1,1-Dimethyl-1H-indene-5-carbonitrile | 124369-43-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 茚和异茚
• 英文名称: 1,1-Dimethyl-1H-indene-5-carbonitrile
• 英文别名: 1,1-Dimethylindene-5-carbonitrile
• CAS: 124369-43-3
• 化学式: C₁₂H₁₁N
• 分子量: 169.226
• InChiKey: LSOATDNEOGKFBR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  23.8
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1,1-Dimethyl-1H-indene-5-carbonitrile 在 palladium on activated charcoal N-溴代丁二酰亚胺(NBS) 、 sodium azide 、 偶氮二异丁腈 、 氢气 作用下， 以 四氯化碳 、 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 25.0 ℃ 、101.33 kPa 条件下， 反应 4.5h， 生成 3-amino-5-cyano-1,1-dimethylindane
  参考文献：
  名称：

  Cardioselective Antiischemic ATP-Sensitive Potassium Channel Openers. 2. Structure-Activity Studies on Benzopyranylcyanoguanidines; Modification of the Benzopyran Ring

  摘要：

  The ATP-sensitive potassium channel (K-ATP) openers are of considerable interest as myocardial protecting agents. However, there exists a narrow window of safety for the use of first-generation compounds as antiischemic agents due to their powerful peripheral vasodilating effects, which can result in underperfusion of the area already at risk. We have recently disclosed the discovery of benzopyranylcyanoguanidine type K-ATP openers (BMS-180448) which are more selective for the ischemic myocardium compared to the first-generation compounds. This publication deals with structure-activity relationships for the antiischemic activity of the lead compound 8. The presence of an electron-withdrawing group at C6, an sp(3) center at C4, and a gem-dimethyl group at C2 appears to be essential for antiischemic activity. Cyanoguanidine can be replaced with a urea moiety. The results reported here support the hypothesis that distinct structure-activity relationships exist for antiischemic and vaso:relaxant activities of compounds related to 8 and cromakalim. The trifluoromethyl analog 10 is 550-fold more selective in vitro for the ischemic myocardium compared to the first-generation agent cromakalim. The reasons for the selectivity of these compounds for the ischemic myocardium are not clear at the present time. They may be related to the existence of receptor subtypes in smooth muscle and the myocardium.

  DOI：

  10.1021/jm00011a016
• 作为产物：
  描述：

  5-Cyano-1,1-dimethyl-indan-3-ol 在 对甲苯磺酸 作用下， 以 甲苯 为溶剂， 反应 16.0h， 生成 1,1-Dimethyl-1H-indene-5-carbonitrile
  参考文献：
  名称：

  一系列新的钾通道激活剂：3-酰胺基-1,1-二甲基茚满-2-醇的合成和平滑肌松弛活性。

  摘要：

  描述了一系列新的平滑肌松弛剂的合成，所述平滑肌松弛剂已显示出通过钾通道的开放或激活起作用。已经评估了化合物抑制豚鼠分离的气管中自发音的能力，并讨论了结构-活性关系。一种化合物，特别是1,1-二甲基-5-硝基-3-（2-吡啶-1-基）茚满-2-醇（16）被确定为体外气道平滑肌的有效缓和剂，IC50 =攻击前30-45分钟口服0.15 microM，可显着抑制清醒豚鼠的组胺诱导的呼吸困难。

  DOI：

  10.1021/jm00107a008

文献信息

• BUCKLE, DEREK R.;ARCH, JONATHAN R. S.;EDGE, COLIN;FOSTER, KEITH A.;HOUGE-+, J. MED. CHEM., 34,(1991) N, C. 919-926
  作者：BUCKLE, DEREK R.、ARCH, JONATHAN R. S.、EDGE, COLIN、FOSTER, KEITH A.、HOUGE-+

  DOI：——

  日期：——