25016-02-8Relevant academic research and scientific papers
AMINE-SUBSTITUTED HETEROCYCLIC COMPOUNDS AS EHMT2 INHIBITORS, SALTS THEREOF, AND METHODS OF SYNTHESIS THEREOF
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Paragraph 01565, (2019/05/10)
The present disclosure relates to amine-substituted heterocyclic compounds. The present disclosure also relates to pharmaceutical compositions containing these compounds and methods of treating a disorder (e.g., cancer) by administering an amine-substituted heterocyclic heterocyclic compound disclosed herein or a pharmaceutical composition thereof to subjects in need thereof. The present disclosure also relates to the use of such compounds for research or other non-therapeutic purposes.
Design, synthesis and biological evaluation of antimicrobial diarylimine and –amine compounds targeting the interaction between the bacterial NusB and NusE proteins
Qiu, Yangyi,Chan, Shu Ting,Lin, Lin,Shek, Tsun Lam,Tsang, Tsz Fung,Barua, Nilakshi,Zhang, Yufeng,Ip, Margaret,Chan, Paul Kay-sheung,Blanchard, Nicolas,Hanquet, Gilles,Zuo, Zhong,Yang, Xiao,Ma, Cong
, p. 214 - 231 (2019/06/14)
Discovery of antimicrobial agents with a novel model of action is in urgent need for the clinical management of multidrug-resistant bacterial infections. Recently, we reported the identification of a first-in-class bacterial ribosomal RNA synthesis inhibitor, which interrupted the interaction between the bacterial transcription factor NusB and NusE. In this study, a series of diaryl derivatives were rationally designed and synthesized based on the previously established pharmacophore model. Inhibitory activity against the NusB-NusE binding, circular dichroism of compound treated NusB, antimicrobial activity, cytotoxicity, hemolytic property and cell permeability using Caco-2 cells were measured. Structure-activity relationship and quantitative structure–activity relationship were also concluded and discussed. Some of the derivatives demonstrated improved antimicrobial activity than the hit compound against a panel of clinically important pathogens, lowering the minimum inhibition concentration to 1–2 μg/mL against Staphylococcus aureus, including clinical strains of methicillin-resistant Staphylococcus aureus at a level comparable to some of the marketed antibiotics. Given the improved antimicrobial activity, specific inhibition of target protein-protein interaction and promising pharmacokinetic properties without significant cytotoxicity, this series of diaryl compounds have high potentials and deserve for further studies towards a new class of antimicrobial agents in the future.
Shining new light on the spiropyran photoswitch: A photocage decides between cis-trans or spiro-merocyanine isomerization
Fleming, Cassandra L.,Li, Shiming,Grotli, Morten,Andréasson, Joakim
supporting information, p. 14069 - 14072 (2018/10/31)
Photochromic molecules from the spiropyran family are known to undergo light-induced interconversion between the colorless spiro- and the colored merocyanine forms. Here, we show for the first time that small structural modifications open up for an additional photoisomerization mode: reversible cis-trans isomerization of the merocyanine. Moreover, the introduction of a photocage allows for light-activated switching between the two modes.
BICYCLIC HETEROARYL SUBSTITUTED COMPOUNDS
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Page/Page column 721, (2018/03/25)
Disclosed are compounds of Formula (I) to (VIII): (I) (II) (III) (IV) (V) (VI) (VII) (VIII); or a stereoisomer, tautomer, pharmaceutically acceptable salt, solvate or prodrug thereof, wherein R3 is a bicyclic heteroaryl group substituted with zero to 3 R3a; and R1, R2, R3a, R4, and n are defined herein. Also disclosed are methods of using such compounds as PAR4 inhibitors, and pharmaceutical compositions comprising such compounds. These compounds are useful in inhibiting or preventing platelet aggregation, and are useful for the treatment of a thromboembolic disorder or the primary prophylaxis of a thromboembolic disorder.
Synthesis of nitroolefins and nitroarenes under mild conditions
Zarei, Mahmoud,Noroozizadeh, Ehsan,Moosavi-Zare, Ahmad R.,Zolfigol, Mohammad A.
, p. 3645 - 3650 (2018/04/14)
1,3-Disulfonic acid imidazolium nitrate {[Dsim]NO3} was prepared and characterized as a new ionic liquid and nitrating agent for the ipso-nitration of various arylboronic acids and nitro-Hunsdiecker reaction of different α,β-unsaturated acids and benzoic acid derivatives, by in situ generation of NO2 to give various nitroarenes and nitroolefins without using any cocatalysts and solvents under mild conditions.
H-Bond Self-Assembly: Folding versus Duplex Formation
Nú?ez-Villanueva, Diego,Iadevaia, Giulia,Stross, Alexander E.,Jinks, Michael A.,Swain, Jonathan A.,Hunter, Christopher A.
supporting information, p. 6654 - 6662 (2017/05/29)
Linear oligomers equipped with complementary H-bond donor (D) and acceptor (A) sites can interact via intermolecular H-bonds to form duplexes or fold via intramolecular H-bonds. These competing equilibria have been quantified using NMR titration and dilution experiments for seven systems featuring different recognition sites and backbones. For all seven architectures, duplex formation is observed for homo-sequence 2-mers (AA·DD) where there are no competing folding equilibria. The corresponding hetero-sequence AD 2-mers also form duplexes, but the observed self-association constants are strongly affected by folding equilibria in the monomeric states. When the backbone is flexible (five or more rotatable bonds separating the recognition sites), intramolecular H-bonding is favored, and the folded state is highly populated. For these systems, the stability of the AD·AD duplex is 1-2 orders of magnitude lower than that of the corresponding AA·DD duplex. However, for three architectures which have more rigid backbones (fewer than five rotatable bonds), intramolecular interactions are not observed, and folding does not compete with duplex formation. These systems are promising candidates for the development of longer, mixed-sequence synthetic information molecules that show sequence-selective duplex formation.
Metal-Free Diaryl Etherification of Tertiary Amines by Ortho-C(sp2)-H Functionalization for Synthesis of Dibenzoxazepines and -ones
Jamsheena, Vellekkatt,Mahesha, Chikkagundagal K.,Joy, M. Nibin,Lankalapalli, Ravi S.
supporting information, p. 6614 - 6617 (2017/12/26)
A phenyliodine(III) diacetate mediated umpolung reactivity of the tertiary amines with suitably substituted o-hydroxybenzyl and phenyl groups is exploited to facilitate o-C(sp2)-H functionalization to afford diaryl ethers. The presence of an o-
Reaction of 3-arylidenepropenoic acid derivatives with triethylamine and other amines; Unexpected reductions and vinylogations
Harisha, Attimogae Shivamurthy,Nayak, Suresh Parameshwar,Nagarajan, Kuppuswamy,Row, Tayur Narasingarow Guru,Hosamani, Amar A.
, p. 2880 - 2889 (2016/05/24)
Exposure of ethyl 2-cyano-3-(2-methoxy-5-nitrophenyl)acrylate 1f to triethylamine in hot ethanol resulted in the formation of the dihydro derivative 2f and vinylogue 3f in high yields. Single crystal X-ray data are provided for 3f. Similar reactions were observed for various analogues. The reaction was studied changing aryl substituent, amines and solvents. Pyridyl, thienyl analogues were also examined. The study was extended to cyclic molecules incorporating such systems like thiazolidinedione 8, 3-cyanocoumarin 9 and 4-arylidene-isoquinoline-2,4-diones 11. The last group gave vinylogated products, 4-cinnamylidene-isoquinolinediones and 4-hydroxylated species. A few examples of arylidene derivatives from malononitrile, ethyl acetoacetate, acetyl acetone and ethyl methylsufonylacetate were investigated. Ethyl cinnamate and β-nitrostyrene were unaffected. The reaction is considered to be possibly radical mediated, since addition of free radical quencher suppressed the reaction. Contrary to the effects of thermal conditions, irradiation of 1f in ethanol at 254 and 365 nm gave complex mixtures. A few other interesting observations in this study are noted: vinylogation of 1f with acetaldehyde to 3f; formation of 3f from 1f by the treatment with triethylamine, palladium carbon and reduction of 1f to 2f by triethylammonium formate in DMF.
Highly Active Multidentate Catalysts for Efficient Alkyne Metathesis
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Paragraph 0166; 0167, (2013/10/08)
The invention relates to highly active and selective catalysts for alkyne metathesis. In one aspect, the invention includes a multidentate organic ligand wherein one substrate-binding site of the metal center is blocked. In another aspect, the invention includes N-quaternized or silane-based multidentate organic ligands, capable of binding to metals. In yet another aspect, the invention includes N-quaternized or silane-based multidentate catalysts. The catalysts of the invention show high robustness, strong resistance to small alkyne polymerization and significantly enhanced catalytic activity compared to their corresponding non-quaternized or non-silane-based multidentate catalyst analogues.
Introducing a podand motif to alkyne metathesis catalyst design: A highly active multidentate molybdenum(VI) catalyst that resists alkyne polymerization
Jyothish, Kuthanapillil,Zhang, Wei
supporting information; experimental part, p. 3435 - 3438 (2011/05/04)
Podand prevents polymers: The molybdenum(VI) propylidyne catalyst 1 with a podand triphenolamine ligand shows high activity in the metathesis of a variety of alkyne substrates, including heterocycles that contain donor moieties. With one substrate-binding site blocked by the multidentate ligand, the undesired polymerization of small alkynes that occurs with non-podand-ligand complex 2 is completely inhibited. Copyright
