Enantiotech Corporation Ltd.

Zhongshan, China

Enantiotech Corporation Ltd.

Zhongshan, China

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Xu L.,Sun Yat Sen University | Xu L.,Enantiotech Corporation | Huang Z.-H.,Enantiotech Corporation | Sandoval C.A.,Enantiotech Corporation | And 2 more authors.
Organic Process Research and Development | Year: 2014

A novel efficient asymmetric hydrogenation (AH) process was developed for the preparation of (R)-1-(3,5-bis(trifluoromethyl)phenyl)ethanol (3), using a catalyst Ru/(4R,5R)-(+)-4,5-bis(diphenylphosphinomethyl)-2,2-dimethyl-1,3-dioxoane-(R,R-Diop)-2R-(α-methylmethanamine)-4,7-dimethyl-1H-benzo[d]imidazole (R-D-Me-BIMAH) in toluene in the presence of potassium t-butoxide. Various hydrogenation parameters, such as ligand, solvent, and substrate-to-catalyst (S/C) ratio, were investigated. The hydrogenation was carried out for four times on a 5 kg scale at 30 atm and 25 C with S/C of 20000 with an enantiomeric excess of >89%. © 2014 American Chemical Society.


Liao S.-R.,Chinese Academy of Sciences | Qin X.-C.,Guangzhou Institutes of Biomedicine and Health | Wang Z.,Guangzhou Institutes of Biomedicine and Health | Li D.,Sun Yat Sen University | And 4 more authors.
European Journal of Medicinal Chemistry | Year: 2016

A series of novel N-1-monoallylated 2,5-diketopiperazine derivatives were designed, synthesized, and evaluated as cytotoxic agents against eight cancer cell lines by using CCK8 assay. These derivatives were substituted with methoxyphenyl groups at C-6 position, and various long alkyl side chains at C-3-position of the 2,5-diketopiperazine ring. The cytotoxic results showed that 4-methoxyphenyl group was better than 2-methoxyphenyl group as optimal substitutive group, while 3-methoxyphenyl group was not a suitable one. When the number (n value) of the methylene groups for the long alkyl side chain was 3 (compounds 1c and 3c), the derivatives had the strongest cytotoxicities. Compound 3c substituted with 4-methoxyphenyl group and pentylidene side chain exhibited strong activity (IC50=0.36-1.9 μM) against all cancer cell lines, and could obviously induce apoptosis of cancer cell line U937 at 1.0 μM after 48 h treatment. © 2016 Elsevier Masson SAS.


PubMed | Chinese Academy of Sciences, CAS South China Sea Institute of Oceanology, Sun Yat Sen University and Enantiotech Corporation
Type: | Journal: European journal of medicinal chemistry | Year: 2016

A series of novel N-1-monoallylated 2,5-diketopiperazine derivatives were designed, synthesized, and evaluated as cytotoxic agents against eight cancer cell lines by using CCK8 assay. These derivatives were substituted with methoxyphenyl groups at C-6 position, and various long alkyl side chains at C-3-position of the 2,5-diketopiperazine ring. The cytotoxic results showed that 4-methoxyphenyl group was better than 2-methoxyphenyl group as optimal substitutive group, while 3-methoxyphenyl group was not a suitable one. When the number (n value) of the methylene groups for the long alkyl side chain was 3 (compounds 1c and 3c), the derivatives had the strongest cytotoxicities. Compound 3c substituted with 4-methoxyphenyl group and pentylidene side chain exhibited strong activity (IC50=0.36-1.9M) against all cancer cell lines, and could obviously induce apoptosis of cancer cell line U937 at 1.0M after 48h treatment.


Matsuoka A.,Nagoya University | Sandoval C.A.,Enantiotech Co. | Uchiyama M.,RIKEN | Uchiyama M.,University of Tokyo | And 2 more authors.
Chemistry - An Asian Journal | Year: 2015

The global reaction route mapping (GRRM) methods conveniently define transition states in asymmetric hydrogenation and transfer hydrogenation of aromatic ketones via the [RuH{(S,S)-TsNCH(C6H5)CH(C6H5)NH2}(η6-pcymene)] intermediate. Multiple electrostatic CH/π interactions are the common motif in the preferred diastereometric structures. © 2015 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.


Li Y.,CAS Shanghai Institute of Organic Chemistry | Zhou Y.,Enantiotech Corporation Ltd. | Shi Q.,CAS Shanghai Institute of Organic Chemistry | Ding K.,CAS Shanghai Institute of Organic Chemistry | And 2 more authors.
Advanced Synthesis and Catalysis | Year: 2011

Readily available and modular hybrid amine/benzimidazole-based 1H-benzimidazole-2-methanamine (BIMA) ligands in combination with 2,3-O-isopropylidene-2,3-dihydroxy-1,4-bis(diphenylphosphino)butane (DIOP) afford efficient catalytic systems for the ruthenium(II)-catalyzed asymmetric hydrogenation (AH) of a number of aryl ketones. The AH proceeds smoothly with substrate-to-catalyst (S/C) molar ratios of up to 100,000 (TOF of 6500ah -1, 8aatm) giving chiral alcohols in up to 99% ee. © 2011 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.


Liao S.,CAS South China Sea Institute of Oceanology | Xu Y.,Shenzhen University | Tang Y.,CAS South China Sea Institute of Oceanology | Wang J.,CAS South China Sea Institute of Oceanology | And 3 more authors.
RSC Advances | Year: 2015

A small library of soluble 2,5-diketopiperazine derivatives were designed, synthesized and evaluated as antifouling agents against two species of marine organisms: Balanus amphitrite and Bugula neritina by larval attachment assay. The results showed that different derivatives had different antifouling activities. Among these compounds, 3a (EC50 = 2.5 μg mL-1), 3b (EC50 = 3.2 μg mL-1) and 3d (EC50 = 1.6 μg mL-1) had strong activities, and 2d (EC50 = 20.5 μg mL-1), 3l (EC50 = 25.0 μg mL-1) and 3m (EC50 = 18.5 μg mL-1) had moderate activities against Balanus amphitrite, but other compounds had no activities. Differently, compounds 3d (EC50 = 3.1 μg mL-1) and 3i (EC50 = 2.3 μg mL-1) exhibited strong activities, and 3a (EC50 = 11.3 μg mL-1) and 3c (EC50 = 17.2 μg mL-1) showed moderate activities against Bugula neritina, whereas other compounds had no activities. All of the active compounds had stronger antifouling activities than those of the natural product cyclo-(l-Phe-l-Pro). Compound 3d could be a new template molecule for further development as an antifouling agent because of its strong inhibitory activities against both species of fouling organisms with low or no toxicity to the environment. © The Royal Society of Chemistry 2015.


Liao S.-R.,CAS South China Sea Institute of Oceanology | Du L.-J.,Jinan University | Qin X.-C.,Chinese Academy of Sciences | Xu L.,Enantiotech Corporation | And 5 more authors.
Tetrahedron | Year: 2016

A one-pot multicomponent approach was established for site selective synthesis of novel 1,3,6-trisubstituted 3,6-diunsaturated (3Z,6Z)-2,5-diketopiperazine derivatives with high stereoselectivity. The computational studies revealed that the steric hindrances between the 2-hydrogen atoms on the aromatic rings and the carbonyl, as well as the steric repulsions between the hydrogen atoms of the CH group in the benzylidene and the CH2 group in the N-alkylative part might be responsible for the Z/E selectivity. Compound (3Z,6Z)-3h (IC50=11 nM) has a close activity to the positive compound plinabulin (IC50=15 nM) against the cancer cell line HL60. © 2015 Elsevier Ltd. All rights reserved.


Sun M.,Anhui Medical University | Lv N.,Anhui Medical University | Li Z.,Anhui Medical University | Xiong Q.,Anhui Medical University | And 2 more authors.
Journal of the Iranian Chemical Society | Year: 2016

Expanding our studies on the anti-angiogenesis activities of 2,4-disubstituted quinazoline derivatives [8], a series of novel N-(2-(quinazolin-2-yl)phenyl)benzamide (SZ) derivatives were designed and synthesized. Cytotoxicity assays indicated that most of these compounds displayed similar cytotoxicity against tumor cells in comparison with our previously reported, but showed a higher cytotoxicity against HUVECs. The SZ derivatives showed a remarkable inhibitive effect against the migration and adhesion of HUVECs, in addition to demonstrating significant in vivo anti-angiogenesis activities in the chick embryo chorioallantoic membrane (CAM) assay. The results proved that the introduction of an aryl group with a basic amide side chain on the 4′ position linked to the amide of the C-2 substituted quinazoline scaffold is an effective approach to improve the anti-angiogenic activity of quinazoline derivatives. © 2015 Iranian Chemical Society.

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