cis-1,10b-Dihydronarciclasin | 40042-04-4

• 分子结构分类: 有机化合物 - 生物碱及其衍生物 - 石蒜科生物碱
• 英文名称: cis-1,10b-Dihydronarciclasin
• 英文别名: cis-Dihydronarcidasin；cis-dihydronarciclasine；(4aR)-2t,3c,4c,7-tetrahydroxy-(4ar,11bc)-1,3,4,4a,5,11b-hexahydro-2H-[1,3]dioxolo[4,5-j]phenanthridin-6-one；(2S,3R,4S,4aR,11bS)-2,3,4,7-tetrahydroxy-2,3,4,4a,5,11b-hexahydro-1H-[1,3]dioxolo[4,5-j]phenanthridin-6-one
• CAS: 40042-04-4
• 化学式: C₁₄H₁₅NO₇
• 分子量: 309.276
• InChiKey: SBTGHBALOCEVOR-GUHAZCHASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.6
• 重原子数：
  22
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  129
• 氢给体数：
  5
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  cis-1,10b-Dihydronarciclasin 在 对甲苯磺酸 、 原甲酸三乙酯 、 silver(l) oxide 作用下， 生成 (3aS)-6,12c-dimethoxy-2,2-dimethyl-(3ar,3bt,10bt,12ac)-3b,4,10b,11,12,12a-hexahydro-3aH-bis[1,3]dioxolo[4,5-c;4',5'-j]phenanthridin-5-one
  参考文献：
  名称：

  Mondon,A.; Krohn,K., Chemische Berichte, 1975, vol. 108, p. 445 - 463

  摘要：

  DOI：
• 作为产物：
  描述：

  水仙环素 在 barium dihydroxide 作用下， 以 乙醇 为溶剂， 生成 cis-1,10b-Dihydronarciclasin
  参考文献：
  名称：

  Mondon,A.; Krohn,K., Chemische Berichte, 1975, vol. 108, p. 445 - 463

  摘要：

  DOI：

文献信息

• Antineoplastic Agents. 454. Synthesis of the Strong Cancer Cell Growth Inhibitors <i>trans</i>-Dihydronarciclasine and 7-Deoxy-<i>trans</i>-dihydronarciclasine
  作者：George R. Pettit、Sylvie Ducki、Stephen A. Eastham、Noeleen Melody

  DOI：10.1021/np9001948

  日期：2009.7.24

  To further pursue the antineoplastic leads offered by Our isolation of trans-dihydronarciclasine (1a) and 7-deoxy-trans-dihydronarciclasine (1c) from two medicinal plant species of the Amaryllidaceae family, a practical palladium-catalyzed hydrogenation procedure was developed for the synthesis of these isocarbostyrils from narciclasine (2a) and 7-deoxynarciclasine (2c).
• PRO-DRUGS OF AMARYLLIDACEAE ISOCARBOSTYRIL PRODUCTS AND THEIR USE AGAINST BRAIN TUMORS
  申请人：Mathieu Veronique

  公开号：US20130053347A1

  公开（公告）日：2013-02-28

  The present invention relates to the biology and mechanism of action of the naturally occurring compound Narciclasine, especially as an anti-cancer agent for brain tumors. The invention provides new insights on the target molecule of Amaryllidaceae isocarbostyril derivatives as for example Narciclasine and provides new prodrugs of these Amaryllidceae isocabostyril constituents for treating cancer, specifically cancers or tumors located in the brain.
• Mondon,A.; Krohn,K., Chemische Berichte, 1975, vol. 108, p. 445 - 463
  作者：Mondon,A.、Krohn,K.

  DOI：——

  日期：——
• Human Cytochrome P450 Liability Studies of <i>trans</i>-Dihydronarciclasine: A Readily Available, Potent, and Selective Cancer Cell Growth Inhibitor
  作者：James McNulty、Amol Thorat、Nesrin Vurgun、Jerald J. Nair、Emilija Makaji、Denis J. Crankshaw、Alison C. Holloway、Siyaram Pandey

  DOI：10.1021/np100657w

  日期：2011.1.28

  The cytochrome P450 activities of the naturally occurring Amaryllidaceae alkaloid narciclasine (3), isolated from Narcissus pseudonarcissus, and synthetic derivative trans-dihydronarciclasine (5) are reported. While narciclasine was found to possess potent inhibitory activity to human CYP3A4, its dihydro analogue was inactive. This study revealed that the C1-C10b double bond is required for inhibition of this crucial metabolizing enzyme. Compound 5 also demonstrated no inhibition of the related human cytochromes CYP19 and CYPIA1. This study elevates the status of trans-dihydronarciclasine (5) as a highly privileged, readily available molecule, with potent and selective anticancer activity.