(6R,11R)-6,11-Dimethyl-3-(3-methyl-but-2-enyl)-1,2,3,4,5,6-hexahydro-2,6-methano-benzo[d]azocin-8-ol

• 分子结构分类: 有机化合物 - 生物碱及其衍生物 - 6,7-苯并吗啡烷
• 英文名称: (6R,11R)-6,11-Dimethyl-3-(3-methyl-but-2-enyl)-1,2,3,4,5,6-hexahydro-2,6-methano-benzo[d]azocin-8-ol
• 英文别名: (1R,13R)-1,13-dimethyl-10-(3-methylbut-2-enyl)-10-azatricyclo[7.3.1.02,7]trideca-2(7),3,5-trien-4-ol
• 化学式: C₁₉H₂₇NO
• 分子量: 285.429
• InChiKey: VOKSWYLNZZRQPF-WGLYWHLYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  23.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (6R,11R)-6,11-Dimethyl-3-(3-methyl-but-2-enyl)-1,2,3,4,5,6-hexahydro-2,6-methano-benzo[d]azocin-8-ol 在 lithium aluminium tetrahydride 、 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.01h， 生成 Thiobenzoic acid S-[(6R,11R)-6,11-dimethyl-3-(3-methyl-but-2-enyl)-1,2,3,4,5,6-hexahydro-2,6-methano-benzo[d]azocin-8-yl] ester
  参考文献：
  名称：

  Hori, Mikio; Ban, Masatoshi; Imai, Eiji, Heterocycles, 1983, vol. 20, # 12, p. 2359 - 2362

  摘要：

  DOI：
• 作为产物：
  描述：

  1,2,3,4,5,6-Hexahydro-cis-6,11-dimethyl-2,6-methano-3-benzazocin-8-ol 、 1-溴-3-甲基-2-丁烯 在 potassium hydrogencarbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以62%的产率得到(6R,11R)-6,11-Dimethyl-3-(3-methyl-but-2-enyl)-1,2,3,4,5,6-hexahydro-2,6-methano-benzo[d]azocin-8-ol
  参考文献：
  名称：

  （±）-顺式-N-去甲甲唑嗪的分辨率提高

  摘要：

  顺式-N-去甲甲唑啉的旋光异构体是合成许多药理上有用的化合物的起始原料。报道了获得这些异构体的改进的拆分方法。

  DOI：

  10.1002/jhet.5570270753

文献信息

• Method for inhibiting growth of cancer cells
  申请人：Pain Therapeutics, Inc.

  公开号：US10363239B2

  公开（公告）日：2019-07-30

  A method of inhibiting the growth of cancer cells is disclosed in which cancer cells that contain an enhanced amount relative to non-cancerous cells of one or more of phosphorylated mTOR, Akt1, ERK2 and serine2152-phosphorylated filamin A are contacted with an FLNA-binding effective amount of a compound or a pharmaceutically acceptable salt thereof that binds to the pentapeptide of filamin A (FLNA) of SEQ ID NO: 1 and exhibits at least about 60 percent of the FITC-labeled naloxone binding amount when present at a 10 μM concentration and using unlabeled naloxone as the control inhibitor at the same concentration. A compound that binds to the FLNA pentapeptide preferably also contains at least four of the six pharmacophores of FIGS. 19-24.

  本发明公开了一种抑制癌细胞生长的方法，该方法是将含有磷酸化的 mTOR、Akt1、ERK2 和丝氨酸 2152 磷酸化的丝胺 A 中的一种或多种含量相对于非癌细胞有所增加的癌细胞，与 FLNA 结合有效量的化合物或其药学上可接受的盐接触，该化合物或其药学上可接受的盐与 SEQ ID NO：1的五肽（FLNA）结合的化合物或其药学上可接受的盐，并且在10 μM浓度下，以相同浓度的未标记纳洛酮作为对照抑制剂时，显示出至少约60％的FITC标记纳洛酮结合量。与 FLNA 五肽结合的化合物最好还含有图 19-24 中六种药效团中的至少四种。
• METHOD FOR INHIBITING GROWTH OF CANCER CELLS
  申请人：Pain Therapeutics, Inc.

  公开号：US20150148318A1

  公开（公告）日：2015-05-28

  A method of inhibiting the growth of cancer cells is disclosed in which cancer cells that contain an enhanced amount relative to non-cancerous cells of one or more of phosphorylated mTOR, Akt1, ERK2 and serine2152-phosphorylated filamin A are contacted with an FLNA-binding effective amount of a compound or a pharmaceutically acceptable salt thereof that binds to the pentapeptide of filamin A (FLNA) of SEQ ID NO: 1 and exhibits at least about 60 percent of the FITC-labeled naloxone binding amount when present at a 10 μM concentration and using unlabeled naloxone as the control inhibitor at the same concentration. A compound that binds to the FLNA pentapeptide preferably also contains at least four of the six pharmacophores of FIGS. 19 - 24.
• US9433604B2
  申请人：——

  公开号：US9433604B2

  公开（公告）日：2016-09-06
• Hori, Mikio; Ban, Masatoshi; Imai, Eiji, Heterocycles, 1983, vol. 20, # 12, p. 2359 - 2362
  作者：Hori, Mikio、Ban, Masatoshi、Imai, Eiji、Iwata, Noriyuki、Baba, Yutaka、et al.

  DOI：——

  日期：——
• An improved resolution of (±)-<i>cis-N</i>-normetazocine
  作者：G. A. Brine、B. Berrang、J. P. Hayes、F. I. Carroll

  DOI：10.1002/jhet.5570270753

  日期：1990.11

  The optical isomers of cis-N-normetazocine are the starting materials for the synthesis of a number of pharmacologically useful compounds. An improved resolution procedure for obtaining these isomers is reported.

  顺式-N-去甲甲唑啉的旋光异构体是合成许多药理上有用的化合物的起始原料。报道了获得这些异构体的改进的拆分方法。