2,4,9,9-tetramethyl-4,5,9,10,11,12-hexahydro-1,6-dioxa-3-aza-dicyclopenta[a,c]phenanthrene | 367523-19-1

• 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: 2,4,9,9-tetramethyl-4,5,9,10,11,12-hexahydro-1,6-dioxa-3-aza-dicyclopenta[a,c]phenanthrene
• 英文别名: 2,4,9,9-tetramethyl-4,5,9,10,11,12-hexahydro-1,6-dioxa-3-aza-dicyclopenta[a,c]phenantrene；5,9,17,17-Tetramethyl-3,10-dioxa-8-azapentacyclo[10.8.0.02,6.07,11.013,18]icosa-1(12),2(6),7(11),8,13(18),19-hexaene
• CAS: 367523-19-1
• 化学式: C₂₁H₂₃NO₂
• 分子量: 321.419
• InChiKey: MYLKWIZRUARODK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6
• 重原子数：
  24
• 可旋转键数：
  0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  35.3
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  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
• 作为产物：
  描述：

  (+/-)-cryptotanshinone 、 乙胺 以 乙醇 、 水 为溶剂， 反应 24.0h， 以23%的产率得到2,4,9,9-tetramethyl-4,5,9,10,11,12-hexahydro-1,6-dioxa-3-aza-dicyclopenta[a,c]phenanthrene
  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

• Reaction of tanshinones with biogenic amine metabolites in vitro
  作者：Lin-Kun An、Xian-Zhang Bu、Hai-Qiang Wu、Xin-Dong Guo、Lin Ma、Lian-Quan Gu

  DOI：10.1016/s0040-4020(02)01414-x

  日期：2002.12

  The reaction of cryptotanshinone and tanshinone IIA with several biogenic amine metabolites involved in the pathogenic pathways of hepatic encephalopathy are investigated and eleven 1,2,3,4,-tetrahydrophenanthrene derivatives, 2–10, 14 and 16, are obtained. The probable mechanisms on reaction are discussed.

  隐和丹参酮IIA的与参与肝性脑病的致病途径几个生物胺的代谢物的反应进行了研究和11 1,2,3,4，-tetrahydrophenanthrene衍生物，2 - 10，14和16获得。讨论了可能的反应机理。
• DITERPENE DERIVATIVES FOR THE TREATMENT OF CARDIOVASCULAR, CANCER AND INFLAMMATORY DISEASES
  申请人：Dev Inderjit Kumar

  公开号：US20070207989A1

  公开（公告）日：2007-09-06

  The present invention relates to useful diterpenes and pharmaceutical compositions containing them of the formula: for use in the treatment of cardiovascular and inflammatory diseases and for cancers susceptible to an NF-κB inhibitor and an endothelin receptor inhibitor. The present invention also relates to compounds and methods useful to inhibit cell proliferation and for the induction of apoptosis.

  本发明涉及有用的二萜化合物及包含它们的药物组合物，用于治疗心血管和炎症性疾病，以及对NF-κB抑制剂和内皮素受体抑制剂敏感的癌症。本发明还涉及用于抑制细胞增殖和诱导凋亡的化合物和方法。
• Synthesis of new 1,1-dimethyl-1,2,3,4-tetrahydrophenanthrene derivatives
  作者：Xian-Zhang Bu、Zhi-Shu Huang、Min Zhang、Lin Ma、Gui-Wu Xiao、Lian-Quan Gu

  DOI：10.1016/s0040-4039(01)01034-6

  日期：2001.8

  Four new 1,1-dimethyl-1,2,3,4-tetrahydrophenanthrene derivatives. 1-amino-2-(1-hydroxy-2-propyl)-8,8-dimethyl-5,6,7,8-tetrahydrophenanthrene-3,4-dione. 2. 3-amino-2-(1-hydroxy-2-propyl)-8,8-dimethyl-5,6,7,8-tetrahydrophenanthrene-1,4-dione. 3. 1,4,9,0-tetramethyl-4,5,9,10,11,12-hexahydro-1H-6-6oax-1,3-diaza-dicyclopenta[a,c] phenanthrene 4. 2,4,9,9-tetramethyl-4,5,9,10,11,12-hexahydro-1,6-dioxa-3-aza-dicyclopenta[a,c]phenanthrene 5. were synthesized by reactions of cryptotanshinone 1. a bioactive component from Salvia miltiorrhiza bunge, with amino compounds. (C) 2001 Elsevier Science Ltd. All rights reserved.
• 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.