反式-查耳酮

应用制备生物活性体外研究反式-查耳酮试剂级价格

反式-查耳酮

CAS号:614-47-1
英文名:trans-Chalcone
中文名:反式-查耳酮
CBNumber:CB7746253
分子式:C15H12O
分子量:208.26
MOL File:614-47-1.mol

反式-查耳酮化学性质

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
储存条件 :Sealed in dry,Room Temperature
溶解度 :Chloroform (Slightly)
形态 :Solid
颜色 :Pale Yellow
气味 (Odor) :at 100.00 %. floral balsam herbal
香型 :floral
水溶解性 :Soluble in chloroform, ether, benzene, and ethanol (slightly). Insoluble in water.
Merck :14,2037
BRN :509985
LogP :4.013 (est)
CAS 数据库 :614-47-1(CAS DataBase Reference)
NIST化学物质信息 :Benzalacetophenone(614-47-1)

安全信息

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

反式-查耳酮 MSDS

1,3-Diphenyl-2-propen-1-one

反式-查耳酮性质、用途与生产工艺

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.