70709-65-8Relevant academic research and scientific papers
A Bisphenolic Honokiol Analog Outcompetes Oral Antimicrobial Agent Cetylpyridinium Chloride via a Membrane-Associated Mechanism
Ochoa, Cristian,Solinski, Amy E.,Nowlan, Marcus,Dekarske, Madeline M.,Wuest, William M.,Kozlowski, Marisa C.
, p. 74 - 79 (2019/11/20)
Targeting Streptococcus mutans is the primary focus in reducing dental caries, one of the most common maladies in the world. Previously, our groups discovered a potent bactericidal biaryl compound that was inspired by the natural product honokiol. Herein, a structure activity relationship (SAR) study to ascertain structural motifs key to inhibition is outlined. Furthermore, mechanism studies show that bacterial membrane disruption is central to the bacterial growth inhibition. During this process, it was discovered that analog C2 demonstrated a 4-fold better therapeutic index compared to the commercially available antimicrobial cetylpyridinium chloride (CPC) making it a viable alternative for oral care.
Synthesis of potential bisphenol A substitutes by isomerising metathesis of renewable raw materials
Trita,Over,Pollini,Baader,Riegsinger,Meier,Goo?en
supporting information, p. 3051 - 3060 (2017/07/15)
Isomerising metathesis is introduced as a sustainable method to produce dihydroxystilbene derivatives from eugenol, a clove oil ingredient, and cardanol from cashew nut shell liquid. Hydrogenation of the dihydroxystilbenes provided their di(hydroxyphenyl)ethane analogues. Initial studies to convert these monomers into polycarbonates and thiol-ene polymers support their potential to replace the petrol-derived bisphenol A (BPA). The estrogenic activity of the monomers derived from cardanol was found to be in the same range as that of BPA, a known endocrine disruptor. In contrast, eugenol-derived materials were found to be non-estrogenic, opening up new perspectives for bio-based food packaging materials.
Inhibitory effect of cytotoxic stilbenes related to resveratrol on the expression of the VEGF, hTERT and c-Myc genes
Martí-Centelles, Rosa,Falomir, Eva,Murga, Juan,Carda, Miguel,Marco, J. Alberto
supporting information, p. 488 - 496 (2015/10/05)
A group of thirty-nine stilbene derivatives, prepared by means of Heck coupling reactions, has been investigated for their cytotoxicity, as well as for their ability to inhibit the production of the vascular endothelial growth factor (VEGF) and the activation of telomerase. The ability of these compounds to inhibit proliferation of two tumoral cell lines (HT-29 and MCF-7) and one non tumoral cell line (HEK-293) was first determined. Subsequently, we determined the capacity of the compounds to inhibit the secretion of VEGF in the aforementioned cell lines and to downregulate the expression of the VEGF, hTERT and c-Myc genes, the two latter involved in the control of the activation of telomerase. One of the synthetic stilbenes, (E)-4-(4-methoxystyryl)aniline, showed strong cytotoxicity and proved able to cause a marked decrease both in the secretion of VEGF and in the expression of the hTERT and c-Myc genes, in all cases at concentrations in the low nanomolar range.
Identification of novel SAR properties of the Jak2 small molecule inhibitor G6: Significance of the para-hydroxyl orientation
Baskin, Rebekah,Gali, Meghanath,Park, Sung O.,Zhao, Zhizhuang Joe,Keser, Gy?rgy M.,Bisht, Kirpal S.,Sayeski, Peter P.
supporting information; experimental part, p. 1402 - 1407 (2012/04/04)
In this study, we analyzed the structure-activity relationship properties of the small molecule Jak2 inhibitor G6. We synthesized a set of derivatives containing the native para-hydroxyl structure or an alternative meta-hydroxyl structure and examined their Jak2 inhibitory properties. We found that the para-hydroxyl derivative known as NB15 had excellent Jak2 inhibitory properties in silico, in vitro, and ex vivo when compared with meta-hydroxyl derivatives. These results indicate that NB15 is a potent derivative of the Jak2 inhibitor G6, and that maintaining the para-hydroxyl orientation of G6 is critical for its Jak2 inhibitory potential.
Ionic-liquid-influenced expeditious and stereoselective synthesis of olefins
Bhilare, Sachin V.,Darvatkar, Nitin B.,Deorukhkar, Amol R.,Rasalkar, Meghana S.,Salunkhe, Manikrao M.
, p. 3111 - 3117 (2008/02/12)
1-Butyl-3-methylimidazolium chloroaluminate, [bmim]Cl·.AlCl3 (molar fraction, N=0.67), ionic liquid has been used in combination with metallic Zn for the reductive coupling of carbonyl compounds to synthesize symmetrical olefins, with the Z-isomer formed predominantly. The ionic liquid played a dual role of Lewis acid catalyst and solvent. Copyright Taylor & Francis Group, LLC.
A facile and catalytic method for selective deprotection of tert-butyldimethylsilyl ethers with copper(II) bromide
Bhatt, Suchitra,Nayak, Sandip K.
, p. 8395 - 8399 (2007/10/03)
Copper(II) bromide is found to be a simple and efficient catalyst for selective deprotection of tert-butyldimethylsilyl ethers of alcohols/phenols at ambient temperature. Various labile functional groups such as ketal, alkene, ketone, OTBDPS, OTHP and allyl and benzyl ethers are found to be compatible under the reaction conditions.
Synthesis and Protein-Tyrosine Kinase Inhibitory Activity of Polyhydroxylated Stilbene Analogues of Piceatannol
Thakkar, Kshitij,Geahlen, Robert L.,Cushman, Mark
, p. 2950 - 2955 (2007/10/02)
A series of hydroxylated trans-stilbene related to the antileukemic natural product trans-3,3',4,5'-tetrahydroxy stilbene (piceatannol) (1) has been prepared and tested for inhibition of the lymphoid cell lineage-specific protein-tyrosine kinase p56lck, which plays an important role in lymphocyte proliferation and immune function.A number of the analogues displayed enhanced enzyme inhibitory activity relative to the natural product.Reduction of the double bond bridging the two aromatic rings and benzylation of the phenolic hydroxyl groups was found to decrease activity significantly.The most potent compounds in the series proved to be trans-3,3',5,5'-tetrahydroxystilbene, trans-3,3',5-trihydroxystilbene, and trans-3,4,4'-trihydroxystilbene.
Synthesis and nematocidal activity of hydroxystilbenes
Ali,Kondo,Tsuda
, p. 1130 - 1136 (2007/10/02)
Various (E)-hydroxystilbenes were synthesized from (E)/(Z) mixtures of methoxystilbenes through a new (Z)-(E) isomerization method followed by demethylation. The nematocidal activity appears when methoxystilbenes are demethylated to hydroxystilbenes. For this activity, a hydroxy group at the C-2 or C-3 position is necessary. Thus, 2-hydroxy-, 3-hydroxy-, 2,6-dihydroxy-, 3,4-dihydroxy-, 3,5-dihydroxy-, 2,2'-dihydroxy-, 3,3'-dihydroxy-, 3,4'dihydroxy-, 2-hydroxy-4-methoxy-, 5-hydroxy-2-methoxy-, 2-hydroxy-6-methoxy-, 6-allyloxy-2-hydroxy-, 3-hydroxy-5-methoxy-, and 5-allyloxy-3-hydroxystilbenes showed rather potent nematocidal activity. The activity of 5-allyloxy-3-hydroxystilbene was the strongest [minimal lethal concentration (MLC) = 30 μM]. The activities of the (E) and (Z) isomers were comparable. The activities were also retained, though they were weaker, in the dihydro derivatives, hydroxybibenzyls.
