3-<3-<(ethoxycarbonyl)methyl>pyridin-4-yl>propionic acid ethyl ester | 147646-16-0

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 3-<3-<(ethoxycarbonyl)methyl>pyridin-4-yl>propionic acid ethyl ester
• 英文别名: ethyl 3-(3-carbethoxymethylpyrid-4-yl)propionate；Ethyl 3-[3-(2-ethoxy-2-oxoethyl)pyridin-4-yl]propanoate
• CAS: 147646-16-0
• 化学式: C₁₄H₁₉NO₄
• 分子量: 265.309
• InChiKey: CYTUGKWOVIUAQQ-UHFFFAOYSA-N

物化性质

• 沸点：
  370.7±32.0 °C(Predicted)
• 密度：
  1.115±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  19
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  65.5
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-<3-<(ethoxycarbonyl)methyl>pyridin-4-yl>propionic acid ethyl ester 在 盐酸 、 sodium hydride 作用下， 生成 5,8-二氢-6H-异喹啉-7-酮
  参考文献：
  名称：

  Synthesis and binding of 6,7,8,9-tetrahydro-5H-pyrido[3,4-d]azepine and related ring-opened analogs at central nicotinic receptors

  摘要：

  6,7,8,9-Tetrahydro-5H-pyrido[3,4-d]azepine (5a) and its N-7-methyl derivative 5b were synthesized and evaluated as potential nicotinic acetylcholinergic receptor (nAChR) ligands. On the basis that 6,7,8,9-tetrahydro-5H-pyrido[3,4-c]azepine (4a), which binds at nAChRs with low affinity (K-i = 1100 nM), possesses an internitrogen distance (4.6 Angstrom) that may be less than optimal, we designed compound 5a due to its similar shape but longer internitrogen distance (5.5 Angstrom). Compound 5a (K-i = 45 nM) was found to bind with enhanced affinity. However, unlike what is seen with nornicotine/nicotine, N-methylation of 5a reduced affinity (5b; K-i = 268 nM) rather than enhancing it. The results suggest that 5 may interact at nicotine receptors in a manner that is somewhat different from that of nicotine. Ring-opening of the pyrido[3,4-d]azepine ring led to a series of 3-(2-aminoethyl)pyridines 21 that retained the affinity of the cyclic compound. Subsequent modification, including further chain lengthening (e.g. aminopropylpyridines 22) and introduction of unsaturation, ultimately led to the development of a series of 3-(2-aminethoxy)pyridines 27. Simple N-substituted derivatives of 27 were found to bind with K-i values of 20 to 35 nM. Because parallel structural changes in several series of related compounds did not result in parallel shifts in nAChR affinity, it is unlikely that all the investigated compounds bind in a similar fashion at these receptors. Nevertheless, some of these compounds represent novel classes of nAChR ligands. (C) Elsevier, Paris.

  DOI：

  10.1016/s0223-5234(99)80051-8
• 作为产物：
  描述：

  3-吡啶乙酸乙酯 在 sulfur 作用下， 以 xylene 为溶剂， 生成 3-<3-<(ethoxycarbonyl)methyl>pyridin-4-yl>propionic acid ethyl ester
  参考文献：
  名称：

  Facile synthesis of two pyridine alkaloids via functionalized 3,4-dialkylpyridines

  摘要：

  DOI：

  10.1021/jo00063a043

文献信息

• Synthesis and binding of 6,7,8,9-tetrahydro-5H-pyrido[3,4-d]azepine and related ring-opened analogs at central nicotinic receptors
  作者：Yun-Xing Cheng、Malgorzata Dukat、Matthew Dowd、Wolfgang Fiedler、Billy Martin、Mohamed  Imad Damaj、Richard A Glennon

  DOI：10.1016/s0223-5234(99)80051-8

  日期：1999.2

  6,7,8,9-Tetrahydro-5H-pyrido[3,4-d]azepine (5a) and its N-7-methyl derivative 5b were synthesized and evaluated as potential nicotinic acetylcholinergic receptor (nAChR) ligands. On the basis that 6,7,8,9-tetrahydro-5H-pyrido[3,4-c]azepine (4a), which binds at nAChRs with low affinity (K-i = 1100 nM), possesses an internitrogen distance (4.6 Angstrom) that may be less than optimal, we designed compound 5a due to its similar shape but longer internitrogen distance (5.5 Angstrom). Compound 5a (K-i = 45 nM) was found to bind with enhanced affinity. However, unlike what is seen with nornicotine/nicotine, N-methylation of 5a reduced affinity (5b; K-i = 268 nM) rather than enhancing it. The results suggest that 5 may interact at nicotine receptors in a manner that is somewhat different from that of nicotine. Ring-opening of the pyrido[3,4-d]azepine ring led to a series of 3-(2-aminoethyl)pyridines 21 that retained the affinity of the cyclic compound. Subsequent modification, including further chain lengthening (e.g. aminopropylpyridines 22) and introduction of unsaturation, ultimately led to the development of a series of 3-(2-aminethoxy)pyridines 27. Simple N-substituted derivatives of 27 were found to bind with K-i values of 20 to 35 nM. Because parallel structural changes in several series of related compounds did not result in parallel shifts in nAChR affinity, it is unlikely that all the investigated compounds bind in a similar fashion at these receptors. Nevertheless, some of these compounds represent novel classes of nAChR ligands. (C) Elsevier, Paris.
• Facile synthesis of two pyridine alkaloids via functionalized 3,4-dialkylpyridines
  作者：Min Jen Shiao、Win Long Chia、Chin Jen Peng、Chien Chang Shen

  DOI：10.1021/jo00063a043

  日期：1993.5