8,9-Dihydrobenzo[g][1,3]benzodioxole-6-carbonitrile | 102035-29-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 8,9-Dihydrobenzo[g][1,3]benzodioxole-6-carbonitrile
• CAS: 102035-29-0
• 化学式: C₁₂H₉NO₂
• 分子量: 199.209
• InChiKey: VSLDXLMCJNRCDL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  15
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  42.2
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  8,9-Dihydrobenzo[g][1,3]benzodioxole-6-carbonitrile 在 sodium tetrahydroborate 、 lithium diisopropyl amide 作用下， 以 乙醇 为溶剂， 反应 1.67h， 生成 1-cyano-1-methyl-5,6-(methylenedioxy)tetralin
  参考文献：
  名称：

  Conformationally defined adrenergic agents. 3. Modifications to the carbocyclic ring of 5,6-dihydroxy-1-(2-imidazolinyl)tetralin: improved separation of .alpha.1 and .alpha.2 adrenergic activities

  摘要：

  A series of modifications to positions 1, 2, and 4 of the tetralin ring of 5,6-dihydroxy-1-(2-imidazolinyl)tetralin (1, A-54741) succeeded in improving the separation of the potent alpha 1 and alpha 2 adrenergic agonism observed for the parent compound 1. In particular 5,6-dihydroxy-4,4-dimethyl-1-(2-imidazolinyl)tetralin (7) was found to be a specific alpha 1 adrenergic agonist, and 7,8-dihydroxy-4-(2-imidazolinyl)chroman (2) was found to have improved alpha 2 adrenergic agonistic selectivity relative to the parent compound 1.

  DOI：

  10.1021/jm00158a016
• 作为产物：
  描述：

  5,6-亚甲基二氧基-1-四酮 在 盐酸 、 zinc(II) iodide 作用下， 以 乙醇 为溶剂， 生成 8,9-Dihydrobenzo[g][1,3]benzodioxole-6-carbonitrile
  参考文献：
  名称：

  Structure−Activity Studies for a Novel Series of N-(Arylethyl)-N-(1,2,3,4-tetrahydronaphthalen-1-ylmethyl)-N-methylamines Possessing Dual 5-HT Uptake Inhibiting and α₂-Antagonistic Activities

  摘要：

  In search of an alpha(2)-antagonist/5-HT uptake inhibitor as a potential new class of antidepressant with a more rapid onset of action, compound 3 was prepared and observed to possess high affinity for the alpha(2)-receptor (K-i = 6.71 nM) and the 5-HT uptake site (20.6 nM). A series of tertiary amine analogs of 3 were synthesized and assayed for their affinity at both the alpha(2)-receptor and the 5-HT uptake site. The structure-activity relationship reveals that a variety of structural modifications to the arylethyl fragment are possible with retention of this dual activity. On the tetralin portion, 5-OMe substitution and the (R) stereochemistry at C-l are optimal with alternate substitutions producing compounds retaining high affinity for the alpha(2)-receptor but lacking affinity for the 5-HT uptake site. Data for several rigidified 5-O-alkyl analogs suggests that the favored orientation of the oxygen lone pairs may be away from the g-position of the tetralin.

  DOI：

  10.1021/jm960723m

文献信息

• Biogenic amine uptake inhibitors
  申请人：ABBOTT LABORATORIES

  公开号：EP0461353A1

  公开（公告）日：1991-12-18

  Compounds of the formula: or a pharmaceutically acceptable salt thereof, wherein m is 0, 1 or 2 and n is 0 or 1; R1 is hydrogen or lower alkyl; R2 is C1-C6-alkyl substituted with a heterocyclic group or C7-C16-arylalkyl, wherein the aryl group is unsubstituted or substituted with from one to three non-hydrogen members independently selected from the group consisting of halogen, C1-C6-alkyl, halo-C1-C6-alkyl, C1-C6-alkoxy, hydroxy, amino and C1-C6-alkylamino; R3, R4, R5 and R6 are independently selected from the group consisting of hydrogen, C1-C6-alkoxy, C1-C6-alkyl, halogen, and halo-C1-C6-alkyl, or any two of R3, R4, R5 and R6 taken together form a methylenedioxy group; and R7 is hydrogen or C1-C6-alkyl. These compounds are useful as inhibitors of the neuronal uptake of biogenic amines and for the treatment of affective disorders, such as, for example, depression.

  式化合物 或其药学上可接受的盐、 其中 m 为 0、1 或 2，n 为 0 或 1； R1 是氢或低级烷基 R2 是被杂环基团或 C7-C16 芳烷基取代的 C1-C6 烷基，其中芳烷基未被取代或被 1 至 3 个独立选自卤素、C1-C6-烷基、卤代-C1-C6-烷基、C1-C6-烷氧基、羟基、氨基和 C1-C6- 烷基氨基的非氢成员取代； R3、R4、R5 和 R6 独立地选自氢、C1-C6-烷氧基、C1-C6-烷基、卤素和卤代-C1-C6-烷基组成的组，或任意两个 R3、R4、R5 和 R6 共同组成亚甲基二氧基；以及 R7 是氢或 C1-C6- 烷基。 这些化合物可作为神经元摄取生物胺的抑制剂，用于治疗情感障碍，例如抑郁症。
• DEBERNARDIS J. F.; WINN M.; ARENDSEN D. L.; KERKMAN D. J.; KYNCL J. J., J. MED. CHEM., 29,(1986) N 8, 1413-1417
  作者：DEBERNARDIS J. F.、 WINN M.、 ARENDSEN D. L.、 KERKMAN D. J.、 KYNCL J. J.

  DOI：——

  日期：——
• 1-Aminomethyl-1,2,3,4-tetrahydronaphthalenes and -indanes
  申请人：ABBOTT LABORATORIES

  公开号：EP0325963B1

  公开（公告）日：1993-09-22
• 1-AMINOMETHYL-1,2,3,4-TETRAHYDRONAPHTHALENES
  申请人：ABBOTT LABORATORIES

  公开号：EP0395734A1

  公开（公告）日：1990-11-07
• EP0395734A4
  申请人：——

  公开号：EP0395734A4

  公开（公告）日：1991-01-02