(7S)-1,2,3,10-テトラメトキシ-7α-(メチルアミノ)-5,6-ジヒドロベンゾ[a]ヘプタレン-9(7H)-オン
コレミド · Santavy物質F · デメコルシン · (-)-デメコルチン · コルセミド · [S,(-)]-6,7-ジヒドロ-1,2,3,10-テトラメトキシ-7-(メチルアミノ)ベンゾ[a]ヘプタレン-9(5H)-オン · N-デアセチル-N-メチルコルヒチン · デスメコルヒン
![(7S)-1,2,3,10-テトラメトキシ-7α-(メチルアミノ)-5,6-ジヒドロベンゾ[a]ヘプタレン-9(7H)-オン の分子構造式](/img/chemical/220401.png)
識別子と物理属性
| CAS No. | 477-30-5 |
|---|---|
| 分子式 | C21H25NO5 |
| 平均分子量 | 371.433 g/mol |
| 単同位体質量 | 371.1732729 g/mol |
| SMILES | CN[C@H]1CCc2cc(OC)c(OC)c(OC)c2-c2ccc(OC)c(=O)cc21 |
| InChIKey | NNJPGOLRFBJNIW-HNNXBMFYSA-N |
| PubChem CID | 220401 |
| ChEMBL | CHEMBL312862 |
| ChEBI | CHEBI:4393 |
| EC No. | 207-514-6 |
| DTXSID | DTXSID7020342 |
| 現地名 | (7S)-1,2,3,10-テトラメトキシ-7α-(メチルアミノ)-5,6-ジヒドロベンゾ[a]ヘプタレン-9(7H)-オン |
化学・物理的性質
| 融点 | 73-75°C |
|---|---|
| 比旋光度 | D20 -129.0° (c = 1 in chloroform) |
| 沸点 | 501.11°C (rough estimate) |
| 密度 | 1.2350 (rough estimate) |
| 屈折率 | 1.5614 (estimate) |
| 貯蔵条件 | 2-8°C |
| 溶解度 | DMSO: 10 mg/mL |
| 外観・状態 | 粉 |
| pKa（酸解離定数） | 8.48±0.40(Predicted) |
| 色 | White to off-white |
| BRN | 2822892 |
| 安定性 | Hygroscopic |
| InChI | 1S/C21H25NO5/c1-22-15-8-6-12-10-18(25-3)20(26-4)21(27-5)19(12)13-7-9-17(24-2)16(23)11-14(13)15/h7,9-11,15,22H,6,8H2,1-5H3 |
| InChIKey | NNJPGOLRFBJNIW-UHFFFAOYSA-N |
| SMILES | N(C1CCc2c(c(c(c(c2)OC)OC)OC)C3=CC=C(C(=O)C=C31)OC)C |
化学的特性
Faintly Yellow Crystalline Powder
安全性と法規制
| F | 8-10-23 |
|---|---|
| 水環境危害等級（WGK） | 3 |
| RTECS 番号 | GH0800000 |
| 輸送番号（UN） | UN 2811 6.1/PG 2 |
| 毒性 | LD50 oral in mouse: 25530ug/kg |
| 危険文句（R） | 25-26/27/28 |
| 危険表示 | T,T+ |
| 安全措置（S） | 22-24/25-45-36/37/39 |
| 危険等級 | 6.1(a) |
| 包装等級 | II |
用途
説明
Colcemid is a colchicine derivative that inhibits tubulin polymerization as potently as colchicine (IC50 = 2.1 and 2.4 μM, respectively) but is less toxic. At very low (nanomolar) concentrations, colcemid suppresses microtubule dynamicity and inhibits cell migration, while at micromolar levels it blocks microtubule assembly, arresting cells in metaphase. Mitotic block by colcemid is used to synchronize cells and for karyotyping in cytogenetic studies. Prolonged exposure to colcemid can activate p53, leading to apoptosis.
使用
An antimitotic agent that disrupts microtubles by binding to tubulin and preventing its polymerization. Stimulates the intrinsic GTPase activity of tubulin. Induces apoptosis in several normal and tumor cell lines and activates the JNK/SAPK signaling pathway.
一般的な説明
Colcemid is also known as demecolcine. Its generic name is N-methyl-N-deacetyl-colchicine. Colcemid depolymerizes microtubules and blocks mitosis at metaphase.
製法・合成法
純化方法
Colcemide is purified by chromatography on silica and eluting with CHCl3/MeOH (9:1), and by recrystallisation from EtOAc/Et2O to form yellow prisms. UV in EtOH has max 243nm ( 30,200) and 350nm ( 16,3000). [Synthesis, IR, NMR, MS: Capraro & Brossi Helv Chim Acta 62 965 1979, Beilstein 8 IV 3319.]