7496-46-0Relevant articles and documents
Alkaloids from plants of the Nitraria genus. structure of sibiridine
Tulyaganov,Allaberdiev
, p. 292 - 293 (2003)
The new alkaloid sibiridine was isolated from the aerial parts of Nitraria sibirica and N. schoberi. Its structure was established using spectral data and chemical transformations. Its synthesis was carried out.
A new diaza-18-crown-6 ligand containing two quinolin-8-ylmethyl side arms: Crystal structures and characterization of the ligand, the protonated ligand and its mononuclear Barium(II) and dinuclear copper(II) complexes
Dalley,Xue,Bradshaw,Xian Xin Zhang,Harrison,Savage,Krakowiak,Izatt
, p. 1 - 9 (2001)
A new 7,16-bis(quinolin-8-ylmethyl)-1,4,10,13-tetraoxa-7,16-diazacyclooctadecane ligand, L, has been prepared and its crystal structure reported. In addition, the structure of the protonated ligand H2L has been determined. H2L is of interest because of interatomic interactions between the ligand and perchlorate ions. The mononuclear Ba(II) (BaL), and dinuclear Cu(II) (Cu2L) complexes of L have been prepared and their crystal structures determined. Stability constants and other thermodynamic data valid in methanol at 23 or 25° for these and several other complexes of L have been obtained. Among the metal ions studied, L forms the most stable complex with Ba2+. In addition, L selectively binds Cu2+ over Ni2+ by about 3 orders of magnitude. Some of the complexes have been studied using nmr and uv-vis spectroscopic techniques. Crystal data are given for L, space group, P21/c, a = 8.8325(14) A, b = 13.808(3) A, c = 13.310(3) A; β = 94.72(2)° Z=2, R = 0.0727; for H2L, space group, P21/c, a = 14.685(3) A, b = 15.035(6) A, c = 17.369(4) A, β = 90.366(12)°, Z = 4, R = 0.0781; for BaL, space group, Pbcn, a = 17.314(3) A, b = 9.539(2) A, c = 22.081(3) A, Z = 4, R = 0.0354; and for Cu2L, space group, Cc, a = 19.762(2) A, b = 14.413(2) A, c = 14.935(2) A, β = 98.753(12)°, Z = 4, R = 0.0564. Cu2+ forms a hydroxo-bridged dinuclear complex with L while Ba2+ forms a mononuclear complex with L in which its two side arms are not involved in complexation.
New 1,4,7,10-Tetraazacyclotridecane-11,13-dione Ligands appended with Additional Donor(s) 8-Methylquinoline(s): Crystal Structures and Characterization of their Copper(II) Complexes
Bu, Xian He,An, Dao Li,Chen, Yun Ti,Shionoya, Mitsuhiko,Kimura, Eiichi
, p. 2289 - 2296 (1995)
Two macrocyclic dioxotetraamine ligands 4-(quinolin-8-ylmethyl)-1,4,7,10-teraazacyclotridecane-11,13-dione (H2L1) and 4,7-bis(quinolin-8-ylmethyl)-1,4,7,10-tetraazacyclotridecane-11,13-dione (H2L2) have been synthesized.The resulting dioxomacrocycles readily co-ordinate Cu(2+) with concomitant double deprotonation of the ligands.The solution behaviour of the copper(II) complexes 1> 1 and 2> 2 has been studied by ESR, UV/VIS and cyclic voltammetric techniques.Remarkable red shifts were observed for the absorption band maxima of the electronic spectra of these copper(II) complexes (598 nm for 1 and 600 nm for 2) in comparison to that of unsubstituted (1,4,7,10-tetraazacyclotridecane-11,13-dione)copper(II) species (516 nm).The crystal structures of 1 and 2 (which crystallised in the form 2)2>*3H2O*MeCN) have been determined by X-ray diffraction analysis.Crystallographic data: 1, orthorhombic, space group Pcab, a = 16.260(3), b = 7.739(2), c = 27.530(9) Angstroem, Z = 8, R' = 0.061 for 2594 observed reflections with I > 3?(I); 2, triclinic, space group P, a = 12.288(3), b = 14.734(4), c = 18.005(4) Angstroem, α = 102.26(2), β = 104.26(2), γ = 107.02(2) deg, Z = 2, R' = 0.090 for 2284 observed reflections with I > 3?(I).In complex 1, the Cu atom is five-co-ordinate and forms a distorted square pyramid in which N(11) of the quinoline pendant is at the apical site.The Cu-N(11) bond is longer than the basal Cu-N bond lengths .In complex 2, the Cu(II) centre is also five-co-ordinate, with one of the quinoline pendants co-ordinating to Cu(II) from the apical position and the other pendant remaining unco-ordinated.
Effect of the linking position of a side chain in bis(quinolylmethyl)ethylenediamine as a DNA binding agent
Mikata, Yuji,Onchi, Yoko,Kishigami, Maki,Yano, Shigenobu
, p. 477 - 479 (2000)
Two bisquinoline derivatives, N,N'-bis(2-quinolylmethyl)ethylenediamine (2-BQME) and N,N'-bis(8-quinolylmethyl)ethylenediamine (8-BQME) have been synthesized, and their ability to bind to duplex DNA was studied. 8-BQME bound to DNA more strongly than 2-BQME, judging from the extent of increase in the melting temperature of duplex DNA, the UV-vis spectral change, and ethidium displacement assay. These compounds exhibited apparent AT- specificity suggesting minor groove binding in addition to intercalation.
THERAPEUTIC COMPOUNDS AND METHODS TO TREAT INFECTION
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Paragraph 0468-0469, (2019/02/13)
Disclosed herein are compounds of formula I: or a salt thereof and compositions comprising a compound of formula I or a pharmaceutically acceptable salt thereof. Also disclosed herein are methods for treating or preventing a bacterial infection in an animal comprising administering to the animal a compound of formula I or a pharmaceutically acceptable salt thereof, alone or in combination with a bacterial efflux pump inhibitor.
Metal-Free Oxidative B?N Coupling of nido-Carborane with N-Heterocycles
Yang, Zhongming,Zhao, Weijia,Liu, Wei,Wei, Xing,Chen, Meng,Zhang, Xiao,Zhang, Xiaolei,Liang, Yong,Lu, Changsheng,Yan, Hong
supporting information, p. 11886 - 11892 (2019/07/18)
A general method for the oxidative substitution of nido-carborane (7,8-C2B9H12?) with N-heterocycles has been developed by using 2,3-dichloro-5,6-dicyanobenzoquinone (DDQ) as an oxidant. This metal-free B?N coupling strategy, in both inter- and intramolecular fashions, gave rise to a wide array of charge-compensated, boron-substituted nido-carboranes in high yields (up to 97 %) with excellent functional-group tolerance under mild reaction conditions. The reaction mechanism was investigated by density-functional theory (DFT) calculations. A successive single-electron transfer (SET), B?H hydrogen-atom transfer (HAT), and nucleophilic attack pathway is proposed. This method provides a new approach to nitrogen-containing carboranes with potential applications in medicine and materials.
A general method for the metal-free, regioselective, remote C-H halogenation of 8-substituted quinolines
Motati, Damoder Reddy,Uredi, Dilipkumar,Watkins, E. Blake
, p. 1782 - 1788 (2018/02/23)
An operationally simple and metal-free protocol for geometrically inaccessible C5-H halogenation of a range of 8-substituted quinoline derivatives has been established. The reaction proceeds under air, with inexpensive and atom economical trihaloisocyanuric acid as a halogen source (only 0.36 equiv.), at room temperature. Exceptionally high generality with respect to quinoline is observed, and in most instances, the reaction proceeded with complete regioselectivity. Quinoline with a variety of substituents at the 8-position gave, exclusively, the C5-halogenated product in good to excellent yields. Phosphoramidates, tertiary amides, N-alkyl/N,N-dialkyl, and urea derivatives of quinolin-8-amine as well as alkoxy quinolines were halogenated at the C5-position via remote functionalization for the first time. This methodology provides a highly economical route to halogenated quinolines with excellent functional group tolerance, thus providing a good complement to existing remote functionalization methods of quinolin-8-amide derivatives and broadening the field of remote functionalization. The utility of the method is further showcased through the synthesis of several compounds of biological and pharmaceutical interest.
Unprecedented Reaction Pathway of Sterically Crowded Calcium Complexes: Sequential C?N Bond Cleavage Reactions Induced by C?H Bond Activations
Yang, Yang,Wang, Haobing,Ma, Haiyan
, p. 239 - 247 (2017/02/05)
Five bis(quinolylmethyl)-(1H-indolylmethyl)amine (BQIA) compounds, that is, {(quinol-8-yl-CH2)2NCH2(3-Br-1H-indol-2-yl)} (L1H) and {[(8-R3-quinol-2-yl)CH2]2NCH(R2)[3-R1-1H-indol-2-yl]} (L2–5H) (L2H: R1=Br, R2=H, R3=H; L3H: R1=Br, R2=H, R3=iPr; L4H: R1=H, R2=CH3, R3=iPr; L5H: R1=H, R2=nBu, R3=iPr) were synthesized and used to prepare calcium complexes. The reactions of L1–5H with silylamido calcium precursors (Ca[N(SiMe2R)2]2(THF)2, R=Me or H) at room temperature gave heteroleptic products (L1, 2)CaN(SiMe3)2 (1, 2), (L3, 4)CaN(SiHMe2)2 (3 a, 4 a) and homoleptic complexes (L3, 5)2Ca (D3, D5). NMR and X-ray analyses proved that these calcium complexes were stabilized through Ca???C?Si, Ca???H?Si or Ca???H?C agostic interactions. Unexpectedly, calcium complexes ((L3–5)CaN(SiMe3)2) bearing more sterically encumbered ligands of the same type were extremely unstable and underwent C?N bond cleavage processes as a consequence of intramolecular C?H bond activation, leading to the exclusive formation of (E)-1,2-bis(8-isopropylquinol-2-yl)ethane.
Pd(OAc)2-catalyzed lactonization of arylacetamides involving oxidation of C-H bonds
Uemura, Takeshi,Igarashi, Takuya,Noguchi, Moe,Shibata, Kaname,Chatani, Naoto
supporting information, p. 621 - 623 (2015/05/20)
The reaction of arylacetamides that contain a quinolin-8-ylmethylamine as the directing group with PhI(OAc)2, in the presence of Pd(OAc)2 as the catalyst, results in lactonization to give γ-lactones, the formation of which involves activation of the ortho C-H bonds, with concomitant cleavage of the directing group.
Synthesis and anti-norovirus activity of pyranobenzopyrone compounds
Pokhrel, Laxman,Kim, Yunjeong,Nguyen, Thi D.T.,Prior, Allan M.,Lu, Jianyu,Chang, Kyeong-Ok,Hua, Duy H.
supporting information; experimental part, p. 3480 - 3484 (2012/07/03)
During the last decade, noroviruses have gained media attention as the cause of large scale outbreaks of gastroenteritis on cruise ships, dormitories, nursing homes, etc. Although noroviruses do not multiply in food or water, they can cause large outbreaks because approximately 10-100 virions are sufficient to cause illness in a healthy adult. Recently, it was shown that the activity of acyl-coenzyme A:cholesterol acyltransferase-1 (ACAT1) enzyme may be important in norovirus infection. In search of anti-noroviral agents based on the inhibition of ACAT1, we synthesized and evaluated the inhibitory activities of a class of pyranobenzopyrone molecules containing amino, pyridine, substituted quinolines, or 7,8-benzoquinoline nucleus. Three of the sixteen evaluated compounds possess ED50 values in the low micrometer range. 2-Quinolylmethyl derivative 3A and 4-quinolylmethyl derivative 4A showed ED50 values of 3.4 and 2.4 μM and TD50 values of >200 and 96.4 μM, respectively. The identified active compounds are suitable for further modification for the development of anti-norovirus agents.
