Silvestrol aglycone; (1R,2R,3S,3aR,8bS)-2,3,3a,8b-四氢-1,6,8b-三羟基-8-甲氧基-3a-(4-甲氧基苯基)-3-苯基-1H-环戊并[b]苯并呋喃-2-甲酸甲酯 | 960365-65-5

分子结构分类

有机化合物 - 有机杂环化合物 - 苯并呋喃

中文名称

Silvestrol aglycone; (1R,2R,3S,3aR,8bS)-2,3,3a,8b-四氢-1,6,8b-三羟基-8-甲氧基-3a-(4-甲氧基苯基)-3-苯基-1H-环戊并[b]苯并呋喃-2-甲酸甲酯

中文别名

(1R,2R,3S,3AR,8BS)-2,3,3A,8B-四氢-1,6,8B-三羟基-8-甲氧基-3A-(4-甲氧基苯基)-3-苯基-1H-环戊并[B]苯并呋喃-2-甲酸甲酯

英文名称

(1R,2R,3S,3aR,8bS)-methyl 1,6,8b-trihydroxy-8-methoxy-3a-(4-methoxyphenyl)-3-phenyl-2,3,3a,8b-tetrahydro-1H-cyclopenta[b]benzofuran-2-carboxylate

英文别名

(1R,2R,3S,3aR,8bS)-methyl 1,6,8b-trihydroxy-8-methoxy-3a-(4-methoxyphenyl)-3-phenyl-2,3,3a,8b-tetrahydro-1H-benzo[b]-cyclopenta[d]furan-2-carboxylate；Silvestrol aglycone；methyl (1R,2R,3S,3aR,8bS)-1,6,8b-trihydroxy-8-methoxy-3a-(4-methoxyphenyl)-3-phenyl-2,3-dihydro-1H-cyclopenta[b][1]benzofuran-2-carboxylate

Silvestrol aglycone; (1R,2R,3S,3aR,8bS)-2,3,3a,8b-四氢-1,6,8b-三羟基-8-甲氧基-3a-(4-甲氧基苯基)-3-苯基-1H-环戊并[b]苯并呋喃-2-甲酸甲酯化学式

CAS

960365-65-5

化学式

C₂₇H₂₆O₈

mdl

——

分子量

478.499

InChiKey

HYLOONIBWUNKDH-PXIJUOARSA-N

BEILSTEIN

——

EINECS

——

物化性质

熔点：

127-129℃
沸点：

645.4±55.0 °C(Predicted)
密度：

1.408
溶解度：

二甲基亚砜：≥106mg/mL（221.53mM）

计算性质

辛醇/水分配系数(LogP)：

2.9
重原子数：

35
可旋转键数：

6
环数：

5.0
sp3杂化的碳原子比例：

0.3
拓扑面积：

115
氢给体数：

3
氢受体数：

8

安全信息

储存条件：

2-8℃

制备方法与用途

生物活性

Silvestrol aglycone 是 Silvestrol 的类似物，能够抑制癌细胞蛋白翻译起始。其对蛋白翻译荧光素酶报告基因 yc-LUC 和 tub-LUC 的 EC50 值分别为 10 nM 和 200 nM，并具有抗癌作用。

体外研究

Silvestrol aglycone（化合物4）在72小时后抑制 MDA-MB-231 细胞增殖的半数有效浓度 (E50) 为 20 ± 10 nM。

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
——	[7-benzyloxy-5-methoxy-2-(4-methoxyphenyl)-4-oxochromen-3-yl] 4-methoxybenzoate	1402931-30-9	C₃₂H₂₆O₈	538.554

下游产品

中文名称	英文名称	CAS号	化学式	分子量
(1R,2R,3S,3aR,8bS)-1,8b-二羟基-6,8-二甲氧基-3a-(4-甲氧基苯基)-3-苯基-2,3-二氢-1H-环戊并[b][1]苯并呋喃-2-羧酸甲酯	aglafoline	143901-35-3	C₂₈H₂₈O₈	492.526
——	(1R,2R,3S,3aR,8bS)-methyl 1,8b-dihydroxy-8-methoxy-3a-(4-methoxyphenyl)-3-phenyl-2,3,3a,8b-tetrahydro-1H-benzo[b]-cyclopenta[d]furan-2-carboxylate	1402931-63-8	C₂₇H₂₆O₇	462.499
——	rocagloic acid	190385-15-0	C₂₇H₂₆O₈	478.499
——	(1R,2R,3S,3aR,8bS)-methyl 6-chloro-1,8b-dihydroxy-8-methoxy-3a-(4-methoxyphenyl)-3-phenyl-2,3,3a,8b-tetrahydro-1H-benzo[b]-cyclopenta[d]furan-2-carboxylate	1402931-76-3	C₂₇H₂₅ClO₇	496.944
——	(1R,2R,3S,3aR,8bS)-methyl 1,8b-dihydroxy-8-methoxy-3a-(4-methoxyphenyl)-6-methyl-3-phenyl-2,3,3a,8b-tetrahydro-1H-benzo-[b]cyclopenta[d]furan-2-carboxylate	1402931-64-9	C₂₈H₂₈O₇	476.526
——	(1R,2R,3S,3aR,8bS)-methyl 6-amino-1,8b-dihydroxy-8-methoxy-3a-(4-methoxyphenyl)-3-phenyl-2,3,3a,8b-tetrahydro-1H-benzo[b]-cyclopenta[d]furan-2-carboxylate	1402931-65-0	C₂₇H₂₇NO₇	477.514
——	(1R,2R,3S,3aR,8bS)-methyl 1,8b-dihydroxy-6-((2S,6S)-6-(2-hydroxymethyl)-1,4-dioxan-2-yloxy)-8-methoxy-3a-(4-methoxyphenyl)-3-phenyl-2,3,3a,8b-tetrahydro-1H-benzo[b]cyclopenta[d]furan-2-carboxylate	1402931-58-1	C₃₂H₃₄O₁₁	594.615
——	(1R,2R,3S,3aR,8bS)-methyl 1,8b-dihydroxy-8-methoxy-3a-(4-methoxyphenyl)-6-(methylamino)-3-phenyl-2,3,3a,8b-tetrahydro-1Hbenzo[b]cyclopenta[d]furan-2-carboxylate	1402931-66-1	C₂₈H₂₉NO₇	491.541
——	(1R,2R,3S,3aR,8bS)-methyl 1,8b-dihydroxy-6-((2R,3R,6S)-6-(2-hydroxymethyl)-3-methoxy-1,4-dioxan-2-yloxy)-8-methoxy-3a-(4-methoxyphenyl)-3-phenyl-2,3,3a,8b-tetrahydro-1H-benzo[b]cyclopenta[d]furan-2-carboxylate	1402931-55-8	C₃₃H₃₆O₁₂	624.642
——	(1R,2R,3S,3aR,8bS)-methyl 1,8b-dihydroxy-6-((2R,3S,6S)-6-(2-hydroxymethyl)-3-methoxy-1,4-dioxan-2-yloxy)-8-methoxy-3a-(4-methoxyphenyl)-3-phenyl-2,3,3a,8b-tetrahydro-1H-benzo[b]cyclopenta[d]furan-2-carboxylate	1402931-57-0	C₃₃H₃₆O₁₂	624.642
——	(1R,2R,3S,3aR,8bS)-methyl 1,8b-dihydroxy-6-((2S,3R,6S)-6-(2-hydroxymethyl)-3-methoxy-1,4-dioxan-2-yloxy)-8-methoxy-3a-(4-methoxyphenyl)-3-phenyl-2,3,3a,8b-tetrahydro-1H-benzo[b]cyclopenta[d]furan-2-carboxylate	1402931-54-7	C₃₃H₃₆O₁₂	624.642
——	(1R,2R,3S,3aR,8bS)-methyl 1,8b-dihydroxy-6-((2S,3S,6S)-6-(2-hydroxymethyl)-3-methoxy-1,4-dioxan-2-yloxy)-8-methoxy-3a-(4-methoxyphenyl)-3-phenyl-2,3,3a,8b-tetrahydro-1H-benzo[b]cyclopenta[d]furan-2-carboxylate	1402931-56-9	C₃₃H₃₆O₁₂	624.642
——	(1R,2R,3S,3aR,8bS)-methyl 6-cyano-1,8b-dihydroxy-8-methoxy-3a-(4-methoxyphenyl)-3-phenyl-2,3,3a,8b-tetrahydro-1H-benzo[b]-cyclopenta[d]furan-2-carboxylate	1402931-75-2	C₂₈H₂₅NO₇	487.509
——	(1R,2R,3S,3aR,8bS)-methyl 6-(dimethylamino)-1,8b-dihydroxy-8-methoxy-3a-(4-methoxyphenyl)-3-phenyl-2,3,3a,8b-tetrahydro-1Hbenzo[b]cyclopenta[d]furan-2-carboxylate	1402931-67-2	C₂₉H₃₁NO₇	505.568
——	(1R,2R,3S,3aR,8bS)-methyl 1,8b-dihydroxy-6-(((2S,3R,6S)-6-(2-hydroxyethyl)-3-methoxy-1,4-dioxan-2-yl)oxy)-8-methoxy-3a-(4-methoxyphenyl)-3-phenyl-2,3,3a,8b-tetrahydro-1H-cyclopenta[b]benzofuran-2-carboxylate	1402931-50-3	C₃₄H₃₈O₁₂	638.669
——	(1R,2R,3S,3aR,8bS)-methyl 6-((2S,6R)-6-((R)-1,2-dihydroxyethyl)-1,4-dioxan-2-yloxy)-1,8b-dihydroxy-8-methoxy-3a-(4-methoxyphenyl)-3-phenyl-2,3,3a,8b-tetrahydro-1H-benzo[b]cyclopenta[d]-furan-2-carboxylate	1402931-49-0	C₃₃H₃₆O₁₂	624.642
——	(1R,2R,3S,3aR,8bS)-methyl 1,8b-dihydroxy-6-((2R,3R,6S)-6-(2-hydroxyethyl)-3-methoxy-1,4-dioxan-2-yloxy)-8-methoxy-3a-(4-methoxyphenyl)-3-phenyl-2,3,3a,8b-tetrahydro-1H-benzo[b]cyclopenta[d]furan-2-carboxylate	1402931-51-4	C₃₄H₃₈O₁₂	638.669
——	(1R,2R,3S,3aR,8bS)-methyl 1,8b-dihydroxy-6-((2S,3S,6S)-6-(2-hydroxyethyl)-3-methoxy-1,4-dioxan-2-yloxy)-8-methoxy-3a-(4-methoxyphenyl)-3-phenyl-2,3,3a,8b-tetrahydro-1H-benzo[b]cyclopenta[d]furan-2-carboxylate	1402931-52-5	C₃₄H₃₈O₁₂	638.669
——	(1R,2R,3S,3aR,8bS)-methyl 1,8b-dihydroxy-6-((2R,3S,6S)-6-(2-hydroxyethyl)-3-methoxy-1,4-dioxan-2-yloxy)-8-methoxy-3a-(4-methoxyphenyl)-3-phenyl-2,3,3a,8b-tetrahydro-1H-benzo[b]cyclopenta[d]furan-2-carboxylate	1402931-53-6	C₃₄H₃₈O₁₂	638.669
(1R,2R,3S,3AR,8BS)-6-[[(2S,3R,6R)-6-[(1R)-1,2-二羟基乙基]-3-甲氧基-1,4-二氧己环-2-基]氧基]-2,3,3A,8B-四氢-1,8B-二羟基-8-甲氧基-3A-(4-甲氧基苯基)-3-苯基-1H-环戊烯并[B]苯并呋喃-2-羧酸甲酯	(1R,2R,3S,3aR,8bS)-methyl 6-(((2S,3R,6R)-6-((R)-1,2-dihydroxyethyl)-3-methoxy-1,4-dioxan-2-yl)oxy)-1,8b-dihydroxy-8-methoxy-3a-(4-methoxyphenyl)-3-phenyl-2,3,3a,8b-tetrahydro-1H-cyclopenta[b]benzofuran-2-carboxylate	697235-38-4	C₃₄H₃₈O₁₃	654.668
——	(1R,2R,3S,3aR,8bS)-methyl 6-acetyl-1,8b-dihydroxy-8-methoxy-3a-(4-methoxyphenyl)-3-phenyl-2,3,3a,8b-tetrahydro-1H-benzo[b]-cyclopenta[d]furan-2-carboxylate	1402931-74-1	C₂₉H₂₈O₈	504.537
——	(1R,2R,3S,3aR,8bS)-1,8b-dihydroxy-8-methoxy-2-(methoxycarbonyl)-3a-(4-methoxyphenyl)-3-phenyl-2,3,3a,8b-tetrahydro-1Hbenzo[b]cyclopenta[d]furan-6-carboxylic acid	1402931-69-4	C₂₈H₂₆O₉	506.509
——	(1R,2R,3S,3aR,8bS)-methyl 6-carbamoyl-1,8b-dihydroxy-8-methoxy-3a-(4-methoxyphenyl)-3-phenyl-2,3,3a,8b-tetrahydro-1Hbenzo[b]cyclopenta[d]furan-2-carboxylate	1402931-71-8	C₂₈H₂₇NO₈	505.524
——	(1R,2R,3S,3aR,8bS)-dimethyl 1,8b-dihydroxy-8-methoxy-3a-(4-methoxyphenyl)-3-phenyl-2,3,3a,8b-tetrahydro-1H-benzo[b]-cyclopenta[d]furan-2,6-dicarboxylate	1402931-70-7	C₂₉H₂₈O₉	520.536
——	(1R,2R,3S,3aR,8bS)-methyl 1,8b-dihydroxy-8-methoxy-3a-(4-methoxyphenyl)-6-(methylsulfonamido)-3-phenyl-2,3,3a,8b-tetrahydro-1H-benzo[b]cyclopenta[d]furan-2-carboxylate	1402931-68-3	C₂₈H₂₉NO₉S	555.606
——	(1R,2R,3S,3aR,8bS)-methyl 1,8b-dihydroxy-8-methoxy-3a-(4-methoxyphenyl)-6-(methylcarbamoyl)-3-phenyl-2,3,3a,8b-tetrahydro-1H-benzo[b]cyclopenta[d]furan-2-carboxylate	1402931-72-9	C₂₉H₂₉NO₈	519.551
——	(1R,2R,3S,3aR,8bS)-methyl 6-(dimethylcarbamoyl)-1,8b-dihydroxy-8-methoxy-3a-(4-methoxyphenyl)-3-phenyl-2,3,3a,8b-tetrahydro-1H-benzo[b]cyclopenta[d]furan-2-carboxylate	1402931-73-0	C₃₀H₃₁NO₈	533.578
——	CR-1-31-B	1352914-52-3	C₂₈H₂₉NO₈	507.54
楝酰胺	rocaglamide	84573-16-0	C₂₉H₃₁NO₇	505.568
——	(1R,2R,3S,3aR,8bS)-6-chloro-1,8b-dihydroxy-8-methoxy-3a-(4-methoxyphenyl)-N,N-dimethyl-3-phenyl-2,3,3a,8b-tetrahydro-1H-benzo[b]cyclopenta[d]furan-2-carboxamide	1402931-85-4	C₂₈H₂₈ClNO₆	509.986
——	(1R,2R,3S,3aR,8bS)-1,8b-dihydroxy-6-((2S,6S)-6-(hydroxymethyl)-1,4-dioxan-2-yloxy)-8-methoxy-3a-(4-methoxyphenyl)-N,N-dimethyl-3-phenyl-2,3,3a,8b-tetrahydro-1H-benzo[b]cyclopenta[d]-furan-2-carboxamide	1402931-83-2	C₃₃H₃₇NO₁₀	607.657
——	(1R,2R,3S,3aR,8bS)-6-cyano-1,8b-dihydroxy-8-methoxy-3a-(4-methoxyphenyl)-N,N-dimethyl-3-phenyl-2,3,3a,8b-tetrahydro-1H-benzo[b]cyclopenta[d]furan-2-carboxamide	1402931-84-3	C₂₉H₂₈N₂O₆	500.551

反应信息

作为反应物：

描述：

Silvestrol aglycone; (1R,2R,3S,3aR,8bS)-2,3,3a,8b-四氢-1,6,8b-三羟基-8-甲氧基-3a-(4-甲氧基苯基)-3-苯基-1H-环戊并[b]苯并呋喃-2-甲酸甲酯在 ChiralPak AD-H 作用下，以甲醇、乙醇、甲苯为溶剂，反应 3.0h，生成 (1R,2R,3S,3aR,8bS)-1,8b-二羟基-6,8-二甲氧基-3a-(4-甲氧基苯基)-3-苯基-2,3-二氢-1H-环戊并[b][1]苯并呋喃-2-羧酸甲酯

参考文献：

名称：

合成Silvestrol类似物作为有效的和选择性的蛋白质合成抑制剂

摘要：

蛋白质翻译失调在人类癌症发病机理的许多层面上都起着至关重要的作用。西尔维斯托尔，环戊达[ b]苯并呋喃天然产物通过干扰eIF4F翻译复合物的组装，在起始步骤阻止翻译。Silvestrol具有复杂的化学结构，其官能团的要求尚未得到系统的研究。而且，由于药物样性质差，silvestrol具有有限的发展潜力。在本文中，我们寻求开发Silvestrol关键中间体的实用合成方法，并探索C6位置周围的构效关系。相对于简单的5'UTR，silvestrol和类似物选择性抑制蛋白质翻译的能力（相对于简单的5'UTR，对翻译起始机制（即复杂的5'-非翻译区UTR）有很高的要求）。Silvestrol的简化类似物，例如化合物74与silvestrol相比，它们中的76种和76种具有相似的细胞毒性作用和更好的ADME特性。

DOI：

10.1021/jm3011542
作为产物：

描述：

白杨素在吡啶、