4-(1,2-dihydro-2-oxo-1-pyridyl)-2,2-dimethyl-6-nitro-2H-1-benzopyran | 117545-13-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: 4-(1,2-dihydro-2-oxo-1-pyridyl)-2,2-dimethyl-6-nitro-2H-1-benzopyran
• 英文别名: 1-(2,2-Dimethyl-6-nitro-2H-1-benzopyran-4-yl)-2(1H)-pyridinone；1-(2,2-dimethyl-6-nitrochromen-4-yl)pyridin-2-one
• CAS: 117545-13-8
• 化学式: C₁₆H₁₄N₂O₄
• 分子量: 298.298
• InChiKey: DFCBXKCQXBAPOV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  22
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  75.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-(1,2-dihydro-2-oxo-1-pyridyl)-2,2-dimethyl-6-nitro-2H-1-benzopyran 生成 1-(2,2-dimethyl-6-nitro-1aH-oxireno[2,3-c]chromen-7b-yl)pyridin-2-one
  参考文献：
  名称：

  HAUSLER, GUNTHER;GERICKE, ROLF;WURZIGER, HANNS;BAUMGARTH, MANFRED;LUES, I+

  摘要：

  DOI：
• 作为产物：
  描述：

  1-[(3R,4S)-3-hydroxy-2,2-dimethyl-6-nitro-3,4-dihydrochromen-4-yl]pyridin-2-one 在 sodium hydroxide 作用下， 以 1,4-二氧六环 为溶剂， 反应 0.17h， 以24%的产率得到4-(1,2-dihydro-2-oxo-1-pyridyl)-2,2-dimethyl-6-nitro-2H-1-benzopyran
  参考文献：
  名称：

  4-（1,2-二氢-2-氧代-1-吡啶基）-2H-1-苯并吡喃及相关化合物，新型钾通道活化剂的合成及降压活性。

  摘要：

  描述了4-（1,2-二氢-2-氧代-1-吡啶基）-2H-1-苯并吡喃-3-醇的合成和降压活性。未取代的吡啶酮加合物铅化合物7e具有高活性，吡啶酮环上的取代基导致活性降低。为了获得最佳活性，必须在C-6位上强烈吸电子的取代基。当2-吡啶酮环被其他杂环如4-吡啶酮，嘧啶酮，哒嗪酮，吡嗪酮和1,4-丁烷磺胺取代时，活性得以维持。3-羟基官能团（---- 17a）的去除不会显着降低活性。从苯并二氢吡喃醇中除去水会导致苯并二氢吡喃酮的形成，这是已知最有效的降压药之一。各种取代基，尤其是杂环C-6取代基的影响，以4-（2-氧代-1-吡咯烷基）色满-3-醇系列进行了研究。铬醇在3-羟基处被短链酸酯化，保持其活性。色烯双键的环氧化也产生活性化合物。环氧化物22的重排产生3-酮化合物23和烯醇衍生物25。酮23a的还原产生顺式-苯并二氢吡喃醇7ab及其反式异构体7e。在自发性高血压大鼠中以1 mg / kg

  DOI：

  10.1021/jm00164a005

文献信息

• Chromanderivate
  申请人：MERCK PATENT GmbH

  公开号：EP0346724A1

  公开（公告）日：1989-12-20

  Neue Chromanderivate der Formel I worin X, Y, R¹, R², R⁵, R⁶ und R⁷ die in Patentanspruch 1 angegebenen Bedeutungen haben, sowie ihre Salze zeigen Wirkungen auf das cardiovas­kuläre System und können verwendet werden zur Behandlung bzw. Prophylaxe von Herzinsuffizienz, Angina pectoris, Bluthochdruck, Inkontinenz und Alopezie.

  这段文字是关于一种新的化合物的描述，化合物的名称为 "Neue Chromanderivate"，化学式为 "I"。其中的X、Y、R¹、R²、R⁵、R⁶和R⁷是根据专利权要求1中给出的定义，它们的盐对心血管系统有作用，可以用于治疗或预防心力衰竭、心绞痛、高血压、失禁和脱发。
• 6-Substituted Benzopyrans as Potassium Channel Activators:  Synthesis, Vasodilator Properties, and Multivariate Analysis
  作者：Raimund Mannhold、Gabriele Cruciani、Horst Weber、Horst Lemoine、Andrea Derix、Claus Weichel、Monica Clementi

  DOI：10.1021/jm981047m

  日期：1999.3.1

  During the last 10 years compounds have been discovered which can activate or block K-ATP channels. In particular, K channel activators (KCA)have been found to be smooth muscle relaxants with their main utility in hypertension and bronchodilation. In this paper we describe the synthesis of new KCA of the benzopyran type with a fixed 4-substituent and a systematic variation in the 6-position. The relaxant potency in rat aorta and trachea was used for biological characterization of the benzopyrans. In both biological test systems, they exhibit potency ranges of more than 3 log units. Structure-activity relationships are investigated by principal component analysis (PCA) and partial least-squares (PLS) analysis. Most striking outliers in an initial PLS analysis of the entire database were the unsubstituted 6-H compound 13 as well as 34 and 35. For the remaining set of 31 compounds, a S-component PLS model explains the variance in biological activity to 81% in the aortic and to 82% in the tracheal test system. 6-Substituents influence affinity by a direct (presumably dipolar) interaction with the receptor site. According to the 2D-plot of the partial PLS weights, a strong electronegativity as well as high values for the integy moment and for the heat of formation in water dominate the first component; low values for substituent size (as defined by globularity or surface) are in addition favorable for high potency. High lipophilicity and low minimum energies of interaction dominate the second component. Chemical descriptors for the biological potency of the test set in rat aorta and rat trachea are very similar according to the almost identical projection of the Y-variables onto the X-component space.
• BERGMANN, ROLF;GERICKE, ROLF, J. MED. CHEM., 33,(1990) N, C. 492-504
  作者：BERGMANN, ROLF、GERICKE, ROLF

  DOI：——

  日期：——
• US5387587A
  申请人：——

  公开号：US5387587A

  公开（公告）日：1995-02-07
• US5391751A
  申请人：——

  公开号：US5391751A

  公开（公告）日：1995-02-21