methyl 8-oxo-8-[[(1S,3R,5R,6S,8R,10R,11S,13R,15R,16S,18R,20R,21S,23R,25R,26S,28R,30R,31S,33R,35R,36R,37R,38R,39R,40R,41R,42R,43R,44R,45R,46R,47R,48R,49R)-36,37,38,39,40,41,42,43,44,45,46,47,48,49-tetradecahydroxy-10,15,20,25,30,35-hexakis(hydroxymethyl)-2,4,7,9,12,14,17,19,22,24,27,29,32,34-tetradecaoxaoctacyclo[31.2.2.23,6.28,11.213,16.218,21.223,26.228,31]nonatetracontan-5-yl]methylamino]octanoate | 1434613-10-1

分子结构分类

有机化合物 - 脂质和类脂质分子 - 糖脂

中文名称

——

中文别名

——

英文名称

methyl 8-oxo-8-[[(1S,3R,5R,6S,8R,10R,11S,13R,15R,16S,18R,20R,21S,23R,25R,26S,28R,30R,31S,33R,35R,36R,37R,38R,39R,40R,41R,42R,43R,44R,45R,46R,47R,48R,49R)-36,37,38,39,40,41,42,43,44,45,46,47,48,49-tetradecahydroxy-10,15,20,25,30,35-hexakis(hydroxymethyl)-2,4,7,9,12,14,17,19,22,24,27,29,32,34-tetradecaoxaoctacyclo[31.2.2.23,6.28,11.213,16.218,21.223,26.228,31]nonatetracontan-5-yl]methylamino]octanoate

英文别名

——

methyl 8-oxo-8-[[(1S,3R,5R,6S,8R,10R,11S,13R,15R,16S,18R,20R,21S,23R,25R,26S,28R,30R,31S,33R,35R,36R,37R,38R,39R,40R,41R,42R,43R,44R,45R,46R,47R,48R,49R)-36,37,38,39,40,41,42,43,44,45,46,47,48,49-tetradecahydroxy-10,15,20,25,30,35-hexakis(hydroxymethyl)-2,4,7,9,12,14,17,19,22,24,27,29,32,34-tetradecaoxaoctacyclo[31.2.2.23,6.28,11.213,16.218,21.223,26.228,31]nonatetracontan-5-yl]methylamino]octanoate化学式

CAS

1434613-10-1

化学式

C₅₁H₈₅NO₃₇

mdl

——

分子量

1304.22

InChiKey

GDMYVNZFJCTDSA-DJBQRYOMSA-N

BEILSTEIN

——

EINECS

——

计算性质

辛醇/水分配系数(LogP)：

-13.5
重原子数：

89
可旋转键数：

16
环数：

21.0
sp3杂化的碳原子比例：

0.96
拓扑面积：

589
氢给体数：

21
氢受体数：

37

上下游信息

上游原料

中文名称	英文名称	CAS号	化学式	分子量
单-6-O-氨基-Β-环糊精	6(I)-amino-6(I)-deoxycyclomaltoheptaose	29390-67-8	C₄₂H₇₁NO₃₄	1134.01

下游产品

中文名称	英文名称	CAS号	化学式	分子量
——	N'-hydroxy-N-[[(1S,3R,5R,6S,8R,10R,11S,13R,15R,16S,18R,20R,21S,23R,25R,26S,28R,30R,31S,33R,35R,36R,37R,38R,39R,40R,41R,42R,43R,44R,45R,46R,47R,48R,49R)-36,37,38,39,40,41,42,43,44,45,46,47,48,49-tetradecahydroxy-10,15,20,25,30,35-hexakis(hydroxymethyl)-2,4,7,9,12,14,17,19,22,24,27,29,32,34-tetradecaoxaoctacyclo[31.2.2.23,6.28,11.213,16.218,21.223,26.228,31]nonatetracontan-5-yl]methyl]octanediamide	1434613-14-5	C₅₀H₈₄N₂O₃₇	1305.21

反应信息

作为反应物：

描述：

methyl 8-oxo-8-[[(1S,3R,5R,6S,8R,10R,11S,13R,15R,16S,18R,20R,21S,23R,25R,26S,28R,30R,31S,33R,35R,36R,37R,38R,39R,40R,41R,42R,43R,44R,45R,46R,47R,48R,49R)-36,37,38,39,40,41,42,43,44,45,46,47,48,49-tetradecahydroxy-10,15,20,25,30,35-hexakis(hydroxymethyl)-2,4,7,9,12,14,17,19,22,24,27,29,32,34-tetradecaoxaoctacyclo[31.2.2.23,6.28,11.213,16.218,21.223,26.228,31]nonatetracontan-5-yl]methylamino]octanoate 在羟胺、 potassium hydroxide 作用下，以甲醇、水为溶剂，反应 24.0h，以47%的产率得到N'-hydroxy-N-[[(1S,3R,5R,6S,8R,10R,11S,13R,15R,16S,18R,20R,21S,23R,25R,26S,28R,30R,31S,33R,35R,36R,37R,38R,39R,40R,41R,42R,43R,44R,45R,46R,47R,48R,49R)-36,37,38,39,40,41,42,43,44,45,46,47,48,49-tetradecahydroxy-10,15,20,25,30,35-hexakis(hydroxymethyl)-2,4,7,9,12,14,17,19,22,24,27,29,32,34-tetradecaoxaoctacyclo[31.2.2.23,6.28,11.213,16.218,21.223,26.228,31]nonatetracontan-5-yl]methyl]octanediamide

参考文献：

名称：

A cyclodextrin-capped histone deacetylase inhibitor

摘要：

We have synthesized a beta-cyclodextrin (beta CD)-capped histone deacetylase (HDAC) inhibitor 3 containing an alkyl linker and a zinc-binding hydroxamic acid motif. Biological evaluation (HDAC inhibition studies) of 3 enabled us to establish the effect of replacing an aryl cap (in SAHA (vorinostat,)) 1 by a large saccharidic scaffold "cap''. HDAC inhibition was observed for 3, to a lesser extent than SAHA, and rationalized by molecular docking into the active site of HDAC8. However, compound 3 displayed no cellular activity. (C) 2013 Elsevier Ltd. All rights reserved.

DOI：

10.1016/j.bmcl.2013.03.084
作为产物：

描述：

甲基8-氯-8-氧代辛酸、单-6-O-氨基-Β-环糊精在吡啶作用下，反应 24.0h，以44%的产率得到methyl 8-oxo-8-[[(1S,3R,5R,6S,8R,10R,11S,13R,15R,16S,18R,20R,21S,23R,25R,26S,28R,30R,31S,33R,35R,36R,37R,38R,39R,40R,41R,42R,43R,44R,45R,46R,47R,48R,49R)-36,37,38,39,40,41,42,43,44,45,46,47,48,49-tetradecahydroxy-10,15,20,25,30,35-hexakis(hydroxymethyl)-2,4,7,9,12,14,17,19,22,24,27,29,32,34-tetradecaoxaoctacyclo[31.2.2.23,6.28,11.213,16.218,21.223,26.228,31]nonatetracontan-5-yl]methylamino]octanoate

参考文献：

名称：

A cyclodextrin-capped histone deacetylase inhibitor

摘要：

We have synthesized a beta-cyclodextrin (beta CD)-capped histone deacetylase (HDAC) inhibitor 3 containing an alkyl linker and a zinc-binding hydroxamic acid motif. Biological evaluation (HDAC inhibition studies) of 3 enabled us to establish the effect of replacing an aryl cap (in SAHA (vorinostat,)) 1 by a large saccharidic scaffold "cap''. HDAC inhibition was observed for 3, to a lesser extent than SAHA, and rationalized by molecular docking into the active site of HDAC8. However, compound 3 displayed no cellular activity. (C) 2013 Elsevier Ltd. All rights reserved.

DOI：

10.1016/j.bmcl.2013.03.084

点击查看最新优质反应信息

文献信息

A cyclodextrin-capped histone deacetylase inhibitor

作者：Jahangir Amin、Antonino Puglisi、James Clarke、John Milton、Minghua Wang、Ronald M. Paranal、James E. Bradner、John Spencer

DOI：10.1016/j.bmcl.2013.03.084

日期：2013.6

We have synthesized a beta-cyclodextrin (beta CD)-capped histone deacetylase (HDAC) inhibitor 3 containing an alkyl linker and a zinc-binding hydroxamic acid motif. Biological evaluation (HDAC inhibition studies) of 3 enabled us to establish the effect of replacing an aryl cap (in SAHA (vorinostat,)) 1 by a large saccharidic scaffold "cap''. HDAC inhibition was observed for 3, to a lesser extent than SAHA, and rationalized by molecular docking into the active site of HDAC8. However, compound 3 displayed no cellular activity. (C) 2013 Elsevier Ltd. All rights reserved.

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