536974-71-7Relevant articles and documents
Design and synthesis of π-extended resveratrol analogues and in vitro antioxidant and anti-inflammatory activity evaluation
Damodar, Kongara,Gim, Ji Geun,Jeon, Seong Ho,Lee, Jeong Tae,Lee, Yeontaek,Nam, Ki Yoon,Park, Jae Phil,Park, Lee Seul
supporting information, (2021/06/14)
The research on resveratrol (1) has been conducted intensively over a long time due to its proven antioxidant activity and disease-fighting capabilities. Many efforts have also been made to increase these biological effects. In the present study, six new extended aromatic resveratrol analogues containing naphthalene (2) and its bioisosteres quinoline (3 and 4), isoquinoline (5) quinoxaline (6) and quinazoline (7) scaffolds were designed and synthesized using an annulation strategy. The antioxidant and anti-inflammatory activities of these compounds were investigated. All compounds showed better antioxidant activity than resveratrol in ABTS assay. As for the anti-inflammatory test, 5 and 7 exhibited better activity than resveratrol. It is worth noting that nitrogen substitution on the extended aromatic resveratrol analogues has a significant impact on cell viability. Taking the antioxidant activities and NO inhibition activities into consideration, we conclude that isoquinoline analogue 5 may qualify for the further investigation of antioxidant and anti-inflammatory therapy. Furthermore, our study results suggest that in order to improve the biological activity of polyphenolic compounds, extended aromaticity and nitrogen substitution strategy could be a viable method for the design of future drug candidates.
Nickel-Catalyzed Amination of α-Aryl Methyl Ethers
Patel, Purvish,Rousseaux, Sophie A. L.
, p. 492 - 496 (2020/03/13)
α-Aryl amines are prevalent in pharmaceutically active compounds and natural products. Herein, we describe a Ni-catalyzed protocol for their synthesis from readily available α-aryl ethers. While α-aryl ethers have been used as electrophiles in Ni-catalyzed C-C bond formations, their use in C-heteroatom bond formation is much less prevalent. Preliminary mechanistic insight suggests that oxidative addition is facilitated by an anionic ligand and that reductive elimination is a reversible process.
Bicyclic derivatives of the potent dual aromatase-steroid sulfatase inhibitor 2-bromo-4-{[(4-cyanophenyl)(4H-1,2,4-triazol-4-yl)amino]methyl} phenylsulfamate: Synthesis, SAR, crystal structure, and in vitro and in vivo activities
Wood, Paul M.,Woo, L. W. Lawrence,Labrosse, Jean-Robert,Thomas, Mark P.,Mahon, Mary F.,Chander, Surinder K.,Purohit, Atul,Reed, Michael J.,Potter, Barry V. L.
experimental part, p. 1577 - 1593 (2011/12/01)
The design and synthesis of a series of bicyclic ring containing dual aromatase-sulfatase inhibitors (DASIs) based on the aromatase inhibitor (AI) 4-[(4-bromobenzyl)(4H-1,2,4-triazol-4-yl)amino] benzonitrile are reported. Biological evaluation with JEG-3 cells revealed structure-activity relationships. The X-ray crystal structure of sulfamate 23 was determined, and selected compounds were docked into the aromatase and steroid sulfatase (STS) crystal structures. In the sulfamate-containing series, compounds containing a naphthalene ring are both the most potent AI (39, IC50AROM=0.25 nm) and the best STS inhibitor (31, IC50STS=26 nm). The most promising DASI is 39 (IC50AROM= 0.25 nm, IC50STS=205 nm), and this was evaluated orally in vivo at 10 mgkg-1, showing potent inhibition of aromatase (93%) and STS (93%) after 3 h. Potent aromatase and STS inhibition can thus be achieved with a DASI containing a bicyclic ring system; development of such a DASI could provide an attractive new option for the treatment of hormone-dependent breast cancer.
Construction of a pH-driven supramolecular nanovalve
Nguyen, Thoi D.,Leung, Ken C.-F.,Liong, Monty,Pentecost, Cari D.,Stoddart, J. Fraser,Zink, Jeffrey I.
, p. 3363 - 3366 (2007/10/03)
The versatility of supramolecular chemistry has been exploited in constructing nanovalves based on mesoporous silica MCM-41 and the mutual recognition between secondary dialkylammonium ions and dibenzo[24]crown-8 (DB24C8). Naphthalene-containing dialkylam
NOVEL COMPOUNDS AND THEIR USE IN MEDICINE, PROCESS FOR THEIR PREPARATION AND PHARMACEUTICAL COMPOSITIONS CONTAINING THEM
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Page/Page column 46-47, (2010/02/11)
The present invention relates to novel compounds of formula (I) and their pharmaceutically acceptable salts thereof, pharmaceutical compositions containing them. The present invention also relates to a process for the preparation of the above said novel compounds.
Alpha substituted carboxylic acids
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, (2008/06/13)
Alpha substituted carboxylic acids of formula (I):
FURAN OR THIOPHENE DERIVATIVE AND MEDICINAL USE THEREOF
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Page/Page column 87-88, (2008/06/13)
The present invention provides a compound represented by the formula (I): [wherein R is an optionally substituted hydrocarbon group or an optionally substituted heterocyclic group, p is 0, 1 or 2, and when p is 2, each R may be the same or different, R1 is a hydrogen atom or an optionally substituted hydrocarbon group, R2 is an optionally substituted aromatic group, Ring A is an optionally substituted monocyclic aromatic ring or optionally substituted bicyclic aromatic fused ring, X1 is an oxygen atom or a sulfur atom, X2 is a bond, an oxygen atom or -S(O)n- (wherein n is 0, 1 or 2), Y is a bond, an oxygen atom, -S(O)m-, -C(=O)-N(R3)- or -N(R3)-C(=O)- (R3 is a hydrogen atom, an optionally substituted hydrocarbon group or an optionally substituted heterocyclic group, and m is 0, 1 or 2), M1, M2 and M3 may be the same or different and are each independently a bond or an optionally substituted divalent aliphatic hydrocarbon group, and M4 is an optionally substituted divalent aliphatic hydrocarbon group] or a salt thereof, which is useful as a prophylactic and/or therapeutic agent for lipid metabolism abnormality, arteriosclerotic disease and sequelae thereof, diabetes mellitus and the like.
ALPHA SUBSTITUTED CARBOXYLIC ACID AS PPAR MODULATORS
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Page 134-135, (2010/02/09)
Alpha substituted carboxylic acids of formula (I): wherein R' and R2 are as defined in the specification and R3 is A) formula (II); B) formula (III); C) formula (IV); and D) formula (V); wherein Y, Art, Are, AP, R4, R5, R6, R7, R6, R9, R9a, R10, R", R12, R17, ring A, and p are as defined in the specification; pharmaceutical compositions containing effective amounts of said compounds or their salts are useful for treating PPAR, specifically PPAR α/y related disorders, such as diabetes, dyslipidemia, obesity and inflammatory disorders.