neosalvianen | 790673-00-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 菲及其衍生物
• 英文名称: neosalvianen
• 英文别名: 5,9,17,17-tetramethyl-3,10-dioxa-8-azapentacyclo[10.8.0.02,6.07,11.013,18]icosa-1(12),2(6),4,7(11),8,13(18),19-heptaene
• CAS: 790673-00-6
• 化学式: C₂₁H₂₁NO₂
• 分子量: 319.403
• InChiKey: XIEAHUZPQQITDN-UHFFFAOYSA-N

物化性质

• 熔点：
  213-215 °C
• 沸点：
  474.8±40.0 °C(Predicted)
• 密度：
  1.190±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  24
• 可旋转键数：
  0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  39.2
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 储存条件：
  存储条件：2-8°C，干燥且密封。

制备方法与用途

Neosalvianen 是一种含氮化合物，对 HeLa、HepG2 和 OVCAR-3 细胞系均表现出细胞毒活性，其 IC50 值分别为 63.9 μM、59.2 μM 和 74.6 μM。

反应信息

• 作为产物：
  描述：

  2,4,9,9-tetramethyl-4,5,9,10,11,12-hexahydro-1,6-dioxa-3-aza-dicyclopenta[a,c]phenanthrene 在 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 苯 为溶剂， 反应 48.0h， 以56%的产率得到neosalvianen
  参考文献：
  名称：

  Nitrogen-Containing Compounds from Salvia miltiorrhiza

  摘要：

  Five new N-containing compounds, neosalvianen (1), salvianen (2), salvianan (3), salviadione (4), and 5-(methoxymethyl)-1H-pyrrole-2-carbaldehyde (5), were isolated from Salvia miltiorrhiza. Their structures were mainly established by spectroscopic methods. Neosalvianen (1) and its analogues (6a, 6b) were synthesized for spectroscopic data comparison. Compounds 1, 2, 4, and 6a were evaluated for their cytotoxic activities against selected cancer cell lines. Among these components, salvianen (2) exhibited the most potent cytotoxicity with a CD50 range of 30.4-39.5 mu M against HeLa (cervical epitheloid carcinoma), HepG2 (hepatocellular carcinoma), and OVCAR-3 (ovarian adenocarcinoma) cell lines in a dose-dependent manner. The cytotoxicities of the tested compounds were not specific and showed similar activities to the selected cancer cell lines.

  DOI：

  10.1021/np0500934

文献信息

• Nitrogen-Containing Compounds from <i>Salvia </i><i>m</i><i>iltiorrhiza</i>
  作者：Ming-Jaw Don、Chien-Chang Shen、Yun-Lian Lin、Wan-Jr Syu、Yi-Huei Ding、Chang-Ming Sun

  DOI：10.1021/np0500934

  日期：2005.7.1

  Five new N-containing compounds, neosalvianen (1), salvianen (2), salvianan (3), salviadione (4), and 5-(methoxymethyl)-1H-pyrrole-2-carbaldehyde (5), were isolated from Salvia miltiorrhiza. Their structures were mainly established by spectroscopic methods. Neosalvianen (1) and its analogues (6a, 6b) were synthesized for spectroscopic data comparison. Compounds 1, 2, 4, and 6a were evaluated for their cytotoxic activities against selected cancer cell lines. Among these components, salvianen (2) exhibited the most potent cytotoxicity with a CD50 range of 30.4-39.5 mu M against HeLa (cervical epitheloid carcinoma), HepG2 (hepatocellular carcinoma), and OVCAR-3 (ovarian adenocarcinoma) cell lines in a dose-dependent manner. The cytotoxicities of the tested compounds were not specific and showed similar activities to the selected cancer cell lines.