甲异靛
| 中文名称 | 甲异靛 |
|---|---|
| 中文同义词 | N-甲基-(3,3'-双-二氢吲哚)-2,2'-二酮;甲异靛;异甲靛;甲异靛, >96%;1-甲基-[3,3'-联吲哚基] -2,2'-二酮;1-甲基-[3,3'-联吲哚啉亚基] -2,2'-二酮;(E)-1-甲基-[3,3-联亚二氢吲哚基]-2,2-二酮;甲异靛,10 MM DMSO 溶液 |
| 英文名称 | Meisoindigo |
| 英文同义词 | 1-METHYL-3,3'-BIINDOLE-2,2'(1H,1'H)-DIONE;3-(1,2-dihydro-2-oxo-3h-indol-3-ylidene)-1,3-dihydro-1-methyl-2h-indol-2-one;MEISOINDIGO;N-methylisoindigotin;Dian III;Methylisoindigotin;Natura-α;Meisoindigo 3-(1,2-Dihydro-2-oxo-3H-indol-3-ylidene)-1,3-dihydro-1-methyl-2H-indol-2-one |
| CAS号 | 97207-47-1 |
| 分子式 | C17H12N2O2 |
| 分子量 | 276.29 |
| EINECS号 | 200-256-5 |
| 相关类别 | 小分子抑制剂;小分子抑制剂，天然产物;医药化工中间体;标准品;中药对照品;Inhibitors |
| Mol文件 | 97207-47-1.mol |
| 结构式 |  |
甲异靛 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 | 不溶于水；不溶于乙醇；超声波检测下 DMSO 中≥25.85 mg/mL |
| 形态 | 粉末晶体 |
| 酸度系数(pKa) | 11.62±0.20(Predicted) |
| 颜色 | 橙色到棕色到深红色 |
| InChI | InChI=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) |
| InChIKey | QNOCRUSVMMAKSC-UHFFFAOYSA-N |
| SMILES | N1(C)C2=C(C=CC=C2)C(=C2C3=C(NC2=O)C=CC=C3)C1=O |
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. |
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. |
59-48-3
2058-74-4
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
安全信息
| 海关编码 | 2933.79.1500 |
|---|
| 更新日期 | 产品编号 | 产品名称 | CAS号 | 包装 | 价格 |
|---|---|---|---|---|---|
| 2026/03/03 | S5327 | 甲异靛 Meisoindigo | 97207-47-1 | 5mg | 1204.85元 |
| 2026/03/03 | S5327 | 甲异靛 Meisoindigo | 97207-47-1 | 25mg | 3849.67元 |