2,3,5,6,7,8-hexahydro-5,5,8,8-tetramethyl-1H-benzindole | 121866-13-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 2,3,5,6,7,8-hexahydro-5,5,8,8-tetramethyl-1H-benzindole
• 英文别名: 2,3,5,6,7,8-hexahydro-5,5,8,8-tetramethyl-1H-benz[f]-indole；5,5,8,8-tetramethyl-2,3,6,7-tetrahydro-1H-benzo[f]indole
• CAS: 121866-13-5
• 化学式: C₁₆H₂₃N
• 分子量: 229.365
• InChiKey: BSQSCDUQKRHETF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  17
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  12
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2,3,5,6,7,8-hexahydro-5,5,8,8-tetramethyl-1H-benzindole 在 吡啶 、 4-二甲氨基吡啶 、 氢氧化钾 作用下， 以 甲醇 为溶剂， 反应 0.5h， 生成 4-(5,5,8,8-Tetramethyl-2,3,5,6,7,8-hexahydro-benzo[f]indole-1-carbonyl)-benzoic acid
  参考文献：
  名称：

  Retinobenzoic acids. 4. Conformation of aromatic amides with retinoidal activity. Importance of trans-amide structure for the activity

  摘要：

  N-Methylation of two retinoidal amide compounds, 4-[(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthalenyl)carbamoyl]benz oic acid (3, Am80) and 4-[[(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2- naphthalenyl)carbonyl]amino]benzoic acid (5, Am580), resulted in the disappearance of their potent differentiation-inducing activity on human promyelocytic leukemia cell line HL-60. Studies with 1H NMR and UV spectroscopy indicated that large conformational differences exist between the active secondary amides and the inactive N-methyl amides. From a comparison of the spectroscopic results of these amides with those of stilbene derivatives, the conformations of the active amides are expected to resemble that of (E)-stilbene, whereas the inactive amides resemble the Z isomer: 3 (Am80) and 5 (Am580) have a trans-amide bond and their whole structures are elongated, while the N-methylated compounds [4 (Am90) and 6 (Am590)] have a cis-amide bond, resulting in the folding of the two benzene rings. These structures in the crystals were related to those in solution by 13C NMR spectroscopic comparison between the two phases (solid and solution).

  DOI：

  10.1021/jm00130a011
• 作为产物：
  描述：

  5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-1H-benzindole 在 sodium cyanoborohydride 作用下， 以 溶剂黄146 为溶剂， 反应 2.0h， 生成 2,3,5,6,7,8-hexahydro-5,5,8,8-tetramethyl-1H-benzindole
  参考文献：
  名称：

  Retinobenzoic acids. 4. Conformation of aromatic amides with retinoidal activity. Importance of trans-amide structure for the activity

  摘要：

  N-Methylation of two retinoidal amide compounds, 4-[(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthalenyl)carbamoyl]benz oic acid (3, Am80) and 4-[[(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2- naphthalenyl)carbonyl]amino]benzoic acid (5, Am580), resulted in the disappearance of their potent differentiation-inducing activity on human promyelocytic leukemia cell line HL-60. Studies with 1H NMR and UV spectroscopy indicated that large conformational differences exist between the active secondary amides and the inactive N-methyl amides. From a comparison of the spectroscopic results of these amides with those of stilbene derivatives, the conformations of the active amides are expected to resemble that of (E)-stilbene, whereas the inactive amides resemble the Z isomer: 3 (Am80) and 5 (Am580) have a trans-amide bond and their whole structures are elongated, while the N-methylated compounds [4 (Am90) and 6 (Am590)] have a cis-amide bond, resulting in the folding of the two benzene rings. These structures in the crystals were related to those in solution by 13C NMR spectroscopic comparison between the two phases (solid and solution).

  DOI：

  10.1021/jm00130a011

文献信息

• Tricyclic retinoids, methods for their production and use
  申请人：LIGAND PHARMACEUTICALS INCORPORATED

  公开号：EP0933350A1

  公开（公告）日：1999-08-04

  Tricyclic retinoids having activity for retinoic acid receptors and/or retinoid X receptors are provided. Also provided are pharmaceutical compositions incorporating such tricyclic retinoid compounds and methods for their therapeutic use.

  本研究提供了对维甲酸受体和/或维甲酸 X 受体具有活性的三环类维甲酸。此外，还提供了含有此类三环类维甲酸化合物的药物组合物及其治疗方法。
• TRICYCLIC RETINOIDS, METHODS FOR THEIR PRODUCTION AND USE
  申请人：LIGAND PHARMACEUTICALS, INC.

  公开号：EP0800504A1

  公开（公告）日：1997-10-15
• [EN] TRICYCLIC RETINOIDS, METHODS FOR THEIR PRODUCTION AND USE<br/>[FR] RETINOIDES TRICYCLIQUES ET LEURS PROCEDES DE PRODUCTION ET D'UTILISATION
  申请人：LIGAND PHARMACEUTICALS INCORPORATED

  公开号：WO1996020914A1

  公开（公告）日：1996-07-11

  (EN) Tricyclic retinoids having activity for retinoic acid receptors and/or retinoid X receptors are provided. Also provided are pharmaceutical compositions incorporating such tricyclic retinoid compounds and methods for their therapeutic use.(FR) L'invention concerne des rétinoïdes tricycliques présentant une capacité d'activation des récepteurs d'acide rétinoïque et/ou des récepteurs de rétinoïdes X. Elle concerne également des compositions pharmaceutiques comprenant ces composés rétinoïdes tricycliques, ainsi que leurs procédés d'utilisation thérapeutique.