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97207-47-1

中文名称 甲异靛
英文名称 Meisoindigo
CAS 97207-47-1
分子式 C17H12N2O2
分子量 276.29
MOL 文件 97207-47-1.mol
更新日期 2025/08/13 14:38:03
97207-47-1 结构式 97207-47-1 结构式

基本信息

中文别名
异甲靛
甲异靛
甲异靛, >96%
1-甲基-[3,3'-联吲哚基] -2,2'-二酮
N-甲基-(3,3'-双-二氢吲哚)-2,2'-二酮
英文别名
CS-1454
Natura-α
Dian III
MEISOINDIGO
Meisoindigo, >96%
Methylisoindigotin
Meisoindigo, >=98%
Meisoindigo(Natura-
N-methylisoindigotin
Meisoindigo USP/EP/BP
所属类别
原料药:抗代谢类抗肿瘤药

物理化学性质

熔点236-237°C
沸点482.0±45.0 °C(Predicted)
密度1.381±0.06 g/cm3(Predicted)
储存条件Sealed in dry,Room Temperature
溶解度insoluble in H2O; insoluble in EtOH; ≥25.85 mg/mL in DMSO with ultrasonic
酸度系数(pKa)11.62±0.20(Predicted)
形态粉末晶体
颜色橙色到棕色到深红色
InChIInChI=1S/C17H12N2O2/c1-19-13-9-5-3-7-11(13)15(17(19)21)14-10-6-2-4-8-12(10)18-16(14)20/h2-9H,1H3,(H,18,20)
InChIKeyQNOCRUSVMMAKSC-UHFFFAOYSA-N
SMILESN1(C)C2=C(C=CC=C2)C(=C2C3=C(NC2=O)C=CC=C3)C1=O

安全数据

危险性符号(GHS)GHS hazard pictograms
GHS07
警示词警告
危险性描述H302-H315-H319-H335
海关编码2933.79.1500

制备方法

方法1
2-吲哚酮

59-48-3

1-甲基靛红

2058-74-4

甲异靛

97207-47-1

通用方法:将1-甲基靛红(1, 1.0 mmol)、2-吲哚酮(2, 1.0 mmol)和四氯化锆(ZrCl4, 23 mg, 0.1 mmol)的混合物在无水乙醇(5 mL)中于回流条件下加热。反应进程通过薄层色谱(TLC)监测,待反应物完全消失(通常需要8-12小时)后,将反应混合物缓慢冷却至室温。析出的红色固体通过过滤收集,并用少量无水乙醇洗涤,得到纯的1-甲基-[3,3'-联吲哚啉亚基]-2,2'-二酮(3)。

参考文献:

[1] Tetrahedron Letters, 2016, vol. 57, # 52, p. 5856 - 5858

[2] Bulletin de la Societe Chimique de France, 1914, vol. <4> 15, p. 335

[3] Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences, 1913, vol. 156, p. 1385

甲异靛价格(试剂级)
报价日期产品编号产品名称CAS号包装价格
2025/05/22HY-13680甲异靛
Meisoindigo
97207-47-15mg800元
2025/05/22HY-13680甲异靛
Meisoindigo
97207-47-110mM * 1mLin DMSO973元
2025/05/22HY-13680甲异靛
Meisoindigo
97207-47-110mg1100元

常见问题列表

生物活性
Meisoindigo (Dian III) 是 Indirubin (HY-N0117) 的衍生物,可以造成急性髓细胞性白血病 (AML) 细胞周期在 G0/G1 期停滞,并诱导凋亡。Meisoindigo 具有很高的抗肿瘤活性。
体外研究

Meisoindigo (Dian III; 5-20 μM; for 24 hours) inhibits growth of the AML cell lines.
Meisoindigo (10 μM; for 24 hours) induces apoptosis of acute myeloid leukemia.
Meisoindigo (5-10 μM; for 24 hours) causes cell-cycle arrest.
Meisoindigo (5-10 μM; for 24 hours) increases the cleaved caspase-3 and pro-apoptotic Bak, and decreases Bcl-2 and Bcl-xL levels in HL-60 cells.
Meisoindigo (10, 30, 50, 100, 150 μM; 24 hours) interdicts LPS-induced (1 μg/mL) NLRP3 inflammasome activation and M1/M2 polarization through down-regulation of TLR4 pathways after OGD/R in HT-22 and BV2 cells.

Cell Viability Assay

Cell Line: HL-60, NB4, U937 leukemic cell lines
Concentration: 5, 10, 15, 20 μM
Incubation Time: For 24 hours
Result: Inhibited growth of the AML cell lines in a dose- and time-dependent manner.

Apoptosis Analysis

Cell Line: HL-60 cells
Concentration: 10 μM
Incubation Time: For 24 hours
Result: Induced apoptosis of acute myeloid leukemia.

Cell Cycle Analysis

Cell Line: HL-60 cells
Concentration: 5, 10 μM
Incubation Time: For 24 hours
Result: Caused cell-cycle arrest, with more cells in sub-G1 and G0/G1 phases and fewer cells in the S phase, in a dose-dependent manner.

Western Blot Analysis

Cell Line: HL-60 cells
Concentration: 5, 10 μM
Incubation Time: For 24 hours
Result: Increased the cleaved caspase-3 and pro-apoptotic Bak, and decreased Bcl-2 and Bcl-xL levels in HL-60 cells.
体内研究

Meisoindigo (Dian III; 50-150 mg/kg; IP; daily; for 14 days) has anti-leukemic activity in vivo.
Meisoindigo (2, 4, 8, 12 mg/kg; IP; before MCAO and 2 h after reperfusion) significantly reduces infarct volume, ameliorates neurological deficits 3 days after middle cerebral artery occlusion (MCAO) in Wild-type C57BL/6J mice (25-30 g). Meisoindigo reduces edema and lowers AQP4 expression in the brain.

Animal Model: NOD/SCID mice, 6-8 weeks old, with HL-60 leukemic cells
Dosage: 50, 100, 150 mg/kg
Administration: IP; daily; for 14 days
Result: Had anti-leukemic activity in vivo.
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