(13aR,14R)-9,11,12,13,13a,14-hexahydro-3,6,7-trimethoxydibenzo[f,h]pyrrolo[1,2-b]isoquinolin-14-ol | 1034896-75-7

• 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: (13aR,14R)-9,11,12,13,13a,14-hexahydro-3,6,7-trimethoxydibenzo[f,h]pyrrolo[1,2-b]isoquinolin-14-ol
• 英文别名: (13aR,14R)-14-hydroxytylophorine；O-methyl-tylophorinidine；Dibenzo[f,h]pyrrolo[1,2-b]isoquinolin-14-ol, 9,11,12,13,13a,14-hexahydro-3,6,7-trimethoxy-, (13aS-cis)-；(13aR,14R)-3,6,7-trimethoxy-9,11,12,13,13a,14-hexahydrophenanthro[9,10-f]indolizin-14-ol
• CAS: 1034896-75-7
• 化学式: C₂₃H₂₅NO₄
• 分子量: 379.456
• InChiKey: LAWAARLALKUFQQ-XXBNENTESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  28
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  51.2
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (13aR,14R)-9,11,12,13,13a,14-hexahydro-3,6,7-trimethoxydibenzo[f,h]pyrrolo[1,2-b]isoquinolin-14-ol 在 三乙基硅烷 、 三氟乙酸 作用下， 反应 10.0h， 以97%的产率得到(R)-deoxytylophorinine
  参考文献：
  名称：

  Parham型环酰化反应高效、手性特异性合成菲-吲哚里西啶生物碱

  摘要：

  以 Parham 型环酰化为关键步骤的简洁、高效和模块化的路线已被用于合成六种对映体纯的菲-吲哚里西啶生物碱 1a-c。大规模制备对映体纯的泰洛弗拉生物碱及其类似物现在是可行的。醇中间体8a-c难以通过其他合成方法制备，通过金属化-环化-还原序列以优异的产率合成。

  DOI：

  10.1002/ejoc.200900920
• 作为产物：
  描述：

  在 sodium tetrahydroborate 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 为溶剂， 反应 9.0h， 以1.3 g的产率得到(13aR,14R)-9,11,12,13,13a,14-hexahydro-3,6,7-trimethoxydibenzo[f,h]pyrrolo[1,2-b]isoquinolin-14-ol
  参考文献：
  名称：

  Parham型环酰化反应高效、手性特异性合成菲-吲哚里西啶生物碱

  摘要：

  以 Parham 型环酰化为关键步骤的简洁、高效和模块化的路线已被用于合成六种对映体纯的菲-吲哚里西啶生物碱 1a-c。大规模制备对映体纯的泰洛弗拉生物碱及其类似物现在是可行的。醇中间体8a-c难以通过其他合成方法制备，通过金属化-环化-还原序列以优异的产率合成。

  DOI：

  10.1002/ejoc.200900920

文献信息

• Asymmetric synthesis of phenanthroindolizidine alkaloids with hydroxyl group at the C14 position and evaluation of their antitumor activities
  作者：Takashi Ikeda、Takashi Yaegashi、Takeshi Matsuzaki、Syusuke Hashimoto、Seigo Sawada

  DOI：10.1016/j.bmcl.2010.11.008

  日期：2011.1

  The asymmetric total synthesis of the strongly cytotoxic phenanthroindolizidine alkaloid 3 was achieved. Using the same route, various derivatives were also synthesized. Cytotoxicity of those synthetic compounds was evaluated and compounds 19, 23, and 27 demonstrated potent cytotoxicities similar to that of 3. The in vivo antitumor efficacy of selected compounds was also evaluated and 23 demonstrated moderate antitumor efficacy. (C) 2010 Elsevier Ltd. All rights reserved.
• AGENTS FROM FICUS HISPIDA FOR THE AMELIORATION OF METABOLIC SYNDROME AND RELATED DISEASES
  申请人：GOKARAJU Ganga Raju

  公开号：US20120128808A1

  公开（公告）日：2012-05-24

  The invention discloses herbal ingredient(s) derived from Ficus hispida comprising herb powder(s), extract(s), fraction(s), pure compound(s) or mixtures thereof and their compositions for alleviating metabolic disorders selected from metabolic syndrome, obesity, diabetes, atherosclerosis, endothelial dysfunction and other metabolic disorders or conditions; the for amelioration of different biological marker proteins and metabolic processes associated metabolic disorders.
• METHOD OF ISOLATING PHENANTHROINDOLIZIDINE ALKALOIDS FROM TYLOPHORA ATROFOLLICULATA WITH HIF-1 INHIBITORY ACTIVITY, COMPOSITIONS COMPRISING THEM AND THEIR USE
  申请人：Macau University of Science and Technology

  公开号：US20170312266A1

  公开（公告）日：2017-11-02

  A method of isolating at least one phenanthroindolizidine alkaloid, in particular with HIF-1 inhibitory activity, from Tylophora atrofolliculata is used to isolate and obtain for example about 22 phenanthroindolizidine alkaloids, including at least 11 new phenanthroindolizidine alkaloids which have not been previously isolated. Experimental tests confirmed an exceptional HIF-1 inhibitory activity of the phenanthroindolizidine alkaloids isolated. A pharmaceutical composition includes at least one phenanthroindolizidine alkaloid and at least one pharmaceutical tolerable excipient. A method of treating a subject suffering from cancer includes administering at least one phenanthroindolizidine alkaloid isolated from Tylophora atrofolliculata . A method of treating a subject suffering from cancer includes administering at least one phenanthroindolizidine alkaloid to the subject.
• US8703215B2
  申请人：——

  公开号：US8703215B2

  公开（公告）日：2014-04-22
• US9782401B1
  申请人：——

  公开号：US9782401B1

  公开（公告）日：2017-10-10