160169-11-9Relevant articles and documents
Selectivity control in one-pot myrtenol amination over Au/ZrO2 by molecular hydrogen addition
Demidova, Yu. S.,Suslov,Simakova,Mozhajcev,Korchagina,Volcho,Salakhutdinov,Simakov,Murzin, D. Yu.
, p. 60 - 67 (2017)
The one-pot myrtenol amination was studied over Au (3 wt.%)/ZrO2 catalyst under mixed N2/H2 atmosphere (9 bar). The effect of hydrogen addition was explored with the aim to increase selectivity to the target amines. Hydrogen addition timing depending on myrtenol conversion and hydrogenation temperature affected selectivity to the reaction products. Hydrogen addition (1 bar) after almost complete myrtenol conversion at 100 °C increased the yield to amine up to 68% preserving C[dbnd]C bond in the initial myrtenol structure. Hydrogen addition at 180 °C irrespective of the myrtenol conversion level provoked reduction of both C[dbnd]C and C[dbnd]N bonds with formation of two diastereomers (yield up to 93%), with trans-isomer formation being preferred when hydrogen was added at almost complete myrtenol conversion. It was shown, that in the presence of a gold catalyst controlled hydrogenation of competitive C[dbnd]C and C[dbnd]N groups can be performed during one-pot alcohol amination by regulation of the reaction conditions.
The development of tyrosyl-DNA phosphodyesterase 1 (TDP1) inhibitors based on the amines combining aromatic/heteroaromatic and monoterpenoid moieties
Mozhaitsev, Evgenii,Suslov, Evgenii,Demidova, Yuliya,Korchagina, Dina,Volcho, Konstantin,Zakharenko, Alexandra,Vasil’eva, Inna,Kupryushkin, Maksim,Chepanova, Arina,Ayine-Tora, Daniel Moscoh,Reynisson, Jóhannes,Salakhutdinov, Nariman,Lavrik, Olga
, p. 597 - 605 (2019/08/26)
Background: Inhibition of the DNA repair enzyme, tyrosyl-DNA phosphodiesterase 1 (TDP1), may increase the efficacy of cancer drugs that cause damage to tumor cell DNA. Among the known TDP1 inhibitors, there are compounds containing moieties of natural substances, e.g., monoterpenoids. In this work, we synthesized several compounds containing aromatic/ heteroaromatic amines and monoterpenoid groups and assessed their TDP1 inhibition potential. Methods: Structures of all the synthesized compounds were confirmed by1H and13C NMR as well as HRMS. The TDP1 inhibitory activity of the amines was determined by real-time fluorescence oligonucleotide biosensor. Results: The synthesized secondary amines had TDP1 inhibitory activity IC50 in the range of 0.79-9.2 μM. The highest activity was found for (–)-myrtenal derivatives containing p-bromoaniline or m-(trifluoromethyl)aniline residue. Conclusion: We synthesized 22 secondary amines; of these, 17 amines are novel chemical structures. Many of the amines inhibit TDP1 activity in the low micromolar range. Therefore, these compounds are promising for further study of their antiproliferative activity in conjunction with DNA damaging drugs.
Pinane-Type Tridentate Reagents for Enantioselective Reactions: Reduction of Ketones and Addition of Diethylzinc to Aldehydes
Cherng, Yie-Jia,Fang, Jim-Min,Lu, Ta-Jung
, p. 3207 - 3212 (2007/10/03)
The reduction of aryl and alkenyl methyl ketones using lithium aluminum hydride modified with (1R,2S,3S,5A)-(+)-10-anilino-3-ethoxy-2-hydroxypinane (10b) afforded chiral secondary alcohols in 83-96% chemical yields and 50-91% ee with dominance of R enantiomers. The reduction of acetophenone in the presence of lithium iodide gave the alcohol product with higher ee. On the other hand, the addition reaction of diethylzinc to benzaldehyde using the pinane-based diols 5-9 as promoters gave 1-phenylpropanol in favor of the S enantiomer up to 88% ee. Using the pinane-based alcohols 10a-e as promoters, the R enantiomer was obtained as the major product. The addition reactions of diethylzinc to various substituted benzaldehydes, employing the diol ligands 5c and 8e, afforded predominantly the corresponding (S)-alcohols. The chiral modifiers 5-10 were prepared from (1R)-(-)-myrtenol and were readily recovered (>90%) after the asymmetric reactions. In this study, LAH reduction and Et2Zn addition are complementary methods for the preparation of optically active secondary alcohols. The ligand 10-butylanilino-2,3-dihydroxypinane 5c promoted the Et2Zn additions effectively, whereas the modifier 10-anilino-3-ethoxy-2-hydroxypinane 10b induced the LAH reductions in a highly enantioselective manner.
A New Pinane-Type Tridentate Modifier for Asymmetric Reduction of Ketones with Lithium Aluminum Hydride
Cherng, Yie-Jia,Fang, Jim-Min,Lu, Ta-Jung
, p. 89 - 92 (2007/10/02)
The reduction of aryl and alkenyl ketones using lithium aluminum hydride modified with (1R,2S,3S,5R)-(+)-10-anilino-3-ethoxy-2-hydroxypinane (3), afforded chiral secondary alcohols in 83-96percent yields and 53-97percent optical yields.The modifier 3 was
Asymmetric Reduction Using Lithium Aluminum Hydride Modified with Chiral Ligands Prepared from (1R)-(-)-β-Pinene
Lu, Ta-Jung,Liu, Shew-Wen
, p. 467 - 472 (2007/10/03)
The reduction of prochiral ketones using chiral reducing reagents, prepared from lithium aluminum hydride and (-)-(1R,2S,3S,5R)-10-anilinopinanediol (5) and (-)-(1R,2S,3S,5R)-10-N-methylanilinopinanediol (6), affords chiral secondary alcohols in useful ch
