15547-43-0Relevant academic research and scientific papers
Strong Br?nsted acid promoted asymmetric hydrogenation of isoquinolines and quinolines catalyzed by a Rh-thiourea chiral phosphine complex: Via anion binding
Wen, Jialin,Tan, Renchang,Liu, Shaodong,Zhao, Qingyang,Zhang, Xumu
, p. 3047 - 3051 (2016)
Rhodium catalyzed asymmetric hydrogenation of both isoquinolines and quinolines provides a new method to synthesize chiral tetrahydroisoquinolines and tetrahydroquinolines. By introducing strong Br?nsted acid HCl, anion binding between the substrate and t
Rare-earth-metal complexes supported by new chiral tetra-azane chelating ligands: Synthesis, characterization, and catalytic properties for intramolecular asymmetric hydroamination
Zhang, Yanyu,Yao, Wei,Li, He,Mu, Ying
, p. 4670 - 4679 (2012)
A number of new chiral tetra-azane proligands (1R,2R)-N,N′-bis(o- arylamino-benzylidene)-1,2-diaminocyclohexane ((1R,2R)-[(ArHN)C 6H4CH=N]2C6H10, Ar = 2,6-Me2C6H3 (L1H2), 2,6-Et2C6H3 (L2H2), 2,6-iPr2C6H3 (L3H 2)) have been synthesized via a nucleophilic displacement of the two fluorine atoms in (o-C6H4FCH=N)2C 6H10 with the lithium salt of the corresponding aniline derivative. Their rare-earth-metal complexes L1ScCl 2Li(THF)3 (1), L1YCl2Li(THF) 3 (2), L2YCl2Li(THF)3 (3), and L3YCl2Li(THF)2 (4) were synthesized in good yields via the salt metathesis of MCl3 (M = Sc, Y) with the dilithium salts of the ligands L1Li2(THF)4, L 2Li2(THF),4, and L3Li 2(THF)4, respectively. Further more, the two diethylamido complexes L1Y(NEt2)ClLi(THF)3 (5) and L 3Y(NEt2)ClLi(THF)2 (6) were also synthesized from reactions of the corresponding chloride complexes 2 and 4 with diethylamidolithium. The new proligands L1H2-L 3H2 and their rare-earth-metal complexes 1-6 have been characterized by elemental analyses and 1H and 13C NMR spectroscopy. The structures of complexes 1, 2, and 4 have been further confirmed by single-crystal X-ray diffraction analysis. The molecular structural analysis reveals that the metal centers in complexes 1, 2, and 4 acquire a distorted-octahedral coordination environment in their solid-state structures by sharing the chloride with a LiCl(THF)n moiety. After in situ treatment with nBuLi or Me3SiCH2Li, complexes 1-4 show reasonable catalytic activity and good enantioselectivity (up to 90%) for intramolecular asymmetric hydroamination reactions of terminal aminoalkenes. The amido complexes 5 and 6 can catalyze the intramolecular hydroamination reaction directly and show catalytic activities and enantioselectivities similar to those of the in situ formed alkyl complexes.
NEW ISOINDOLINE OR ISOQUINOLINE COMPOUNDS, A PROCESS FOR THEIR PREPARATION AND PHARMACEUTICAL COMPOSITIONS CONTAINING THEM
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Page/Page column 36, (2015/02/19)
Compounds of formula (I): (I) wherein Het, R3, R4, R5, R7, R8, R9, T, p, p', q, and q' are as defined in the description are pro-apoptotic agents useful in the treatment of cancers and of a
A Chiral Synthesis of Four Stereoisomers of 1,3-Dimethyl-1,2,3,4-tetrahydroisoquinoline, an Inducer of Parkinson-like Syndrome
Toda, Jun,Matsumoto, Shinobu,Saitoh, Toshiaki,Sano, Takehiro
, p. 91 - 98 (2007/10/03)
Four stereoisomers of 1,3-dimethyl-1,2,3,4-tetrahydroisoquinoline, an inducer of Parkinson-like syndrome, were synthesized by applying a new method of 1,2,3,4-tetrahydroisoquinoline (TIQ) synthesis utilizing the Pummerer reaction as a key step. The chiral centers at C-1 and C-3 were constructed by two routes starting from alaninol (3) and 1-phenylethylamine (4) as a chiral source. Enantiomerically pure 1,3-dimethyl-TIQs (1R,3S)-(1), (1S,3R)-(ent-1), (1S,3S)-(2), and (1R,3R)-(ent-2) were prepared in a stereochemically unambiguous manner from 3 in 11 steps (route I) and from 4 in 6 steps (route II). The conformations of tetrahydroisoquinoline ring in 1-methyl, 3-methyl, and 1,3-dimethyl-TIQs were discussed on the basis of their CD, 1H-NMR spectra, and steric energies.
Effect of ring size or an additional heteroatom on the potency and selectivity of bicyclic benzylamine-type inhibitors of phenylethanolamine N- methyltransferase
Grunewald, Gary L.,Dahanukar, Vilas H.,Ching, Piao,Criscione, Kevin R.
, p. 3539 - 3546 (2007/10/03)
In the search for potent and selective inhibitors of the enzyme phenylethanolamine N-methyltransferase (PNMT; EC 2.1.1.28), we examined the effect of ring size or an additional heteroatom in the conformationally- restricted benzylamine-type PNMT inhibitors. Based on semiempirical calculations (MNDO) and molecular modeling studies, PNMT-inhibitory activity of these compounds seemed to be dependent on (a) the torsion angle between the plane of the aromatic ring and the endo N atom lone pair (τ2 angle), with the optimal value of τ2 being about -75°, and (b) the amount of steric bulk about the 3-position of 1,2,3,4-tetrahydroisoquinoline (5, THIQ). 2,3,4,5-Tetrahydro-1H-2-benzazepine (6) was found to have the highest selectivity (PNMT K(i) = 3.34 μM, α2 K(i) = 11 μM, selectivity = 3.2) as compared to other homologues of THIQ (PNMT K(i) = 9.67 μM, α2 K(i) = 0.35 μM, selectivity = 0.036). The higher PNMT-inhibitory activity of 6 was attributed to favorable steric interactions of the puckered methylene groups in the putative bioactive conformation of 6 at the PNMT active site, whereas unfavorable interactions of these puckered methylene groups at the α2- adrenoceptor were thought to be the cause of reduced α2 affinity of 6. No further enhancement of the selectivity of the benzazepine ring system could be obtained via introduction of a second heteroatom (N, O, S) at the 5- position in this ring system.
CD OF PRIMARY AMINES AND 1- OR 3-SUBSTITUTED TETRAHYDROISOQUINOLINES IN PRESENCE OF
Diener, Wolfgang,Frelek, Jadwiga,Snatzke, Guenther
, p. 954 - 965 (2007/10/02)
The syntheses of (S)-(-)-1,2-dimethyl-1,2,3,4-tetrahydroisoquinoline (IX) and S-(+)-2,3-dimethyl-1,2,3,4-tetrahydroisoquinoline (XVI) in optically pure form and with known absolute configuration is described.The CD and NMR spectra of these compounds and of most of their intermediates are given, and from these data could be deduced, that the N-methyl groups of the two bases IX and XVI adopt different conformations in solution, but the same (viz. axial) in their complexes with .
