2,2-dimethyl-2H-pyrano<3,2-c>pyridine | 108031-09-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃吡啶类
• 英文名称: 2,2-dimethyl-2H-pyrano<3,2-c>pyridine
• 英文别名: 2,2-Dimethyl-2H-pyrano[3,2-c]pyridine；2,2-dimethylpyrano[3,2-c]pyridine
• CAS: 108031-09-0
• 化学式: C₁₀H₁₁NO
• mdl: MFCD18802992
• 分子量: 161.203
• InChiKey: KZFPXYSAYXMXGD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  22.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2,2-dimethyl-2H-pyrano<3,2-c>pyridine 在 potassium tert-butylate 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 24.5h， 生成 (3R,4S)-2,2-Dimethyl-4-(pyridin-2-yloxy)-3,4-dihydro-2H-pyrano[3,2-c]pyridin-3-ol
  参考文献：
  名称：

  Relaxant activity of 4-amido-3,4-dihydro-2H-1-benzopyran-3-ols and 4-amido-2H-1-benzopyrans on guinea pig isolated trachealis

  摘要：

  A series of 4-amido-3,4-dihydro-2H-1-benzopyran-3-ols and 4-amido-2H-1-benzopyrans related to the potassium channel activator cromakalim have been prepared and evaluated for their relaxant activity in guinea pig isolated tracheal spirals. Several analogues show enhanced relaxant activity relative to cromakalim in this preparation and the rank order of potency for those substituents investigated at C-6 was CF3 greater than CN greater than C2H5 greater than aza greater than or equal to CH3. One compound, trans-3,4-dihydro-2,2-dimethyl-4-(2-oxopiperidin-1-yl)-7-(trifluor omethyl)-2H- 1-benzopyran-3-ol (24), was resolved into its two enantiomers and the activity was shown to reside essentially in the (+)-isomer, adding further support to the suggestion that the smooth muscle receptor for these potassium channel activators is stereoselective.

  DOI：

  10.1021/jm00173a019
• 作为产物：
  描述：

  4-(2-Methylbut-3-yn-2-yloxy)pyridine 以 邻二氯苯 为溶剂， 反应 1.0h， 以50%的产率得到2,2-dimethyl-2H-pyrano<3,2-c>pyridine
  参考文献：
  名称：

  Evans, John M.; Stemp, Geoffrey, Synthetic Communications, 1988, vol. 18, # 10, p. 1111 - 1118

  摘要：

  DOI：

文献信息

• Anti-hypertensive pyranopyridine compounds
  申请人：Beecham Group p.l.c.

  公开号：US04812459A1

  公开（公告）日：1989-03-14

  A compound of formula (I) or a pharmaceutically acceptable salt thereof: ##STR1## wherein all the symbols are defined in the specification; having pharmacological activity, including blood pressure lowering activity, a process and intermediates for their preparation and their use as pharmaceuticals.

  一种式子为(I)的化合物或其药学上可接受的盐：##STR1## 其中所有符号均在说明书中定义；具有药理活性，包括降低血压的活性，以及制备它们的过程和中间体，以及它们作为药物的用途。
• Discovery and structure–activity relationships of a novel series of benzopyran-based KATP openers for urge urinary incontinence
  作者：Xuqing Zhang、Yuhong Qiu、Xiaojie Li、Sheela Bhattacharjee、Morgan Woods、Patricia Kraft、Scott G. Lundeen、Zhihua Sui

  DOI：10.1016/j.bmc.2008.11.055

  日期：2009.1

  A novel series of benzopyran derivatives were synthesized and evaluated as K(ATP) channel openers. Structure-activity relationships were investigated around 4-position of the benzopyran nucleus. Optimization of 4-substituent with some heterocyclic rings led to compound 13b bearing a benzo[d] isoxazol-3-one moiety as a potent and selective KATP channel opener in vitro. In two anesthetized rat models of myogenic bladder overactivity, compound 13b was found to inhibit spontaneous bladder contractions. (C) 2008 Elsevier Ltd. All rights reserved.
• Variation in the aromatic ring of cromakalim: antihypertensive activity of pyranopyridines and 6-alkyl-2H-1-benzopyrans
  作者：Gordon Burrell、Frederick Cassidy、John M. Evans、Diane Lightowler、Geoffrey Stemp

  DOI：10.1021/jm00173a018

  日期：1990.11

  The synthesis and antihypertensive activity in the spontaneously hypertensive rat of two new series of analogues related to cromakalim (1) are described. In the first series, where the benzopyran nucleus has been replaced by a pyranopyridine nucleus, the position of the nitrogen atom has been found to be critical for activity, and the most potent compounds are the pyrano[3,2-c]pyridines. In the second series, where the powerful electron-withdrawing cyano group of compound 1 has been replaced by alkyl and phenyl groups, the order of antihypertensive potency is ethyl, isopropyl, tert-butyl greater than propyl, cyclopentyl greater than methyl greater than phenyl.
• BURRELL, GORDON;CASSIDY, FREDERICK;EVANS, JOHN M.;LIGHTOWLER, DIANE;STEMP+, J. MED. CHEM., 33,(1990) N1, C. 3023-3027
  作者：BURRELL, GORDON、CASSIDY, FREDERICK、EVANS, JOHN M.、LIGHTOWLER, DIANE、STEMP+

  DOI：——

  日期：——
• EVANS, JOHN M.;STEMP, GEOFFREY, SYNTH. COMMUN., 18,(1988) N 10, C. 1111-1118
  作者：EVANS, JOHN M.、STEMP, GEOFFREY

  DOI：——

  日期：——