23950-59-6Relevant academic research and scientific papers
Stereoselective formation of eight-membered rings by radical cyclization of silylenedioxy-tethered bis-methacrylate derivatives
Meng, Fan-Yi,Huang, Shou-Ling,Liu, Yi-Hung,Hu, Ziqiang,Lai, Guoqiao,Luh, Tien-Yau
, p. 2869 - 2873 (2015)
Radical-initiated addition of CCl4, Cl3CBr, PhSH, and (TMS)3SiH to (bisisopropyl)silylenedioxy-tethered bis-methacrylate derivatives gives the corresponding eight-membered ring cyclic adducts stereoselectively. Hydrolysis
Asymmetric Total Synthesis of (-)-Spirochensilide A
Liang, Xin-Ting,Chen, Jia-Hua,Yang, Zhen
, p. 8116 - 8121 (2020)
An asymmetric total synthesis of (-)-spirochensilide A has been achieved for the first time. The synthesis features a semipinacol rearrangement reaction to stereoselectively construct the two-vicinal quaternary chiral centers at C8 and C10, a tungsten-med
Macrocycle embrace: Encapsulation of fluoroarenes by m-phenylene ethynylene host
Popov, Ilya,Chen, Teng-Hao,Belyakov, Sergey,Daugulis, Olafs,Wheeler, Steven E.,Miljani, Ognjen .
, p. 2750 - 2754 (2015)
We report structural characterization of a new member of m-phenylene ethynylene ring family. This shape-persistent macrocycle also co-crystallizes with hexafluoro-, 1,2,4,5-tetrafluoro-, 1,3,5-trifluoro, and 1,4-difluorobenzene. The four complexes are alm
Staphylococcus aureus rnpa inhibitors: Computational-guided design, synthesis and initial biological evaluation
Suigo, Lorenzo,Chojnacki, Michaelle,Zanotto, Carlo,Sebastián-Pérez, Victor,Morghen, Carlo De Giuli,Casiraghi, Andrea,Dunman, Paul M.,Valoti, Ermanno,Straniero, Valentina
, (2021/05/04)
Antibiotic resistance is spreading worldwide and it has become one of the most important issues in modern medicine. In this context, the bacterial RNA degradation and processing machinery are essential processes for bacterial viability that may be exploited for antimicrobial therapy. In Staphylococcus aureus, RnpA has been hypothesized to be one of the main players in these mech-anisms. S. aureus RnpA is able to modulate mRNA degradation and complex with a ribozyme (rnpB), facilitating ptRNA maturation. Corresponding small molecule screening campaigns have recently identified a few classes of RnpA inhibitors, and their structure activity relationship (SAR) has only been partially explored. Accordingly, in the present work, using computational modeling of S. aureus RnpA we identified putative crucial interactions of known RnpA inhibitors, and we used this information to design, synthesize, and biologically assess new potential RnpA inhibitors. The present results may be beneficial for the overall knowledge about RnpA inhibitors belonging to both RNPA2000-like thiosemicarbazides and JC-like piperidine carboxamides molecular classes. We evaluated the importance of the different key moieties, such as the dichlorophenyl and the piperidine of JC2, and the semithiocarbazide, the furan, and the i-propylphenyl ring of RNPA2000. Our efforts could provide a foundation for further computational-guided investigations.
Synthesis of N-trifluoromethyl amides from carboxylic acids
Flavell, Robert R.,Liu, Jianbo,Parker, Matthew F. L.,Toste, F. Dean,Wang, Sinan,Wilson, David M.
supporting information, p. 2245 - 2255 (2021/08/12)
Found in biomolecules, pharmaceuticals, and agrochemicals, amide-containing molecules are ubiquitous in nature, and their derivatization represents a significant methodological goal in fluorine chemistry. Trifluoromethyl amides have emerged as important functional groups frequently found in pharmaceutical compounds. To date, there is no strategy for synthesizing N-trifluoromethyl amides from abundant organic carboxylic acid derivatives, which are ideal starting materials in amide synthesis. Here, we report the synthesis of N-trifluoromethyl amides from carboxylic acid halides and esters under mild conditions via isothiocyanates in the presence of silver fluoride at room temperature. Through this strategy, isothiocyanates are desulfurized with AgF, and then the formed derivative is acylated to afford N-trifluoromethyl amides, including previously inaccessible structures. This method shows broad scope, provides a platform for rapidly generating N-trifluoromethyl amides by virtue of the diversity and availability of both reaction partners, and should find application in the modification of advanced intermediates.
Organocatalytic Nitroaldol Reaction Associated with Deuterium-Labeling
Yamada, Tsuyoshi,Kuwata, Marina,Takakura, Ryoya,Monguchi, Yasunari,Sajiki, Hironao,Sawama, Yoshinari
supporting information, p. 637 - 641 (2017/12/13)
A deuterium-labeling reaction of nitroalkanes in deuterium oxide and the subsequent nitroaldol reaction have been accomplished under basic and organocatalytic conditions to provide the deuterium-labeled β-nitroalcohols in high yields and high deuterium contents. β-Deuterated β-nitroalcohols could be smoothly obtained from the reaction of nitroalkanes and various electrophiles using the easily-removal basic resin WA30. Furthermore, the asymmetric nitroaldol reaction using nitromethane and α-keto esters as electrophiles in the presence of a quinine-derived organocatalyst in deuterium oxide could provide the desired β-deuterated nitroalcohol derivatives with high enantioselectivities. (Figure presented.).
Hydroxybiphenylamide GroEL/ES Inhibitors Are Potent Antibacterials against Planktonic and Biofilm Forms of Staphylococcus aureus
Kunkle, Trent,Abdeen, Sanofar,Salim, Nilshad,Ray, Anne-Marie,Stevens, McKayla,Ambrose, Andrew J.,Victorino, José,Park, Yangshin,Hoang, Quyen Q.,Chapman, Eli,Johnson, Steven M.
supporting information, p. 10651 - 10664 (2019/01/04)
We recently reported the identification of a GroEL/ES inhibitor (1, N-(4-(benzo[d]thiazol-2-ylthio)-3-chlorophenyl)-3,5-dibromo-2-hydroxybenzamide) that exhibited in vitro antibacterial effects against Staphylococcus aureus comparable to vancomycin, an antibiotic of last resort. To follow up, we have synthesized 43 compound 1 analogs to determine the most effective functional groups of the scaffold for inhibiting GroEL/ES and killing bacteria. Our results identified that the benzothiazole and hydroxyl groups are important for inhibiting GroEL/ES-mediated folding functions, with the hydroxyl essential for antibacterial effects. Several analogs exhibited >50-fold selectivity indices between antibacterial efficacy and cytotoxicity to human liver and kidney cells in cell culture. We found that MRSA was not able to easily generate acute resistance to lead inhibitors in a gain-of-resistance assay and that lead inhibitors were able to permeate through established S. aureus biofilms and maintain their bactericidal effects.
COMPOSITIONS AND METHODS FOR INHIBITION OF CATHEPSINS
-
Paragraph 0216; 0217, (2017/03/14)
This present disclosure is directed to compound of Formula I and methods of using these compounds in the treatment of conditions in which modulation of a cathepsin, particularly cathepsin L, cathepsin K, and/or cathepsin B, will be therapeutically useful.
Synthesis and biological evaluation of a water-soluble phosphate prodrug salt and structural analogues of KGP94, a lead inhibitor of cathepsin L
Parker, Erica N.,Odutola, Samuel O.,Wang, Yifan,Strecker, Tracy E.,Mukherjee, Rajeswari,Shi, Zhe,Chaplin, David J.,Trawick, Mary Lynn,Pinney, Kevin G.
supporting information, p. 1304 - 1310 (2017/06/19)
The magnitude of expression of cathepsin L, often upregulated in the tumor microenvironment, correlates with the invasive and metastatic nature of certain tumors. Inhibition of cathepsin L represents an emerging strategy for the treatment of metastatic ca
METHYLAMINE DERIVATIVES AS LYSYSL OXIDASE INHIBITORS FOR THE TREATMENT OF CANCER
-
Paragraph 00884, (2017/09/08)
Provided are compounds of the Formula (I), or a pharmaceutically acceptable salt thereof, wherein W, X, Y, Z, x, R1, R2, R3, x and n are defined in the specification. The compounds are inhibitors of lysyl oxidase (LOX) and lysyl oxidase-like (LOXL) family members (LOXL1, LOXL2, LOXL3, LOXL4) and are useful in therapy, particularly in the treatment of cancer. Also disclosed are LOX inhibitors for use in the treatment of a cancer associated with EGFR and biomarkers that predict responsiveness to a LOX inhibitor.
