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
发表期刊TETRAHEDRON
卷号72期号:8页码:1051-1057
摘要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. (C) 2015 Elsevier Ltd. All rights reserved.
部门归属[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
关键词One-pot 2 Multicomponent 5-diketopiperazines Site Selectivity Adol Condensation
学科领域Chemistry
文献类型期刊论文
条目标识符http://ir.scsio.ac.cn/handle/344004/15495
专题中科院海洋生物资源可持续利用重点实验室
通讯作者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.
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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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