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9-hydroxy-6-(4-hydroxyphenyl)-2,2-diphenyl-8H-1,3-dioxolo[4,5-g][1]benzopyran-8-one | 1105056-24-3

分子结构分类

有机化合物 - 苯丙烷和聚酮 - 二芳基庚烷

中文名称

——

中文别名

——

英文名称

9-hydroxy-6-(4-hydroxyphenyl)-2,2-diphenyl-8H-1,3-dioxolo[4,5-g][1]benzopyran-8-one

英文别名

9-hydroxy-6-(4-hydroxyphenyl)-2,2-diphenyl-8H-[1,3]dioxolo[4,5-g]chromen-8-one；9-Hydroxy-6-(4-hydroxyphenyl)-2,2-diphenyl-[1,3]dioxolo[4,5-g]chromen-8-one

9-hydroxy-6-(4-hydroxyphenyl)-2,2-diphenyl-8H-1,3-dioxolo[4,5-g][1]benzopyran-8-one化学式

CAS

1105056-24-3

化学式

C₂₈H₁₈O₆

mdl

——

分子量

450.447

InChiKey

OXBONCWOPORCFV-UHFFFAOYSA-N

BEILSTEIN

——

EINECS

——

物化性质

熔点：

284-286 °C
沸点：

679.0±55.0 °C(Predicted)
密度：

1.434±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

辛醇/水分配系数(LogP)：

5.8
重原子数：

34
可旋转键数：

3
环数：

6.0
sp3杂化的碳原子比例：

0.04
拓扑面积：

85.2
氢给体数：

2
氢受体数：

6

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
野黄芩素	scutellarein	529-53-3	C₁₅H₁₀O₆	286.241
红盏花素	scutellarin	27740-01-8	C₂₁H₁₈O₁₂	462.367
灯盏花乙素甲酯	scutellarin methyl ester	119262-68-9	C₂₂H₂₀O₁₂	476.394

下游产品

中文名称	英文名称	CAS号	化学式	分子量
——	6-(4-(benzyloxy)phenyl)-9-hydroxy-2,2-diphenyl-8H-[1,3]dioxolo[4,5-g]chromen-8-one	1402607-40-2	C₃₅H₂₄O₆	540.572
——	9-hydroxy-6-(4-(2-morpholinoethoxy)phenyl)-2,2-diphenyl-8H-[1,3]dioxolo[4,5-g]chromen-8-one	1436402-36-6	C₃₄H₂₉NO₇	563.607
——	N,N-dimethylcarbamic acid 4-(9-hydroxy-8-oxo-2,2-diphenyl-8H-1,3-dioxolo[4,5-g][1]benzopyran-6-yl)phenyl ester	——	C₃₁H₂₃NO₇	521.526
——	7-(benzyloxy)-2-(4-(benzyloxy)phenyl)-5-hydroxy-6-methoxy-4H-chromen-4-one	28736-83-6	C₃₀H₂₄O₆	480.517
——	5-hydroxy-6,7-bis(methoxymethoxy)-2-[4-(phenylmethoxy)phenyl]-4H-1-benzopyran-4-one	1619254-61-3	C₂₆H₂₄O₈	464.472
——	7-(benzyloxy)-2-(4-(benzyloxy)phenyl)-5,6-dihydroxy-4H-chromen-4-one	62252-32-8	C₂₉H₂₂O₆	466.49
——	5-hydroxy-2-(4-hydroxyphenyl)-6,7-bis(methoxymethoxy)-4H-1-benzopyran-4-one	1619254-63-5	C₁₉H₁₈O₈	374.347
——	2-(4-(benzyloxy)phenyl)-5,6,7-trihydroxy-4H-chromen-4-one	1351585-69-7	C₂₂H₁₆O₆	376.365
蓟黄素	salvigenin	6601-62-3	C₁₇H₁₄O₆	314.295
——	5-hydroxy-6,7-bis(methoxymethoxy)-2-[4-[2-(4-morpholinyl)ethoxy]phenyl]-4H-1-benzopyran-4-one	1619254-65-7	C₂₅H₂₉NO₉	487.507
柳穿鱼黄素	pectolinarigenin	520-12-7	C₁₇H₁₄O₆	314.295
高车前素	hispidulin	1447-88-7	C₁₆H₁₂O₆	300.268
——	4-(5,6,7-trihydroxy-4-oxo-4H-chromen-2-yl)phenyl 4-((diethylamino)methyl)benzoate	——	C₂₇H₂₅NO₇	475.498
——	4-(5,6,7-trihydroxy-4-oxo-4H-chromen-2-yl)phenyl 4-((4-methylpiperazin-1-yl) methyl)benzoate	——	C₂₈H₂₆N₂O₇	502.524
——	4-(5,6,7-trihydroxy-4-oxo-4H-chromen-2-yl)phenyl 4-(piperidin-1-ylmethyl)benzoate	——	C₂₈H₂₅NO₇	487.509
——	4-(5,6,7-trihydroxy-4-oxo-4H-chromen-2-yl)phenyl 4-(pyrrolidin-1-ylmethyl)benzoate	——	C₂₇H₂₃NO₇	473.482
——	4-(5,6,7-trihydroxy-4-oxo-4H-chromen-2-yl)phenyl 4-(morpholinomethyl)benzoate	——	C₂₇H₂₃NO₈	489.482
——	4'-Methylscutellarin-triacetat	6563-68-4	C₂₂H₁₈O₉	426.38
——	5,6,7-trihydroxy-2-(4-methoxyphenyl)-4H-chromen-4-one	6563-66-2	C₁₆H₁₂O₆	300.268
——	5-(4-(5-hydroxy-6,7-dimethoxy-4-oxo-4H-chromen-2-yl)phenoxy)pentyl 4-(bis(2-chloroethyl)amino)benzoate	——	C₃₃H₃₅Cl₂NO₈	644.549
——	5,6,7-trihydroxy-2-(4-ethoxyphenyl)-4H-chromen-4-one	——	C₁₇H₁₄O₆	314.295
——	2-(4-(2-(dimethylamino)ethoxy)phenyl)-5,6,7-trihydroxy-4H-chromen-4-one	——	C₁₉H₁₉NO₆	357.363
——	2-(4-(2-(diethylamino)ethoxy)phenyl)-5,6,7-trihydroxy-4H-chromen-4-one	——	C₂₁H₂₃NO₆	385.417
——	5,6,7-trihydroxy-2-[4-[2-(4-morpholinyl)ethoxy]phenyl]-4H-1-benzopyran-4-one	1436398-09-2	C₂₁H₂₁NO₇	399.4
——	N,N-dimethylcarbamic acid 4-(5,6,7-trihydroxy-4-oxo-4H-1-benzopyran-2-yl)phenyl ester	——	C₁₈H₁₅NO₇	357.32
——	2-(4-(3-(dimethylamino)propoxy)phenyl)-5,6,7-trihydroxy-4H-chromen-4-one	——	C₂₀H₂₁NO₆	371.39
——	N,N-dimethyl-2-(4-(5,6,7-trihydroxy-4-oxo-4H-chromen-2-yl)phenoxy)acetamide	——	C₁₉H₁₇NO₇	371.346
野黄芩素	scutellarein	529-53-3	C₁₅H₁₀O₆	286.241
——	N,N-diethylcarbamic acid 4-(5,6,7-trihydroxy-4-oxo-4H-1-benzopyran-2-yl)phenyl ester	——	C₂₀H₁₉NO₇	385.373
——	N,N-diethyl-2-(4-(5,6,7-trihydroxy-4-oxo-4H-chromen-2-yl)phenoxy)acetamide	——	C₂₁H₂₁NO₇	399.4
——	5,6,7-trihydroxy-2-(4-(3-morpholinopropoxy)phenyl)-4H-chromen-4-one	——	C₂₂H₂₃NO₇	413.427
——	5,6,7-trihydroxy-2-(4-(2-morpholino-2-oxoethoxy)phenyl)-4H-chromen-4-one	——	C₂₁H₁₉NO₈	413.384
——	N,N-bis(1-methylethyl)carbamic acid 4-(5,6,7-trihydroxy-4-oxo-4H-1-benzopyran-2-yl)phenyl ester	——	C₂₂H₂₃NO₇	413.427
——	3-(4-(5,6,7-trihydroxy-4-oxo-4H-chromen-2-yl)phenoxy)propyl 4-(bis(2-chloroethyl)amino)benzoate	——	C₂₉H₂₇Cl₂NO₈	588.441
——	4-(5,6,7-trihydroxy-4-oxo-4H-chromen-2-yl)phenyl morpholine-4-carboxylate	——	C₂₀H₁₇NO₈	399.357
——	4-(5,6,7-trihydroxy-4-oxo-4H-chromen-2-yl)phenyl 4-methylpiperazine-1-carboxylate	——	C₂₁H₂₀N₂O₇	412.399

反应信息

作为反应物：

描述：

9-hydroxy-6-(4-hydroxyphenyl)-2,2-diphenyl-8H-1,3-dioxolo[4,5-g][1]benzopyran-8-one 在 palladium 10% on activated carbon 、氢气、三乙胺作用下，以四氢呋喃、乙醇为溶剂， 20.0 ℃ 、101.33 kPa 条件下，反应 12.0h，生成 4-(5,6,7-trihydroxy-4-oxo-4H-chromen-2-yl)phenyl 4-chlorobutanoate

参考文献：

名称：

作为电压门控 Nav1.5 和 Cav1.2 通道阻滞剂的新型黄芩素类似物的合成和体内抗心律失常活性评价

摘要：

恶性心律失常具有较高的发病率和死亡率，对人类健康构成重大威胁。黄芩素是从黄芩中分离得到的黄芩素的代谢产物，对心血管疾病具有良好的治疗作用，并且可以进一步代谢为甲基化形式。基于灯盏乙素体内代谢物，设计了一系列22种新型羟基取代的灯盏乙素衍生物，通过灯盏乙素支架与FDA批准的抗心律失常药物药效团的结合合成，并通过大鼠数量分析评价其抗心律失常活性。心律失常恢复时间，对应于氯化钡诱发心律失常大鼠模型中的恢复时间和维持时间，以及乌头碱诱发心律失常大鼠模型中诱发VP、VT、VF和CA所需的乌头碱累积剂量。所有设计的化合物均能缩短氯化钡诱导的心律失常连续时间，表明灯盏花素的4'-羟基取代基具有快速起效的抗心律失常作用。此外，几乎所有化合物都能使 HR、RR、QRS、QT 和 QTc 间期以及 P/T 波振幅正常化。最有前途的化合物10e表现出最好的抗心律失常活性，具有长期疗效和极低的细胞毒性，优于阳性对

DOI：

10.3390/molecules28217417
作为产物：

描述：

红盏花素在盐酸作用下，以二苯醚、乙醇、水为溶剂，反应 36.5h，生成 9-hydroxy-6-(4-hydroxyphenyl)-2,2-diphenyl-8H-1,3-dioxolo[4,5-g][1]benzopyran-8-one

参考文献：

名称：

Efficient Chemical Synthesis of a Scutellarein Derivative Containing Morpholine Ring

摘要：

黄芩苷（1）[5,6-二羟基-2-（4-羟基苯基）-4-氧代-4H-1-苯并吡喃-7-基 β-D-吡喃葡萄糖苷酸]在我国临床治疗脑梗塞和冠心病方面疗效显著。药代动力学研究表明，黄芩苷（1）在吸收前很容易在肠道中被β-葡萄糖醛酸酶代谢为黄芩苷（2）[5,6,7-三羟基-2-（4-羟基苯基）-4H-1-苯并吡喃-4-酮]。为了提高黄芩苷（1）的生物活性，我们课题组根据其体内代谢机制合成了多种黄芩苷衍生物。结果表明，与黄芩苷（1）相比，C-7 或 C-8 位取代的吗啉环具有更好的抗氧化活性、水溶性和抗凝血活性。本文报告了一种构建 5,6,7-三羟基-2-[4-[2-(4-吗啉基)乙氧基]苯基]-4H-1-苯并吡喃-4-酮（5）的高效合成方法。该合成路线将促进在 C- 4'位置含有胺侧链的黄芩苷衍生物的合成。

DOI：

10.2174/1570178611666140421230118

点击查看最新优质反应信息

文献信息

Concise synthesis and antidiabetic activity of natural flavonoid glycosides, oroxins C and D, isolated from the seeds of Oroxylum indium

作者：Gang Li、Guanghui Wang、Yangliu Tong、Junheng Zhu、Tongtong Yun、Xiaoping Ye、Fahui Li、Shengli Yuan、Qingchao Liu

DOI：10.1177/1747519820927966

日期：2021.1

The first concise synthesis of natural flavonoid glycosides, oroxins C (1) and D (2), which were isolated from the seeds of Oroxylum indicum, was efficiently achieved by a convergent strategy. The ...

从 Oroxylum indicum 的种子中分离出的天然黄酮苷类化合物 C (1) 和 D (2) 的首次简洁合成是通过收敛策略有效实现的。这 ...
Synthesis of scutellarein derivatives with antiproliferative activity and selectivity through the intrinsic pathway

作者：Tong Han、Yan Wang、Mingying Wang、Xu Li、Keguang Cheng、Xiang Gao、Zhanlin Li、Jiao Bai、Huiming Hua、Dahong Li

DOI：10.1016/j.ejmech.2018.09.047

日期：2018.10

To explore antitumor agents with potent efficacy and low toxicity, scutellarein derivatives with benzoic acid mustard (10a−c, 11a−c and 13a−c) were designed and synthesized. The antiproliferative activities of the target derivatives against A549, MCF-7 and Bel-7402 cancer cell lines were tested. Compound 10a showed the strongest potency with an IC50 value of 1.50 μM against MCF-7 cell line, and displayed

为了探索有效且低毒的抗肿瘤药，设计并合成了具有苯甲酸芥子气的黄cut苷衍生物（10a - c，11a - c和13a - c）。测试了目标衍生物对A549，MCF-7和Bel-7402癌细胞系的抗增殖活性。化合物10a对MCF-7细胞系的效能最强，IC 50值为1.50μM，对人肝L-O2正常细胞的毒性低（IC 50  > 50μM），显示了正常细胞与恶性细胞之间的特异性。机理研究表明10a它可能以浓度依赖的方式诱导MCF-7细胞凋亡，将MCF-7细胞周期阻滞在G1期并引起线粒体功能障碍。此外，促凋亡蛋白caspase-9，caspase-3，Bax和细胞色素c的表达增强，以及抗凋亡蛋白Bcl-2的表达降低，证实了10a诱导了MCF-7细胞内在的凋亡途径。。强大的抗增殖活性和良好的选择性保证10a是进一步发展为抗癌治疗剂（尤其是乳腺癌）的先导化合物。
Application ofN-substituted (aminomethyl)benzoate Strategy in Design of Scutellarein Derivatives with Improved Caco-2 Cell Permeability andIn VitroAntioxidative Activity

作者：Ze-Qin Dai、Hang Su、Min Luo、Yu Ou、Xiao-Zhong Fu、Yong-Xi Dong、Yu-Feng Cha、Shun Zhang、Yong Huang、Yong-Lin Wang

DOI：10.1002/bkcs.10377

日期：2015.8

A series of 4′‐N‐substituted (aminomethyl)benzoate derivatives of scutellarein were designed and synthesized. Evaluation of their physiochemical properties showed that the designed target compounds 5a–e exhibit higher chemical stability and aqueous solubility than scutellarin and scutellarein. The permeability (P app AP to BL ) of 5c–e in Caco‐2 cells were 2.8, 8.1, and 12.6 times higher than that

设计并合成了一系列黄cut素的4'- N-取代（氨基甲基）苯甲酸酯衍生物。对它们的理化性质的评估表明，所设计的目标化合物5a–e与黄cut苷和黄cut苷相比，具有更高的化学稳定性和水溶性。Caco-2细胞中5c–e的渗透率（P app AP 对 BL）分别比黄素高2.8、8.1和12.6倍，比黄re素高1.3、4.1和6.0倍。特别是5e具有最高的P app AP到BL值（7.19±0.31×10 -6 cm / s）和最低的ER（P app BL to AP / P app AP to BL）值0.17。体外抗氧化评估结果表明5e可以通过减轻线粒体膜电位损失并减少H 2 O 2诱导的活性氧（ROS）的产生来防御H 2 O 2诱导的PC12细胞的氧化损伤。
Efficient Synthesis of 6-O-methyl-scutellarein from Scutellarin via Selective Methylation

作者：Min-Zhe Shen、Zhi-Hao Shi、Nian-Guang Li、Hao -Tang、Qian-Ping Shi、Yu-Ping Tang、Jian-Ping Yang、Jin-Ao Duan

DOI：10.2174/15701786113109990046

日期：2013.11

Scutellarin (1) possesses distinguished efficacy in the clinical therapy of cerebral infarction, coronary heart disease, and angina pectoris. Scutellarin (1) is readily converted in vivo, therefore, synthetic methods for the construction of its metabolites will be very important in the near future. In this work, an efficient and first synthetic method for 6-O-methyl- scutellarein (3), one metabolite of scutellarin in vivo, is developed. Dichlorodiphenylmethane in diphenyl ether is used firstly to protect the dihydroxy groups at C-6 and C-7 in scutellarein (2). Then, benzyl bromide is used to selectively protect the hydroxy groups at C-4' and C-7 in 10. 6-O-Methyl-scutellarein (3) is obtained in high yield through seven steps.

黄芩苷（1）在脑梗塞、冠心病和心绞痛的临床治疗中具有显著疗效。黄芩苷（1）在体内很容易转化，因此，合成其代谢物的方法在不久的将来将非常重要。在这项工作中，首次开发出了黄芩苷的一种代谢物--6-O-甲基黄芩苷（3）的高效合成方法。首先用二苯醚中的二氯二苯甲烷保护黄芩苷（2）中 C-6 和 C-7 的二羟基。然后用溴化苄选择性地保护 10 中 C-4' 和 C-7 的羟基。通过七个步骤，便可高产获得 6-O-甲基黄芩苷（3）。
Permeability of novel 4′-N-substituted (aminomethyl) benzoate-7-substituted nicotinic acid ester derivatives of scutellarein in Caco-2 cells and in an in vitro model of the blood-brain barrier

作者：Yu Ou、Min Luo、Yong-Xi Dong、Hang Su、Xiao-Zhong Fu、Yu-Feng Cha、Shun Zhang、Yong-Long Zhao、Yong-Jun Li、Yong-Lin Wang

DOI：10.1007/s00044-016-1659-y

日期：2016.10

A series of 4′-N-substituted (aminomethyl) benzoate-7-substituted nicotinic acid ester derivatives of scutellarein was designed and synthesized. Evaluation of physiochemical properties showed that the newly designed compounds had greater chemical stability and aqueous solubility than scutellarin or scutellarein. The permeabilities (P app AP to BL) of compounds 7b and 7e in Caco-2 cells were 5.9-fold

一系列的4' - ñ -取代的（氨基甲基）野黄芩素的苯甲酸-7-取代烟酸酯衍生物设计并合成。理化性质的评估表明，新设计的化合物比黄苷或黄cut苷具有更高的化学稳定性和水溶性。化合物7b和7e在Caco-2细胞中的渗透率（P app AP对BL）比黄素高5.9倍和3.7倍，比黄cut素高3.7倍和2.4倍。化合物7b和7e的磁导率（P app AP到BL）在体外模型中，血脑屏障比黄cut素高9.7倍和5.9倍，比黄cut素高9.2倍和5.6倍。