3-(4',4'-dimethyl-4',5'-dihydro-oxazol-2'-yl)-4-phenylpyridine | 68981-85-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 3-(4',4'-dimethyl-4',5'-dihydro-oxazol-2'-yl)-4-phenylpyridine
• 英文别名: 3-(4,4-dimethyl-4,5-dihydrooxazol-2-yl)-4-phenyl-pyridine；4-phenyl-3-(4,5-dihydro-4,4-dimethyl-2-oxazolyl)pyridine；3-(4,4-dimethyloxazolin-2-yl)-phenylpyridine；3-(4,4-dimethyl-4,5-dihydro-oxazol-2-yl)-4-phenyl-pyridine；3-(4,5-dihydro-4,4-dimethyl-2-oxazolyl)-4-phenylpyridine；4,4-dimethyl-2-(4-phenylpyridin-3-yl)-5H-1,3-oxazole
• CAS: 68981-85-1
• 化学式: C₁₆H₁₆N₂O
• 分子量: 252.316
• InChiKey: IPBZAMXDVBJBIO-UHFFFAOYSA-N

物化性质

• 熔点：
  85-86 °C
• 沸点：
  75-82 °C(Press: 0.025 Torr)
• 密度：
  1.12±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  34.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-(4',4'-dimethyl-4',5'-dihydro-oxazol-2'-yl)-4-phenylpyridine 在 盐酸 、 氯化亚砜 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 32.0h， 生成 4-phenylpyridine-3-carboxylic acid methyl ester
  参考文献：
  名称：

  Identification and Characterization of m1 Selective Muscarinic Receptor Antagonists

  摘要：

  A series of esters of 1,4-disubstituted tetrahydropyridine carboxylic acids (I) has been synthesized and characterized as potential mi selective muscarinic receptor antagonists. The affinity of these compounds for the five human muscarinic receptor subtypes (Hm1-Hm5) was determined by the displacement of [H-3]-NMS binding using membranes from transfected Chinese hamster ovarian cells. One of the most potent and selective compounds of this series is an analogue of I [11, R-1 = (CH2)(5)CH3], which has an IC50 value of 27.3 nM at the m1 receptor and possesses 100-fold (m2), 48-fold (m3), 74-fold (m4), and 19-fold (m5) selectivities at the other receptors. Thus, this analogue appears to be more selective on the basis of binding than the prototypical mi antagonist, pirenzepine. Functional data, such as the inhibition of carbachol-stimulated phosphatidylinositol hydrolysis, on selected analogues confirmed the muscarinic antagonistic properties of this chemical series.

  DOI：

  10.1021/jm980067l
• 作为产物：
  描述：

  3-(4,4-二甲基-4,5-二氢-1,3-氧唑-2-基)吡啶 在 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 乙醚 、 苯 为溶剂， 反应 4.0h， 生成 3-(4',4'-dimethyl-4',5'-dihydro-oxazol-2'-yl)-4-phenylpyridine
  参考文献：
  名称：

  Hauck, Albert E.; Giam, Choo-Seng, Journal of the Chemical Society. Perkin transactions I, 1980, p. 2070 - 2076

  摘要：

  DOI：

文献信息

• Nicotinic Acid Adenine Dinucleotide Phosphate Analogues Containing Substituted Nicotinic Acid: Effect of Modification on Ca²⁺ Release
  作者：Pooja Jain、James T. Slama、LeRoy A. Perez-Haddock、Timothy F. Walseth

  DOI：10.1021/jm1007209

  日期：2010.11.11

  in potency for competition ligand binding assays using [32P]NAADP. In contrast, several 5-substituted NAADP derivatives showed high potency for binding and full agonist activity for Ca2+ release. 5-Azido-NAADP was shown to release calcium from sea urchin egg homogenates at low concentration and to compete with [32P]NAADP in a competition ligand binding assay with an IC50 of 18 nM, indicating that this

  在烟酸部分的 4 位或 5 位位置被取代的烟酸腺嘌呤二核苷酸磷酸 (NAADP) 的类似物已使用Aplysia californica ADP-核糖基环化酶或哺乳动物 NAD 糖水解酶从 NADP 酶促合成。烟酸的 4 位取代导致从海胆卵匀浆中释放 Ca 2+ 离子的激动剂效力丧失，并导致使用 [ 32 P]NAADP进行竞争配体结合测定的效力丧失。相比之下，几种 5-取代 NAADP 衍生物显示出对 Ca 2+ 的高结合力和完全激动剂活性释放。5-叠氮基-NAADP 以低浓度从海胆卵匀浆中释放钙，并在竞争配体结合试验中与[ 32 P]NAADP 竞争，IC 50为 18 nM，表明该化合物可能是一种潜在的光探针可用于 NAADP 受体的特异性标记和鉴定。
• Convergent and efficient synthesis of spiro[benzofuran-3(2H),4'-piperidines]
  作者：Saul H. Rosenberg、Henry Rapoport

  DOI：10.1021/jo00175a011

  日期：1984.1
• Substitutions of pyridines activated by oxazolines via nucleophilic additions for metalation-alkylation
  作者：A. I. Meyers、Richard A. Gabel

  DOI：10.1021/jo00134a024

  日期：1982.6
• Meyers,A.I.; Gabel,R.A., Heterocycles, 1978, vol. 11, p. 133 - 138
  作者：Meyers,A.I.、Gabel,R.A.

  DOI：——

  日期：——
• Hauck, Albert E.; Giam, C. S., Journal of the Chemical Society. Perkin transactions I, 1984, # 10, p. 2227 - 2232
  作者：Hauck, Albert E.、Giam, C. S.

  DOI：——

  日期：——