4834-72-4Relevant academic research and scientific papers
Inducing apoptosis through upregulation of p53: structure–activity exploration of anthraquinone analogs
Agbowuro, Ayodeji A.,Anifowose, Abiodun,Lu, Wen,Tan, Chalet,Tripathi, Ravi,Wang, Binghe,Yang, Xiaoxiao
, p. 1199 - 1210 (2020/06/17)
We previously reported a series of p53-elevating anthraquinone compounds with considerable cytotoxicity for acute lymphoblastic leukemia (ALL) cells. To further develop this class of compounds, we examined the effect of a few key structural features on the anticancer structure–activity relationship (SAR) in ALL cells. The active analogs showed comparable cytotoxicity and upregulation of p53 but did not induce significant downregulation of MDM2 as seen with the lead compound AQ-101, indicating the importance of the anthraquinone core scaffold for MDM2 regulation. The result from the current study not only contributes to the SAR framework of these anthraquinone derivatives but also opens up new chemical space for further optimization work.
Discovery of Cytochrome P450 4F11 Activated Inhibitors of Stearoyl Coenzyme A Desaturase
Winterton, Sarah E.,Capota, Emanuela,Wang, Xiaoyu,Chen, Hong,Mallipeddi, Prema L.,Williams, Noelle S.,Posner, Bruce A.,Nijhawan, Deepak,Ready, Joseph M.
, p. 5199 - 5221 (2018/06/13)
Stearoyl-CoA desaturase (SCD) catalyzes the first step in the conversion of saturated fatty acids to unsaturated fatty acids. Unsaturated fatty acids are required for membrane integrity and for cell proliferation. For these reasons, inhibitors of SCD represent potential treatments for cancer. However, systemically active SCD inhibitors result in skin toxicity, which presents an obstacle to their development. We recently described a series of oxalic acid diamides that are converted into active SCD inhibitors within a subset of cancers by CYP4F11-mediated metabolism. Herein, we describe the optimization of the oxalic acid diamides and related N-acyl ureas and an analysis of the structure-activity relationships related to metabolic activation and SCD inhibition.
Coumarin-surfactant modified polyoxometalate catalyzed cross dehydrogenative coupling of benzyl alcohol with the: Para -C-H of unprotected aniline
Xu, Qian,Yu, Gang,Liu, Min,Peng, Chang,Banks, M. Katherine,Xu, Weijian,Wu, Ruoxi,Lu, Yanbing
, p. 5133 - 5136 (2018/10/24)
This paper presents a novel method for synthesizing para-aminobenzophenone and its derivatives (p-ABPs) using a coumarin-surfactant modified polyoxometalate as the catalyst. Preliminary mechanistic studies indicate that the reaction has undergone an oxidative cross dehydrogenative coupling process. This method has the advantages of an easy process, a convenient raw material source, safe and green oxidants, and tolerances of several functional groups.
Direct preparation of new organozinc reagents, aminophenylzinc iodides, and their applications
Jung, Hye-Soo,Kim, Seung-Hoi
, p. 1004 - 1006 (2015/02/19)
New organozinc reagents, 4-aminophenyl zinc iodide (A) and 3-aminophenyl zinc iodide (B), have been generated easily and effectively by the direct insertion of active zinc to iodoanilines which possess acidic protons. The subsequent coupling reactions of the organozincs with various acid chlorides turned out to be an efficient tool for the preparation of aminophenyl ketones.
An air-tolerant approach to the carbonylative suzuki-miyaura coupling: Applications in isotope labeling
Ahlburg, Andreas,Lindhardt, Anders T.,Taaning, Rolf. H.,Modvig, Amalie E.,Skrydstrup, Troels
, p. 10310 - 10318 (2013/11/06)
Carbonylative Suzuki-Miyaura coupling conditions have been developed that proceed without the exclusion of oxygen and in the presence of nondegassed and nondried solvents. By adapting the method to a two-chamber setup, the direct handling of carbon monoxide, produced from stable CO precursors, is avoided. The protocol afforded the desired benzophenones with excellent functional group tolerance and in good yields. Substituting the CO precursor, in the CO-producing chamber, with its carbon-13 labeled version generated the corresponding carbon-13 labeled benzophenones. Finally, the developed system was applied in the synthesis and isotope labeling of two pharmaceuticals, nordazepam and Tricor.
Synthesis, molecular modelling and biological evaluation of 4-amino-2(1H)-quinazolinone and 2,4(1H,3H)-quinazolidone derivatives as antitumor agents
Richter, Stephanie,Gioffreda, Barbara
experimental part, p. 810 - 820 (2012/03/08)
A series of 6-benzoyl-, 6-arylthio- and 6-arylsulfonyl-4-amino-2(1H)- quinazolinones and -2,4(1H,3H)-quinazolinediones were prepared. They were evaluated in vitro for their cytotoxicity against the NCI-60 cancer cell lines. A series of 6-benzoyl-, 6-arylthio- and 6-arylsulfonyl-4-amino-2(1H)- quinazolinones and -2,4(1H,3H)-quinazolinediones were prepared. They were evaluated in vitro for their cytotoxicity against the NCI-60 cancer cell lines. Copyright
Efficient one-pot Friedel-Crafts acylation of benzene and its derivatives with unprotected aminocarboxylic acids in polyphosphoric acid
Ivanov, Iliyan,Nikolova, Stoyanka,Statkova-Abeghe, Stela
, p. 1405 - 1411 (2007/10/03)
A number of aminobenzophenones have been synthesized by acylation of benzene and its derivatives with different 2-,3-,4-aminobenzoic and 4-aminophenyl-acetic acids in polyphosphoric acid via Friedel-Crafts reaction as compounds with expected antitumor activity. Copyright Taylor & Francis Group, LLC.
CHEMICAL COMPOUNDS
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Page/Page column 133, (2008/06/13)
The present invention relates to novel compounds with a variety of therapeutic uses, more particularly novel substituted cyclic alkylidene compounds that are particularly useful for selective estrogen receptor modulation.
Envirocat EPIC(R) as a novel catalyst for acylation of anisole using benzoic acids
Bandgar,Sadavarte
, p. 2587 - 2590 (2007/10/03)
Friedel-Crafts acylation of anisole has been carried out using Envirocat EPIC(R) as a novel heterogenous catalyst and benzoic acids under reflux condition. This method is suitable for regioselective acylation of activated aromatics with benzoic acids having electron-donating substituents.
Synthesis and receptor-binding affinity of fluorotamoxifen, a possible estrogen-receptor imaging agent
Shani,Gazit,Livshitz,Biran
, p. 1504 - 1511 (2007/10/02)
Aminotamoxifen was totally synthesized from p-nitrobenzoyl chloride via a Friedel-Crafts acylation. Then, by means of a Balz-Schiemann reaction, aminotamoxifen was converted into fluorotamoxifen. The triazene variation of this conversion, with a 25% yield, enables a rapid, one-step diazotization, incorporating a fluorine atom into the phenyl ring of the tamoxifen. This reaction may be useful for the preparation of low specific activity 18F-labeled tamoxifen, for distribution, and for estrogen-receptor studies. For these in vivo and in vitro studies, fluorotamoxifen was also synthesized from p-fluorobenzoyl chloride, and its chemical intermediates were compared with estradiol and hexestrol, for their receptor binding and competition, as well as for their uterotropic activity. It is demonstrated that tamoxifen and fluorotamoxifen are strong estradiol agonists and partial hexestrol agonists, while aminotamoxifen is a weak estradiol and hexestrol agonist.
