyran-4-ones and a comparison of their antitumor activities with the activities of related 2-phenylbenzothiazoles
Vasselin, David A.,Westwell, Andrew D.,Matthews, Charles S.,Bradshaw, Tracey D.,Stevens, Malcolm F. G.
, p. 3973 - 3981 (2007/10/03)
A new series of fluoro-, methoxyl-, and amino-substituted isoflavones have been synthesized as potential antitumor agents based on structural similarities to known flavones and isoflavones (quercetin and genistein respectively) and antitumor 2-phenylbenzothiazoles. Target compounds were synthesized using palladium-catalyzed coupling methodologies to construct the central aryl carbon-carbon single bond. The new isoflavone derivatives were tested for in vitro activity in human breast (MDA-MB-468 and MCF-7) and colon (HT29 and HCT-116) cancer cell lines. Low micromolar GI50 values were obtained in a number of cases, with the MDA-MB-468 cell line being the most sensitive overall. Notably, significant potentiation of growth inhibitory activity (GI50 1 μM for 12d, 12f, 12h, 12k, 121, 12o but not the methylene-bridged derivative 12i) was observed when MDA-MB-468 cells were co-incubated with TBDD, a powerful inducer of cytochrome P450 (CYP)-1A1 activity, suggesting that isoflavone derivatives can act as substrates for CYP1A1 bioactivation.
A general method for the synthesis of isoflavones by oxidative rearrangement of flavanones using thallium (III) perchlorate
Singh, Om V.,Kapil, Randhir S.
, p. 911 - 915 (2007/10/02)
Oxidation of flavanones with thallium(III) perchlorate in acetonitrile or dimethoxyethane leads to 2,3-aryl migration providing a general method for the synthesis of isoflavones having electron relasing as well as electron withdrawing substituents at C2-aryl ring and the mechanism in relaltion to in vivo is discussed.
