反式-查耳酮

中文名称:

反式-查耳酮

中文同义词:

苯丙烯酰苯;苯基苯乙烯基甲酮;苯苏合香稀甲酮;苯乙烯基本基甲酮;苄差苯乙酮;亚苄基代苯乙酮;查尔酮;1,3-二苯-2-丙烯-1-酮

英文名称:

trans-Chalcone

英文同义词:

PHENYL STYRYL KETONE;(2E)-1,3-DIPHENYLPROP-2-EN-1-ONE;2-BENZALACETOPHENONE;2-BENZYLIDENEACETOPHENONE;3-PHENYLACRYLOPHENONE;TRANS-BENZYLIDENEACETOPHENONE;TRANS-CHALCONE;1,3-DIPHENYL-2-PROPEN-1-ONE

CAS号:

614-47-1

分子式:

C15H12O

分子量:

208.26

EINECS号:

210-383-8

相关类别:

羰基化合物;医药中间体;有机原料;中间体;合成;格氏试剂;化工原料;有机中间体;化工中间体工业原料

Mol文件:

614-47-1.mol

熔点 

55-59 °C

沸点 

208 °C25 mm Hg(lit.)

密度 

1.0712

折射率 

1.5361 (estimate)

闪点 

>230 °F

水溶解性 

Soluble in chloroform, ether, benzene, and ethanol (slightly). Insoluble in water.

Merck 

14,2037

BRN 

509985

CAS 数据库

614-47-1(CAS DataBase Reference)

NIST化学物质信息

Benzalacetophenone(614-47-1)

应用

反式-查耳酮是一种不饱和酮类化合物，浅黄色斜方棱柱体结晶。有文献报道其是一种小分子GPR52拮抗剂。反式-查耳酮可由苯乙酮和苯甲醛一步反应制备得到。

制备

在氮气下，将[Ni（dmpymt）2] 6（5 mol％Ni），KOH（1.0 mmol），苯甲醇（1.5 mmol）和1-苯基乙醇（1.0 mmol）与甲苯（2.5 mL）/ t-BuOH（0.5 mL）加入50毫升Schlenk试管中，将试管置于70°C油浴中，在缓慢，稳定的氮气流中搅拌混合物36小时，将混合物冷却至室温，加水（10毫升）。 用CH2Cl2（3×10 mL）萃取水溶液，用无水Na2SO4干燥合并的萃取液，除去溶剂，在短时间快速柱色谱上纯化粗产物得到反式-查耳酮。

生物活性

trans-Chalcone 是从Aronia melanocarpa 果皮中分离出来的，是类黄酮前体的双酚核心结构。trans-Chalcone 是有效的脂肪酸合酶 (FAS) 和 α-淀粉酶 (b>α-amylase) 抑制剂。trans-Chalcone 引起细胞周期停滞并诱导乳腺癌细胞系 MCF-7 凋亡。trans-Chalcone 具有抗真菌和抗癌活性。

体外研究

trans-Chalcone competitively inhibits porcine pancreatic α-amylase with a Ki of 48 μM. trans-Chalcone (30.23-98.03 μM; 24 hours) induces cell cycle arrest and apoptosis in MCF-7 cells. trans-Chalcone (30.23-98.03 μM; 24 hours) reduces the expression of the apoptosis-related protein Bcl-2 and induces the expression of the CIDEA gene. trans-Chalcone (58.25 μM; 6, 24 hours) has greater inhibition of Bcl-2, induction of APAF1 and BAX, and strong induction of CIDEA in 24 hours. trans-Chalcone (24 hours) inhibits MCF-7 cell viability (IC 20 =30.23 μM; IC 50 =58.25 μM; IC 80 =98.03 μM). trans-Chalcone (48 h) has IC 50 s of 41.53 μM and 48.41 μM for MCF-7 and 3T3 cell lines, respectively. trans-Chalcone exhibits a pronounced cytotoxicity activity. Apoptosis Analysis Cell Line: MCF-7 cell Concentration: 30.23, 58.25, 98.03 μM Incubation Time: 24 hours Result: Induced apoptosis of the breast cancer cell line. Cell Cycle Analysis Cell Line: MCF-7 cell Concentration: 30.23, 58.25, 98.03 μM Incubation Time: 24 hours Result: Caused cell cycle arrest in G1. Western Blot Analysis Cell Line: MCF-7 cell Concentration: 20, 40, 80 μM Incubation Time: 24, 48 hours Result: Reduced the expression of the apoptosis-related protein Bcl-2 and induced the expression of the CIDEA gene. There was marked degradation of cyclin D1 at 48 h. RT-PCR Cell Line: MCF-7 cell Concentration: 58.25 μM Incubation Time: 6, 24 hours Result: Had greater inhibition of Bcl-2, induction of APAF1 and BAX, and strong induction of CIDEA in 24 hours.

Cell Line:

MCF-7 cell

Concentration:

30.23, 58.25, 98.03 μM

Incubation Time:

24 hours

Result:

Induced apoptosis of the breast cancer cell line.

Cell Line:

MCF-7 cell

Concentration:

30.23, 58.25, 98.03 μM

Incubation Time:

24 hours

Result:

Caused cell cycle arrest in G1.

Cell Line:

MCF-7 cell

Concentration:

20, 40, 80 μM

Incubation Time:

24, 48 hours

Result:

Reduced the expression of the apoptosis-related protein Bcl-2 and induced the expression of the CIDEA gene. There was marked degradation of cyclin D1 at 48 h.

Cell Line:

MCF-7 cell

Concentration:

58.25 μM

Incubation Time:

6, 24 hours

Result:

Had greater inhibition of Bcl-2, induction of APAF1 and BAX, and strong induction of CIDEA in 24 hours.

危险品标志 

Xn,Xi

危险类别码 

22-36/37

安全说明 

22-36/37/39-45

WGK Germany 

3

RTECS号

UD5576750

海关编码 

29143990