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Site selective synthesis of cytotoxic 1,3,6-trisubstituted 3,6-diunsaturated (3Z,6Z)-2,5-diketopiperazines via a one-pot multicomponent method
Liao, Sheng-Rong; Du, Li-Juan; Qin, Xiao-Chu; Xu, Liang; Wang, Jun-Feng; Zhou, Xue-Feng; Tu, Zheng-Chao; Li, Juan; Liu, Yong-Hong; Liu, YH (reprint author), Chinese Acad Sci, South China Sea Inst Oceanol, CAS Key Lab Trop Marine Bioresources & Ecol, Guang Dong Key Lab Marine Mat Med,Res Ctr Marine, Guangzhou 510301, Guangdong, Peoples R China.; Li, J (reprint author), Jinan Univ, Dept Chem, Guangzhou 510632, Guangdong, Peoples R China.
2016
Source PublicationTETRAHEDRON
Volume72Issue:8Pages:1051-1057
AbstractA 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. (C) 2015 Elsevier Ltd. All rights reserved.
Department[Liao, Sheng-Rong; Wang, Jun-Feng; Zhou, Xue-Feng; Liu, Yong-Hong] Chinese Acad Sci, South China Sea Inst Oceanol, CAS Key Lab Trop Marine Bioresources & Ecol, Guang Dong Key Lab Marine Mat Med,Res Ctr Marine, Guangzhou 510301, Guangdong, Peoples R China; [Du, Li-Juan; Li, Juan] Jinan Univ, Dept Chem, Guangzhou 510632, Guangdong, Peoples R China; [Qin, Xiao-Chu; Tu, Zheng-Chao] Chinese Acad Sci, Guangzhou Inst Biomed & Hlth, Lab Mol Engn, Guangzhou 510530, Guangdong, Peoples R China; [Qin, Xiao-Chu; Tu, Zheng-Chao] Chinese Acad Sci, Guangzhou Inst Biomed & Hlth, Lab Nat Prod Synth, Guangzhou 510530, Guangdong, Peoples R China; [Xu, Liang] Enantiotech Corp Ltd, Zhongshan Torch Hitech, Ind Dev Zone 528437, Zhongshan, Peoples R China ; LMB
KeywordOne-pot 2 Multicomponent 5-diketopiperazines Site Selectivity Adol Condensation
Subject AreaChemistry
Document Type期刊论文
Identifierhttp://ir.scsio.ac.cn/handle/344004/15495
Collection中科院海洋生物资源可持续利用重点实验室
Corresponding AuthorLiu, YH (reprint author), Chinese Acad Sci, South China Sea Inst Oceanol, CAS Key Lab Trop Marine Bioresources & Ecol, Guang Dong Key Lab Marine Mat Med,Res Ctr Marine, Guangzhou 510301, Guangdong, Peoples R China.; Li, J (reprint author), Jinan Univ, Dept Chem, Guangzhou 510632, Guangdong, Peoples R China.
Recommended Citation
GB/T 7714
Liao, Sheng-Rong,Du, Li-Juan,Qin, Xiao-Chu,et al. Site selective synthesis of cytotoxic 1,3,6-trisubstituted 3,6-diunsaturated (3Z,6Z)-2,5-diketopiperazines via a one-pot multicomponent method[J]. TETRAHEDRON,2016,72(8):1051-1057.
APA Liao, Sheng-Rong.,Du, Li-Juan.,Qin, Xiao-Chu.,Xu, Liang.,Wang, Jun-Feng.,...&Li, J .(2016).Site selective synthesis of cytotoxic 1,3,6-trisubstituted 3,6-diunsaturated (3Z,6Z)-2,5-diketopiperazines via a one-pot multicomponent method.TETRAHEDRON,72(8),1051-1057.
MLA Liao, Sheng-Rong,et al."Site selective synthesis of cytotoxic 1,3,6-trisubstituted 3,6-diunsaturated (3Z,6Z)-2,5-diketopiperazines via a one-pot multicomponent method".TETRAHEDRON 72.8(2016):1051-1057.
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