27701-23-1Relevant academic research and scientific papers
Multidimensional optimization of promising antitumor xanthone derivatives
Azevedo, Carlos M.G.,Afonso, Carlos M.M.,Sousa, Diana,Lima, Raquel T.,Helena Vasconcelos,Pedro, Madalena,Barbosa, Jo?o,Corrêa, Arlene G.,Reis, Salette,Pinto, Madalena M.M.
, p. 2941 - 2959 (2013)
A promising antitumor xanthone derivative was optimized following a multidimensional approach that involved the synthesis of 17 analogues, the study of their lipophilicity and solubility, and the evaluation of their growth inhibitory activity on four human tumor cell lines. A new synthetic route for the hit xanthone derivative was also developed and applied for the synthesis of its analogues. Among the used cell lines, the HL-60 showed to be in general more sensitive to the compounds tested, with the most potent compound having a GI50 of 5.1 μM, lower than the hit compound. Lipophilicity was evaluated by the partition coefficient (Kp) of a solute between buffer and two membrane models, namely liposomes and micelles. The compounds showed a log Kp between 3 and 5 and the two membrane models showed a good correlation (r2 = 0.916) between each other. Studies concerning relationship between solubility and structure were developed for the hit compound and 5 of its analogues.
Regioselective Fluorination of Acenes: Tailoring of Molecular Electronic Levels and Solid-State Properties
Bischof, Daniel,Tripp, Matthias W.,Hofmann, Philipp E.,Ip, Chun-Ho,Ivlev, Sergei I.,Gerhard, Marina,Koert, Ulrich,Witte, Gregor
supporting information, (2022/01/08)
Optoelectronic properties of molecular solids are important for organic electronic devices and are largely determined by the adopted molecular packing motifs. In this study, we analyzed such structure-property relationships for the partially regioselectiv
Transition-Metal-Free Decarboxylative Iodination: New Routes for Decarboxylative Oxidative Cross-Couplings
Perry, Gregory J. P.,Quibell, Jacob M.,Panigrahi, Adyasha,Larrosa, Igor
supporting information, p. 11527 - 11536 (2017/08/30)
Constructing products of high synthetic value from inexpensive and abundant starting materials is of great importance. Aryl iodides are essential building blocks for the synthesis of functional molecules, and efficient methods for their synthesis from chemical feedstocks are highly sought after. Here we report a low-cost decarboxylative iodination that occurs simply from readily available benzoic acids and I2. The reaction is scalable and the scope and robustness of the reaction is thoroughly examined. Mechanistic studies suggest that this reaction does not proceed via a radical mechanism, which is in contrast to classical Hunsdiecker-type decarboxylative halogenations. In addition, DFT studies allow comparisons to be made between our procedure and current transition-metal-catalyzed decarboxylations. The utility of this procedure is demonstrated in its application to oxidative cross-couplings of aromatics via decarboxylative/C-H or double decarboxylative activations that use I2 as the terminal oxidant. This strategy allows the preparation of biaryls previously inaccessible via decarboxylative methods and holds other advantages over existing decarboxylative oxidative couplings, as stoichiometric transition metals are avoided.
Bismuth trichloride–mediated cleavage of phenolic methoxymethyl ethers
Obaro-Best, Oghale,Reed, Jack,Norfadilah, Alya A. F. B.,Monahan, Ryan,Sunasee, Rajesh
supporting information, p. 586 - 593 (2016/06/08)
A simple and efficient method for removal of phenolic methoxymethyl ethers in the presence of 30?mol% of bismuth trichloride in acetonitrile/water is described. Notable features of the cleavage protocol entail use of an ecofriendly bismuth reagent, ease of handling, low cost, operational simplicity, and good functional group compatibility. A number of structurally varied phenolic methoxymethyl ethers were cleaved in good to excellent yields.
Pyranoxanthones: Synthesis, growth inhibitory activity on human tumor cell lines and determination of their lipophilicity in two membrane models
Azevedo, Carlos M.G.,Afonso, Carlos M.M.,Soares, José X.,Reis, Salette,Sousa, Diana,Lima, Raquel T.,Vasconcelos, M. Helena,Pedro, Madalena,Barbosa, Jo?o,Gales, Luís,Pinto, Madalena M.M.
, p. 798 - 816 (2013/10/22)
The benzopyran and dihydrobenzopyran moieties can be considered as "privileged motifs" in drug discovery being good platforms for the search of new bioactive compounds. These moieties are commonly found fused to the xanthonic scaffold belonging to the bio
Design, synthesis, and biological evaluation of β-ketosulfonamide adenylation inhibitors as potential antitubercular agents
Vannada, Jagadeshwar,Bennett, Eric M.,Wilson, Daniel J.,Boshoff, Helena I.,Barry III, Clifton E.,Aldrich, Courtney C.
, p. 4707 - 4710 (2007/10/03)
(Chemical Equation Presented) The antitubercular nucleoside antibiotics 1 and 2 were recently described that inhibit the adenylate-forming enzyme MbtA and disrupt biosynthesis of the virulence-conferring siderophore known as mycobactin in Mycobacterium tu
Synthesis and structure-activity relationship study of lamellarin derivatives
Ishibashi, Fumito,Tanabe, Shinji,Oda, Tatsuya,Iwao, Masatomo
, p. 500 - 504 (2007/10/03)
Ten derivatives (3-12) of marine alkaloid lamellarin D (1) were synthesized and evaluated for cytotoxicity against a HeLa cell line in an effort to examine their structure-activity relationships. It appeared that the hydroxyl groups at positions C-8 and C-20 of 1 were important structural requirements for cytotoxic activity, while the hydroxyl group at C-14 and the two methoxy groups at C-13 and C-21 were not necessary for the activity.
Radicicol derivatives
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, (2008/06/13)
Radicicol derivatives represented by the following formula (I) having tyrosine kinase inhibition activity or pharmacologically acceptable salts thereof: wherein R1and R2are the same or different, and each represents hydrogen, alkanoy
Synthesis of chromanes using pyruvic acid dimethylhydrazone dianion
Tapia, I.,Alcazar, V.,Moran, J. R.
, p. 2190 - 2191 (2007/10/02)
Chromanes were prepared in medium yield from methyl salicylate and the dianions of pyruvic or α-oxobutyric acid dimethylhydrazones.
